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craigrcannon · 3 years

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Employee #1: Yahoo

Employee #1 is a series of interviews focused on sharing the often untold stories of early employees at tech companies.

Tim was the first employee at Yahoo, its Chief Product Officer for eight years, and is now a partner at YC, so we thought it would be fitting to kick things off with him.

Discussed: Meeting the Founders, Writing Yahoo’s Business Plan, Leaving Harvard Business School Early, Creating the Banner Ad, Yahoo’s First Ad Sales, Being an Early Employee After a Management Change, and Founder vs. Early Employee Differences.

Craig : What did you do before Yahoo?

Tim : Before Yahoo, I learned that I preferred working at small companies. I really didn’t think of it as entrepreneurship at that point. My first work experience out of school was at Motorola – a big company. And at the time, in the early ’90s, Motorola was held up as a model of a well-run company. Every business magazine at the time portrayed Motorola up as the ideal.

I went there with a positive attitude. The work was interesting. It was rewarding and intellectually challenging. But after a few months, I remember looking at my boss and my boss’ boss, and my boss’ boss’ boss, and saying to myself, “You know what? I don’t want any of their jobs.” I saw how they spent their time and didn’t find it interesting or very rewarding. They spent their time managing meetings and office politics.

This wasn’t my vision of what work was. To me, work was doing and making things and being able to see the fruits of that labor. At the end of the day or at least after a short period of time, I need to point to something and say to myself ‘that’s what I’ve been building.’

My experience in this big company was very different from that idea. If I rose up the managerial ranks in this big company, I could easy see myself going home and asking myself, “What did I do today?” and not having a very satisfying answer.

Craig : You couldn’t point at stuff.

Tim : That’s right. It‘s not that these managers weren’t doing things, but everything was so time inefficient. In big companies, time scales are longer. And the bullshit factor of office politics is high. For me, maintaining passion for your work when the feedback mechanism is that slow is difficult.

Once I internalized that big companies weren’t my cup of tea, I decided to go to business school in order to make a change.

Craig : But you ended up leaving Harvard Business School for Yahoo, right?

Tim : That’s right. I left in the middle of my second year. The whole point of going to business school was to figure out what I wanted to do and get exposed to a lot. The case study method was great for that.

I soon concluded that small companies were where I would thrive. I also thought that it would be great to work with friends. What could be more rewarding that working hard and doing something important with friends? And so here I was in business school thinking this when my friend Jerry Yang calls and says, “Hey, I want you to come out and join me and my co-founder start a company.”

Craig : That was the opportunity.

Tim : Exactly.

Craig : Just to rewind for a second, how did you guys meet?

Tim : Undergrad. Jerry and I were both double E’s [electrical engineers]. We spent 4 years studying together.

Craig : Cool. So Jerry calls and you’re thinking, “Oh, this might be it.” Did you know that Yahoo would be a thing, or did you just feel like this is a good first step?

Tim : The latter. I didn’t know it would be a big thing. Jerry came to visit me at the beginning of my second year at HBS. At the time he was a PhD student in EE at Stanford. He knew I was looking for a new job, and I told him, “I want something small.”

He called me a couple of months later and said, “Hey, a buddy of mine, my research partner and I started this thing. You should check it out,” and he showed me the world wide web for the first time. There was almost nothing online at that point, but I clearly remember a website company called Satchel.com, which published live sports scores.

I’m a sports junkie. So before I found this website, I used to sit and watch ESPN just for the score ticker that runs across the bottom of the screen. At the time, it only came on twice an hour. I was pathetic. I literally would just sit there and wait 30 minutes for the damn ticker to get the live score for Detroit Piston games. There was no other way.

Craig : Hahaha.

Tim : So Jerry showed me this site and I asked, “You mean I can just hit refresh and I get the live score instantly?” Okay, I got it.

Craig : That’s how you got the internet?

Tim : That’s how I got the internet.

Craig : That’s the best example I’ve ever heard.

Tim : After that, I was hooked. Jerry and his cofounder, David, had built a directory of the world wide web, which was finite at that point. Given where the internet is today, it’s hard to imagine. It was largely just double Es and technical folks posting their dissertations and sharing their papers. Only gradually did they make sites about their hobbies and quirky things, because they realized, “Hey, it doesn’t have to be just dissertations.” So Jerry and Dave started collecting these things and organizing them for everyone.

And so when Jerry called me at school, he said, “Hey, I have no idea if this is going to be big, but I know you’re looking for a job. So how about if you join David and me? Come out to Silicon Valley and get a regular 9 to 5 at a place like at SGI [Silicon Graphics], and then you can moonlight with us. And we’ll see where it goes.” I’m like, “Sounds good.”

Craig : And so where does this fall? Is this the summer before your second year?

Tim : No, this is November of my second year. And I’m thinking, “Sounds good. I’ll ramp up my job search in Silicon Valley, at SGI or Intel or wherever.”

Craig : Yeah, there are plenty of places like that.

Tim : Yes, plenty of places. But that’s also the time when internet usage started to take off.

A couple weeks later Jerry calls me and says, “Hey, we’re going to go raise some money. We need a business plan. Can you help us write a business plan?”

So I flew out to Stanford for Christmas break. I spent two weeks with them, wrote the business plan, then went back to school. They took the business plan, which they probably really didn’t need, it was mostly just a formality at that point, and they raised money from Sequoia Capital.

But in those two weeks I learned a ton from them about the opportunity and put it into a business plan format.

Again, that was about the same time that internet usage started to take off. So a couple weeks after I returned to school, Jerry called and said, “Ah, you know what? This thing is taking off. It might not be a moonlighting job by the time you graduate. It might be a full-time gig.” I’m like, “Fine by me.”

Craig : That just saved me time.

Tim : Exactly, I wouldn’t have to look for another job.

So a few weeks later Jerry calls and says, “Sequoia is going to give us money and we’re going to go for it.” I’m thinking,

“That’s awesome. I’m in. I will see you in June right after graduation.”

Two weeks later, Mike Moritz, a partner at Sequoia, calls me, “Tim, we have a problem.” “I’ll be out after my graduation on June 8th. What’s the problem?”

“We don’t need you in June.”

“Huh? Jerry said I’m in. What’s changed?”

“Well, this ship is sailing. You either need to get on now or don’t bother coming.”

“What’s that mean?”

“We need you in February, not June. Your position will be filled by June.”

So I’m like, “I’m in.”

Craig : Wow. So you just ditched business school?

Tim : It was a little more involved than that. It included a very uncomfortable phone call with my parents, who paid for business school. Luckily, I did end up graduating.

Craig : Nice. So what was your day-to-day when you moved out?

Tim : It was whatever needed to be done. I was an EE, but the other three were all more technical than me. They hired me as the business person so I had to do all the operations and business stuff – including figuring out if there was even an ad market. No one had ever sold advertising on the Internet.

Craig : So advertising was the clear strategy from the very beginning for you. That was in the business plan.

Tim : That was in the business plan. I shouldn’t say that nobody had sold ads online before though. Other people had sold advertising on the Internet, but not at scale and not as their primary business.

I think it was Wired Magazine that was the first one to sell an ad online. So there were the beginnings of something, but Wired was an offline magazine company. It wasn’t their primary business. There wasn’t much else being sold online.

So we came up with the traditional banner ad size that still exists today and tried to figure out how to sell it. At the time, the only people that used the Internet were traditionalists. And what I mean by that is the internet was used exclusively for the non-commercial sharing of information at the time. The idea of commercializing the internet wasn’t accepted by the very people using the internet. Of course, the number of people and the demographics of those people were rapidly changing.

Craig : So your job was to shift how that community was thinking or bring other people online or both?

Tim : Both.

Craig : And so you are cold calling people to sell ads? What were you doing?

Tim : Jerry and I tried to figure out the business side of things and we quickly realized that we were not the best people to sell ads. So we hired an outside agency in L.A. and convinced them to try to sell ads on the internet.

We decided we’ll sell every page on our site, except the home page, to five advertisers for a million bucks a pop. That made us $5,000,000, but they were the same 5 ads on the site for an entire month. Our users hated it.

Craig : What was the traffic at that point?

Tim : I can’t remember the exact number, but it was a double digit percentage of the traffic on the web. It was a big number.

Once we got advertising going, I was thinking, “Oh my god, we’re in the ad business. I’m an engineer, not an ad sales guy. As much as I’d love to pull an ad sales guy out of me, I’m not that guy.”

Jerry realized he wasn’t an ad sales guy either so we hired a CEO, a guy by the name of Tim Koogle. He came on in August of 1995 and helped us build an ad-supported media company. But that was a full seven months after I got there. Traffic on the site was growing at an amazing rate, but we were really struggling to build an organization that could keep up with the growth.

We knew we were on to something potentially really, really big and we knew we didn’t have enough experience to execute it alone.

Craig : So what interests me is throughout this phase it sounds like because you’re buddies with the founders and you’re sort of treated as this co-founder-type guy. How did that dynamic work?

Tim : Jerry and David were the founders and when a big decision needed to be made, like who to raise money from, they would lock themselves in a room and come back with a decision. That said, the day-to-day operational decisions were all made by consensus at the time. There were four of us, and in that sense, I certainly felt like a co-founder.

Craig : After you closed those first ad sales were you all still freaking out over if this would be viable to not?

Tim : It was probably a full year of discomforting uncertainty. Even after we brought Tim Koogle in, it wasn’t a sure thing. The Internet was a sure thing but Yahoo wasn’t a sure thing. It probably took until the end of ’95 to guarantee that.

Craig : Interesting. Did how you feel about the company change as you scaled?

Tim : Nope. I was all in the whole time.

Craig : How long did you stick around?

Tim : I was there until 2003.

Craig : How was it to ride that wave, especially when the bottom fell out in 2000?

Tim : When things are going well and you’re in a growth industry, you don’t have to deal with many difficult issues. It’s the old cliche, winning solves everything.

Craig : For sure.

Tim : It’s really true. It solves everything… or maybe better said, it masks all your mistakes. A lot of the mistakes you make get masked because you receive almost no negative feedback.

But then the bottom fell out and the board let Tim Koogle go. The upper ranks of management emptied out pretty quick, except for me and the CTO who stuck around. We got a new CEO and set of peers in upper management. Let me just say, I learned a whole lot more about business on the way down than I did on the way up.

Craig : When you think back on your time at Yahoo, how do you feel about it?

Tim : Well, I definitely made some of my closest friends there. I compare them to childhood friends. I can pick up the phone and call any of 50 people and talk to them as if no time had passed. It’s a pretty cool feeling.

Craig : That’s really neat.

Tim : It was formative in so many different ways. Granted it was early in my career, but then again most of the entrepreneurs at YC are early in their careers, too. It’s this intense experience where for the first time in your life where you’re defining your own test and seeing if you measure up. You find out a lot about yourself in that environment.

Craig : I imagine it really builds confidence.

Tim : It does.

It was certainly career defining. The financial success was nice, but it was way more than that. The entire process helps define who you are, what you’re good at, what you want to do, and what you think is important.

Craig : When it does work out for someone in your shoes, I feel like it really helps solidify your belief in how you understand people and markets.

I’ve been wondering if through these interviews we’ll find a strong correlation between early employees and people who are good investors. The way I see it, someone like you, you’re like, “Ok, good people, good product, and I can add value. I’m in.” Founders might be much more singularly focused. You know what I mean?

Tim : I do.

I guess Imagine K12 is the exception because that was my idea with Geoff, but Yahoo wasn’t my idea and QuestBridge wasn’t my idea. It was me recognizing a good idea and then being able to contribute to it, and I did that twice in a row. Even with Imagine K12, you could say, “Well, PG is really the one that kind of defined how to help companies… I just applied it in a different realm.”

Craig : Yeah, exactly.

Tim : But I guess you could say that about almost any idea.

I’ve never felt like an idea had to be mine in order for me to be passionate about it or want to contribute. I hope that helps me be a better advisor and investor.

Craig : I think whatever that quality is, that is the exact differentiator between the person who needs to start something and the person who’s comfortable accepting risk but will work on someone else’s idea.

Tim : You think so?

Craig : I think it can be easier to do your own thing, even if it’s a bad idea, because it feels cooler.

Tim : I think there’s social cache to starting your own company now. Back in the 90s, it wasn’t like that. There was no social backdrop to it. You didn’t go to bars and talk about it.

On one hand, I guess it could be seen as a lack of confidence to not do your own thing. But on the other hand, it could be seen as not letting your ego get in the way of recognizing a good idea. I can see both sides and honestly, I don’t know where the truth lies.

For me, my sweet spot is when I can say, “That’s a great idea. It’s just getting started. Count me in.”

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craigrcannon · 3 years

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Employee #1: Reddit

Employee #1 is a series of interviews focused on sharing the often untold stories of early employees at tech companies.

Chris Slowe was the first employee at Reddit. He worked at Reddit for five years, then Hipmunk for five years, and now he’s back at Reddit, writing code.

Discussed: YC’s First Batch, Meeting The Founders, Finishing a PhD While Working at a Startup, Keyser Söze, Reddit as Vocation, Maintaining a Life Outside a Startup, and Returning to Reddit.

Craig : You’re back at Reddit now. What’s your role at this point?

Chris : It’s kinda two things. I started off working on some front page redesign stuff that we’ve got planned. I’m also working on a new version of our algorithm. Our current version is about eight years old. I also wrote that algorithm.

Craig : [Laughter]

Chris : Practically speaking, we’re probably a hundred times bigger than we were when we wrote that, so that was my initial task. I’m also forging one of our new engineering teams, which we internally call “Anti-Evil.” We’re anti-spam, anti-abuse, and sort of anti-cheating. I guess we’re anti-everything. Pro-freedom!

Craig : Right on. And prior to re-joining Reddit you were at Hipmunk. How was it working there?

Chris : I really enjoyed it. I think the thing we learned most of all there was that breaking into travel is really hard. There are a lot of big players and most travel companies aren’t technology companies. I can’t tell you how many times I was on a call and the other person on the phone was referring to their engineering staff as “IT.”

Craig : [Laughter]

Chris : It was like, “Oh, we’re having one of those calls.”

Craig : “Let me get the nerds in here and they’ll figure it out.”

Chris : Yeah!

Craig : That’s hilarious. Ok, so could you give me the rundown of how you ended up at Reddit?

Chris : Sure. I was in Y Combinator’s first batch, along with Steve Huffman and Alexis Ohanian. I was working at a different startup and we were doing desktop search. This was at a time before desktop search was a thing. What kind of killed us that summer was Apple coming out with Spotlight, then Google Desktop came out so we had a hard problem with so many players in the field.

At the end of that summer, my cofounder decided to go to grad school. This was the first YC batch so it was totally different. It was sort of a three month trial to build a product and see what happens. We were at the first demo day, which was actually kind of fun. Something like 20 people showed up.

Craig : Wow. So how did you connect with Steve and Alexis?

Chris : By the end of the summer I had two free bedrooms in my apartment. I was good friends with both of them at that point. I think they originally planned to move back to Virginia but I believe Paul Graham talked them out of it. So they had basically given up on their flat and now needed a place to stay. My cofounder from YC, Zak Stone, was like, “Want to stay with Chris?”. And they were like, “Okay, great.”

Craig : And at what point did you start working on Reddit?

Chris : I want to say like three months later. I was in grad school at the time and I had much more grown-up hours, where I would wake up at 7 or 8 in the morning, go to work, and come back then work on projects at night. Steve and Alexis would sleep in then work until like 4 in the morning.

Because I was up early I’d check Reddit and when it was down I’d knock on Steve’s door and be like, “Hey, site’s down.” After the third time that happened, he just showed me how to log in and start it back up.

Craig : That’s great.

Chris : So I guess my first job at Reddit was in ops. But yeah, at that point it was still Steve writing code and Alexis doing everything else. We were friends and he asked me if I wanted to join, and I did. That was probably six months after Reddit started.

Craig : You were still in grad school studying physics, right?

Chris : Yeah. That’s when I was in my fifth year of grad school.

Craig : And did you have to pause everything to make that happen?

Chris : No. So I’d go to lab and work from 8 to 6 then come home, eat dinner, and join them in the living room to hack for a while. The nice thing is, I was given work that was sort of independent of what everyone else was working on so I wasn’t a blocker.

I think the first thing I worked on was traffic monitoring. This was at a time before Google Analytics. It was like processing access logs and generating summaries and trying to figure out how to do this at scale. I must have rebuilt that damn thing eight times in the first four years.

The thing about that time was we were all learning how to program web apps while we were building them and there wasn’t really a standard operating procedure or anything.

Craig : So you were essentially working part-time?

Chris : Part-time in startup hours but it was like a full-time job. I would normally work from 6 to 2. Then go to sleep, get back up, and do it again.

You know, your 20s are a magical period of time. I could get by on four or five hours of sleep without any major side effects. Basically it was like that for all of 2006. It was like two full-time jobs. The kicker is I somehow managed to meet my wife during that period.

Craig : That’s amazing. So what happens next?

Chris : Well, the four of us – Steve, Alexis, me, and Aaron Swartz – worked on it until the acquisition, which was around Halloween 2006. And it all happened really fast. We were a 15-month-old startup.

I remember the next night I was making pizza with my girlfriend, now wife, and I called Steve and was like, “Hey, we’re making pizza, Do you want to come over?” And he was like, “I am in California.”

Craig : Whoa.

Chris : Yeah. So I was like, “Oh, well, okay then.”

Craig : [Laughter] And so how long did it take before you moved to California?

Chris : I looked for apartments in January and we moved out early February. Part of the agreement with Condé Nast was that — I think it actually said this in the contract — “Chris gets to finish his PhD.”

So I got to the point where I could leave Cambridge and write my thesis remotely. It was kind of a fun transition, going from a full-time job as a researcher and a second full-time job in a startup to a full-time job at an acquired company where I could spend my nights writing a thesis.

Craig : So let’s step back a little bit. Did you think that you would be interested in working with the Reddit guys when they moved into your apartment? Or were you just buddies?

Chris : Probably a little bit of both. At the time it was just because they were buddies and they needed a place. I had no particular plans at all. I was coming off of the failure of my first startup. We were trying to solve this problem of basically like, “I can’t find anything on my hard drive. I have all these areas I can’t search!” What happened practically is that the problem doesn’t come up any more because there is almost nothing on my hard drive that doesn’t exist in some state online.

Craig : Yeah, exactly. So what about Steve and Alexis compelled you to want to work with them?

Chris : At the time it was actually interesting just to be working as a web dev to be honest. Getting into the web scene was kind of a neat thing. I also liked Reddit.

Here’s a funny story. That summer everyone in the first YC batch was a beta tester for Reddit. This was before comments existed, so it was just a bunch of links.

Eventually it kind of opened up and we got a few people Steve didn’t know personally. But for like four months most of the content on the front page was from one of the alt accounts Steve and Alexis had. They were basically populating it as a way to make it seem like there were more people there. Because nobody wants to walk into an empty room. Right?

Craig : Right.

Chris : So my username on Reddit is KeyserSosa, which is a misspelling of Keyser Söze, which is the Usual Suspects villain.

I remember a day, probably in November, when Steve took a day off. He came back a couple hours later and there was new content on the front page and he hadn’t done anything. It was like this moment of like, “Oh, my God! It’s walking!”

Craig : [Laughter]

Chris : And he’s like, “Great! There are actually people on the site who I don’t know and they are posting all the time. There’s this one guy, KeyserSosa, who’s super active!”

They we’re like, “KeyserSosa? Who is KeyserSosa?”

And I’m like, “Oh, hi guys.”

Craig : [Laughter] That’s so good.

Chris : Anyhow. I achieved my peak on Reddit probably in the first year, in terms of being one of the top posters. And then you know, it was all downhill from there.

Craig : Yeah. I was wondering what your relationship with Reddit is now. Not the company, but the community.

Chris : I’ve definitely become much more of a lurker. My use was definitely a side effect of working on it. When I was originally here for the first five years, at the time there was never more than four or five of us working on the site.

Craig : Oh, wow.

Chris : We were kind of professionally understaffed. At least at that point we were really understaffed and always growing at a really phenomenal rate–like doubling every six months. So we were kind of wearing a lot of hats as engineers. We were engineers, and also the community team, and also infrastructure.

I am an introvert who has become an extrovert via the Internet, or something like that. I feel like lots of talking and thinking in that vein is much more draining than sitting and doing engineering work. That definitely contributed to me leaving.

Craig : Yeah, that makes sense.

Chris : So when I left the first thing I did was go on a six-month Reddit detox. Essentially I was like, “Alright. I just can’t look.” And I didn’t look at it.

The thing is, it was and still is like my baby. And I can say that, I have kids now.

When one thing goes wrong, I take it personally. In 2010 I was basically in charge, so everything was either my fault or something I had to deal with. I think the only way to not feel completely attached to all the things that were happening, or whatever mistakes were being made, or whatever drama was happening, was to step away for a little while. You kinda have to do it.

Craig : So how did your relationship with the founders and the early team change over time?

Chris : I don’t think very much, actually. The team was always small so we were and still are a group of friends. I think there’s no other option than to be like comrades in arms in that case. At the very worst, we were the 300 holding back the hordes.

I think because we got acquired so early we had to really justify our budget and keep the team small. We couldn’t get an infusion of cash to grow because we were already bought and so it sort of stunted growth initially. Another side effect is that the look of the site has kind of been the same for a very long time. There’s a whole bunch we have to kind of rebuild.

The flip side of that is that we got really nimble and good at a bunch of things. But we’re now up to I think 120 people. And we’re independent again.

Craig : So now do you have startup-like growth goals?

Chris : We’re kind of acting like a three-year-old startup with ten years of legacy and some good standard operating procedures, which is nice.

Craig : When you look back and consider the early days, how do you feel about Reddit?

Chris : It’s overall positive. It’s been a lot of fun. I mean, it’s been a lot of stress, but it’s also been a lot of fun. Since I’m back now, it’s almost like it’s not so much a part of my career as it’s become my career. Maybe “vocation” is a better word. I still take a lot of the stuff really personally even though I’ve only been back for about six months.

Our fingerprints are everywhere. I think it is fair to say that the snarky tone that still pervades Reddit is an outcropping of Steve. That’s his personality and he kind of imprints it on the community. I think in the same way a company’s tone and culture is a reflection of the founders, so to is the community it creates.

Craig : You’ve been around so many startups. Do you ever have thoughts of doing your own thing again?

Chris : I am very content to be first employee in all things. I’m close enough to be able to hear about the fundraising, and the acquisitioning, and the business side of things. But I do not get invited to any of those meetings, which is just wonderful as far as I’m concerned. Right now, my job here is as an engineering manager. I have a team of like six and honestly, that is a good size for me. I would rather be an engineer who is a manager, rather than a managing engineer, or an office manager, or C-something. I actually enjoy doing the work.

Craig : Right on. Are there any signs that you would advise someone to look for if they are considering being a first employee?

Chris : I would say the first three to six months is gonna be a slog. It’s gonna be a tough slog. That said, startups have culturally matured in the last ten years and it’s been fun to watch. When the first batch started at YC, there was all this talk like, “Oh, yeah, you should work 16 hours and day and not feel bad.”

What’s really great to see is that all those people who were working 16 hours have now grown into their thirties and realized that, “Oh, sleep is really cool.”

Craig : [Laughter]

Chris : And, “You should probably date.” And, “Do you know what is also awesome? Kids. And do you know what kids don’t let you do? Work.” So there’s been this kind of progression from just working all the time to still working hard while also having a life.

Because there are only a few people around in the beginning you have to be willing to switch hats really quickly. Especially for the startups, traffic is irregular, and you’re not up-scaled, and you have to kinda deal with that stuff live.

You’ll also have a responsibility to set the tone for the company. The same holds true with the founders.

Craig : What about the founders? Do you think there any traits successful founders share?

Chris : It sounds trite but determination. Ideas are important. Luck is important. But follow-through is really important. This is sort of separate from the founders but there’s also timing.

After we started, everyone compared us to Digg for five years before Digg had its problems. But we didn’t even know about Digg when we started.

We were a dime a dozen for a while. It was actually funny. There was us and a bunch of Digg clones, which was amusing.

Craig : Right on. Let’s stop there. Any last words of wisdom?

Chris : The internet has a long memory!

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craigrcannon · 3 years

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Employee #1: General Assembly

A conversation with Mimi O Chun, General Assembly’s first employee.

Employee #1 is a series of interviews focused on sharing the often untold stories of early employees at tech companies.

Mimi O Chun was the first employee at General Assembly, an education company operating in 15 cities with over 25,000 graduates worldwide. She is currently a founder, advisor, investor, and consultant for a number of early-stage startups.

Discussed: Switching From Consultant to Employee, Career Paths for a Designer, Being Older Than the Founders, Being the Only Woman at a Startup, Working With Four Founders, and Determining Where You Can Have the Most Influence.

Craig : So how did you meet the General Assembly guys?

Mimi : I met Adam [Pritzker] while I was working at IDEO. He was at a bit of a crossroads—simultaneously applying to business school, thinking about starting something, and applying at IDEO.

He ended up withdrawing himself from consideration because I think he realized entrepreneurship was his calling. He comes from a family of entrepreneurs so I think he knew, even though he was looking at these other paths, the lure of entrepreneurship was too tempting for him to do anything else.

We ended up staying in touch. When you meet someone at IDEO in general, whether you’re a candidate or an employee, the conversations tend to be around what inspires you and what you’re drawing your references from. Adam and I very quickly developed a rapport because he could make business references AND fine art references. We just had a common dialogue, so we ended up staying in touch, getting drinks from time to time.

When he told me more about what he and his partners were planning to do with General Assembly—which at the time was called Superconductor—I was like, “Oh, this is really fascinating. I know nothing about this. I’d be happy to help you with brand strategy and design.”

Craig : As a friend or contractor?

Mimi : Kind of both. I did it for a really reduced rate. I would have helped anyway, but then the scope became big. By that point, once I was producing a lot more stuff, we had to formalize things a bit more.

I never presumed that I would leave IDEO to join General Assembly. I like to describe it as waking up in Vegas with a wedding ring on my finger by the time I finally joined full-time. I think there were a lot of life events for me that happened—I was getting a divorce and I was moving out of my apartment. I was doing a bunch of things that also made me a lot more, I think, open. I knew I needed change and I’m not a good tweaker, so I just kind of changed everything and ended up leaving IDEO to join General Assembly full-time.

Craig : Okay, just so I get this timeline right, when did you meet Adam and when did you join GA?

Mimi : So Adam came into IDEO in February of 2010. I think GA launched in January of 2011. We didn’t start collaborating until the summer of 2010. I remember we would have drinks at the Standard Biergarten in the Meatpacking District. We started talking in earnest about developing the brands. I was helping on nights and weekends while I was working at IDEO and then I ended up leaving formally in October of 2010.

Craig : Okay, so it wasn’t very long at all between meeting and launching.

Mimi : It all happened in stages. We were at 902 Broadway, doing the build-out on the fourth floor.

Matt [Brimer] and Brad [Hargreaves] had essentially built our inaugural class of startups who would form our membership—participating in the community and renting desks. When construction ended up getting delayed, we rented a temporary space on the seventh floor of the building in November of 2010, but we were under a press embargo. Nobody could post anything on social media about it until we did our official launch for the Times in January of 2011.

Craig : Okay, gotcha. All right, it initially started out with renting desks. Was that the very beginning?

Mimi : When the founders first started GA, it was initially structured as an LLC — it was supposed to be everybody’s side job. It was primarily coworking, but specifically designed for people working on startups.

The founders had looked at the market and at the time there were a bunch of coworking spaces popping up in Dumbo and whatnot, but in those scenarios you have an accountant sitting next to a freelance writer with absolutely nothing in common, and GA was about creating a tighter community with a lot more in common.

I don’t think anybody really thought of it as coworking because the benefits of being in a space like that were really about knowledge-sharing. It wasn’t really a real estate play, I’ll put it that way. We were breaking even on the desks at the time. It was about creating something bigger and a more sort of osmotic transfer of knowledge between teams, but also to have teams that are in various stages of their growth, all in a shared space.

In the beginning, everyone who joined the community would be asked to contribute back to the community in some way—whether it was writing a blog post or teaching a short class or doing a quick fireside chat. It was really about trying to instill those values from the get-go.

The formalized education happened later, not that much later, but later. If you look at the actual footprint of that first space in 902 Broadway, I think it was 16,000 square feet. And of that 16,000 square feet, we designed one classroom that was relatively small. It was a small fraction of the total space.

This is the thing with creating non-tech startups. If you have an actual physical space, you can really only iterate with your next campus. That first campus, yeah, you can see how it evolved from there. And now I would say that with most of the other locations, 90% of the footprint is dedicated to educational space.

Craig : Okay. What’s Adam’s relationship with the other guys? Who grabbed who?

Mimi : Adam initially met Matt and Brad at New York Tech Meetup, I believe. And Matt brought Jake [Schwartz] in.

Craig : And so how did it go the first time you met all of them?

Mimi : That was probably when we started the brand development process. I worked most closely with Adam but I spent a lot of time with all of them (Adam, Brad, Matt, and Jake) in the beginning because I was trying to synthesize many different perspectives on what this thing could be.

We all came to the project with a certain bias or a certain passion or a certain conviction, and that was very evident from the beginning. And so one of the first things I did with the team, with the founders, was articulate the brand values and craft the value proposition. We weren’t exactly sure how to talk about General Assembly, so I ran them through an exercise. This was me putting my consultant hat on, running an exercise to get at what was the one- or two-sentence way to describe General Assembly. So that was the first thing.

We basically repeated those exercises to name it and design the identity—the visual, verbal, and spatial identity. All of that was culled from numerous conversations that I had with all of the founders.

Craig : What hooked you in the beginning about GA?

Mimi : I think I had thought about it specifically through the lens of a designer because I’d been on the board of AIGA, I’d been a lecturer and critic at schools, and so I’m always thinking about career paths that are available to young designers.

At the time I think I thought of the design profession as having two paths: client services or in-house. I guess working for a startup is in-house, but as we both know, it’s a totally different beast to be involved from a foundational level as a designer. There’s a lot of authorship and a lot of opportunity that young designers have by pursuing a path of entrepreneurship. So that was probably my primary motivation.

Craig : Just to pause you, you liked the idea of helping other people follow this path? Or you’re doing it for yourself or both?

Mimi : I think it was both. I was also curious about this New York tech community that I had no idea existed.

This is the curse of the consultant, having been one for pretty much the majority of my career prior to GA. You work on projects in really weird industries that you would never before consider. It’s like light embedding. And when you lightly embed into that industry, you can learn a shit ton about them. And so for me, it seemed like a natural way, by helping GA’s founders with brand strategy, I could simultaneously learn about the tech industry. It’s a natural way to do research. Just do a project and it’ll be interesting and productive at the same time.

Craig : When does it become like, “Oh, maybe I want to do this for real?” Was that at a particular meeting or anything like that?

Mimi : I left IDEO not because I was necessarily thinking that GA was going to become what it eventually became, but more because, in the early days of GA, with all of those inaugural startups there, I was like, “Oh, I can consult for the inaugural startups that are in GA.” I think our realization that there was a need to really build out GA as an educational company happened later.

Craig : So you were thinking, “Okay, this is a very cool project that I can leave IDEO for and essentially run as my full-time job. And in this project, I can potentially garner even more projects as a startup consultant.”

Mimi : It’s like Inception.

Craig : [Laughter]

Mimi : It’s the first time I’ve actually talked about it. It’s funny, because yeah, there is a realization attached to it that I wasn’t super risky and prophetic in seeing what GA would become. It very much happened in an incremental way. I was not about to take a lot of financial risks at the time.

Craig : So back to when you were working as a consultant. How did the name come about?

Mimi : At the time, the working title was Superconductor and one of my caveats to working with Adam was, “I will totally help you with brand strategy and design if you let me change the name.” And Adam was like, “Okay, I think I can do that.” But he said it without realizing necessarily how attached a couple of the other founders were to the name. They had already been talking about it within the tech community and people liked it.

The reason why I was adverse to the name Superconductor was because it sounded almost like an accelerator program. It sounded more like it was about us rather than about our community. I knew that it had to be about our community in order for people to feel welcomed and to feel like it was their home and to take ownership of the community themselves. So General Assembly came out of three inspirations. One was the idea of factories and places where things get made. The second was around schools, like when you have your school-wide assembly. And then the third came from self-governing bodies. Could you create a community where those three ideas were prevalent? So that’s where the name came from.

Craig : Did the risk of startups kind of lure you in at all when you were at IDEO? What was interesting about the startups?

Mimi : I think I can say this about IDEO designers in general, but there’s a certain type of person who goes to work there. They’re designers whose greatest priority is impact. I always believe you can create impact at scale with market leaders at a place like IDEO or you can create impact at the other end of the spectrum as a startup. The middle is less interesting. It’s a little bit more incremental. They’re thinking a little bit more near-term.

In other words, you can have massive impact if you’re innovating at Walmart or you can have massive impact if you’re creating a startup, right? Those two ends of the spectrum have always been far more interesting to me than the middle.

And New York startups—in the beginning and probably still to this day—are different from the Valley’s in that there are a lot more non-technical founders in New York. A lot of people who come out of media and marketing, a lot of people who saw a problem and wanted to solve it versus a tech-first approach of “How can I turn this innovation into a viable business?”

You have these legacy industries in New York, whether it’s publishing, fashion, art. And we started seeing these startups pop up, like Artsy or Of a Kind, trying to disrupt these sort of New York legacy industries. And I think that’s what was interesting to me.

Craig : Let’s talk about what it was like working there as the first employee. How did the interpersonal dynamics work out between you, the founders, and the rest of the team?

Mimi : For a really long time, it was the four founders plus myself. I had a non-trivial piece of equity, so technically I guess that made me a partner, which meant that I would join the founders for some of the early planning meetings once we were actually in the space.

Dynamic-wise, I worked primarily with Adam on stuff. I don’t know if I actually reported to Adam or if I reported to Jake. No, I must have reported to Adam technically, though it never felt that way. I think not having a founder title was actually really good for me.

Craig : That’s what I was wondering.

Mimi : I didn’t need the accountability, but in many ways, I had the most tangible skill set. I think having four founders is actually pretty rare for a startup because there can be too much overlap. Each of GA’s four founders are so distinctly different in terms of both their personalities, their passions, and what they’re all individually good at, that it’s pretty evident to me where their energies naturally went, but I don’t think it was always that way in the beginning.

Craig : Do you think that not being a founder made your work more satisfying?

Mimi : I definitely looked at it as a really positive experience. My perspective is I’ve always been more comfortable behind the scenes than out in front. It’s not that I would be unwilling to take on that role, and I certainly subsequently have, but I think, for my first introduction to a startup, it’s definitely good to be first employee.

Craig : So how did that play out when you started hiring more and more people?

Mimi : When you’re at a high-growth company and somebody’s been there for a long time, you can go to that person for a lot of institutional knowledge that your colleague who was hired three months before you were doesn’t have. I felt a certain responsibility being an early employee to welcome new hires. And I was also the only woman.

Craig : Yeah, I was holding out for that question.

Mimi : I was also the oldest by a good margin. I think Jake is around seven years younger than me and he was the oldest of the founders. So there was definitely a little bit of a mom, den mom sort of thing. Tiger mom? I don’t know.

Craig : [Laughter] Yeah, that’s a tricky role. I’m interested in how you viewed both that dynamic and the dynamic of the company at the time. Were there any moments when you were like “I don’t know about this?”

Mimi : Yeah, there were. A lot of designers want to have palpable impact. As a consultant, you do a lot of these vision decks that get thrown in a file cabinet somewhere. One of the first things that happened was when we had built out the space, we had a press embargo, we knew the New York Times story was gonna come out January 26th or whatever it was, and so everybody was walking around on eggshells. Everybody was super stressed about this launch. The space was pretty much finished but there was a lot of glass in that inaugural campus and people kept running into the glass, like literally running into the glass.

One of the startups [renting space at GA] had a friend come over and he literally smacked his head on a glass wall. It happened a number of times. I would hear people talking about how other people were running into glass and then two seconds later they themselves would run into glass. So I eventually got this frosted adhesive to put on the glass but for a good day or two, I was freaking out, putting Post-Its on every single glass surface. I remember having this oh shit moment of “I wanted to have palpable impact on users and this is what it means to be accountable for it.”

Craig : [Laughter] Was there anything that surprised you about the experience of being a first employee?

Mimi : As a first employee, for better or worse, the thing about joining a startup is that it’s not a meritocracy, right? If you’re disappointed in a decision that’s made, or if you feel the founders aren’t leading the way that you would lead an organization, it can be incredibly frustrating. It’s actually tricky to be a first employee because you identify both with the founders and the employees.

Craig : And so I wonder how you start to reconcile that, assuming you get a fair equity deal, how you feel about ownership, how you feel about managing people.

Mimi : I think you do feel some ownership. I think you do feel some accountability, but I guess, for me, being pretty functional in my role and pretty discreet around what was my domain probably helped with that.

I stopped being operationally involved a good number of years ago, so when I go back and step into a GA location now, I’ve actually been really pleasantly surprised and at times proud of how well the brand has managed to weather.

Craig : Yeah. Do you think that makes you feel better about the experience as a whole because you have a tangible legacy?

Mimi : As a designer, it would be so easy for me to go into straight-up marketing. One of the reasons why I’ve never chosen that path is because I’m not interested in putting lipstick on a pig. I’m not interested in creating spin for a sub-optimal product experience.

For me, product, environment, experience, and the communications and design around it are all so interwoven that I could create the most beautiful brand in the world, but if it’s a sub-optimal experience for people, it doesn’t mean anything. It just means we’re really good at fronting.

Craig : So kind of closing things off, since leaving GA, how do you think about it?

Mimi : I think in some ways I’m more comfortable in the role of a first employee than I am as a founder. But I’m not personally interested in joining a startup late. I guess it depends on what you’re motivated by or what you’re looking for in your job. I have always known that I identify with early stage startups.

New was always much more interesting to me. For me, I’m most interested in taking a nebulous idea, taking a very fuzzy hypothesis and turning it into something concrete, whether that’s for P&G or whether that’s for this as-of-yet unnamed startup. I like figuring it out.

I think that the tech community in general is so overspecialized for mid-stage or mature companies. I remember meeting a designer from Apple whose job it was to design icons, day in and day out. And I was like, “Wow, okay.” He was this lauded designer and obviously very skilled at it, but I think I was spoiled in my career in that I felt like I had license to weigh in on anything from product to marketing to brand. I can have opinions about all of those things and try and prototype ideas around all of that stuff. And that’s one of the benefits of being an early-stage employee that you wouldn’t get if you joined as the 800th, right?

Craig : Yeah, definitely. That autonomy is huge. All right, so do you have any general advice for someone who’s a first employee?

Mimi : I think if there’s anything, it’s having a good amount of self-awareness and a fair amount of clarity. Ask your founders where the buck stops in decision-making. Find out what you own and ask yourself, “Am I comfortable with this? Am I comfortable with this part of the pie?” Just getting clarity around that, I think, will be helpful. It sets the stage.

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craigrcannon · 3 years

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Employee #1: Airbnb

A conversation with Nick Grandy, Airbnb’s first employee.

Employee #1 is a series of interviews focused on sharing the often untold stories of early employees at tech companies.

Nick Grandy was the first employee at Airbnb. He is currently building Outschool, which helps parents find and book learning activities for their kids.

Discussed: Closing Down Your Startup, Finding a Startup to Join, Meeting the Founders, Interviewing at Airbnb, Growing From Four to 500, Leaving Airbnb, and Hiring Your First Employee.

Craig : Could you just start by explaining how you ended up at Airbnb?

Nick : Yeah, for sure. I had come out to Silicon Valley with the intention of getting into the startup world though, to be honest, at the time I didn’t know anything about Silicon Valley or startups. I just knew I wanted to explore that world.

I moved out to San Francisco at the same time I joined YC in the winter of 2008. I was working on this company, Wundrbar, with a friend of mine and had a fantastic experience in YC and learned a ton and met a lot of people.

I think actually my high-level plan was “Okay, I’m going to go do this startup, I’m going to do YC, I’m going to figure it out, this is going to be awesome and that’s Plan A. And if that doesn’t work out, well, Plan B is that hopefully I’ll join some other cool company and get into a startup that way.”

Plan A didn’t work out. We shut down the company after about a year and that’s when I started looking around for other startups to join. I think I had the appetite at that point to join an early-stage company so I still had a pretty high risk tolerance but I also wanted to work on something where I felt more assured that my efforts would be put to good use and that there were actually customers and users.

I was meeting with various early-stage companies and ran into the Airbnb guys at a YC event, actually. I met Brian [Chesky] at one and then at a separate event met Nate [Blecharczyk], and the conversation continued from there.

Craig : Were you interviewing with other companies?

Nick : Yeah, I was interviewing elsewhere. Another company I interviewed with was a brain-training game company. I actually worked in a neuroscience lab previously and had an interest in that realm as well. They offered me a job but I passed. I wasn’t fully convinced.

At the same time I was talking to some other people about starting a new company where I would be CTO. But again, I think it was too early, too risky, and I didn’t want to spin wheels for another year trying to get something going. Whereas with the Airbnb guys, they were super early and small but they had a product, a V1, that was up and running. And the product was working. I used it as part of my application process and was like “Yes, this is super cool, this works, I can totally envision this growing and taking over the world and I want to help do that.”

Craig : In terms of interviewing, what was that like?

Nick : I met them socially then swung by the office one day for a pretty casual chat, sort of like “get to know you.” We went to the roof and chatted and had an introductory conversation. Then there was a take-home coding test. Which was basically building a web app. They wanted an answer to, “Can you be productive immediately?”

And then there was an in-person interview with each of the founders. Lastly there was what at the time was termed “the beer test” though now it has more appropriate names.

Craig : Was there anything in particular about the founders that made you want to join Airbnb or was it the product entirely?

Nick : I think it was both. I knew that I’d be working with those three guys very closely. I had to be impressed by them and excited about the prospect of working with them and I was. I was at a point where I was looking for both a product and a vision that I was excited about in addition to the people.

Craig : In terms of the early days, how long was it before there was another employee?

Nick : It actually wasn’t long. They had been looking to hire a first engineer for a long time and the product was starting to take off in such a way that it was then like, “Okay, we need to scale.”

At the time that I joined, there were some sales contractors who were there and pretty soon after, we brought on support contractors. I think actually the second full-time hire came on like a month after I did and then probably the next full-time hires came on maybe like a month or two after that. And then it just picked up steam.

Craig : When it was just four of you, what was that environment like?

Nick : It was the four of us around a giant desk–like four desks pushed together in the middle of a living room.

I think that they, as the founders, they remained more concerned with the corporate questions. I was brought on as an engineer specifically so I had a pretty specific domain. But for things like product questions – “How do we fix this problem?” or, “How do we do this?” – I think those questions were fairly collaborative.

At the time we had weekly product meetings where we talked about the work in progress, challenges, priorities, and how we were going to invest them. It was a fairly collaborative environment.

Craig : You were there for several years, how did the environment change over the course of your time there?

Nick : It definitely evolved. I think that as the company grew, more separation was created. Initially The founders would independently talk about the high-level priorities and then Nate and I would talk about engineering priorities–what we’re going to build, how we’re going to sequence it, and the allocation of work. As the company grew, early employees, myself included, had larger responsibilities in terms of onboarding new people, setting product direction, and defining the direction of the company. I was basically an individual contributor engineer in my first year, an engineering manager / product manager in my second, and a general manager in my third.

Craig : How did your opinion of the company change as you came into this role where you were managing other people?

Nick : The company definitely scaled very quickly. I was there for three years and when I left it was about 500 employees globally. In the last year that I was there, we basically opened like 10 international offices and hired a ton of people because it was just this incredibly rapid growth.

I preferred the small company vibe and was less interested in being a senior manager at a larger company. My favorite stages at Airbnb were when we were around 10, 15 people plus or minus, where there was some focus and specificity of roles but the whole team was also really intimate and you knew exactly what was going on. There was a very fun feel to working at the company. It had this sort of Wild West feel then.

Craig : I’ve noticed that desire among a few first employees. They seem to like that stage where it’s kind of in-between. Do you know what I mean?

Nick : Yeah, totally. I was going to say that by comparison I also worked at Clever. I was there immediately before Outschool. I joined when they were about 20 people and left when they were around 80 people. I started to have the same feelings in relation to the size of the company. That said, Clever is an awesome place and I actually would have stayed except that the time was right to start Outschool with Amir [Nathoo] and Mikhail [Seregine].

Craig : So what was the trigger for you to leave Airbnb?

Nick : There wasn’t one trigger in particular. I was and remain super excited about the company but it was basically the organization growth. Scaling from four to 500 people in three years is super chaotic, and I was less excited about being part of a large company.

Craig : You picked a winner in joining Airbnb. You could have tried to do that again. What made you feel that you wanted to start your own thing?

Nick : That’s a bug that I had prior to being in Airbnb. I had gone through YC. I wanted to start my own thing. Where that came from, I’m not really sure.

I think it’s just different strokes for different folks. Some people would be really thrilled to pick a winner and join a hot startup early on, then grow and become a senior executive at that company. For whatever reason, that wasn’t the vision that was exciting to me. The vision was to create something from the ground up.

Being at Airbnb also created a really tough baseline. Airbnb’s such an awesome business. It’s a really great business model, it’s really fun and it’s exciting and romantic. There are so few businesses like that. It’s particularly difficult when comparing it to other businesses that I’ve looked at and considered joining or starting.

Craig : I assume you learned a lot at Airbnb. How are you translating that now into Outschool?

Nick : There are a lot of parallels in the two-sided peer-to-peer market. I think pretty much every day there’s some parallel or learning I think back to or recall for Outschool.

In terms of product, marketplace dynamics, and organizational growth, learnings are applied every day. Actually, working at Clever was also a fantastic experience because it showed me that it’s possible to have a high-growth company with a totally different culture and different approach. That was a great learning experience and one I’m glad I did before starting a new company again.

Craig : Have you hired someone yet as a first employee?

Nick : Actually we’re in the process of that right now.

Craig : So what are you doing? How’s it going?

Nick : There’s all of that tension around how much you optimize for every hire. And I think Airbnb sort of optimized very carefully and it was really painstaking in the early days of hiring me and then also hiring subsequent employees. We were really careful vetting and then on the other hand you have the advice to, “hire fast, fire fast.” I think actually my approach is going to be a little closer to that.

Craig : Are you narrowing in on a person?

Nick : We have two roles: a customer success manager and an engineer. We’re in the interview process for both of those and we’ve had a pretty good response. We’re interviewing people in person so hopefully we’ll have a hire in a matter of weeks, hopefully not months.1

Craig : What are you looking for in a first hire?

Nick : The thing that we’re screening for in the first hire are someone who’s comfortable with a dynamic environment and comfortable with change. They need to recognize that week-by-week there might be differences in the company. You just have to be comfortable with that or it’s not going to work.

We also want somebody who wants to help build a company from the ground up. Not just someone who’s just looking for a job, somebody who’s really excited about the idea of helping to build an organization.

Those are sort of critical for any role, independent of the particular skill sets. And then also things like being an independent thinker and being able to solve problems on their own, because we can’t oversee everything.

At this point we’re essentially looking for partners as opposed to people who are simply hired to do a 9-5 task and then go home.

Craig : What about somebody who’s looking at companies and thinking about being a first employee? What should someone know if they’re going to do that?

Nick : That’s a good question. I think a lot of that’s pretty context-dependent by where the company is at. I joined Airbnb at a time when we were just starting this very aggressive growth curve and the whole organization scaled very quickly. That’s different than if I had joined early on and for a year we struggled to find product/market fit and didn’t hire anybody else.

Those are very different things and imply different relationships. I think for a lot of YC companies there is a pretty big distinction between the founder role and an employee role where the founders are thinking about corporate-level things and a different set of problems than any particular employee will who is brought in to solve a particular problem for the company.

Craig : Is there anything someone should know about setting or managing their expectations when joining a company as a first employee?

Nick : Generally, it’s a super risky thing to do. The sweet spot generally comes later where there’s more clarity that a company is on a great path and has a great growth curve. For very early employees often that’s not clear, let alone how long the company will be around or what things are going to look like in six months or a year.

I think that anyone looking for an early role needs to be comfortable with that high level of risk and needs to be particularly excited about the benefits of being super early, such as being able to touch all parts of the company and see all the parts clearly. There’s also the team intimacy, the Wild West feel, the lack of process, and then the immediacy of doing anything that comes along when your team is then only four people or ten people large.

Craig : Thinking back on Airbnb, how do you feel about your time there?

Nick : I feel incredibly fortunate that I got connected with the company at the time. It was a fantastic experience in growth and I’m itching to have that experience again.

1 Since speaking with us Outschool has hired their first employee. ↩

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craigrcannon · 3 years

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Employee #1: Tumblr

A conversation with Marc LaFountain, Tumblr’s first employee.

Employee #1 is a series of interviews focused on sharing the often untold stories of early employees at tech companies.

Marc LaFountain was the first employee at Tumblr. He currently works on Uber’s EMEA support tools in Amsterdam.

Discussed: Being a User First and an Employee Second, Cold Emailing David Karp, Customer Support as First Employee, Scaling a Support Team, Building an Office in Richmond, VA, Developer/Support Dynamics, and Working in Startups Overseas.

Craig : You live in Switzerland now, right?

Marc : I’m actually in Amsterdam, though I live in Switzerland. While we were in the U.S. my wife got a job offer in Switzerland and I wanted to support her in that so yeah, that’s how I ended up overseas. Then I got an opportunity to work with Uber in Amsterdam, so that’s where I work. I fly from Geneva to Amsterdam every Monday morning and then I do the reverse every Friday afternoon.

Craig : Oh my god.

Marc : [Laughter] Yeah, it’s pretty crazy. I’m gonna get platinum status on KLM in another few months, which is gonna be very exciting.

Craig : [Laughter] Congrats man. So what are you doing at Uber?

Marc : I do tools and system stuff. We’ve got a worldwide organization that does tech support for riders and drivers and eaters. I’m one of the folks that makes the tools and systems for that support organization–making the help desk run, all of that kind of stuff. We run Europe, Middle East, and Africa out of Amsterdam.

Craig : Very cool. Ok, let’s talk about Tumblr. How did you get involved?

Marc : Very serendipitously, in terms of luck and timing. Tumblr started in 2007 and I was among the earliest users. I probably started using Tumblr within three months of it launching. I was in the first few hundred thousand users. At the time it felt like a community in the truest sense of the word. If you were a really active Tumblr blogger then you kind of felt like you knew everybody, in a way. Not literally everybody, but you know what I mean.

So I felt like a part of the community and at the time it was just two people running it. David Karp and Marco Arment were doing everything. They were designing everything, they were coding everything, they were testing everything, they were doing any tech support, any abuse response, and any PR. They were a two man shop and Tumblr was just growing at just a ridiculous hockey stick kind of pace.

It got to this point where they did all their own support through [email protected] and it sort of felt like anything you sent was going into a black hole. And I didn’t blame them, Tumblr was a free service, being run by two guys, and it was growing like crazy. They couldn’t respond to every email. They couldn’t even read everything. It was just way too much.

I didn’t know David or Marco and I lived in Richmond, Virginia, but I just sent [email protected] an email and said, “Hey I’m one of your earlier and more passionate users. I have a tech support background. I love Tumblr. I love support. I think you guys probably need somebody to start working on support and I would love to be that somebody.”

I’ll admit I didn’t really expect anything. I thought they probably wouldn’t even read the message and then even if they did, they probably already knew so many people in New York that could help. It was a total shot in the dark. David, luckily, read that email and I think appreciated that I made it very clear that I loved the platform. I really spoke to what it meant to me, how innovative it was, how I had met people through it, and just how special it was to me. I think that’s what most caught his eye. Not just that I was looking for a job but that I was very much looking for a job at Tumblr. So he emailed me back.

We ended up speaking by phone. Not even something like FaceTime or Skype. Phone. And he made me an offer to be a part-time contractor. I think I did like 10 or 15 hours a week initially doing support for them. I used my own computer in my own home in Richmond. I did it on nights and weekends and kept my day job. It was small enough then, there were a few thousand e-mails that had kind of stacked up but once I got that down, I was able to manage. That got us about six months.

Craig : Ok. I have a couple questions at this point. What were you doing before?

Marc : Before Tumblr I changed jobs like every one to two years. My wife was so tired of it, she just rolled her eyes every time. When I started using Tumblr I was working for a government agency in Virginia that does emergency preparedness, doing PR for them. Then like right when David hired me I worked very briefly for a city government in Richmond. Basically I have a little bit of tech background and a little bit of a PR background. What was your other question?

Craig : What was your Tumblr?

Marc : Oh, my Tumblr is just marc.tumblr.com. It’s just personal stuff. I’ve never had a blog that was overly political or edgy or anything like that. I would blog news and geekery that was interesting to me. I would blog about travels I was taking. I would blog pretty photos I had taken, but basically it was just about me as a person. There wasn’t really an agenda per se.

Craig : Was there a particular community that you were following on Tumblr?

Marc : I followed a lot of people that I viewed as prominent bloggers or prominent geeks. Essentially because I wanted to kind of learn more about that world and that space. In 2007 it was clear to me that social media and the influence of these people was becoming real, which almost seems passé to say now, but in early 2007 it wasn’t really. I’ve forgotten when Facebook let non .edu people in, but in 2007, social media actually wasn’t that big of a deal yet. It was early days. I think Twitter had just started in ’06. Everything that we now think of as social media with the possible exception of Facebook was in its infancy.

Craig : Okay, so to jump back, you make it through the first couple thousand emails and then you’re contracting 10 to 15 hours a week. What happens next?

Marc : I think it was December of 2007. I started and the volume just kept going up, so finally, I think it was probably in April of 2008, I was just like, “There’s too much to be done in 10 to 15 hours a week. So either we’re gonna have to start auto-responding, not responding, or I’m gonna have to go full-time.” It wasn’t like I could just tack on another five hours. I needed to quit my day job and really like commit to it if I was gonna do it. So we had another couple phone calls about that. At the time I still hadn’t met David or Marco in person.

Craig : [Laughter] That’s so good. Richmond really isn’t that far from New York. Anyway, keep going.

Marc : We did a few more phone calls and then they sent me a full-time contract via email. I think I worked for them for like another four to six weeks then finally, I think it was June of ’08, I flew to New York and met them in person, which was bizarre.

This was at a weird time where I had more than 15 hours of support work but less than 40+ full-time startup hours. I was sort of wondering how to spend that time so they created a portion of the site to feature Tumblr blogs and Tumblr posts. I think it was /browse at the time. I would spend a lot of time finding new posts to feature, new blog posts to feature–basically trying to help with the engagement aspects of things, which was maybe one of the most stressful things that I ever did there.

I would be browsing around Tumblr and there were some people who would really love the posts that I featured. Then I would see these posts that would be like, “Who the hell is running Tumblr browse? This is so boring.” And I’d think to myself, “Their opinion also counts”, so I would try to mix it up.

Anyway, I did that kind of stuff for a while. That got us another six months, maybe eight months. Then I hired a second person at Richmond to help with support. Unfortunately by the year mark, we were starting to get more into abuse issues. Once you get big enough you have people doing all sorts of harassment, libel, just all kinds of nasty stuff. So we brought on a second person to help. Not only did we need the bandwidth, we needed 24 hour coverage.

The thing is, once abuse gets reported, if you jump on it right then and you nip it in the bud, it’s probably not gonna become that big of a deal. But if you finish for the day at 7 PM and abuse gets reported at 7:15 and you don’t take action on it until 9 AM or whenever you start work, it will just fester all night. It’ll get re-blogged, it will get screenshotted. Before you know it, you wake up and you’re like, “shit.”

Craig : Yeah, that makes sense. Were you also doing technical support? At what point could people customize their Tumblrs?

Marc : That was actually a very early feature. You had the ability to do custom HTML and CSS. When I signed up, maybe three months in, you could do that. People were incorporating FeedBurner and doing all kinds of stuff. It was tricky for me in that I got progressively out of my depth, so people would write in to me about complicated JavaScript issues and I was like, “Well… here’s the thing.”

Craig : [Laughter]

Marc : [Laughter] Yeah, it was an issue. When we released a formal API it got really hard. Marco was our only developer and while he certainly could answer most questions, he didn’t have the time. Fortunately password reset issues, not JS stuff, was the number one issue.

So yeah, that’s the way it worked at the two person level. I was at Tumblr a little under five years and by the end, we were 30 people in Richmond doing support and safety. It got pretty big. We were supporting, I think, 12 languages by the end. Now, when I say 12 languages, we would literally have one person who could speak a lot of the languages, so it was not like it was 24/7 or even seven days a week support in all the languages. But it became a pretty big operation by the end of my time there.

Craig : Is that office still there in Richmond?

Marc : The office is still there. I think one of the reasons that David was interested in hiring me in Richmond and letting me grow out Richmond is that compared to somewhere like Manhattan or Silicon Valley or San Francisco, Richmond is pretty cost-effective. It’s not like outsourcing to a foreign country cost-effective, but if you want to have full-time, benefitted employees in the U.S. doing support and trust and safety work, Richmond is a cost-effective place to get that.

You can pay them a fair, reasonable wage without breaking the bank. You can get some pretty cool office space without breaking the bank. So far they’ve maintained that office and I think they largely maintained the staffing levels in that office. I think economically it works out pretty well. As Yahoo’s future unfolds we’ll see if that continues to be the case, but that seems to be what’s going on right now.

Craig : I wonder if it’s had a ripple effect. Have other support offices bubbled up in Richmond because Tumblr is there?

Marc : Definitely. One of the guys that I worked with at Tumblr, Jim Coe, has opened The Yeomen and they are a support outsourcing consultancy. I worked for Jim at The Yeomen for a year. And there’s a company called Mobelux that does mobile application and website development. They actually did the early version of the Tumblr apps, and they’re based in Richmond. I do think some good things kind of came out of Tumblr being there.

Craig : So you said you’d done some tech stuff before you were at Tumblr. Did you guys talk about equity and shares when you signed on?

Marc : Not really. To be clear, David was not only fair to me, but very kind to me from an equity standpoint. But, we didn’t talk much about equity at the time. They sent me a sheet of paper, it had some shares on it, I signed it. I basically knew nothing about equity. I knew nothing about investing. I knew nothing about different types of options. I knew nothing about any of it.

The other thing is Tumblr ended up getting acquired for a large sum of money, but it in 2007…it sounds weird to say this, equity just wasn’t even on my radar. The idea that six years later Tumblr was gonna get acquired for major money and that that might matter to me just wasn’t even something I was consciously thinking about.

I’m not much of a negotiator when it comes to job stuff. My biggest thing was making sure I would make as much as I was making at my prior job so my wife wouldn’t kill me. That was literally my biggest concern.

Craig : [Laughter] Then you negotiated effectively.

Marc : Yeah. It’s not something that we went into terribly in detail. What’s funny is I’ve been at several companies since then, and I know more about equity now, and I think it’s wild how differently different companies do it. There are some companies that will tell you, “This is exactly how many shares overall there are in the company. This is how many you’ll be getting. This is the percentage it represents. Therefore based on our most recent valuation, this is how much we think it represents.”

And then there are others where it just feels like a black box. It’s like you know that you’re getting X number of shares but what percentage of the company that represents, what the company’s valuation is may not even be something that you are aware of. You know what I mean? I don’t know that one way is necessarily better or worse but it’s just interesting to me how differently companies handle it.

I definitely understood more as my time at Tumblr went on and Tumblr did new rounds of financing. I would read articles about the financing and whatnot. I had a growing awareness of what the company was worth but it still wasn’t very concrete for me.

Craig : Yeah, it’s tricky even if you know the mechanics because ultimately it’s impossible to know how it will play out. So were you there through the acquisition?

Marc : I was actually not there. I left in, I think it was October of 2012, and I think it got acquired in May or June of 2013, or something in that ballpark. I definitely stayed in touch with them and came back to Manhattan once during that period and visited the office. I’m still in touch with a lot of them on Tumblr and other networks, but I was not there for the acquisition.

Craig : I’m interested in how you think about your first employee experience given you weren’t a developer or designer. You’re the first support person we’ve had in this series.

Marc : Yeah, so one thing I would say, I don’t know if David and Marco would consider Marco the first employee. I’ve seen articles where Marco is considered a cofounder and I’ve seen articles which refer to David as the founder. Marco was definitely present at the creation. He was definitely present at the creation of Tumblr. I definitely was not present at the creation of Tumblr.

So, I feel just really lucky that David read my email, that it connected with him, that he was willing to take a chance on me even though I was remote, and he let me build up the office. I feel very lucky and blessed.

But in general, when you get in early you kind of get to wear more hats. You have a broader role. In fact, you’re gonna be actively encouraged to take on as much stuff as possible and get as broad as possible because there’s just so much to be done.

That can really grow on you and stretch you personally and professionally. To a degree you can define your own job. There’s so much that needs to be done. You can just kind of look around and say, “Well, that needs to be done, or I’m interested in that and that and that, too.” You can just kind of like cobble together a job that you like.

I do think all companies have a lifecycle and get to the point where things are a bit complex, where you do have a more tightly defined job, where you have to stay in your lane more. But I think it’s nice to get there in the early days because it is broad and so flexible.

Craig : Were there ever any tensions between you and later employees who were developers or designers?

Marc : Having worked at several startups now I think there’s an inherent tension between people who work in support and people who work in the product and engineering side of the house. They want to build beautiful, shiny, new things, you know I mean? They want to sign up more users, they want to increase engagement for additional users. They have things that they’re focused on and fixing a bug isn’t that. Building tools for support that users don’t even see isn’t at the top of their list. So we were constantly like, “Hey, quit building that shiny, new thing. We need this tool or we need this bug fixed.” There’s an inherent tension there, all the time.

And I’ve seen the same dynamic at, gosh, three different companies that I’ve worked with now. I think it’s just kind of the nature of the relationship. It is more fun to build things than to fix things. But when I say tensions, it’s not like people yelling and screaming, and throwing things, but it just takes some arm twisting to get support stuff handled.

When you think about it, Tumblr is free to use. And support is a cost center not a revenue center. Do I think that providing good support could help you to retain and engage users? Definitely. But so can launching new features. So it was kind of an ongoing discussion.

And to answer the seniority part of the question. I think in most organizations people tend to respect tenure. Given that I was the third one, even an engineer who might have viewed me as fairly non-technical would kind of feel like, “Well you’re a non-technical support guy but you’re also one of the three people that helped build this up in the early years and I respect that.”

Craig : Say I’m a founder and I’m going to hire my first support person, how can I set up a system so that the developers respect the support people and the support people don’t feel like they’re always pushing a rock uphill to get stuff done?

Marc : Well, I’m not saying that I have lived this personally, but when I was running support at Tumblr I would go to conferences for support people and the way that Automattic [Wordpress] handles that I thought was really fascinating. I have no idea, by the way, if this is still the case today. I heard this story probably seven or eight years ago, but at the time they had two full-time engineers who did nothing but fix bugs and build support. I heard that one of them was a core engineer on WordPress–one of the people who built it initially.

So, to think that they took it seriously enough that they threw two engineers at it full-time, with one of them having that level of seniority and experience, I think really spoke to how seriously they took support. At the end of the day, resourcing is how you show that something matters.

Really it always depends on the size of your operation, but if you get to the scale of a Tumblr or a WordPress, you probably need at least one good engineer who feels like it’s their mission in life to be killing these bugs and building support tools. It may not be perceived as sexy as building the new features that the company is working on but it’s important. So I think that you will show the support people that you care if you give them the engineering and design resources to make their jobs easier.

Craig : I think that’s great advice. Ok, so if I’m going to be a first employee, what should I know?

Marc : So I think having passion for the product is really everything. Maybe there are people out there who can be hired guns who can just parachute into any job – whether they actually use the product or not – and do a good job at it. I am definitely not that person. I think having a deep passion for the product is everything.

I put in some brutal hours. I dealt with some significant problems and fires. I don’t think I could have gotten through it if I didn’t love and use the product as much as I did. So find a product and/or a company that you truly believe in and have a passion for would be the biggest thing.

I would also say that you have to, at some point, set limits. And this isn’t just for a startup hire. It’s any startup, it’s any company. Nobody at Tumblr was gonna turn to me and be like, “Dude, you’re working too many hours, chill, take time, sleep.” No one ever turned to me and said that, ever. And it’s not like everybody else wasn’t working as hard or harder as I was. I’m not playing my little violin, but I think being at a successful startup means you literally could work 100 hours a week, indefinitely.

There’s just an infinite amount of work that could be done and, at some point, you have to prioritize and just say, “I’m gonna set reasonable limits for myself. I’m gonna focus on what matters most.”

Craig : What about vetting founders?

Marc : I look for great personal rapport. David is such a lovely person and I’m not just saying that to be nice. David is really a lovely person and one of the brightest people that I’ve ever met. What I maybe love most about David is that he can make you feel like you alone are responsible for this amazing success even though intellectually you’re like, “Well I just do support. I wasn’t actually here when it was created, and I’m probably not responsible for the success.” Great founders can give you that kind of warm glow that makes you feel like you’re special and you’re doing amazing work. And it’s very, very motivating.

So I think personal rapport with the founder is key. If you are the first hire or even among the first hires, you’re going to be working relatively closely with that person. If you don’t like them, if you don’t respect them, if you don’t like their work style, things will go south very, very quickly. And so I think personal connection is super important.

Craig : I’ve been wondering, what are some of the more insane or hilarious support requests you’ve had to field?

Marc : Oh gosh. There are so many stories. I’m not gonna go into who because I still to this day think it’s important to like protect confidentiality but Tumblr got big enough that celebrities would use it and would write in for tech support.

You would be having like a really regular Monday, kind of scrolling through the Help Desk, and be like, “Wow, that name looks really familiar. Oh, wow.” [Laughter]

Richard Branson ended up coming to speak in Richmond at some event and I knew the organizers of it and because of that they asked David to come and speak. And so David and Richard ended up hitting it off and he ended up investing in Tumblr and this is all in Richmond, Virginia. I just remember standing there and watching the two interact thinking, “I am watching David Karp and Richard Branson strike up a friendship in Richmond, Virginia.” It’s so surreal and weird and so there are a lot of very cool stories like that.

Craig : Man, that’s great. Do have any favorite Tumblrs?

Marc : Oh gosh, I mean, obviously, DavidsLog.com is amazing. I love a lot of the Tumblr people’s blogs. Amanda Lynn Ferri is hysterical. She used to work at Bustedtees and Connected Ventures and never fails to crack me up. Katherine Barna who runs PR there, she has ALittleSpace.Tumblr.com. I love Katherine’s blog. She has such an awesome New York life that I enjoy following. I love following the blogs of all the folks that I used to work with in Richmond because not only do I love following their lives, they post lots of stuff from work so there are times when I almost kind of feel like I’m still there. That’s a familiar scene.

I found it was a really weird dichotomy, I tended to either follow the blogs of people that I knew in person or the blogs of people who were really prominent in something that I was interested in. So, there is a venture capitalist named Fred Wilson [[Tumblr]109][[Blog]11]. He’s one of the partners at Union Square Venture and was a Tumblr investor. Fred doesn’t even probably know who I am, by the way. But I follow Fred to this day because I find him so interesting.

Craig : How do you think about your work at Uber in relation to your work at Tumblr?

Marc : It’s in some ways so similar and in some ways so different. Uber has always charged for the service that it provides. Tumblr, when I was there, sold a few premium features but for the most part did not charge for the service that it was providing. And I think the rules and regulations change when you’re actually dealing with money. There’s a level of service that you’re kind of obligated to provide. And support is a literally 24/7 here at Uber. At Tumblr, we did all the support in Richmond, Virginia and we would do some extended hours type stuff but we didn’t do 24/7 support.

Tumblr is interesting in that Tumblr is a community and you’ve got people in that community who are interacting with each other in a very long-term, ongoing way. Uber is much more transactional. You take a ride with a driver and those two people may never interact again in life, you know what I mean? That is very different and it can be both positive and negative. People in the Tumblr community can get really close, but the people in the Tumblr community can also get a little mean. You had to balance that kind of togetherness and, sometimes, rudeness.

Craig : Do you notice any differences between the European and American startup environments?

Marc : I’m trying to think of the best way to answer that question. I’ve spent a little time in Berlin. I’ve visited SoundCloud and whatnot. I definitely think that there’s a big and growing startup scene in Europe.

I do think that Europeans can bring a different mindset to the table. Something that I have found so fascinating while living here is that in a lot of Europe, nothing is open Sunday and nothing is open late at night. Nothing is open on holidays and the 24/7 nature of life in the U.S., the life that startups in the U.S. kind of exacerbate, just isn’t here as much.

There really are people who take their six weeks of vacation. Even at Uber, there are people who take their six weeks of vacation, which I think is a good thing, by the way. Like, that’s the European standard and I think in a lot of the countries they even require it. I think work-life balance may be a bit healthier here, but then again, certain attitudes are also just part of European culture.

Craig : Do you have any closing words? Anything we haven’t talked about?

Marc : I guess the only thing that I would say for anybody who ends up reading this, is that I wanna make sure that I come across with the proper degree of humility here. I feel tremendously lucky. My email to David was a shot in the dark that he did not have to read or respond to. And then I worked hard at Tumblr. I think I did a pretty good job at Tumblr, but I don’t doubt that there are many, many other people who could have done as good or better at the job. Life is really about trying to make the most of the luck that you have. And I think startups are that way, too.

Thanks to Matt Hackett for introducing us to Marc.

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craigrcannon · 3 years

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Employee #1: Dropbox

A conversation with Aston Motes, Dropbox’s first employee.

Employee #1 is a series of interviews focused on sharing the often untold stories of early employees at tech companies.

Aston Motes was the first employee at Dropbox. He’s now a startup advisor and investor, and he currently is focused on multiple projects at the intersection of music and technology.

Discussed: Studying at MIT, Learning About Startups, Interning in Silicon Valley, Meeting The Founders, The Y-Scraper, Building Dropbox, Learning From Success and Failure, Going Through YC After Dropbox, Choosing Companies as an Employee vs. as an Investor.

Craig : What were you doing before Dropbox and how did you get involved?

Aston : I’ll go back to when I got to MIT. So, I fully expected to be a professional software engineer and to work at a big company after graduation. I assumed I would go to Microsoft or Google or maybe Amazon. Those were great jobs and a lot of my peers were going to those companies. They seemed like pretty fun places to be. You know, they had free drinks in their refrigerators! And that was kind of my ideal situation after college.

Halfway through MIT I started reading the essays of this guy named Paul Graham [PG] and learned that there was this whole other world of Silicon Valley, the startup world. Obviously, all those companies that I was just talking about came up in this culture of the venture capital backed startup, but that startup world wasn’t visible to me at the time.

I actually went to a talk by PG he gave at MIT. And I just became an acolyte of his, based on his blog posts. They shifted my perspective, and I eventually I decided I really wanted to start a startup rather than work at one of those big companies The only problem was, I didn’t have any great startup ideas. The closest my friends and I got to a real startup was, we built this book exchange website for MIT students called bookX (which is now defunct).We thought that it might be a business, but turned out it wasn’t.

So on my way out of MIT, I was looking to join startups and subsequently ended up in New York City at OkCupid. I actually had interned previously in Silicon Valley and decided that maybe it was too much tech for me. I wanted to experience New York where there were, I guess, other cultural things.

Once I got to New York I realized I missed having a bunch of geeks around everywhere. I found my pocket of geeks in New York at OkCupid, and I had a roommate who was also a software engineer. So I had that network, but I did miss the Valley. There’s a different energy in Silicon Valley versus New York, especially in 2007 when I was there.

Craig : So how long did you end up staying at OkCupid?

Aston : I stayed at OkCupid for just six months, and those six months were really, really great. But actually, for almost all six months I was being recruited by Dropbox. Essentially what happened was one of the people that I had worked on bookX with, Arash [Ferdowsi], ended up going to YC and co-founding Dropbox with Drew [Houston]. They started working on Dropbox together a few months before I went OkCupid.

The whole time I was at OkCupid I was hearing about their exploits. When they started they were working out of an office in Cambridge so I hung out with them there. But, just as they went through Y Combinator in the summer of 2007, I heard news from them about how well they were doing and how many people in YC loved what they were doing.

I think they ended up getting voted as one of the best startups in the batch by their peers. By the end of the summer they finagled a round from Sequoia Capital. When I heard how much it was, I was blown away. They were like, “Yeah, we just raised a million dollars.”

And I’m like, “That’s incredible.” I didn’t know they gave a million dollars to…I mean, literally, kids.

Drew is a couple of years ahead of me, but I still felt like a kid, so I thought certainly “that guy is a kid.” In reality, Drew had spent a bunch of time building companies and was working at a startup at the time, so he had a lot more experience than I appreciated at the time. And Arash felt like a kid as well. Arash is a year younger than me and I actually TA’d him when I was at MIT.

Craig : [Laughter]

Aston : I mean, it’s one of those things where my vision of what Silicon Valley could be was really in front of me. It went from PG writing, “Hey, you know, college students can build interesting businesses” to, “Here are people that you know from your school that are not only building something awesome, but they’re also getting the same type of respect more established people in the Bay Area get.”

That was a really big moment in terms of my understanding of what Dropbox was. Before that it was just this cool thing they were working on. Then it was like, “Oh they’re building a business.” And around that time period they were looking for a first employee.

Craig : Was there anything in particular that excited you about Dropbox?

Aston : So, obviously, those guys. Drew and Arash are super, super smart and great engineers. To this day, I’ll hold Drew as one of the best Windows programmers I have ever met. And Arash is just sick at all things backend. They were this perfect pairing. So, as far as the team went, I was certain that these guys were going to be great people to work with.

For the longest time I had seen product demos that were just video. But once I played with the product I was like, “Oh, this thing works. I really like this product and it would be awesome to get a chance to work with these guys, on this thing.” It was a product that, as an MIT student, it matched my expectations for how something should work.

Craig : What does that mean?

Aston : MIT has this thing called Athena, which is a very old networked computing system. Basically, you can go to any computer on campus, log in with your username and password, and the computer’s desktop, comes up the same with all your applications and files.

It’s a super awesome system that you got used to at MIT. If I needed to print something on the run, I could drop into any computing block and my stuff is right there.

Craig : That’s really cool.

Aston : Yeah, definitely. So from the product perspective, Dropbox made a lot of sense to me. If I didn’t have Athena on my laptop I couldn’t get to my files but with Dropbox I could. Maybe not this whole desktop experience, but at least my documents and my photos and all that stuff.

That’s about as far I thought about the marketability of it. Basically, “There are people out there like us and they’re going to love this thing.”

But the Sequoia check definitely solidified my belief in the fact that this could be a real startup; it wasn’t just a project that was going to end very quickly. So I actually tried to help Drew and Arash recruit someone else as first employee, assuming I would just join later.

I was like, “You guys are going to be around. Now that you have this check, you guys are going to exist for a couple of years. I’ll just come on later. Let me try to help you find someone else who doesn’t have a job,” because I was working at OkCupid and really liked my job and didn’t want to up and quit. I had a year-long lease in New York that I didn’t feel super excited about paying for while living in another city. So it was like, “I’m probably not the right person to do this. I’m not really in a position to do this.” But my recruitment efforts failed and their recruitment efforts succeeded.

Craig : [Laughter]

Aston : That whole time they had been working on me and I didn’t even notice that they were recruiting me. And I would say the nail in the coffin was, they flew me out to San Francisco to see what was going on. I got to see the apartment, which was not very glamorous, but it was the apartment they were living in and working out of, with a great view of the bay.

You could see the Golden Gate Bridge and Alcatraz and of all that. So, it was a cool place to be working and it was just them. The idea that it would be just us working on it was also attractive. And the other thing that was really cool was the community that was around at the time.

Their building was nicknamed the “Y-Scraper” because it’s a towering monstrosity in North Beach and it was full of YC companies. That whole neighborhood is low-rises except for this 12 story tower. It sticks out like a sore thumb, but does have great views. At the time Justin.tv, Weebly, Scribd, Etherpad, Disqus and more YC companies were all living in that building. There were a ton of companies.

The density of startup people was so high that it ended up being this really impressive thing for me. Like, there wasn’t just Dropbox and this team that I was working on. Around me I was going to have other similarly-minded people. At that point I realized not only would Dropbox be a cool team to work with and a cool product to work on, but it was going to be an opportunity for me to really learn what it was like to start my own company, which as I mentioned before, was always a goal.

Craig : What made you not start your own company then? What made you decide to be an employee?

Aston : Well, the immediate thing was that I didn’t have any great ideas. I think related to that was I didn’t have a ton of confidence about my ability to run a company, having never have done one before. So I reckoned that being an employee would be the best way to see it, and if it failed, I would learn a bunch. I would learn a bunch, and it wouldn’t necessarily be my fault–I’d just be like that guy who was around. And from those lessons I’d be able to learn all the things to avoid and when it was time to do mine, I would be super prepared.

Craig : Totally. So you join Dropbox and move out. What’s it like?

Aston : It was just like I expected. It was awesome.

Craig : Did it feel like you lived in a dorm?

Aston : It didn’t have a dorm feel per se, because everyone was working so hard. You wouldn’t see people randomly during the day. We had pretty weird hours. We would start in the early afternoon and would work until well into the low numbers in the morning. So we didn’t overlap with a lot of the other companies during the week because everybody was working on their own thing. They were maybe a couple occasions I can think of where someone visited us during the day. But on weekends, yes, definitely. It was one of those things where everybody’s personality type is “work hard, play hard” and almost all the companies would take one day to get away from everything and do something interesting.

Craig : So what were you actually working on? What part of the product?

Aston : So when Dropbox first came out, the demo video had this desktop part and this web part. Drew built the first version of everything. And then when Arash came on they ended up splitting it with Drew on desktop and Arash on web and servers. And then when I came, we split it again so it was Drew on desktop, Arash on servers and me on web.

So I built the more modernized version of the web stack and that involved a number of website redesigns. We started the site in an era where IFRAMEs were cool and by the time I left the company we were well into AJAX/XHR and dynamic everything on the client side.

I also had a hand in choosing a bunch of technologies that Dropbox ended up sticking with, for better or for worse. Drew picked Python on the web, and he also picked Python on the desktop. But I ended up picking Mercurial for the distributed version control system, which we were definitely wrong on that one–should have picked Git. I also picked Prototype.JS for the web. We were wrong on that one, too and should have picked jQuery.

But this is just like a long line of interesting things that happen when you have a startup, where you look at the things that are trending, you look at things that are hot, and you pick the ones that feel good, and then six months later it turns out that your pick wasn’t the right one and everyone is doing this other thing.

By now, I think Dropbox has moved away from Prototype.js and potentially also from Mercurial. But it’s funny how long these early decisions stick around the company.

Craig : What choices worked out well?

Aston : There’s a long line of things we didn’t do that I think ended up being good. And that was generally from being a pretty conservative engineering culture. We tried to avoid things that were trendy and, in general, we just chose things that worked for us that weren’t super complicated. So I think for the most part we ended up have never having to do a complete overhaul of something that was not working.

Craig : It’s an interesting point. In the other interviews we actually haven’t talked about the implications of their technical choices. Do you have any broader thoughts on how someone should thinking about those decisions?

Aston : My advice for most companies is just use whatever you’re comfortable with. I think a lot of that stuff ends up being “six of one, half a dozen of another.” That said, I’m really happy that Drew chose Python. I wasn’t familiar with Python before I got there. Primarily, I had been coding web stuff in PHP, which Facebook ended up using a lot of. At OkCupid, we were actually using C++. That’s just to say that I was open to whatever language stuff needed to be built in. And I think Python is a really great compromise in terms of programmer productivity and performance.

In general, my thing is, again, in keeping with Dropbox’s conservative culture, if you can use languages and tools and databases and frameworks that are 10 years old or older, you’re probably doing pretty good.

Craig : And so then what were the challenges in the beginning?

Aston : For the first year we were not publicly available and primarily we were just trying to actually deliver all the features we claimed we would have. We had a pretty solid mailing list built through interest in a couple screencast videos that Drew had made.

One screencast went to the top of Digg and Reddit and Hacker News. It was still just us three and we had stuff like that. Basically, we had this huge group of people who wanted to try the software based on what we showed it could do so we were like, “Okay, well let’s actually build that. Let’s actually make it work like that.”

It could work like that for one computer for sure, but we wanted it to work like that super smoothly for everyone who used it, across all platforms, and to have a website that complements all that functionality. In fact, for a long time the desktop client had almost no UI so most of the difficult operations, like sharing a folder, happened on the web.

So we put in a lot of work building up that experience. And we didn’t launch it until a while after I joined. I forget the exact timing, but around a year in we were ready to launch. So yeah, it was all the stuff that goes into any launch but add on the complexity of having not just the web client but also Windows, Mac, Linux, all talking to the same servers, and we had built the majority of this on Amazon Web Services, but at the time they were… not quite as reliable as they are now and definitely not as extensive. I think they just had EC2 and S3 back then.

Once we actually launched, work became fighting fires around customers problems or us needing to ship features and things like that. The first year or so was calmer. It was just a lot of heads down work.

Craig : Did you have a certain number of users in mind when you were writing V1? Like, “Okay, we can handle, whatever, a million people with this.” Anything like that?

Aston : Oh, interesting. Yeah, I actually didn’t spend that much time thinking about how many people we would reach, but it was certainly a consideration, primarily on the folks who were for doing scalability stuff. I was more concerned about the user experience and what would make Dropbox successful.

Just to set context here, there were a lot of companies we were competing against in backup and file sharing. Ultimately, I think what differentiated Dropbox was user experience and really never screwing up, like deleting a file or anything like that. And if you were using Dropbox you could be pretty certain that whatever you were doing, the interaction was going to be easy. So that was a super big focus for me.

When I thought about scale, it was more about how many people are going to run into this crappy case? Or how bad would it be if we did something in a funky way that worked 90% of the time? Because we also needed to, obviously, ship.

A specific example was backend records when someone added and then deleted files. Dropbox didn’t at the time track renames whatsoever. And a rename would encompass a move as well. So, when I joined the company, if you moved a file from directory A to directory B, you deleted this file and then you added this file. From a technical perspective that’s weird and doesn’t match what actually happened: It was actually moved on disk, not added, then deleted.. But also it mismatches anybody’s reasonable expectation of what they would see there.

We spent time trying to apply heuristics to try to understand when people moved files. In that simple case, since the file contents don’t change and the add and delete come together in a small time window, it’s pretty easy to tell that the file just moved from A to B. But when someone moves a directory with 5,000 files and directories, they don’t all come in one file change set, they come split across multiple change sets. And it’s not all at the same time. You can naively compare all the file contents but it ends up being really slow.

We went through multiple versions of this movement matching thing before we got to something we felt was performant. But it’s a good example of where performance issues sneak in around scale. And it’s not people-scale, it’s like file systems-scale, which is a different dimension.

Craig : What were the fires after you launched?

Aston : The first one’s hilarious. We launched publicly at TC 50, which later became TechCrunch Disrupt. Basically the format of this is, you’re on stage in an auditorium with thousands of people watching. Also on stage is a panel of judges – respected entrepreneurs, journalists, venture capitalists – and you get your X number of minutes to pitch, and then at the end of it they give you feedback… in front of everyone.

They were streaming it online so when Drew went to pitch with Arash everybody was in the office watching the live stream. But actually what we were watching is our computers with logs of the server. We were deathly afraid that this demo would fail in some way.

So we’re watching the live stream and the server logs look great. We’re monitoring Drew’s account specifically to make sure everything’s going through. We’re ready to fake it if we need to–like throw a file in there from our side. Then partway through the pitch Dropbox seems to stop working on the live stream.

Everybody is freaking out like, “What went wrong? What can we do to fix it?” It seemed like everything was fine and then we realized that the WiFi was out at TC 50. Drew had obviously counted on the WiFi working. Dropbox actually doesn’t need the WiFi to work that well to do its thing but, you know, it has to be on. [Laughter]

Craig : [Laughter] So how did the demo go?

Aston : So by the end of Drew’s like, “If the internet were working, this is what you would have seen.” But it really killed the magic.

One of the judges was like, “I don’t get it.” And this was a legit person who we respected and thought would love it. Then we just got creamed on stage. It didn’t help that the presentation before us was Swype, which was this awesome, magical keyboard. They had the best demo in the world and then ours didn’t work. So, we started out with fighting fires from day one.

Craig : And what about when the users arrived?

Aston : Yeah. We definitely had scalability issues, we had bugs, the same stories everyone does. I think for the most part, Dropbox had a very blessed experience. One of the ways we were blessed is we really didn’t screw up in the worst way possible, which is lose a bunch of people’s files all at once, in unrecoverable ways. We had built out the system such that when we did delete something, we left a time when we could do recovers. We had written the clients well enough so that we were unlikely to mess up the bits and prompting of the server.

But there were definitely incidents where data got deleted and we had to go recover it. There were definitely incidents where stuff would just not work for people, which is obviously no fun. The funniest one wasn’t really harmful to consumers but it was harmful to our business.

The Dropbox desktop client had an auto updater feature and one time we shipped an auto updater that broke the auto updater.

Craig : [Laughter] That’s awesome.

Aston : [Laughter] So yeah, that meant if we found any other bug we couldn’t fix it. Luckily we were staging the roll out and caught it so it didn’t hit everyone. But for those it did we had to apologize and told them, “Go download this other one that will continue to work in the future.”

Craig : I’m surprised you caught it that fast.

Aston : I don’t remember how we caught it, to be honest. But I mean, it’s a reflection of the engineering culture we had. We were all using the product so when there was funny stuff we tended to catch it. And we tended not to ship it out to too many people until we were certain it was rock solid.

Craig : Okay, and so what was the environment like when you launched? I assume you didn’t live in the YC skyscraper forever.

Aston : We got to five or six people in that apartment before it became a hazard to our health. So we rented an office right around the corner in FiDi in San Francisco. Once we moved there it started feeling like a real company. Through that point we had been hiring pretty much the same way I got hired, which was, “I heard there is this guy at MIT who is pretty smart. Aren’t you friends with him?”

“Yeah, I’m friends with him.”

“You want to ask him if he wants to work with us?”

“Yeah, I’ll ask him.” And then fast forward a number of months later and they worked with us.

We had a great recruiting pipeline but a not particularly interesting one. I think of the first 12 or 15 people who joined the company, almost all of them were MIT graduate or MIT students who dropped out to hang with us for a summer.

Craig : So how did your relationship with the founders shift as Dropbox grew?

Aston : Hm. I had been a TA to Arash so in my mind he was like a younger brother, but then he became my boss immediately when I joined the company. Though I think that’s the way the working world works–your relationship with people will change as you work with them. I think that particular relationship ended up fine. Dropbox was super, super flat and allergic to management in the early days, so pretty much everybody just worked on their own stuff and there wasn’t this sense of, “Oh man, this kid is bossing me around again.” It was never like that.

I do think all of us became much better friends but also, because we were spending so much time with each other, got a little bit of cabin fever. But overall, we worked super well with each other and had really high bandwidth communication because we had all come from the same place.

Craig : And how long did you stick around?

Aston : So I spent quite awhile at Dropbox–four and a half years. And the whole time I was like, “One day I’ll do a start up. I want do a start up. I don’t know what it will be, but I know there will be a day when I’ll have to leave the company and go do my own thing.”

The moment just sort of came when it came. I had just finished launching the API V1, which was the grand re-launching of the API. I wrote the original API for Dropbox. I helped work on V0, which is the first one we released publicly. And then V1 was this scaling up of the ambition of the API and also a huge code cleanup. The API was originally for our mobile client and so in opening up for other people we had to change some stuff so that it actually made sense. After releasing the API, I had this moment where I was like, “Oh, I actually could leave.”

Craig : Meaning you’d hit a milestone?

Aston : Yeah, that project was a big milestone and I didn’t have another big project waiting for me at the time. Also, the company had grown such that I didn’t feel like I was a bottleneck. I wasn’t this person who needed to be around to make sure stuff happened, which is what it was like when I first joined.

I thought, “I can give myself permission to leave. The company won’t die, they’ll be fine. And I can go off and do any of the random cool stuff I want to do.” So I left Dropbox and did YC the following summer.

Craig : Cool. What was the startup?

Aston : I was fascinated at the time with what now is literally a joke on “Silicon Valley”–social, mobile, local. The idea that we’ve got these cell phones that are a marvel of technology. And the convergence of the ability to communicate instantly seemed like a natural fit for this thing that was happening to me, which was wanting to hang out with friends at a random moment. It’s Friday night, I’m not doing anything, where is everybody else? I was fascinated by that question and I built a number of apps over the summer to try to address the problem. But I actually didn’t end up even publicly releasing any of them.

I have pretty high standards for what I thought would be super valuable and I just felt like I wasn’t there. I had a really good sense of what the problem was but I didn’t go into the summer with a clear sense of what the solution would be.

I think in general, consumer mobile is tough because what may work for you may not work for other people. Trying to find something that has really, really wide appeal is hard in the first place, then what’s more difficult is finding a business in there.

While building those apps I talked to a number of founders who had dead companies in the space. Just like graveyards worth of people who were trying to work on a similar problem. Some of them ex-YC, some not. Even with all of their wisdom and my own gut instinct, I never really got to a product that I was super proud of.

Craig : So did you demo anything at Demo Day?

Aston : I didn’t. I think I realized it wasn’t working a little bit before Demo Day. I took the last little bit of time before demo day to really reflect on whether or not I wanted to continue trying to solve that particular problem. I realized that if I raised money around solving the problem I wasn’t sure I was ever going get anybody’s money back.

Craig : Wow, awfully moral.

Aston : Yeah, I take all of this stuff pretty seriously and like I said, had a really high bar for what I thought would be valuable. Yeah, just didn’t do it.

You know, I tell people maybe the worst thing about Dropbox was that it went so well. I didn’t learn many bad things. I learned about things that come with success. And a lot of times with startups it’s more valuable to learn the things that come with failure.

Craig : That’s a great point. What other lessons have you learned that Dropbox’s success may have covered?

Aston : I didn’t have as strong of an appreciation as I do now for just how valuable it is to actually pick a great idea that has a great business behind it. It was some youthful naiveté that I think I’m beyond now. It seemed so easy with Dropbox. As far as I knew, Drew woke up one day with this idea and we built it. If you go read the YC application for Dropbox, we built literally what Drew said and almost every competitor Drew called out built exactly what we thought they would. And the only difference between the story there and the story in real life is that we didn’t get killed and that we ended up building a business.

I don’t know if Drew even estimated the business could be a billion dollar business, but he definitely thought that we had the same type of customers as we ended up having in the early days.

Craig : Wow.

Aston : It was an incredible thing to see an idea that we all thought was good actually work. It was a bit of a surprise, I’ll admit, that when I had an idea that I thought was good, it didn’t work! And that’s a way more typical story for startups.

Craig : Do you have any advice on vetting ideas?

Aston : I’m a big believer now in founder/idea fit. I don’t know if that’s the right term but that concept’s definitely a real thing–matching what you’re building to what you want to be building. And I don’t just mean product, I mean company as well, and maybe company is the more important part. There are certain business ideas out there that I think are pretty awesome that I never want run myself for a variety of reasons. Some ideas are really, really sales heavy and I’m not a salesman. Some of them are about scale. There are definitely ideas out there that can make you hundreds of thousands of dollars a year but my ambition is for something bigger.

I think there’s a lot more that goes into committing yourself to a long term project than I appreciated. And I don’t know if Drew and Arash would have committed to Dropbox if they knew it was going to take them a decade. A decade of their lives. I’m sure they love it. I definitely loved being a part of it too. But that’s just to say that, I didn’t fully appreciate the commitment needed to fully see an idea through.

My time in Y Combinator was like my grad school on founder/idea fit. I was working on this idea and on this problem that seemed real to me but wasn’t shaping up to be the type of business I wanted to build. So yeah, I didn’t build it.

Craig : Does that belief ever keep you from jumping onto projects?

Aston : Yes, definitely. I think the coping mechanism for not wanting to do something that doesn’t match your ideal is just as you said, to just not do anything.

What I did to get over that was instead of spending my time trying to the perfect startup idea, I just started playing again. That was on the advice of a number of serial entrepreneurs and people who had had these great exits.

For example, the founders of OkCupid who now are doing Keybase, which is this really awesome public key exchange. The way they got there was basically through this process that they shared with me, which is just play. Just be willing to explore ideas that you think are interesting and don’t worry a ton about how big they’ll be. Then cull them as you go. It’s like, “Okay, well this one was cool but it wasn’t the company we wanted to build, so let it go.”

Before discovering that letting go process – this was partially related fact that I was in Y Combinator – it felt like such a big thing for me to let an idea go. To say, “You know what, this isn’t it. I really want it to be it, but this isn’t it”. Now my mindset is, easy come easy go. I came up with that idea in a day! Why would that be the thing that I would spend the next five years of my life on?

That’s definitely a change of mentality for myself as an entrepreneur. My time since Y Combinator has been filled with lots and lots of little projects that have been extremely valuable for me in terms of learning. Some of them have made some money, some of them have not. None of them yet are the decade-long commitment thing that I would love to get to. But yeah, I think it’s all part of the process.

Craig : Man, I’m very impressed that you’re so astute in a business sense but also morally and technically. It’s cool.

Aston : Oh, thanks.

Craig : Definitely. Ok, so you’re an investor now. Can you explain how you vet companies as an investor versus as an employee?

Aston : Sure. So the reason investors have a portfolio is because it spreads out your risks, right? This company may fail. This company may 10X. This company may 100X. They offset each other. But as an employee and particularly a first employee, you’re really giving your life to this thing for however long it’s going to be alive and that’s a different sort of commitment.

If I were looking to become a first employee, first off, I’ll say that being a first employee is actually a pretty tough role. You’re basically a founder, in terms of the responsibility that you have and in terms of the emotional weight that the company will have on your life. You won’t be able to get away from it the same way employee number 50 or 500 will.

To that end, I think it’s important to make sure your personal life lines up with the company. It’s different for everyone but for me it was my first year out of college and I wanted to make sure I worked with people I really liked and trusted. Because you can write anything in a contract, but when it comes down to it, it’s very easy to break the contract and you have no recourse, right? I trusted Drew and Arash, basically, with my life. I was like, “These guys are great people and I can’t see a future in which they would do me wrong.” You need to really feel like you want to be associated with the company. For better or for worse, Dropbox is going to be on my resume forever.

So far it’s been great but that’s just to say that, you do have a lot of career risk when you go work with a company. If you work with people who aren’t good or aren’t scrupulous or things like that, it can hurt you. Those are the highest bits for me, “Who am I working with? Do I really want to be working with these people?” And then, I think the second thing is certainly, “This product, do I love it? Do I want be working on this business? Am I willing to keep working with these people on something related if this one doesn’t work?”

That last one’s a weird one. I think a lot of people end up working on things where they’re like, “I love this, but anything else, I hate.” That’s a bad attitude for an early employee because I think your responsibility, ultimately, is to stick with it longer than other employees and almost as long as the founders. You can get out a little bit earlier, but it does look bad when early employees are bailing. It hurts companies.

Being a first employee is a really, really big responsibility and you should be ready for it. As a young person I don’t think I understood how much responsibility I was stepping into but I mean, it was pretty easy for me to make that step because I felt so much confidence around the team and around the product. I knew I was going to learn so much that even if it didn’t work, it would be worth it.

Craig : As an investor, how much time do you spend investigating the business versus the founders?

Aston : I care way more about the business than I did as an employee. At Dropbox, I didn’t think very much at all about how much money we would make. And that was probably fine. I mean, like I said, I was happy enough to be working with the people and on the product. If it ended up with us failing on the business side, I was prepared for it, I expected it. I was actually the first person to push for asking for money from customers and I built out the billing system and then I looked over my computer at Drew and I was like, “How much should we charge?”

And he was like, “I don’t know, 10 bucks a month.”

I was like, “Sounds good to me.”

Craig : [Laughter]

Aston : [Laughter] Yeah, that’s level of financial modeling I was experiencing at Dropbox. I’m sure Drew had stuff with the investors that was a bit more sophisticated.

But yeah, as an employee you can’t make a portfolio, which means you would have to be right. And it’s very hard to know if a company is going to work or not. So I don’t think that could be a part of your calculus as an early employee.

Craig : Totally. All you have is the portfolio across your career. You get some amount of chances.

Aston : Yeah. That, I would say, is a good thing about small startups: they tend to fail fast. So, you know, if your company is failing every year and a half or so, you can get a lot in before you start getting up in the years.

Craig : So, related to finding startup opportunities. It seems like at MIT you were at the right place at the right time to meet people. How do you think about meeting new people now ?

Aston : That’s changed a lot since I moved here. My advice, actually, is to move to where you have lots of opportunities to run into interesting people who are doing cool stuff. My move to New York was probably not the best one in terms of networking around startuppy people. I don’t regret going, but if I had I moved immediately from college to Silicon Valley, I would have had way more people around me who were entrepreneurial and would have raised my chances, not only of finding an opportunity like Dropbox, but also potentially finding a co-founder and doing my own thing. I think getting around a place where the people think the way that you want to be thinking is super valuable.

Craig : And what about vetting them?

Aston : That’s tough. MIT is cheating. Going to MIT you end up getting to meet lots of people who are smart and fun to hang out with and you’ll get along with naturally. It’s much harder after school.

Craig : Agreed. Ok, last question. Do you have any book recommendations?

Aston : Let’s see. For business books, I really like Ben Horowitz’s The Hard Thing About Hard Things. It’s like the opposite of my Dropbox story in ways, so for me it was really eye opening. This idea of taking some people who are super experienced entrepreneurs, who have great connections, who have a billion dollar business idea, and then watching how crazy things get and how many ups and downs there can be on the way to success. It’s fascinating. And style-wise I just love it because it’s very casual and easy to read.

On the non-business side, I absolutely have to recommend Ta-Nehisi Coates’ Between the World and Me. He does a great job using his own personal experience as commentary on the rest of America. It may feel a little bit heavy-handed to some readers, but I think it’s heavy-handed on a really important set of issues about institutional racism. It’s about how this whole system that we have impacts a lot of people’s lives in ways that often go unrecognized. It’s a really great book, and it’s pretty short too.

Craig : That’s great to hear. Ok, let’s end there.

Aston : Cool. Good to hang.

Craig : Likewise! Thanks for your time.

0 notes

craigrcannon · 3 years

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Employee #1: Coinbase

A conversation with Olaf Carlson-Wee, Coinbase’s first employee.

Employee #1 is a series of interviews focused on sharing the often untold stories of early employees at tech companies.

Olaf Carlson-Wee was the first employee at Coinbase. He currently runs Polychain Capital, a hedge fund which invests in a portfolio of blockchain-based assets. He is also an angel investor and filmmaker, based in San Francisco.

Discussed: The Early Days of Bitcoin, Interviewing at Coinbase, Finding Employees on R/Bitcoin, Scaling Support at Coinbase, Spotting Fraud, Vetting Founders in a New Field, Launching Polychain Capital.

You can subscribe to The Macro newsletter to receive future conversations.

Craig : What are you currently working on?

Olaf : I actually launched a company yesterday.

Craig : [Laughter] Whoa, congrats.

Olaf : Yeah, thank you. I don’t feel like celebrating quite yet because it’s just the beginning but it’s called Polychain Capital, “chain” here referring to the blockchain. It’s a hedge fund that invests in a diversified portfolio of cryptocurrencies.

Craig : Man, that’s wild. Is it a big team at this point? Is it just you?

Olaf : Just me.

Craig : And how are you picking the currencies?

Olaf : So I’m looking at things like novel uses of cryptography in the protocol. Or is the protocol attempting something that a blockchain has never done before. I’m also looking at core developer team quality, the developer ecosystem, and asking questions like are there a lot of apps being built on this, with GitHub forks, GitHub stars, and then looking at the community ecosystem. What’s the size of the forum? How often do people post relative to other forums? Is it an active community? Stuff like that. So part is core analysis of protocol, and part is quantitative metrics surrounding the use of the protocol.

I’ve launched with five million under management so mostly right now I’m focused on operationally executing the portfolio perfectly. And then making sure that I’m tracking the space and developments at the protocol level. Keep in mind, my last day at Coinbase was eight weeks ago.

Craig : Wow. Did you raise the five in that eight weeks?

Olaf : Yeah, I’ve been on the phone a lot. I have this stupid headset that I wear all the time. [Laughter]

Craig : [Laughter] You’re one of those guys?

Olaf : Yeah. It’s really embarrassing.

Craig : We’ll let it slide. Ok, so let’s talk about Coinbase. How did you find out about them?

Olaf : So I wrote my undergraduate thesis about Bitcoin and the larger implications of open source finance in 2011. I was Coinbase’s 30th user and now we have four million. I literally cold emailed jobs@coinbase and said, “I love bitcoin. Here’s my thesis. I’ll do any job.”

Craig : So you cold emailed these guys a document that was like 60 pages long?

Olaf : Yeah, like 90 pages long. [Laughter] But, to be fair, I clipped the 30 page chapter that was specifically on Bitcoin and cryptocurrency. But yeah, I did. I emailed an annoyingly long and annoyingly academic document.

Craig : And they responded?

Olaf : Fred [Ehrsam] replied in five minutes and said, “Hey, can you hop on Skype?” That’s when I started learning how things work in Silicon Valley. The pace of things.

We got on Skype and talked for 20 minutes. Then I got an email from him that said, “Okay, we wanna do an in-person interview. You’re going to come to the office tomorrow. I want you to have two finished presentations, 15 minutes each. The first should explain something complicated you know very well. The second should outline your vision for Coinbase.”

So I got to work. At the time I was on a road trip and actually was crashing on a friend’s couch in Oakland so the scheduling worked out well.

Craig : Did you study CS in school?

Olaf : I majored in sociology so I’m self-taught on computer science. Though I’m not a great coder. If I’m a building a website, I’m not very good at that. But I do know cryptography pretty well and, in particular, I know game theory well, which is really important in cryptocurrency.

Craig : Gotcha. So what were your presentations?

Olaf : Okay. So the first one was on the pharmacological induction of lucid dreams. It is complicated, but it’s a mechanism to induce lucidity in your dreams. You can control your dream by waking up in the middle of the night and taking an over-the-counter supplement called galantamine, which increases levels of the neurotransmitter acetylcholine in the synapse. Fun fact is that I’ve been writing down my dreams for 11 years.

The second presentation was on Coinbase and my high level strategy for the company. Coinbase had a lot of problems at that time. When I was applying, there were really bad bugs. Actually, on the first day of my work trial, there was a top Hacker News post that said, “My balance is wrong. I lost all this money.” Everything was broken.

My strategy was to clean up PR problems but focus 100% on security. Bad customer experiences will eventually be forgotten but a security incident will not be forgotten. I basically was saying, “Listen, people want us to move faster than we can.” I mean, Brian [Armstrong] was literally building everything. I was saying to Brian, “We cannot hack something together that ends up leading to a security incident. Even though everything is on fire, let’s do this very carefully.” And I think that resonated with them.

But Coinbase, especially in its early days, had a lot of hard tradeoffs between moving really quickly like a traditional startup and operating as a financial institution. Even then we were storing tens of millions of dollars of people’s money. And of course there were security incidents. Fraud was a big problem. People trying to buy bitcoin with stolen identities. We wanted to give good customers high limits and we we wanted to give scammers low or no limits. There are a lot of hard tradeoffs. I basically took the perspective that we need to be a security juggernaut and any bad customer experiences will long-term be forgotten.

On the other hand, if you get hacked or you have a massive fraud incident and lose all your money, it’s catastrophic. The main thing is avoid the catastrophic events. And what’s funny is looking back, that’s really what Coinbase has done. A big way that Coinbase is the leader in the space is just that we didn’t get hacked, honestly. We did many things right. But that is honestly the number one thing.

Craig : Ok, so you do the presentations. Is this to both of them?

Olaf : This is just to Fred. Fred and I probably talked for 45 minutes–a long time. Then Fred gave me a really brutal mathematics problem and said, “Okay, why don’t you figure that out while I go talk to Brian?”

So I knew I had at least on some level passed the first part. I knew he’d walk me out without meeting Brian if it definitely wasn’t working out.

Do you want to know the problem?

Craig : Yeah, absolutely.

Olaf : Okay. So there are 100 lockers in a row. They’re all closed, okay? A kid goes by. He opens every single locker. A second kid goes by. Now he closes every other locker, every second locker. Third kid comes by, every third locker. If it’s open, he closes it. If it closed, he opens it. Then the fourth kid goes by. Every fourth locker, he changes the state. And now 100 kids go by. What is the state of the lockers after 100 kids go by?

Craig : Oh man, I’d definitely need some time for that.

Olaf : Yeah, so don’t try to figure it out because it may take a while. So I’m sitting there and thinking like, “Okay, focus Olaf. If Brian comes down and the first thing you have is the answer to this problem, this is gonna seal the deal.” At least in my head I thought that. In retrospect, that was getting ahead of things a bit much.

To be honest, I don’t know what happened but I had this crazy flash of insight and had the answer. And when Brian came back, we started talking through it and I just figured it out way faster than I reasonably should have.

Craig : Whoa. So what’s the answer?

Olaf : The answer is perfect squares are open. The reason being, they’re the only numbers that have an odd number of factors. So the number of factors determines whether a locker is open or closed because that’s the number of kids that interacted with it. And so the odd number of factors means it’s open and even number of factors means it’s closed. And the only numbers that have an odd number of factors are perfect squares like 16, 25, 36.

Craig : How long were you given to solve that?

Olaf : Oh, probably like three minutes.

Craig : Holy shit, okay.

Olaf : Yeah. It was probably three minutes. I don’t believe in divine intervention or anything. But that was a time in my life when I had an uncanny flash of insight that I would never pretend I could recreate. But anyway, then Brian grilled me for another hour.

Craig : [Laughter]

Olaf : Brian’s questions were really intense. “What do you wanna do with your life?” “What drives you as a person?” “What’s a belief you have that is extremely unpopular?” He wanted to really know me.

I think Fred had gone up to Brian and said, “Listen, Olaf’s at least sort of qualified for this. I talked to him. I think he could do the job. Now we need to figure out do we want to actually work with him.” And Brian went super deep on a lot of really intense questions about my life, what drove me, what mattered to me, why I wanted to do this, all that stuff. And we had a very intense conversation about what it meant to want to do things, what it meant to be a human trying to go about the world.

Craig : Did you feel prepared to answer those questions?

Olaf : I definitely had to think about each question but I tend to have a pretty crystallized ideology about the way I think about the world. It changes, but at any given moment, I know what it is. So yeah, I think it was pretty reasonable for me to say, “Here’s why I wanna do this.”

Craig : Okay, and then how does it wrap up?

Olaf : They say, “Okay, great. We’ll let you know.” And then they walk me out. I heard back, I wanna say, four days later. They said, “You should come in for work trial.” And that was a two week paid trial. I worked really hard because I knew this was the final test. At the end of those two weeks they said, “Okay. You have a formal job offer.”

Craig : What was the actual job?

Olaf : Customer support. Like I said, I came in and was willing to do anything. I did customer support by myself until we had 250,000 users.

It was a marathon. It was like 12-hour days of fast replying. And, to be clear, we did not have good support during that time. I’ll say that as the person who was doing it. You would get an email. It wouldn’t necessarily come right away. It wouldn’t necessarily perfectly answer your question. But we were replying. [Laughter]

Craig : [Laughter] Okay. So then did you become involved in hiring future people?

Olaf : Yes. So basically what happened was we were trying to hire more customer support people, because it was not scaling with just me. We did four work trials for our customer support people to join me in San Francisco. We rejected all of them. Meanwhile the problem is getting worse and worse and worse, right?

The delay in replies and the quality of replies is just going down in a bad way. I think at the peak, the average time to reply was five days. And this is a financial institution. It’s really inappropriate.

So I got really desperate and I posted a Bitcoin SAT on Reddit. What this was was a test, a Bitcoin aptitude test so to speak. And it had questions like, “What is the hash of the genesis block?” That was the first question. And the idea there was if you’re asking yourself, “What does that mean?” this isn’t the job for you. If you have no idea what that is then get out of here.

It was a bunch of Bitcoin-style brainteaser-y questions and I just posted it on Reddit’s /r/bitcoin and Bitcoin Talk and I said, “If you get a perfect score, you get an interview for remote customer support.”

And we got like 250 people to take this test. Skip ahead maybe four months. I have 43 people reporting to me in a distributed team.

Craig : Whoa.

Olaf : This team covers merchant integrations, API support, anti-fraud investigations, compliance investigations, and did customer support. We now have all of these teams at Coinbase. They mostly came from this one Bitcoin SAT. It was so successful that I posted it a second time at some point and got a new round of candidates.

It was a globally distributed team. The first person I hired was in New Caledonia. It’s weird how these things work. Skip ahead two years, he works at Coinbase in San Francisco and is the director of customer support. He’s an amazing guy. He started remote and I remember thinking when we had our first talk – he had a master’s in computer science from George Washington University – and I was like, “Why do you wanna do customer support?”

And he said, “I’m in New Caledonia. This is the best job I could hope for and I love Bitcoin.” And I was like, “Well, you’re hired.”

And that was when I realized that the remote structure was actually going to work really well. There were hard things about it, but I now feel very confident running remote teams. This was when we were using HipChat–before Slack. Then Slack came out and that helped a lot. And then we had Google Hangouts. Basically the tooling was good enough. Like Google Docs where we can all edit something. The tooling really was good enough, just at that moment. I think if were to try to do this distributed team two or three years before, it would’ve fallen on its face.

Craig : So you were managing support but then you eventually ran risk, right? How does that happen?

Olaf : Yup. So I was kind of managing what was really like the whole operational part of the company and it was really burning me out. This was a year and half of 12-hour days without any vacations. I took Sundays off. We scaled to probably 30 or 40 people in San Francisco before I hired a Director of Support and became the Head of Risk.

So as Head of Risk the main things I focused on were account security and fraud prevention. It wasn’t like infrastructure security around preventing hackers. It’s user-facing, like they enter their password on a phishing site.

Basically with security there are two angles: We can get your coins stolen or you can get your coins stolen.

Craig : [Laughter] Right.

Olaf : [Laughter] So yeah, I was responsible for the latter and anti-fraud, i.e. people buying bitcoin with stolen identities. While I was running support I had a huge part in handling all that stuff. And when fraud had gotten bad in early 2013, I designed the Risk Queue that would review people that we thought were stolen identities. At one point I would review every single buy on the website–one by one.

Craig : Whoa.

Olaf : These are things that absolutely don’t scale, but you can build it in one day and start working on it that day. So Brian built it and I would review every single buy. As a result I started to get an incredible eye for stolen identities. Like I had a sixth sense for whether an account was a stolen identity or not.

Craig : Can you explain that a little bit? What are you looking for?

Olaf : Ok, so there are a couple tiers of scammer. Let’s pretend you’re a unsophisticated scammer. You sign up. The email you use is [email protected] and the name you use is Laura Johnson. Then the bank account you use is Alexander Smith. Obviously something’s going on there. So big name mismatches are the easiest to spot.

Then there are patterns. So, for example, scammers would buy dumps–some guy will a hack a site, he’ll get a bunch of bank account numbers and then he’ll use them all. And those dumps will often share certain traits. For example, I’d suddenly see like 20 SunTrust bank accounts get added in 20 minutes and they all share certain formatting rules or the email domain is the same, or something like that. So again, it’s basically pattern recognition.

But then it gets way more complicated because for sophisticated scammers, their entire job hinges on me looking at something and saying, “that’s legit.”

And it can mean massive payouts for them. Our limits at that time were 50 bitcoin a day. So, if you could sneak past me, you could buy 50 bitcoin every day until the real account holder called their bank and said, “I’m seeing all these crazy charges.”

But yeah, I learned a lot very quickly. I learned a lot about traditional payment mechanisms. Before I knew a lot about bitcoin. Now I know a lot about credit cards. And ACH. And bank wires. And all that stuff.

Craig : Yeah, it sounds like you’ve dug in. I assume not everyone who works at Coinbase now has the same degree of knowledge. How do you scale understanding at a company that is based around something inherently technical?

Olaf : In the early days, everyone was a cryptocurrency fanatic. The first two engineering hires were these absolutely brilliant people who basically came to Coinbase because they wanted to work on cryptocurrency. And what’s interesting is a lot of our anti-fraud people are also super into Bitcoin. They’re not people who worked anti-fraud at Stripe. They’re Bitcoin people first.

So yeah, we’d sort of filter for smart people that were passionate about Bitcoin. It’s my opinion that if you’re smart you can learn a new skill and all the details. But passion and innate interest cannot really be learned. We tended to hire people who said, “I love this company. I don’t quite have the experience.” Versus people that said, “I have the experience, but I’m looking at four other places and maybe I’ll pick Coinbase.”

My belief is that the inexperienced, interested person will outperform the experienced, uninterested person over time.

That said, when we started scaling we did have to start trading between interest in Bitcoin and domain experience. The person who runs Compliance, for example, can’t just be winging it.

Craig : What was it that made you want to join Coinbase?

Olaf : Before I was gonna apply, I read all about the founders. There were a bunch of competitors at the time. The massive market share was MtGox, which ended in tragedy, as you may know. And then like there were bunch of other companies that were bigger. BitInstant, Tradehill, these are all defunct. Every single one of them is dead now. But at the time, Coinbase was like the new little company.

Craig : Okay, so the underlying question is how do you vet founders in a new field?

Olaf : Yeah. I have pretty strong feelings on that. I’d say meet them and make sure 100% that you like them, that you could work for them, and that you will run the whole marathon with them. Running a company and scaling a startup is so much stress, so much work. And they’re gonna be sitting next to you the whole time

If you don’t feel like they’re in it 110% and that you can work with them and be friends with them, it’s not gonna work. Especially in a very micro team. I mean, once a company is 40 people, that’s still like a startup but the founder matters for you personally a little less. It does for the company’s success but not for you personally. But if you’re joining like a sub-10-person startup you really need to make sure that the founder is gonna drive this all the way. This needs be a grand slam.

So much of it is about personality and drive. Even if you’re technically brilliant, there are these dark times. And dark like bad things are happening. There’s always gonna be bad events.

You have to ask, are they gonna focus in and just move forward, or are they gonna give up? And it doesn’t matter if they’re technically competent if they’re in the latter category. They could be the best person in the world at this but if at the end of the day they don’t have the drive and spirit to make this happen, it doesn’t matter. So to me the technical competency of course is vital. But if you met someone and said, “Wow, that guy is the number one expert in the world at this,” but you felt like he’s kind of flakey. Pass. Always pass.

With Brian and Fred, they’re two of the smartest, most focused and driven people I have ever met. And I knew that after the interview. I was like, “These guys are really not fucking around.” Seriously, it really made me wanna work there.

Craig : So to your point of the bad things always happening, what were the bad things that happened?

Olaf : Oh, man. I think in 2013 our user base increased 100x. And the price of bitcoin went up 100x. Our volumes went up I think even more than 100x. You know when people talk about like rapid aggressive scaling? That’s exactly what it was and a tiny number of us were scaling all of it. At the beginning of that year it was two people. At the end of that year, just eight.

Craig : Wow.

Olaf : Brian and Fred are very careful about hiring. They only hire people that they truly think are superstars. At Coinbase one thing that gets said a lot is, “On a candidate if you’re not a ‘hell yes’, you’re a ‘no’.” If you’re like, “I like them. I think they’re smart. I think they’re great.” That’s a “no.”

You really have to fight to keep that up. You have to feel like if this person does not get hired, we’re crazy. That’s how you have to feel for someone to get hired at Coinbase.

And that early team was really unique individuals. Like, it was the perfect puzzle pieces. But anyway, the scaling during that time was brutal. It was absolutely brutal. And we had bugs that were really bad.

Here’s the thing, it’s not like having bugs on Twitter where maybe something gets retweeted wrong. When you have a bug on Coinbase, balances are incorrect in what are essentially bank accounts. And transactions that are time sensitive aren’t getting sent out. The stakes are way higher yet you’re still just five people in a room making the whole thing.

One time the ACH file we use with banks got duplicated. That’s means that if you bought $100 of Bitcoin we duplicated the transaction so you’re buying $200 of Bitcoin. When something like that happened I would get a thousand emails in 20 minutes because these are bank accounts and people definitely notice that stuff.

The one thing that’s so lucky is we never had an incident where someone gained access to our infrastructure and pulled out Bitcoin from the hot wallet. That was just the blessing. I think even Brian would probably tell you that there were times in Coinbase’s history that were sort of coin flips. But we survived them. Other companies had incidents like that and had to shut down. We caught things fast enough.

Craig : That’s funny. It’s exactly the same thing Aston said about Dropbox. Basically, “Shit went wrong all the time but the one thing we never did was lose a ton of files.”

Olaf : Exactly. This is exactly Coinbase’s story. In those early days everything went wrong except the one thing that couldn’t go wrong.

Craig : [Laughter] Exactly. So at what point were you like, “Okay. I’m ready to do something else?”

Olaf : Yeah. So I basically saw what, for me, has been the biggest trend in the space I’ve ever seen, and I’ve been in this heads down for five years. People are doing this new behavior where they’re actually raising capital and issuing what is essentially network ownership of their network on the blockchain. So these are like bits of equity in peer-to-peer networks that are built on the blockchain.

A crude example here is imagine if an early user of Facebook gets a thousand shares of Facebook. Now, instead of just normal network effects, there’s also monetary incentive network effects built into this protocol. And these new types of protocols are built on new blockchains or as subtokens of existing blockchains. The opportunity for me was too big to pass up. The trend was too strong. Plus I needed a new adventure. So I left to start Polychain.

And it’s only been eight weeks but Polychain has seen a lot of interest because this trend is really strong. I think that over the next year, there’s gonna be amazing opportunities here. The alternative thing that I could’ve started is a venture fund that invests in companies built on the protocols.

But in this new model, there’s really no place for traditional VCs because the protocol tokens themselves are the issuance of ownership. Not shares on a piece of paper. And as the company wants to raise their Series A, their Series B, their Series C, all that is them holding say 5%, 10% of the protocol tokens and those going up in value as their network becomes more valuable. And then they can sell tokens and become diluted to get liquid cash. It works very well. It’s a lot of similar mechanics to venture capital fundraising, but they can do it all with this native protocol units and crowdfunding, and there’s just no place for paper shares or VCs.

So, instead of betting in companies built on protocol, I’m actually buying units of the protocol. I’m buying scarce blockchain tokens and creating a portfolio of those tokens. I’m basically buying ownership in all of these new 2.0 peer-to-peer protocols.

Craig : That’s wild.

Olaf : Yeah, that’s why Polychain is a hedge fund instead of a venture fund. Because I’m holding solely protocol tokens. To a normal person what I’m doing is extremely esoteric.

Craig : [Laughter] Uh, yes.

Olaf : It absolutely is. That said a lot of smart people in Silicon Valley think it’s on that edge where this is going to grow substantially over the next five years.

Craig : You’re definitely in the right place. Ok, random question. Aside from the Bitcoin readings you recommended, what books do you recommend?

Olaf : I have a couple that come to mind. So I love David Foster Wallace and Infinite Jest is probably my favorite book. His short stories are also amazing.

Another book that comes to mind is House of Leaves. The premise is crazy. So the actual book is a manuscript written by an old man. With annotations by a narrator who has found and reconstructed this book. With annotations by an omnipotent editor. Who is finding the annotations of the person who reconstructed this old man’s book.

Craig : Oh my god.

Olaf : And now this is where it gets even crazier. The old man’s book is a analysis of a movie that doesn’t exist.

Craig : [Laughter]

Olaf : And the narrator who’s annotating and reconstructing this old man’s book is being driven crazy because there’s so much detail and he can’t find this movie. And it like actually doesn’t appear to exist. And the old man, all his sources are fake articles and things. It gets really weird but it’s much more of a page turner than David Foster Wallace.

Anyway, I’d recommend both because they’re super long and once you get into them, they completely consume your brain. They’re my favorite kind of books.

Craig : Right on. Ok, let’s end there. Thanks for your time.

Olaf : Sure thing.

Olaf’s Suggested Reading Blood Meridian by Cormac McCarthy – Probably my other favorite book along with Infinite Jest. Programming and Metaprogramming in the Human Biocomputer by Dr. John Lilly Journey to Ixtlan by Carlos Castaneda Steppenwolf by Herman Hesse

Here are three posts that explain the Polychain thesis well: • App Coins and the dawn of the Decentralized Business Model • The Golden Age Of Open Protocols • Crypto Tokens and the Coming Age of Protocol Innovation

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craigrcannon · 3 years

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Employee #1: Warby Parker

A conversation with Mara Castro, Warby Parker’s first employee.

Employee #1 is a series of interviews focused on sharing the often untold stories of early employees at tech companies.

Mara Castro was the first employee at Warby Parker. She currently is the Director of Customer Experience.

Discussed: Working at a Nonprofit, Finding the Job Posting, Interviewing with the Founders, Starting Part-Time, Figuring Out Operations, Moving to New York, Going into Retail, Building the Brand, and Learning to Manage People.

Craig: So the easiest way to start is just to explain what you were doing before and go from there.

Mara: Sure. So I graduated from Texas A&M then went back to Brazil and was working with a former Formula One racecar driver, helping him set up his nonprofit. At that point I was pretty dead set on wanting to build a nonprofit that was going to do good for the world. So I started in Brazil but knew that I did want to come back to the US.

I was originally from Brazil but my father worked in oil so we lived around the world – UAE, Libya, Singapore, Venezuela – then I ended up moving back to Philly for business school and from there started working at a nonprofit called the Food Trust. So I got a lot of exposure to how nonprofits work in the US.

I loved the work that I was doing but felt like I wanted to do something more with a little bit more of a business background. I felt like I could add more value to the world instead of spending so much time fundraising and policy writing and that kind of stuff. As I was trying to look for something different, Jeff Raider, one of the co-founders of Warby Parker, put out a job description looking for an operations manager.

At that point the four founders were still in business school. It was November of 2009. Warby Parker was really just an idea. They didn’t have a website or anything but they knew that they wanted help from someone to set up customer service and operations in general.

Craig: Where was the job posting? Was it on Craigslist?

Mara: I think they had posted it in quite a few places but because my ex went to Wharton business school, it had been shared there to all of the students and he shared it with me.

Craig: Gotcha. Okay, so you email him and then you meet up. How does that go?

Mara: It was great. Jeff is one of those guys that’s just incredibly charismatic, super fun, really smart. We talked about everything that I had done before, what I was hoping to do in the future and it was just very, very natural–just casual conversation about what my experience was and then what the idea of Warby Parker was at that time.

Craig: And was the idea the same as it is now?

Mara: Yes, that’s one of the special things about Warby Parker is that from day one, they really spent a ton of time thinking through what the pillars were for the brand. They really wanted this company to be a lifestyle brand that was going to be here for the next hundred years. They wanted it to really revolutionize eyewear industry and they wanted to prove that for-profits could do good in the world. Those three main pillars are still the ones that really reign the company to this day.

Craig: Did he convince you with that in the beginning?

Mara: The pitch was really just that they’re four really smart friends with this great idea to sell glasses online, so many other companies were selling products online that never had before –you shouldn’t have to pay the price of an iPhone for glasses.

I started wearing glasses when I was maybe 12 years old and so I knew how expensive glasses were and how limited the options were. It just seemed to make a lot of sense plus, with my background of wanting to work somewhere that was going to do good in the world, it was just awesome to see how it wasn’t a marketing ploy. It was part of the brand and who they really wanted to be from day one.

Neil [Blumenthal], one of our co-founders (and current co-CEOs) was one of the first employees at Vision Spring before he went to business school and he had really set up the whole program and how that nonprofit worked. And we were just going to partner with them so that we could do work in a way that they knew how to do it best and we were just going to help them and achieve that in the best way. It just really felt very authentic, very natural so at that point, I was just like, “Okay, you guys need to hire me.”

Craig: [Laughter] Okay, so what happens next?

Mara: We were still just talking about it because they didn’t even have the glasses yet. They didn’t have a website. It was really just an idea at that point but they knew that they wanted help soon thereafter. And so we continued talking. And I think they received the glasses maybe at the end of December or January of 2009. They started doing some trunk shows with their friends and I came to a couple of them, got to see the glasses, got to meet the other co-founders, and actually did an interview call with Dave Gilboa who is currently my boss. They decided to launch in the beginning of February and I started February 1, 2010.

Craig: Did you move to NY at that point?

Mara: No. So they were still in school in Philly and school was going to go through June. So on February 1st, we were launching but not necessarily the website. It was more of launching the fulfillment process. So we were still doing trunk shows with their friends and I was helping process orders with our tech consultant, set up the whole process through NetSuite which is an ERP [Enterprise Resource Planning] that we were using at the time, and really just help set up the foundation. Then we fully launched on February 15th with the website and features in GQ and Vogue

For the first two weeks in February I was part-time, 15 hours a week, just helping with anything that came up. The launch of the website kind of kicked us into crazy mode. And that’s when my role turned into a hundred hours a week and basically that’s what it’s been since then.

From that point, it was just like, “Okay, this is really going to work. Let’s figure out how to make this work in the best way. I think it was April when we decided we were going to move to New York and started prepping for that move.

Craig: And so were you handling fulfillment in the beginning?

Mara: I was helping with a little bit of everything, right. At first it was just me but then we quickly hired four other people and also I helped train all of the founders’ families everyone we knew could help, because it got really crazy really fast. I was in charge of setting up all of the training materials, managing all of the folks, setting up the culture, working with inventory, supply chain and then helped with all of the talent on HR, setting up all of the assistants as well and office management. It was a startup, right? You do what’s needed.

Craig: Right, exactly. The job description doesn’t exactly match the job. So had you guys raised money at that point?

Mara: No. So it was all from the four founders’ savings at that point.

Craig: Ok. How many styles did you launch with?

Mara: That’s a good question. It was twenty-seven plus our monocle. At that time, a few very big, bold styles which were in at the moment and then a few toned-down frames. And then, of course, the monocle.

Craig: [Laughter] I didn’t even know that was a thing. Do people actually buy it?

Mara: We do get a lot of orders for groomsmen. But, I mean, it’s not our bestseller. [Laughter]

Craig: [Laughter] I figured. Ok, so you moved to New York and then what? Had you lived in New York before?

Mara: I had not, no. I feel like everybody has a dream of living in New York so it was very exciting to move here. So we moved to New York. We worked out of Neil’s wife’s back office. She had a jewelry line that she ran out of the garment district. So it was this tiny inventory room which became one of our first showrooms. Our first showroom was actually Neil’s apartment. [Laughter]

So we moved to her back office and then from there, we moved in August to our first real office in Union Square. At that point I think we had maybe 10 employees or so on our team.

Craig: At that time were you able to get a sense if it would last or if it was just this crazy startup thing that might implode?

Mara: No, we were definitely filling a need in the market for sure. Just from customer conversations I could tell it was a thing. We always wanted to make sure that every employee (and our founders) were interacting with customers. We had phone and email initially and we responded to each and every person individually even when we got the crazy spike in March. We were all working from 7:00 to 4:00 a.m. really responding to every customer. People would reply to the 4:00 a.m. emails being like, “I get it. You’re a startup. That’s totally fine. Take your time, but would love your glasses. This is amazing. This is such a great idea. Don’t know why nobody has tried this before.”

So it definitely felt like we were filling a need in the market and that we just had to figure out the kinks of growing pains to make sure that we had enough inventory for everyone.

Craig: I imagine the actual manufacturing process is pretty time intensive–learning how it all works and figuring it all out, especially in the beginning.

Mara: Yeah, definitely. So Neil did have some experience in manufacturing glasses through Vision Spring, the nonprofit where he had worked. He knew some of it.

The way our manufacturing process works is we get the materials from either Italy or Japan. We manufacture the glasses in China and then we ship them to the US. Now we have six labs across the US. They then cut each lens specifically to each customer and then ship those glasses, the completed glasses, to the customer directly from our labs.

It is a pretty complicated process and, honestly, none of us had worked in retail before, including the four founders. Setting up the technology that was necessary to track all of that inventory, to manage our customer orders in the best way, wasn’t easy. Do you know about the Home Try-On?

Craig: Yeah, but you should explain it anyway.

Mara: Cool. So the Home Try-On program, the way it works is you select five pairs and we ship them to you to try on and then you return them and can purchase your favorite on the site. So the first lab that we ever partnered with was in New York and they used to do not only do fulfillment of the glasses but our Home Try-On program as well. The way that it would work is that they would send out the Home Try-On glasses from their lab and then everything would get returned to Neil’s apartment in Philly.

Initially, it was just me going through everything and double-checking, making sure everything was good, cleaning everything and then putting it all in boxes and just carrying it over to a UPS to send it over to our lab so that they could start the whole process again.

Craig: [Laughter] That’s insane.

Mara: [Laughter] Yeah, it was pretty insane.

Craig: Were there other bottlenecks? How established were the labs and the manufacturers that you were working with?

Mara: The way that labs usually work is that they partner with an optician at a company like LensCrafters and they fulfill the glasses but then send it to that storefront who then dispenses the glasses in person to a customer. Our process was completely new to them. They had never gone through the fulfillment process of quality checking everything and making sure it was the way we wanted it to before sending it to the customer directly. We were definitely establishing that through our company and teaching all of our labs how to do this.

Craig: Were you ever involved in those conversations? Convincing the lab, “Hey, now you do this, too.”

Mara: So the lucky thing about that is there was one person at the first lab that we partnered with that really believed in our idea. It took some convincing with him but then he was really the one that was able to get all of his lab on board. Of course, it took us a lot of work to establish all of the partnerships to set up all the processes in a way we wanted.

Craig: Cool. So back to the story, you moved to New York and things are ramping up. What happens after the summer? How does it go?

Mara: I mean, so we went through the period of just crazy explosive growth in February, March, April. Then we were moving to New York and, of course, in any startup in the beginning you have step function growth, right. With us, we didn’t do any marketing in that first full year. We really grew most through word of mouth, We were really just focused on “How can we learn as much as we can from the experiences that we are providing to our customers? What can we be doing differently?” And that’s what we were really focusing on: so building all of the technology, how to build out and manage all of our inventory, how to make sure that we were running the company in the best way. We were hiring a few more people at that point. We hired our first tech employee.

Craig: Wait, what?

Mara: Yeah, so we were only working with a consultant until the end of 2010.

Craig: [Laughter] So the whole first year was on some consultant guy’s website? That’s amazing.

Mara: Yeah, so it was on NetSuite. Our contact there made it all work. But at that point we were still answering all of our phone calls through Google Voice to our cell phones. Everybody was in one inbox in Gmail.

Craig: [Laughter]

Mara: It was pretty insane. You know the labels that you use in Gmail? We would use labels with our names. Just put a label and say, “Okay. Royce, Brian, Lee, Colleen, Mara.” And you would just assign the top 10, middle 10, things like that. And we would just make it work.

Craig: And so now are you becoming more of a manager?

Mara: In March of 2010, I was already a manager but still very much a doer because I was managing the operations team but still doing office management and talent and inventory and all of that kind of stuff as well. I think it wasn’t until much later on that I was fully able to hire for all of those different roles. It was very much just managing all of our folks within the operations team to make sure that we were just fulfilling orders and managing our customer’s experiences as best as possible.

Craig: You’ve been there for six years at this point. How’s your role changed?

Mara: A lot. I mean, it’s been an awesome journey, lots of learnings along the way. I think what’s been most exciting about Warby Parker is that we continue to grow at this crazy pace and we’re just always going through growing pains and trying to figure out what’s the next big step and how do you deal with that next big step. Going from startup mode and being very reactive to everything that gets thrown your way because you don’t really know when to expect that next big push, that next big craze. It’s been awesome to be able to have more processes in place, better systems that we can count on. We’re not just on one inbox anymore and we have a real phone system with lots of hard data which is awesome.

Craig: Okay, and how many people are you now?

Mara: So companywide, we’re over 900 people and that includes our employees from our 40 retail stores that we now have.

We started thinking we were only going to sell online but then through lots of different experiments with the showrooms we found that our customers did really like getting access to all of the glasses and getting that assistance in person and that we could also learn a lot from those interactions in person with those customers. So we started experimenting with a few stores. We launched our first store in 2013 and then have been expanding since then.

Craig: So what did you learn from customers trying on in a store vs the Home Try-On data?

Mara: First, observing them and what glasses they’re gravitating towards, how they shop. So usually, people in the past have gone through face shape but a lot of people don’t even know what their face shape is. It is a little hard for people to understand that. So do you organize by bolder and more classics? By different color styles? So we were able to see how customers interacted with those glasses and how we were setting them up in person allowed us to further understand how to couple those glasses together and how to talk about them, how to create better stories around those types of glasses.

Craig: Do you have thoughts on what your personal future ambitions are?

Mara: To be honest, I never thought I would stick around at a company for more than two years, right? Everybody jumps around every two years, nowadays especially. So it’s been six and a half years and I continue loving it as much as I did in day one. It’s just a combination of continued learning and growing and the amazing culture. That just keeps me coming back for more and I know that we do have a lot of really exciting plans for the future (we’re opening our own lab in upstate New York soon) plus this continued expansion into retail. We opened our first store in Canada this year.

There’s just so much more that we can do. Our brand awareness in New York, in California, is pretty high but throughout the rest of the country and potentially rest of the world, there’s a huge opportunity there. It really feels like we’re still just getting started. And there are so many more opportunities for the company and so many more opportunities for me to continue to learn and develop myself and continue to add value to the growing organization. So that keeps me around.

Craig: What does that mean? How do you want to continue to develop yourself?

Mara: I mean… I have about a 150 people on my team. I’ve never managed a 150 people before. Actually, Warby Parker was the first experience that I had managing anyone. So continuing to grow my team and scale my team, making sure that we’re investing in our employees in the best way while we continue to learn how to scale the organization in the best way, and the way that I do that is making sure that I’m a better leader every day.

I just continue to expose myself to other companies that have gone through this growth before, have done what we have done before, continue to read a lot of books, just developing myself in any way possible.

Craig: Most people in the world have not managed 150 people. And, I mean, you’re easy to have a conversation with but I imagine there are other things that aren’t your strong suit, right? So what did you have to learn along the way?

Mara: Everything.

Craig: [Laughter] Okay. How about–what was counterintuitive for you?

Mara: I don’t know. Let’s see. That’s a really good question. So I am very much a planner and I like to be very organized in everything that I do. I think in the beginning it was a lot more stressful to not be able to have everything planned out. You just have to roll with the punches and you just have to figure things out as they get thrown at you. And so eventually you then get used to that culture and then you have to break out of that and go into process mode and make sure that you have really great processes in place so everybody in the organization is empowered to take action in a way that’s consistent throughout the entire organization.

A lot of what I learned is around lean, Six Sigma thinking and how to implement it into daily practices. You have to realize that everything isn’t going to be exactly the way you want it and how you would do it. But if you are able to have enough processes in place and enough structure in place with enough guiding posts like strategic objectives and milestone metrics and core values, then you empower everyone to take action, to make decisions and learn on their own. Then you can then help them learn through the great decisions or bad ones and, of course, correct from there.

That’s been more of the learning challenge. As you grow into a leader and, of course, as the team continues to grow, making sure that those ideas seep through to all of the layers of the organization.

Craig: Yeah, each person on a hundred-person team is not as effective or easy to evaluate as each person on a ten person team, right? So you’re not 10X more productive and managing that process does make a lot of sense. As your ambitions scale, do you feel that you have founder-type ambitions in you at some point?

Mara: Potentially? I mean, I’ve learned so much here and I feel like if I did want to, that I would be able to start a company myself. Nothing planned for the moment but potentially, one day.

Craig: Anyway, so the founders were all dudes, right?

Mara: Yep.

Craig: So you were obviously the first female hire. What’s that dynamic like?

Mara: I don’t know. I think it’s just hard to really put myself in those shoes just because in every experience I have had even before Warby, I haven’t had that much of an issue with being the only woman in the workplace and having to just work that much harder to speak up or to assert myself or something like that. Once we moved to New York, the two other guys became board members and stepped out of day to day operations and it was really only the two co-CEOs that stayed on board. And so maybe that’s why it didn’t feel very daunting.

Craig: Interesting. Ok, let’s move on then. What books are you reading right now? Are you a business book person?

Mara: Yes, most recently I’ve been reading a couple of HBRs business books which are compilations of great articles – HBR’s 10 Must Reads on Managing Yourself and HBR’s 10 Must Reads on Managing People – and my personal favorite which I’m having my entire team read right now is How to Win Friends and Influence People.

Craig: Cool. So we usually ask people about lessons learned. Maybe you could break that up into first employee learnings and general learnings?

Mara: Sure. So learnings from early days, first. I think that the most successful people that I’ve seen in startup settings are people that have no ego. They just know that shit needs to get done. You really just need to put your head down and figure things out and just make it work. So hauling boxes to UPS or cleaning glasses or when we got a batch of bad glasses, going through them and realizing that they were all bad and counting them up and then sending them back. So you just need to make the time and you just need to do it and you need to figure out how to do it in the best way. But working at a startup is really hard and it’s more than a hundred hours a week. It’s all consuming and you just have to be ready for it.

I think that those are sort of just my general learnings from startup life. It’s not for everyone. And I guess in terms of growing into the position that I am today and moving forward, I think part of the learnings that I’ve taken away from the last six and a half years in terms of hiring for your team, is that you need to focus more on the behaviors that you’re hiring for.

We really believe in hiring passionate, curious, proactive people rather than people that have the specific skills or experience that maybe you’re hoping to get because in the end, if the person doesn’t fit into at least those three behaviors at Warby Parker, they’re just not going to be successful. And we are a company that moves quickly and we want to be able to depend on everyone to be a problem solver and to think in a proactive manner. You can always teach the other things. I can always give somebody exposure to going to a conference or sitting down with somebody from a different company that has done these specific roles before. But you really do need to hire for behaviors and if you make a mistake, it’s better to call it quits sooner rather than later.

Craig: And what about hiring people that aren’t like you?

Mara: It’s also a very much of a learning process and you have to learn how to manage to everyone’s personality. You have to understand what you’re hiring that person for and then how to manage them in the best way to use those skills that you really hired them for and then supplement what they don’t have.

Craig: Last question. Would you consider yourself a good manipulator of people?

Mara: That is a really bad way of putting it.

Craig: [Laughter]

Mara: You mean like influencing people?

Craig: No. I mean, you can call it whatever you want but I think “manipulation” is unfairly cast in a negative light and is different. I think it’s actually one of the strongest skill sets someone can have. I think “influence” might work toward a similar output but the input is different . Anyway, I look around and there are certain people that are obviously good at it and certain people that aren’t great and certain people where you’re like, “I don’t know if you’re really good or terrible.”

Mara: So, honestly, I’ve learned how to be better in the last six years. I know initially the whole political games in an organization killed me. It really killed me to think you had to speak in a way or you had to manipulate people to get your job done. But through the advice of a colleague I read “How to Win Friends and Influence People” by Dale Carnegie and learned that it’s not necessarily about manipulating people to get your job done, but how to influence others in a way that everyone wins in the end.

It’s hard, but a lot of practice has helped me get better. I think I can still get better, but I’ve definitely made a lot of strides in the last few years. I feel like it’s something that people just have to continue working on…

Craig: Well, I mean, perhaps this is obvious but these things, these interviews, are like therapy sessions for me as I’m figuring shit out.

Mara: [Laughter]

Craig: [Laughter] But really, that challenge of figuring out how steer a group of people that you may not completely vibe with is fascinating to me. Anyway, this has been super fun. Thanks so much for your time.

Mara: This was a lot of fun.

Craig: Totally. Thanks Mara!

0 notes

craigrcannon · 3 years

Text

Employee #1: Kickstarter

Employee #1 is a series of interviews focused on sharing the often untold stories of early employees at tech companies.

Cassie Marketos was the first employee at Kickstarter.

Discussed: Meeting Yancey, Setting Kickstarter’s Tone Through Community Management, Choosing Projects to Feature, Learning How To Manage Up, Moving On, Book Recommendations.

You can subscribe to YC’s newsletter to receive future conversations.

Craig: So how about we start with you talking about your background before Kickstarter.

Cassie: Yeah. There isn’t much of one to be honest. [Laughter]. I went to school in California at UC Santa Cruz. I worked at a radio station and studied literature. Then I pretty much threw a dart at a dartboard to decide where I was going to go after college and ended up in New York.

I started working for this music company managing a thing called White Label for them and selling records. And I worked for a concert company called Bowery Presents at night. So I’d go from daytime office to night time working the door at shows all over the city. It was really fun.

In my first month in New York in 2008 I was at a No Age and Health show at Market Hotel. I was with a guy I had worked with who quit and had gone to work at Emusic. Also at the show was his new boss, Yancey [Strickler]. Me and Yancey really got along. We stood in the back of the show and just talked the whole time. Then, two years later, Yancey wrote me an email and was like, “I’m starting this company. Let’s get meet up.” I was like a baby still. I had only worked at this music company and knew nothing about startups or tech… I had no developed sense of anything.

Craig: Had you guys stayed in touch at all?

Cassie: Not really.

Craig: So he emails you and you’re like, “Alright, let’s meet up.” And what’s that conversation?

Cassie: We got dinner at Sweetwater. I had no idea what I was looking for in my next job or what to expect from the conversation. He was laying out behind what they were trying to do, and it was clear that him and Perry [Chen], who I hadn’t yet met, believed really purely in the why of the idea behind Kickstarter. They cared deeply about enabling all types of people to make creative things and put them in the world. I remember being really moved by his sincerity. And I was like, no matter where this thing goes it’s important to me to be around this kind of energy.

Yancey believed in what they wanted to do so purely. A matter of days later I put in my two weeks at my job and started working for Kickstarter. They didn’t have funding yet, I don’t think.

Craig: Was the product the same thing in the beginning?

Cassie: I mean, the fundamentals were all there. You know, you set a goal and a timeframe. And it’s all or nothing. But there weren’t complex creator goals and engagement tools and resources in the beginning. We didn’t yet know what was going to happen or what was going to be needed.

Craig: So what was your function?

Cassie: I was hired as a customer service person, technically. When Kickstarter first launched, there was no clear indication of how you launched a project. You had to be smart enough or curious enough or ambitious enough to write into customer service and be like, “Hey, I want to get my idea up here. How do I do it?.” So I would field all those requests. Some projects we accepted, but some we didn’t.

Craig: Wild. What were the criteria in the beginning?

Cassie: I mean, I’m not gonna say that we had well-formulated criteria. It was intuitive and I want to say “warm,” because that’s the only word I can think of. There was a really supportive enthusiasm coming from us, we were just so into the things that people wanted to try and do. Personally, I really like people and I like interacting with them. So I loved having a job where the bulk of what I had to do was talk to people and help them coax their creative visions into life.

I think part of the early days was figuring out what we meant when we said Kickstarter was for “creative projects.” And, in the beginning, it was certainly easier to take certain kinds of risks. For example, we accepted this woman, Emily Richmond, who wanted to sail around the world. She promised to send backers photos from her journey and we were so into that. It was her creative pursuit.

Later on things evolved and we had to be a little bit more specific in our parameters to accommodate the influx of attention. With projects like that it became a challenge to figure out where they belonged on the spectrum of creative work.

Craig: And so how many projects were coming through a month?

Cassie: The product evolved and the process for applying for projects evolved as the influx got greater. It’s been such a long time it’s really hard to say, but I just remember that when it hit…it hit hard and there were not that many of us to deal with it all. Actually, my old coworker, Cindy Au, posted this old video of us way, way after hours in the Kickstarter office being so goofy and dancing to oldies in our chairs and rolling around the office. I know we were there because we were backed up approving projects and talking to project creators.

https://youtu.be/ur_4NE4ROt0

Craig: And so what was the point where it actually hit, where it started getting traction?

Cassie: I just remember a before and an after. I remember that Yancey and I did the Renegade Craft Fair, which is this really DIY Brooklyn event. We had a booth and Yancey was there and we were still so small I remember people being like, “What’s Kickstarter?” and I would take a deep breath and get ready to tell them all about it, and then suddenly at some point like a month later I just remember not having to ever explain to anyone what Kickstarter was ever again. I would be like, “I work for Kickstarter,” and they would already know about it.

Honestly, I think it was a combination of well-designed product and fortuitous timing. We were just coming out of a crazy financial crash, people were struggling to figure out how to make their art, and then Kickstarter came along and became a solution.

The traction kind of went project category by project category as these different communities picked up on and figured out how they could best put it to use.

Craig: Were you guys doing any marketing?

Cassie: Not really. We had a press guy who fielded requests, but he was part-time for a long time. Perry and Yancey played it pretty close to the vest. They were very deliberate about the interviews they did grant. They turned down a lot of stuff. I think that really helped contribute to the feeling that Kickstarter was a platform about its users. We did not feel like a “founder first” company.

Perry and Yancey weren’t running any circuits. They weren’t trying to show up at all the conferences. They weren’t trying to network, really. They were very deliberate about what opportunities for promotion they pursued.

Craig: When you met them did it strike you that this was going to work out? Or was it the idea that was just really compelling?

Cassie: You know, what’s embarrassing to admit is that I didn’t actually investigate the idea itself that much. People would tell me, “That’s so smart!” and “That’s so cool”, but it didn’t strike me as this genius thing. The idea itself was so secondary to the type of people I saw that I’d be working for. I was only like 23. I wasn’t looking for a big break. I was just looking for role models and mentorship and the thing that would help me get to the level where I could find “the thing” that I was supposed to be doing

Craig: And so at what point are you working there and you’re like, “Oh man, I work at a startup now?”

Cassie: I didn’t even know what a startup was when I started working there. I think probably when Fred [Benenson] started working there and we rented that loft on the Lower East Side and outfitted it with a whole kitchen and we would make handmade tortillas and stuff. That’s when, in retrospect, I “worked at a startup.”

Craig: And so how long was that before Fred joined?

Cassie: Not that long. Maybe a month or two. Fred didn’t start until we got an office. And I think it was a couple months until we got an office.

Craig: So they hired Fred to do what?

Cassie: I honestly don’t even remember. What I do remember is that Fred was a guy who knew cool people, was good at the internet, and it seemed like a good idea to have him around. That was my impression of his hire — I’m not even sure he got a specific job title right out the gate. I never really had a title in the entire time I worked there.

Craig: So without any title, how did your job shift along the way? Were you always that community person?

Cassie: The scope of the job changed a lot because I was also a good writer and I had good instincts for how communities online functioned, even though I didn’t know that was a thing at the time. I think the joy I took from interacting with people really helped that.

Initially, I was hired to do customer service, which meant accepting projects and doing basic troubleshooting. Then I started writing for our blog. Then the role of accepting projects and working with project creators became more formal. It quickly became a sprawling, unwieldy job that did not really have a title because it fell into so many different camps. Like most first employees at startups, I was just doing a little bit of everything.

Craig: What do you think it is about you that made you good at managing the community?

Cassie: I think I was good at listening to people. I think I genuinely cared about what people had to say, too, which makes people feel heard and — most importantly — it makes them feel understood. Even when you can’t tell somebody what they want to hear, if you make sure they feel understood, you can still make them feel happy and good.

If you give a community a tool to use, they will find their own ways and make their own rules with it. But I think there is always a line. I think rule one of community building is knowing how to respect a community’s right to invent itself, while still being able to quietly guide it from behind.

Craig: Yeah, I kind of wonder how much that role is about being a shepherd-type person. Did you ever have to say, “No, we’re not this or that.”

Cassie: Yeah. I would say a challenge with community — or really anything — is getting people to do something without making them feel like you’re telling them to do it. That’s the challenge I think all digital communities face – finding a way to set a precedent and make people feel empowered to make their own choices, while ensuring they’re making good choices, so everything doesn’t go haywire.

At Kickstarter we worked so closely with all the initial project creators and communicated with them so much and stayed so in touch with them, we had an initial batch of super high quality projects that really demonstrated the best use of the platform. Then the second generation creators coming in and used that initial community as a kind of guidebook and template for project building. And then, over time, the community began to internalize a set of rules and best practices.

The community became self-regulating very fast, but it was because we put that much effort into making sure that the initial projects were really good and really were the best possible use of the product, you know? It took the pressure off of us to tell every creator, “This is what you have to do and how you need to do it.” They were able to find their own way very easily.

Craig: It makes sense but how does it self-regulate when Kickstarter seems to mostly just be about viewing or posting a project?

Cassie: There’s a message box on every project. So you can always get in touch with creators, and what you get is a lot of second gen and third gen creators who are e-mailing people with successful projects and asking for tips. And then slowly creators saw that their experience was a valuable resource, so they started independently talking to people, writing blogs, posting how-to’s, running workshops, etc. The community started helping itself out, very fast.

And most creators have been backers at some point. And at this point, people are backing dozens and dozens of projects. Most people have a really strong sense for what feels good, as a backer, and they aren’t afraid to weigh in about it. Often, even in the early days, we would see project updates getting a lot of feedback from the backer community. And creators would be very responsive and receptive to that feedback. We’d see whole projects change course, you know?

Craig: Do you remember any instances where the community changed the course of the project?

Cassie: I remember there was a videogame where they were trying to make it and they blew through all their money in development and didn’t end up with a product they liked. They were like, “This is where we’re at. We are not happy with the product. We need to do this.” And people stepped out of the backer community and came on as developers and designers and gaming people, and they worked together to try to finish this game so there would be a final product.

A more common example is when somebody wants to self-publish a book and the project ends up being really successful. Then they end up with a book deal they weren’t expecting and all of a sudden the backer community is back-burnered while the author is like, “Now I have to release this book through this company first. They’re going to handle pre-sale and stuff like that.” And the backer community is like, “We should get first access because we supported you first. We are the reason you are so successful.” That can cause issues.

Craig: What did you as the voice of Kickstarter when someone got in too deep?

Cassie: Oh. Well, I think in the beginning the idea of a Kickstarter project exceeding its goal 10 times over and making a million bucks was like, “Ha! That will never happen.” But then once it did start to happen and once we saw the very real trouble that people would get into, that’s when we doubled down on creator resources. And that’s when things like reward caps began to appear in the product.

Craig: Gotcha. Let’s talk about the hardware product statement. Why did it happen?

Cassie: There were just a ton of product projects on the site all of a sudden and the site started getting a reputation in the press for being a place to launch a product, which was not our core mission at all. We were trying to figure out how to walk the line between not shutting down a thriving community and protecting the heart of a place that was supposed to be about little art projects and theater projects and music and all these creative things. We didn’t want everyone to just be flooding Kickstarter coming to launch their product. So, I think that’s what it was.

There was also, of course, a worry with these massive projects that make $1 million and promise a product–where’s the line of accountability for delivering?

On one hand, we were a platform connecting creators and backers and it’s on the backer to practice skepticism and look into something and not just click a button. On the other hand, there are lots of ways for us as people who are creating the product to enable and empower transparency and require creators to provide comprehensive information to their potential backers.

Craig: Especially when there was a sort of proliferation of Kickstarter-like sites. Was the product decision also about differentiation?

Cassie: I’m sure that came into the conversations, but I think the real driving goal was, “How do we maintain this potentially fragile artistic community? How do we not let these hardware products crowd ’em out, but also how do we respect those projects, too?” At the end of the day if a person is like “Me making this cool gadget is my creative endeavor,” is it really our job to say, “No, it’s not,” you know? That’s really hard.

Craig: Totally. Especially when you’re letting the community self-guide and it self-guides towards hardware.

Cassie: Yeah. I think anybody who’s running a digital platform will tell you it can be really hard to reconcile your original intentions with what your community uses your product for. When you make a thing and put it in the world, you do cede a little bit of control. But I also think, right now, the entire world is struggling to negotiate a new boundary line on accountability. It used to be considered very “cool” to let communities self-govern — but now people are (hopefully) starting to come around to the fact of that not working. Now, I think the new conversations starting to happen are about how to build morality, civility, and inclusiveness into a product. They’re about how and where to take a stand.

Craig: Were you part of the curation for the newsletter and front page of the site and that kind of stuff?

Cassie: I sent the newsletter for years, yeah.

Craig: How did you navigate picking projects when there are $10 million and $1,500 projects on the site?

Cassie: We always had to be really careful about selecting them. I think the most important thing that makes a good Kickstarter project is not how much money it raises or how much it’s trying to raise. It’s 100% about – and I know this is like a word as old as time in digital community circles – storytelling. Anyone who’s telling their story in a compelling way, no matter what they’re making or how much money they’re raising, if they’re speaking in a way that resonates, that is what matters. That was the intuition that guided me.

I didn’t want to send out a newsletter with four projects that were like $10 million each, because that’s insane. Then all the people getting that newsletter are going to be like, “If I want to make a project on Kickstarter I have to be able to raise $1 million and I can’t do that.” It was looking for the heart in things, really. There would be projects where a group of kids were making a record in their garage and raising like $5,000 and you’d watch their video and it would be technically “bad,” — but it would also be so charming and funny and reflective of the spirit of the project creators. And then maybe the rewards would be really tongue-in-cheek and you’d laugh out loud reading them and that is totally a project we’d put in the newsletter, because it’s about the people.

Craig: As you became bigger you were sort of hit makers, too, for the little guys.

Cassie: Yes, that’s true. We were turning a really powerful spotlight on these projects. We could certainly have the power to put somebody over the line on their funding goal.

Craig: Totally. So as you were at the company longer, were you involved in hiring people?

Cassie: I would say that at a very early stage, I’ll admit this, I was like, “I don’t want to be a manager responsible for people.” So I’d interview people, sure, but I’d never say that I felt like I was responsible for who’d be hired. I really dodged responsibility. I just wanted to hang out with the product and community. I wanted to spend all my time looking at projects, writing about them, getting into them, going to see them in real life, interviewing the people, curating, and I wanted to live and breathe that. I did not want to be thinking about office management.

Craig: So when you left, was your role similar to what it was in the beginning?

Cassie: When I left I was full-time managing projects, basically. My role had been so many things, that just happened to be what I was doing when I left. I went from customer service to being full-time project manager to being editorial manager back to managing projects because we were getting so many and we really needed people doing that. I was just like, “I’ll do it.” My role sort of did not follow the standard ascension that I think a lot of first employees might say. But there are a lot of reasons for that…

Craig: Full stop.

Cassie: I’m happy to talk about that, I just didn’t know if you wanted to.

Craig: [Laughter] Definitely! Go for it.

Cassie: I was not fiending for management and responsibility. In my head Kickstarter was not the thing I was trying to do with my life. I had all these ambitions like, “I’m doing Kickstarter until X time and then my life begins.” As much as I loved it, I was trying to just learn stuff, be immersed, do it. Afterward my life would really begin and it would be about me and the things that I’m meant to do. I did not reach for it there. But also I just hit a lot of roadblocks in terms of the functionality of the company itself.

Craig: What does that mean?

Cassie: I just don’t think there was an understanding of how to manage me. In other words, not having clearly defined goals, not getting feedback on things–all of those things that help somebody thrive in a workplace, I wasn’t getting and I didn’t know to ask for. I was too naïve to know what I needed.

It was kind of a negative feedback loop at one point where it was really frustrating, but I learned so much. Now I feel like every job I’m in I understand how to assess the environment and manage up instead of waiting for people to tell me what to do. I’m now very comfortable saying: “I’m not getting X in this environment” and then working for it. I can do that now and it’s fucking amazing. It opens so many doors. Wait, can I swear or should we cut that out?

Craig: [Laughter] Don’t worry about it, it’s allowed. I think if you did a text analysis I probably have like 90% of the swears and 10% of the words. I’m very efficient.

Cassie: [Laughter] My whole interview is just a series of swear words.

Craig: [Laughter] “I don’t know, she insisted on printing the eggplant emoji 100 times.”

Cassie: [Laughter] Exactly.

Craig: Anyway, if you were to be there again, would you change anything? How would you have applied those learnings?

Cassie: I think about this all the time. If I was to start over at Kickstarter knowing everything I do now, I’d just dominate. I know so much about how not to internalize external structural issues.. In the early days of Kickstarter, just because I didn’t know any better, anything going wrong around me, I internalized as: I’m doing something wrong, I’m a bad person. I think it’s a huge issue with people in the workplace, especially young people, especially young women. Learning not to do that, oh my god, I feel like I can enter work environments so fearlessly now because it’s not gonna destroy me if things are going wrong at the company.

I would come back with the exact same skill set, intuition, enthusiasm, drive, and dedication I had, which were all aspects that made me a really valuable person for the company in the first place, but I would just be able to separate my sense of self from my workplace and my sense of the workplace. I think I’d be able to get what I needed to succeed a lot better.

I think I would be able to better identify a path through the company. And I wouldn’t get tripped up by all the little things that tripped me up.

Craig: Like what?

Cassie: Like being so self-conscious and not knowing how to stand up for myself and not knowing how to identify structural issues. Not being able to identify what’s going wrong in the room and just fix it instead of taking it personally. I was too young, scared, and uncertain, and I would take a lot of things personally that I just didn’t have to.

Craig: Yeah, though a lot of that is unavoidable. Even if someone told you, like on your first day at Kickstarter, a list of things to think about and do, you’d still have to go through stuff to really learn. At least I have to to internalize things.

Cassie: You totally do. You have to live your experience. There are so many books and articles I’ve read that I thought I was understanding and then I just lived my life and I experienced some of the things that were addressed in it and I was like, “Oh my god, I now get this on a level that I did not get before.”

Craig: Yup. Though an active goal for me is to be sensitive enough to hear those ideas and try and make them click early, but it’s really difficult. I have yet to do it super well. Essentially like before you break your leg, listen to the person saying, “You’re gonna break your leg if you do that.”

Cassie: What I feel like I’ve kind of learned is that you can’t predict anything in life. You can only predict that life is unpredictable. All you can do is feel sure of your ability to deal with it. So my goal in life is not to go out and avoid breaking my leg. It’s just to be confident that my leg will heal itself and be okay. I’ve developed a faith in myself to get through things. So I’m less afraid of what might come that’s bad and I’m not avoiding that anymore. I’m just like, I’m going through this and if X or Y happens, I can deal with it because I have thick skin. Does that make sense?

Craig: Yeah. You’re also now just more mature and confident and you believe in yourself. When you said you were self-conscious, what were the things that were going wrong that you internalized? I’m asking because a lot of people that read these are in similar shoes as employees.

Cassie: Yeah. So, if I would write something and send it to somebody for feedback and they wouldn’t get back to me immediately or they would forget, instead of following up I would feel they thought it was bad. But the reality is everyone’s busy. Sometimes you just have to remind people.

Or when somebody’s in a meeting and they snap at me and I’m like, “Oh my god, it’s because they hate me and I’m doing a really bad job and I have to change everything about myself until I end up getting it right.” It’s like, no. Newsflash, no one is thinking about you. That is the truth of busy companies that are growing. No one is thinking about you. Who knows what is going on in someone’s life that they snapped at you? The best way to deal with everything is head-on and straightforward and just talk to people. If someone is consistently shitty with you for a week, for a month, you need to learn how to sit that person down and be like, “Hey, something is going on here. I want to get along with you. We both need to do it in order to do our jobs well. How can I make this better?”

Just be forward and offer to make change. Like 90% of people will respond to that with incredible gratitude because no one has those conversations with them. If you’re on the receiving end of it, it snaps you out of something, for sure. I’ve done that so many times where I’ve learned to get really good at sitting people down and being like, “Hey, what’s up with X?” People respond really well. I think everyone is used to getting in ruts of passive aggressive behavior, and if you address them in a kind, candid way, people want to come around and get along with you most of the time.

Craig: I have two questions then. One is, how does that effect you managing up, and also are there important nuances there for people to think about as a woman in the workplace? Especially in a tech workplace?

Cassie: So I know what I need to do well in a workplace–I need consistent feedback and I need excruciatingly honest feedback. I don’t want people to tell me things in a nice way. I just want them to be honest with me. So I feel like I have to be really forward about setting that precedent with new managers, where I coach them into not being afraid to tell the hard truths by reacting consistently positively when they have to give me hard feedback. People can be very afraid to tell you something they think you don’t want to hear, but what you’re telling somebody when you give them hard, honest feedback is: “I know you’re really good at this, so I know you can do better.” Which is actually very respectful. We’re just so conditioned to think that to be nice is the only way to be good to people.

With hard feedback from managers, my end of the bargain is that I can’t fall apart and take it personally and get emotional when someone says, “You can do better.” I take that as a sign of faith that they think I can do better, which is good.

In terms of being a woman in the workplace I will say that overwhelmingly more so than young men I talk to in workplaces, young women internalize the work environment and think there’s something wrong with them, and shrink and get stressed out. I just see them suffer from that. Every young woman I’ve ever talked to, I just try to break that cycle with them and show them how the issues they’re facing in the workplace aren’t their personal failures, but they’re actual structural issues. I teach them to build a wall between their sense of self and their idea of failure. Failure is such a constant and, like everyone says, you just have to roll with it. I wish there was a class called Failure where we just saw all the places in history where amazing, well-known people totally fucked up.

Craig: Totally. Ok, so then what inspired you to leave? What made the choice?

Cassie: I had hit a ceiling in terms of what I was learning and I got bored, to be totally honest. I felt like I had a lot of things I wanted to do in my life that I had shelved because Kickstarter had started to take off and became this really big thing. It was this whole crazy ride, but it was coming to an end for me, and I was ready to do other things. I just had stopped learning, and I was hungry for other things. I wrote an essay about it, actually.

I remember when I was making the decision it was really hard. I got off work on Rivington and walked all the way up to 87th street on the east side three nights in a row thinking about it before I was like, this is the right decision, and then I quit. It was like asking for a divorce. I’d just been through so much. I think every employee at a startup has been through that. There’s a golden age and then you bottom out a little and you hit the hard parts. I really struggled for a while with Kickstarter and I struggled through those hard parts and I got back on top again and got to a place where I was like, “I feel really good about my work again, I feel really good about my relationships here, I feel like it’s time to go,” and I wanted to go out on top. I didn’t want to quit because I was frustrated and struggling.

Craig: Then did you immediately leave New York?

Cassie: Yes. My mom works for an airline and I fly for free. The next day I was on a plane to Berlin for a job interview at Soundcloud, though it didn’t really make sense to take that gig, at the time. Then I went to Costa Rica and then I went to Europe and then Southeast Asia and I was just gone for about two years. I just left and didn’t come back. I worked remotely for myself.

Craig: What was it like leaving all of your friends?

Cassie: I wrote a lot of letters while I was traveling and I was really impressed and surprised by how in touch certain people were, like the people I would maybe least expect. I don’t know. I didn’t feel like I was really leaving anything behind. I would say it felt very good.

Craig: How do you feel now about Kickstarter as it currently stands?

Cassie: I don’t think about it anymore ever. I don’t know if there is some kind of filter on my computer that they’ve figured out, but I never see Kickstarter projects, I never get emails. It’s like it never existed in my digital universe at all. I never see it. Kickstarter is like my ex-boyfriend.

Craig: [Laughter] Unfollow.

Cassie: [Laughter] I’m totally over Kickstarter.

Craig: Did you ever see those UX of a Heartbreak gifs? Like the mutual friend count going up on your ex’s partner?

Cassie: I don’t think so…

Craig: They’re awesome. I’ll link them in the interview. Anyway, I’m sure there were tons of good moments at Kickstarter. Do you have any funny memories?

Cassie: Running the Shit Kickstarter Says Twitter before they made me delete it. I ran a Shit Kickstarter Says Twitter feed because we would say the most absurd things out loud when we’d be talking about projects, because it would be like, “We could build the Iron Man suit in the hamster farm,” but it was legitimately what we were talking about. It was just like pure gold.

The first year that we were a company we took a few long weekends together. One of those remains one of my top five memories ever. Yancey, Perry, and I went out early to check in to this house we had rented in Amagansett for all the employees to work from. I remember getting caught in a rainstorm, posting up in a pool hall, staying out late, crashing on deck chairs at a friends house, a million other things. Just beautiful wanderings and being so weird and silly. Things still felt very new then, like Christmas. The excitement and freshness was like that.

Then the first film festival, which was a real big achievement for us. The first time a project won an Oscar, and seeing the film in theaters. That was so exciting!

Then, there were all the times you’d meet somebody who you had helped with their Kickstarter project. Sometimes they would literally cry, because they would have connected you with this profound turning point in their creative career and you’re like, “I don’t deserve this at all. This is all about you. It’s absurd that you would give me any credit.” But knowing that there are thousands of people out there who have that association with you is really crazy!

Craig: I really enjoy doing these interviews because everyone is so completely different. It’s so cool.

Cassie: We’re all really the same.

Craig: [Laughter] Yeah, sorry. You’re all the same. Interview over. But actually, what’s next for you?

Cassie: I’m honestly not sure at the moment. My current job comes to an end in January and I’ve been really re-thinking how I want to spend my time. I’m looking forward to burying myself in new projects and it seems more important than ever to make sure I’m committing myself to civic-orientated work. There’s so much that needs to be done — and it’s really important that people my age are getting involved. So I’m pursuing any opportunity I can that puts me in touch with other young women who are out there trying to make it. I want to be a resource wherever I can. Right now, what we need is to be building support systems for each other — and I want to be actively working to help do that. That seems like the most important thing.

Claire Wasseman, who runs Ladies Get Paid, is really inspiring to me. So are people at companies like Nava and USDS who are using their technical skills to remake government services, like health care, for people. I also love the work of companies like Loyal (founder Sarah Judd Welch, runs an amazing newsletter, too), who are focused on building community in new and smart ways.

Craig: Anyway, the last question I have is are there any books or anything like that you would recommend people check out?

Cassie: One of the most educational books I’ve read about process has nothing to do with tech or startups or anything, but I read Robert Irwin’s biography.

Craig: [Laughter] It’s the book I recommended on the YC’s summer reading list.

Cassie: Wait, seriously? The Lawrence Wechsler biography, seriously?

Craig: Yeah, the conversations with Robert Irwin.

Cassie: Are you kidding?

Craig: No.

Cassie: Really? I’m shocked. Reading that book is magnificent because you see his whole life, his whole creative process, everywhere he failed, everywhere he did everything right. The thing with Robert, is he just found his light — the thing he wanted to do — and he pursued it so deliberately, and with such devotion, and, often, without really understanding his own end goal. That was something that really resonated with me, the love of the thing, the process itself, matters most. Just get in there and do it.

Oliver Sachs has a memoir that I loved reading because he fucked up so much. So much. I remember one anecdote where he committed years to some early research — and in the final hour, he just messed up, I forget, but some tiny, seemingly insignificant detail of an experiment, and he completely fucked up the entire experiment. All of it had to go down the drain. But, you know, he still went on to become one of the most famous and renowned minds of his field. That failure was just incorporated into his life story, just like my failures — anybody’s failures — will be incorporated into theirs, if you just keep the right attitude.

Thanks to Fred Benenson for introducing us to Cassie.

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craigrcannon · 3 years

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Employee #1: Amazon

A conversation with Shel Kaphan, Amazon’s first employee.

Employee #1 is a series of interviews focused on sharing the often untold stories of early employees at tech companies.

Shel Kaphan was the first employee at Amazon. He is currently pursuing personal interests and still living in Seattle.

Discussed: Getting Online, Prior Startups, Vetting Jeff Bezos, Moving to Seattle, Early Versions of Amazon, Finding Traction Through Netscape, Building the Company, Changing Roles, Life After Amazon.

Craig : What were you doing before Amazon?

Shel : I worked as a programmer starting in 1975. My first real programming job was with an MIT spinoff called Information International, Inc. (also known as Triple-I) that was in Los Angeles, Culver City actually. I went there for a summer job in 1975. I was in college at the time, for the second time around, having dropped out once already, but stayed at Triple-I for three years. In 1978 I decided I should finish my undergraduate degree so I went back to school at UC Santa Cruz for a while and stayed in Northern California until I moved up to Seattle.

Craig : Ok, and how did you end up going to Seattle?

Shel : In early 1994, I had been working at a company called Kaleida Labs, which was a joint venture of Apple and IBM. I left there in the spring of 1994. One of the younger guys who had recently come out of university showed me Mosaic, which was brand new back then. The first time I got onto the the ARPANET, the precursor to the Internet as we know it, was 1969 or 70. I always had the feeling that there was something incredibly cool about it, but for some reason very few people seemed to think it was all that exciting. I couldn’t really imagine where it was all going to go eventually.

When I saw Mosaic, something clicked and I knew the Internet was finally going to open up to a much wider audience. Having missed a couple of earlier waves of technology that didn’t seem that interesting to me at the time, I thought this wave was one that was really going to be interesting and I wanted to do something with it. I didn’t know exactly what, but I knew I wanted to be involved. There were already a few new web-related businesses hiring some of the hotshots that I knew at the time. Netscape had been founded and some people I knew were already working there. It didn’t seem like a good fit for me, if I even could have gotten a job there. I wanted to do a startup and be more involved in the early phases of a business.

I was kicking around ideas with a friend of mine in Santa Cruz, who I had worked with at Frox and then Xerox, Herb Jellinek, trying to figure out some business idea that would be attractive to us that we could work on together–one that we thought might possibly work. We started talking to various people in our networks. Herb had gone to grad school at Stanford and one of his friends from there had gone to work at a hedge fund in New York, which happened to be the same one where Jeff Bezos worked at the time. He connected us with Jeff because he knew that Jeff was going to leave to start a web-related business that he had analyzed for this hedge fund. For whatever reason, that company didn’t want to pursue it but Jeff did.

Herb talked to Jeff, and then Jeff flew out to meet us in Santa Cruz. We had breakfast together and Jeff told us about his idea to start an online bookstore. We were even talking about possibly locating it in Santa Cruz. This was in spring of ‘94. Jeff went back home to New York and started thinking about where he wanted to locate. We were looking at office space in Santa Cruz but as he learned more about mail-order business he eventually decided it made more sense to be in a smaller population state or one that didn’t charge sales tax. He narrowed it down to someplace in Nevada or Seattle. I pretty much knew that I wasn’t going to be moving to Nevada. When he finally decided on Seattle, it took him all summer to convince me to move because I had lived in Santa Cruz for nearly 20 years and I liked it there.

Eventually, I decided that there was enough that I wanted to do on the project that it made sense to move. Herb, who had only recently moved to Santa Cruz, decided to stay. At first I was a little bit tentative about it–I kept my house in Santa Cruz and I only moved the minimum amount of stuff I needed to live.

At the time I thought, “Okay, I’m going to be building this website to run a bookstore and I haven’t done that before but it doesn’t sound so hard. When I’m done with that I’m not sure what I’ll do.” At that point there was no idea of doing anything but a bookstore. I thought maybe I would be able to go back to Santa Cruz and monitor it from there. I was pretty wrong about how the business would develop and how ambitious Jeff was. I didn’t know him at the time. We had just met.

Craig : How did you vet each other? Was he technical? Had you worked with many entrepreneurs before?

Shel : I’d worked in a few different startups. We both gave each other references to check out. But I think my choice was mostly based on the sense I had that he was fairly likely to make something work. I had been in a number of startups where there was an absence of people with sufficient business intelligence who understood how to fundraise, market something, and make business plans that weren’t based on hopelessly complicated technology that was super interesting but that nobody was ever going to pay for. I liked the idea that it was a very straightforward sounding business. I liked that I could explain to people who the customers were likely to be, what they were going to be paying for, and how the company could pay its own way.

I liked the guy when I met him. He has a very engaging personality. I was excited about the project so there were other reasons too besides the people involved. At the time there was this confluence of networking, hypertext, graphics and all this stuff that was coming into play with the web for the first time.

I wanted to take Books In Print or something like it and make a hypertext version. I’d been thinking about that before I even met Jeff. I wasn’t thinking about it in the context of selling books, but I was thinking, “Man, I hate going to the library and ruffling through those card catalogues and trying to find that thing that I’m looking for.” Nobody alive probably remembers that anymore. You actually had to go through drawers full of index cards to find books you were interested in. Then you’d walk around the library and browse the shelves to see if maybe the thing you’re interested in would be nearby.

I thought solving that problem was a perfect application for hypertext. There were a couple other online bookstores popping up around that time, too. Nobody seemed to grasp that issue particularly well. So, I thought, “Okay, well, I really want to build this and this project is a chance for me to do it.” Plus, I had worked just after high school in a mail order operation that sold books and other things, so I felt like I was going back to my roots, and that also felt good.

Craig : What was the first thing you guys had to build to get started?

Shel : Well, there was basically nothing except for a little library from NCSA of primitive things that you could use to build slightly interactive websites. I started by building up machines and getting a database system and putting together a little development environment. There weren’t any cloud services or anything like that at the time. It was all build your own and run it yourself. There was precious little in the way of tools or development environments for web stuff or libraries to build things out of. It was all cobbled together. At that point the web was a very static thing–mostly just a collection of pages.

There were hooks in the HTTP servers for running scripts, which is what we were depending on because all of our pages had to be dynamically generated. There was really nothing that existed to build a stateful application. In other words, where you are serving different things to different people and you have to keep track of that person’s progress, as they’re adding things to a shopping basket and going through an ordering process and all that. We pretty much had to figure that out and learn how to do it.

Craig : How did you troubleshoot? Today I use Stack Overflow constantly. What would you do when you ran into a bug that you couldn’t figure out?

Shel : Stay up late.

Craig : [Laughter] Fair enough.

Shel : I don’t recall that we had a lot of help from outside parties. At one point we decided to switch from Sun Microsystems to Digital servers. I was more familiar with Sun’s machines at that time so when we got the Digital machines and had some performance issues at first, Jeff found a professor at UW who could help with kernel tuning, which I was not terribly familiar with.

Everything else was debugging as usual. Technically speaking, Amazon was really pretty straightforward to build in the beginning. Although believe me, we had our share of bugs. But they were mostly relatively straightforward.

Craig : Were you also doing the software for inventory management?

Shel : A month after I got there we hired a guy named Paul Davis who had been in the Computer Science staff at UW, and who was a really great hacker. He and I worked together quite well. I was mostly focused on the website and customer-facing stuff. He was primarily focusing on shipping, receiving, inventory, charging credit cards and all that kind of thing. But we both had our hands on all of the code. He only stayed for a year and a quarter or so. When he left, it was just me for several months before I could hire anybody else. I was doing all of it at that point in time. I remember I worked seven days a week for 3 months straight, and they weren’t 8-hour days. Then we started hiring a few people who could take over specific aspects of the code.

Craig : Do you remember how many orders you were getting per month at the time?

Shel : I don’t remember numbers but it was minuscule by today’s standards. That said, our business was doubling quarterly for about six quarters or more in a row. In the beginning before we got the Digital servers, we ran the whole business on a couple of small Sun desktop machines. That was everything. We didn’t have much of a budget for hardware. We were trying to get absolutely everything we could out of a small number of tiny machines. We were always a little bit behind the curve on adding more hardware as we needed it.

Craig : Did that ever come around to bite you guys?

Shel : Yeah, for sure. We were always up against the limit of what the hardware could do. For one reason or another, sorting out architectural issues to scale more gracefully was something I could never convince Jeff to allocate resources to do. There were always too many customer-facing features that needed to be developed.

There were times when some piece of hardware would crap out and corrupt a database and, of course, some of the backups hadn’t been working. But somehow we survived.

Craig : Were you guys running any kind of analytics at that point?

Shel : No. Not in the beginning. I think it was maybe spring or summer of 1997 when the first people came in that were starting to work on that. In the beginning we were saving our server logs thinking they’d be really interesting to analyze, but not right now.

Craig : When we have a ton of extra money and time.

Shel : Yeah, maybe when we have a thousand extra programmers or something.

Craig : Exactly. So had you been working with Jeff on the product? How was the ship being steered?

Shel : During that time we were just a bookstore, so it didn’t seem to me there was a lot of steering to be done. That said, I don’t know all the things that Jeff might have been doing that I wasn’t aware of at the time. If I think back, I can’t even clearly picture what it was that he was actually doing. He wasn’t working on any of the technical stuff. We never even had a written business plan that I know of.

Craig : [Laughter] Was he sourcing the books?

Shel : He wasn’t doing that. Well, maybe he was at the very, very beginning before we hired people to interact with publishers. At the very beginning we were mostly just working with distributors. But we wanted to have a large catalogue, so we also had to work directly with publishers who weren’t represented by the distributors. That was what allowed us to claim a million titles, which was a big deal back then.

Craig : How were people discovering you guys?

Shel : Well, Google wasn’t around at the time. There are probably other opinions about this but, first off, there weren’t that many websites that were interesting back then. Second, as it turned out, there was a couple who worked at Netscape at the time–Eric and Susan Benson. I had worked with Eric in three different places by then. We had a “friends and family” soft launch in the spring of ‘95. They were among the people that were trying it out. We later hired both of them at Amazon. Susan was working on Netscape’s website in an editorial capacity. I only learned this last year, but when we opened up to the public it was she who put Amazon on their “What’s New” and “What’s Cool” pages. She put us on those lists. Then because the name started with an A, it was above the fold so lots of people saw it. That was, in my opinion, a super important connection for us. It might have happened without the personal connection, but who knows, maybe not.

Craig : That’s wild. Were you shipping to all 50 states in the beginning?

Shel : Yeah, and several foreign countries as well. We had a lot of international orders from fairly early on.

Craig : At what point did you realize, “Maybe I shouldn’t keep my place in Santa Cruz. I might be at Amazon for a while.”

Shel : I think that happened two years in or so. It started to be annoying to have to manage the house remotely, even though it was a friend of mine who was renting it. I was still responsible for it. At that point I also thought, if I do move back there, I’m probably not going to live in that house. It was not a particularly great house. I decided it would make my life a little simpler to get rid of it.

At that time we started extending into different product areas, too. We started having sites in a couple of other countries. Germany and England were the first two. And we started to make acquisitions. I think the acquisitions were probably post-IPO, which was spring of ‘97.

Craig : Whoa. I didn’t realize it was that fast. Three years?

Shel : Yeah, about two and a half.

Craig : What was your role around the time of the IPO?

Shel : My role was always primarily technical with some technical management. At that time I was VP of Development and was responsible for writing the software and keeping the systems up and running. One of the people who were hired to replace me in my original role came in only a month or maybe two before the IPO. The next guy came in September of that year. Early on, the small team of technical folks had been working for me, and I was mainly doing a lot of programming myself, but also system administration, network configuration, and so forth. I was putting disk drives in enclosures and running Ethernet cabling around the building and that kind of thing.

Craig : Not quite the glamorous startup life some people imagine.

Shel : Well, yeah. Those days were still before everything that’s happened with glorifying startups. If you were going to do a startup business, there wasn’t a huge expectation that it was going to be glamorous in any particular kind of way. You were going to work really hard and maybe it was going to work, though probably not.

Craig : Are there any vestiges of your work at Amazon?

Shel : Up until recently, maybe a few years ago, I could have said yes. But I don’t really see anything that looks like it now. It seems highly unlikely that anything I did actually still exists over there anymore.

Craig : What about even design patterns? Like, this is how a shopping cart works.

Shel : I don’t remember learning that from some other website. Though it seems like, as soon as you start thinking about that problem, it’s self-evident what it has to be like. You don’t want to make people go through a transaction every time they pick something. You have to let people go through the site and pick things that they’re interested in, put them somewhere so they can come back and get it all shipped at some point. I remember doing a lot of framing of that process on the website. Putting in text that said you could always take this out of your shopping basket later if you change your mind. So people wouldn’t feel they were overly committed.

Back in those days nobody was used to being a customer of online businesses. You had to be careful to make people feel comfortable and let them know their actions were reversible. Even though I was mainly doing technical things, the appearance of the website and a lot of the text on it were my doing in the early days. I was careful about making things acceptable to what I understood the culture of internet users to be in those days.

Craig : That’s so wild. You were designing for a completely different level of knowledge. You can assume so much more today.

Shel : Yes. Absolutely. Back in those days, it was the very beginning of doing commerce on the internet. There was a whole debate around allowing commercial activity on the internet. At least that’s how I recall it. Many people online were like, “We’re not so sure about commerce on this thing. You better not overdo it. You better be tasteful.”

There were these cases where people doing overtly commercial things were chastised by the community at large. There were some lawyers advertising their services for getting Green Cards and they were doing it by massive spamming activities. It created a huge fuss back then. It’s laughable now because so much stuff like that happens all the time.

And when cookies started being a feature in web browsers a lot of people were really concerned about their privacy, so they would turn them off. So we had to figure out how to make things work without that. Some people were running text-only browsers back then. Plus they were on dial-up. Sending pictures was not a good thing for those people.

Craig : Wait, you could use the early Amazon as a text-only site?

Shel : Yeah, we tested it. It always seemed important for us to make things continue to work, even for people that didn’t have a high bandwidth connection or the latest and greatest computers and all that.

Craig : How long did you end up staying in Amazon?

Shel : I was there for five years.

Craig : At the time you left, was it still a bookstore? What was it like?

Shel : Well, they had branched out into several other product areas. There weren’t any digital products yet. Ebooks hadn’t happened yet. They hadn’t developed any hardware products yet. Their computing services were not public yet. It was still pretty much a retail business. Although it was definitely branching out into other product areas and other countries.

Also around the time of an IPO and afterwards, the kind of people that are attracted to go to a company changes a lot. There were boatloads of MBAs and people like that coming. It was already a big company from my perspective.

Craig : So you’ve observed all these technological shifts. Do you have thoughts about how people should evaluate technologies when they’re about to start building something?

Shel : At this point, I don’t know. It’s a huge subject. For myself, when I look at technology these days, I see that it’s either doing something to connect people or it’s doing something that isolates people. I tend to make value judgments based on that kind of consideration about what is worth working on.

You walk down the streets, you have to weave around people standing there in random orientations in the middle of the sidewalk looking at their cellphones. Then you see people speaking robotically so that their speech recognizer can understand them. Now they are running around in mobs in parks with their phones in front of them trying to catch imaginary animals. I don’t necessarily see all that as a positive development.

I think technology has a role to play but I don’t see it being exploited very carefully in that way. But this is the kind of economy that we live in. And it’s very, very addictive. Even people who complain about it are still subject to it.

Craig : For sure. Where do you see Amazon falling on that spectrum now?

Shel : I think that a lot of what they do is more on the isolating people side. Everything caters to convenience so much that you don’t even have to get out of bed to take care of your day-to-day business. To me, that’s a step too far. Of all the major online businesses, I don’t really think that they extend in that way much beyond what we did very early on by allowing for customer reviews.

Craig : Had you and Jeff stayed close?

Shel : Not really. When he replaced me in my original job and I was moved into the CTO slot, I was nominally in charge of architecture, but in fact that just meant rubber stamping projects that were 95% complete by the time I saw them. That was all after having told me that my job was mine as long as I wanted it. And I didn’t have resources other than myself to work on anything I was interested in either. So I would say we were not really on particularly friendly terms at that point.

Craig : In retrospect, how do you feel about how things unfolded with Jeff and Amazon?

Shel : He’s obviously a super brilliant businessman. If I had any inkling about what kind of a company Amazon would turn into, both in terms of how successful they are and some of their business practices, I probably would have been a little bit more careful about my own relationship to it at the beginning. I also might have decided it wasn’t what I wanted to do.

One thing that the Amazon experience taught me is try to imagine what a project or company would be like if it was more successful than you could ever possibly imagine. It’s very unlikely but it’s possible. You have to think about what the environment will be like if that happens, and how the people involved in it might change. When I was joining Jeff to form Amazon in the beginning, I didn’t even allow myself to go there. I’d worked for a lot of startups so it almost felt like a jinx to think too much about what might happen if it really succeeded in a big way. That was my mentality. I was like, I hope this makes it and is a moderate success. Maybe it even generates enough cash to let us retire at some point. You don’t really want to think about massive success beyond what you can imagine. Then, if it is successful, you have to start thinking, what’s my role in enabling this? Is that something I really want to be doing?

I would say, of all the jobs I had, and I had quite a few between when I started programming and when I left Amazon, the first couple of years at Amazon really were a high point for me. I really, really liked that. A lot of that wasn’t so much because of the technical side of it, it was because of having worked in lots of small businesses that didn’t go anywhere or were the wrong thing at the wrong time or something like that. Being a part of something from the very beginning that engages people and has an astonishing growth curve–being part of making that actually work–was hugely satisfying, and I still look back on those first couple of years as a really exciting and great time in my life.

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craigrcannon · 3 years

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Employee #1: Apple

Employee #1 is a series of interviews focused on sharing the often untold stories of early employees at tech companies.

Bill Fernandez was the first employee at Apple after Steve Jobs, Steve Wozniak, and Mike Markkula incorporated it. He’s currently working on his own startup, Omnibotics.

Discussed: Growing up in Silicon Valley, Introducing Jobs and Woz, Startups Before Startup Media, Apple’s Early Days, Moving to Japan, Returning to Apple, Advice for Early Employees and Founders, and Life After Apple.

Bill : Did you want me to just start a narrative or do you have some questions you want to start with?

Craig : You can just give it a go and I’ll just jump in, if that’s cool.

Bill : Okay, sure. When I was five my parents moved to a street in Sunnyvale, a new little housing tract that was developed primarily for Lockheed engineers. Lockheed had a location adjacent to Moffett Field Naval Air Station. Across the street and three houses over was the Wozniak family. Jerry Wozniak was a mathematician and engineer, he was a real genius and worked on top secret projects at Lockheed. He had two sons and a daughter. His eldest son, Steve Wozniak, was into electronics.

He did ham radio and science fair electronics projects and so forth. He and I both went to Homestead High School which was the local high school. He was four years ahead of me so he got out one year before I got in. But I grew up across the street from him so I kinda knew about him.

My dad and Jerry were friends so Jerry was over a fair amount. But it wasn’t until I was in high school and was seriously an electronic hobbyist that I hooked up with Woz and we became friends and fellow electronics nerds doing projects together. We did a TV jammer, we did an audio oscillator, and one summer we did a computer in my garage. So that was the Woz connection.

When I was in seventh and eighth grade I went to Cupertino Junior High School, which was just behind my backyard fence. I think maybe halfway through seventh grade Steve Jobs came to the school. He and I were both deeply introspective, very philosophical. Neither of us wanted to play the social games that you needed to play to be accepted into any of the numerous cliques that define the social scene for 13 and 14 year olds in junior high school. So we eventually gravitated towards each other and started hanging out. We became fast friends. I got him interested in electronics and so…

Craig : Wait, really?

Bill : Yup.

Craig : Was there a particular thing that you showed him that piqued his interest?

Bill : I don’t remember any one thing specifically. I do remember that in junior high school I was working on electronic locks. I’m not sure what else I was working on then. But we were over at each other’s houses all the time. My mom considers him her fifth son.

Craig : [Laughter]

Bill : It was in our house that he learned about Japanese art, Japanese woodblock prints, spartan design, clean lines and so forth. It was a big influence on his design education and proclivities.

Craig : Neat. So how did Jobs and Woz meet?

Bill : So, I had known of Woz since I was five. Jobs and I became friends when we were like 12 or 13, then we transitioned into high school so Jobs and I both started going to Homestead High School. Maybe my freshman or sophomore year I started doing a lot of projects with Woz.

Across the street from Woz’s house was Mr. Taylor. Mr. Taylor used to have an electronics surplus store. He had closed his store and moved his remaining stock into his garage. I would go across the street and do yard work, like pulling weeds, and we’d keep a little log, and every now and then I’d go over to Mr. Taylor’s house and say, “Mr. Taylor I need a transistor or I need a capacitor.” And I would trade my hours for parts.

So one day Jobs had bicycled over to my house and we were going to hang out and I needed to go to Mr. Taylor’s house to get some parts, so we walked across the street. Woz was out on the street washing his car and I thought to myself, “Well you know, here are two electronics buddies. They might be interested in meeting each other and doing electronics stuff.” So you know, we walked over to the car and I introduced them.

Craig : Amazing. Were they fast friends?

Bill : Well, not in an instant spark of brilliant light, no.

Craig : [Laughter] Sure.

Bill : But you know, they eventually became friends and started doing projects together. It turned out that Woz loved pranks and Jobs had a very countercultural streak. One of the first projects they collaborated on was this huge sign of a hand with the middle finger raised. It was a huge cloth poster and they put it up on the roof of our school and weighted the ends with rocks, I think. This was the end of the building that all of the parents faced during graduation. And the idea was that during graduation they would cut some strings which would release this thing to roll down over the side of the building and it said, “Best Wishes, Class of ’72!” and it was giving them the finger.

Craig : That’s amazing.

Bill : So that was like, their first prank together. And then they went on to doing blue boxes together and so forth.

Craig : So if Woz was four years older than you guys, what was he doing at the time?

Bill : Let’s see, I think he went to Colorado State and got kicked out. Then he worked for a while at places like Call Computing, which was an early timesharing computing company. Then he went to Berkeley and that was the blue box era. It was also the era of Ramar the Mystic.

Craig : What’s that?

Bill : [Laughter] It’s a great story. So Woz was at Berkeley and lived in the second story of a dorm and kinda outside his window out on the street was a telephone booth. This was in the days before cell phones so everyone used telephone booths to make calls. Sometimes, like when a student was entering the telephone booth, Woz would call the telephone booth and it would ring and student would answer it. Then Woz would say, “This is Ramar the Mystic. I see wetness in your future,” and as the guy is saying, “What?” Woz would throw a water balloon at him from the second floor. The guy would be all angry and Woz would say, “Well, Ramar was only trying to help.”

Craig : [Laughter] That’s so good. And what were you doing at the time? Just kind of like electronics hobby stuff in high school?

Bill : Well, let’s see. Yes, I was going through high school and then after high school I worked for Siliconix and then for Antex. Then I went to college and went to Hewlett-Packard for the summer but ended up staying there for three years.

Craig : What were you doing at HP?

Bill : I was the only electronic technician in a research lab of electronic engineers. And that was the division that made handheld scientific calculators. So the HP-35 during my high school years was this breakthrough handheld 10-digit precision scientific calculator for $395, which was an enormous amount but it was all battery-powered and handheld. And then later Woz went to work there as an engineer. I went to college, he called me and asked if I wanted a summer job at that lab and so for the summer I went there and then I stayed for three years. He and I were both working on electronic handheld scientific calculators.

Craig : So at what point do Woz and Jobs come together and decide that they want to start working on Apple?

Bill : Okay, well during this Hewlett-Packard period when Woz and I were both there, Woz in the after hours designed his own Pong game. Pong was the first really popular, you know, video game that bars and pizza shops and restaurants could buy and put it in stores and people would come and put quarters in and play. So he built his own circuitry and used it with a small black and white TV set as the display.

Then a couple of things happened. He started working on building his own computer and he started attending the Homebrew Computer Club that was happening at the Stanford Linear Accelerator Center, SLAC.

So all of those things happened at the same time and then as his computer came together he would take it and show it off after the meetings. At some point there was enough interest shown that Jobs became aware of this. I don’t know if he went to the Homebrew Computer Club or just when he and Woz were together Woz was talking about it. Basically Jobs said, “You know, we could make printed circuit boards and just sell the computer already assembled so people wouldn’t even have to buy all the parts on the open market and figure out how to wire them together. We could just do it for them.” And so that was the beginning of Apple Computer.

Jobs got a printed circuit board made and he figured out where to get all the parts. They decided what to name the company and then, this is funny, Jobs got a front office front. There was a company at 770 Welch Road. If you look at the old literature that was their address, Apple’s mailing address. So there was this company on the second floor that had people who would answer the phone and depending upon what number was called would say, “Hello, this is Apple Computer, how can I help you?” And would receive packages mailed to Apple Computer and would mail things from Apple Computer. Jobs was working in his father’s garage and in his bedroom, you know, and this was like our front to make it look legit.

Craig : [Laughter] That’s fantastic. And so at what point do they call you up and say, “Hey, we need some help?”

Bill : Right after they incorporated. It was like, ’76 or ’77. They incorporated and they needed employees and the first one they wanted to hire was a good electronic technician. Both of them said I was the best that they knew — I think Woz mentioned that in one of his books — so they asked if I’d quit Hewlett-Packard and come work for them in the Jobs family garage.

Craig : How did the pay compare between HP and Apple?

Bill : Well, even with no benefits I thought the pay was good enough. I don’t remember exactly but clearly it was good enough. The major decisions for me were that Hewlett-Packard was the premier electronics company and that was a big plus for an electronics dude, and their benefits were really good and it was very stable. It was very secure. But, you know, I figured that this could be pretty interesting and I was living with my parents and my car was paid off and I was very employable. So I figured that if this fell through that it would be easy for me to get another job and there’s no big loss, right?

Craig : And how old were you at the time?

Bill : Maybe 22. If it was 1976 and I was born in 1954 then I would have been 22 at the time.

Craig : Okay, cool. So you say, “All right, I’ll do this.” Now I’m curious, could you provide any sort of context around how people were thinking about tech startups at the time and why it was attractive to you to jump in on something like this?

Bill : Sure. Well, first is that in those days everything was hardware. There basically were no software startups to a first approximation, okay? And what was then called Silicon Valley became that because there had been a whole bunch of basically hardware startups. There had been Varian up the peninsula, which had built microwave vacuum tubes for transmitters and for radars. There was Fairchild Semiconductor, which was one of the very first semiconductor manufacturers. And then there were a whole bunch of others eventually.

Over the years the peninsula — say from San Jose to San Francisco — had developed an ecosystem that was very hardware oriented. There were a number of electronic surplus stores where people interested in Homebrew and do it yourself stuff could go buy surplus parts and surplus equipment to tear apart. There were a bunch of supporting shops. There were metal shops and PC board shops and a number of the major electronics distributors.

Then we also had a number of major companies like Hewlett-Packard where they did a lot of work to hire a lot of electronics people, primarily electronic engineers and mechanical engineers and so forth. Over the decades that area had built up a bunch of educated people and an ecosystem for supporting the needs of the electronics industry.

Then a sort of history of new businesses being formed by people who spun out of or left big companies for one reason or another was created but that took decades to build up. It started back in the 40s or 50s and now we’re talking about the 60s and 70s. You know, so at least 30 years to build all of that.

So in that environment, Woz and Jobs and I grew up. Woz’s father was an engineer working at Lockheed. I would go up and down the street to engineer neighbors on the street who would mentor me in electronics. We would read Popular Electronics, which was a magazine for hobbyists and do it yourselfers, and before the internet these magazines were like, your main way of learning things.

When you were casting about for something intellectual rather than sports oriented to do, electronics was something you could do as a kid. It’s something you could aspire to, projects that were interesting and so forth. In that environment it was natural for Woz and Jobs and I to build whatever circuits were interesting along the way.

During that period when I was in high school particularly, there were more and more people around the peninsula who wanted their own computers. And there was more and more a sense that maybe it might be possible finally for people to build their own computers. Woz, throughout high school had always wanted his own computers and he was always doodling circuits saying, “You know, if I were going to design a computer this is how I’d do it.”

This built up to a time when in late high school or just right after that, there was the Homebrew Computer Club and there was a lot of surplus computer gear for people to put together. There was a pent-up demand among all the electronics hobbyists, the people who wanted to build their own computers.

It was possible to conceive of how to do these things. Microprocessor integrated circuits had recently come on the market and had recently come down in price enough that a hobbyist could afford them. We were just barely seeing the first semiconductor memory. So, when I was in high school, we dreamed of getting an old magnetic core memory where you have these tiny little doughnuts of magnetic material, like hundreds of them wired together with this little web of woven tiny little wires, you know? And that was the premier memory, you know, and maybe you’d get 500 bits or something, you know? We aspired to find a surplus one of those and get it working so we could build our own computer, see?

Craig : That’s so cool.

Bill : Yeah, so there were a lot of themes that all kind of coalesced. The infrastructure was there so you could say, “I want sheet metal done. I want a printed circuit board made.” You could just go out and someone would do it for you. “I want to buy parts,” someone could do it for you. We had the aspirations of all of these people throughout my high school years and thereafter saying, “Not only do we want our own computer but we think it’s finally possible. You don’t have to build an ENIAC [Electronic Numerical Integrator And Computer] and take up a whole room and have tons of circuits and vacuum tubes.” We had integrated circuits that made all of that circuitry small and lightweight and affordable.

Craig : So the fact that you can get all this with a short trip to all these stores, that makes a ton of sense. The environment makes a ton of sense. Was there anything in particular about the Jobs and Woz that made you think, “I want to work with them,” or did you just think, “Oh, this is kind of neat, it’ll be a fun project regardless”?

Bill : Well, I definitely wanted to work with them. You know, I had worked with Woz and Jobs on projects for years and they were two of my closest friends and we got along well together. And sure, it was great working with my friends. It was also great having the opportunity for us to build our own computer, so yeah. It was great. I just thought, “Let’s go build our own computers. This is awesome.”

Craig : Yeah, I love their mindset. And so what was your job in the very beginning?

Bill : Okay, so technically my title was electronic technician. What that really meant was that I was a very intelligent and capable jack of all trades and gofer. So, Jobs was always sending me around to pick up parts or to deliver things, or in the garage I’d have to build test fixtures and boxes where I’d troubleshoot boards. Pretty much any kind of technical or gofer related thing you know, was my job.

Craig : And how long did that period last?

Bill : Well, we were in the garage for a while and then we moved to our first building. It was an office suite in a little one story office center. It was 20863 Stevens Creek Boulevard Suite, B3.

Craig : [Laughter] You have a great memory.

Bill : Yeah, and it was right next to the first Good Earth Restaurant, which had just been a failed pie restaurant and then Good Earth took over and did their thing. So we’d always eat over there.

Okay, after we outgrew that space we had to rent a second suite just adjacent to it and then we outgrew that and then we rented a building on Bandley Drive a couple of blocks away. That’s where we had our first building, Bandley Drive, and then gradually over the years we ended up with about eight buildings on Bandley Drive. Each time they built a building we’d rent it, because we were growing so fast. And during that time, you know, we built up. In the garage it was just me and Jobs and Woz. Woz was still living in his apartment and still working at Hewlett-Packard. He didn’t want to leave Hewlett-Packard.

Craig : Wild. I didn’t know that.

Bill : Eventually Mike Markkula had to prevail upon him to say, “You have to leave and go full-time. We’ve got this investment and I put my money in and you gotta do it.”

Craig : Yeah, can’t moonlight forever. And so how long has the company been around at this point?

Bill : Well, about a year and a half. We were in the garage and then we moved into our first little office and that’s where we started getting serious. We had a secretary and we had an accountant. We hired some more engineering technicians. We hired a manufacturing guy, we hired an industrial designer. Right between that transition we got Rod Holt from Atari to come and be our head of engineering and so forth. He’s the guy who designed the brilliant power supply for the Apple 2 computer.

Let’s see. Then we moved into Bandley Drive and we had a separate manufacturing area, separate engineering area and a separate administrative area, and we hired a guy and a secretary to do international sales. We were building custom units made in black for Bell & Howell who wanted to sell under their label. We had a marketing guy in addition to our president and our accounting guy.

Craig : Was it uncommon at that point to be growing at that clip?

Bill : I personally don’t know. All I can tell you is that everything I’ve read is that it was phenomenal and unprecedented.

Craig : And so what did you make of it at that point? What did you think of the environment?

Bill : Well, there were a couple of aspects about that. Starting back in the garage era, I would say that there was a tangible sense of magic in the air. Every now and then Woz would come in and he’d say, “You know, I just was at Homebrew last night and look at this piece of software that this guy wrote that runs on our computer.”

At first we had the Apple I and it was all text things, like the Hamurabi game. Then we had the Star Trek text game, then after the Apple II Woz would come in and he’d say, “Look at this amazing color devil that this little high school student named Chris Espinosa made.” And he’d be putting all sorts of colored blocks on the screen and kaleidoscope patterns and stuff, so it was pretty magical. It was really the sense that we were going to bring personal computers to the masses.

Craig : So a year and a half in, what are you doing?

Bill : Well, a year and a half in, everything is growing and diversifying. We have a bigger building, it has more departments, it has more people, we have an international guy as well as a domestic guy, you know, and so forth. Everything was kinda just like, exploding in complexity and diversity. My particular job, it pretty much stayed the same, real electronic grunt work, and I was getting pretty bored with that.

Craig : Okay, so what were your aspirations at that point?

Bill : Yeah, well, I had an engineering mind without the engineering education that a degree would have given me. I went to school for an engineering degree and dropped out so I never finished that degree and never got the range of knowledge that I would need to actually be an engineer. And so I was really working way under my intellectual potential, which became very boring.

Craig : And did you verbalize that you wanted to do more at any point?

Bill : I probably did, although you know, I wasn’t as self-assured then as I am now. I mean, you know, I was just a kid. You know, I’d just gone through high school where everyone chose my courses for me, right?

Craig : Yeah, that insecurity can manifest in different ways. Like some people at 21 admit they don’t really know and others just amp up the ego even though they also don’t know what they’re doing.

Bill : I didn’t really know what my options were at that point and it wasn’t like now where we have a huge social media push for makers, do it yourself, startups, incubators and stuff. None of that existed. None of that mindset, none of that advertising, none of those thought processes, none of these kind of like, dreams or stories about dreams you could have were around. You know, the thought process was basically you find a good company like Hewlett-Packard and you work there for all your life and then you retire. Going to Apple was this huge risk.

It wasn’t like this glamorous thing. It was this huge risk. Basically people would say, “Why would you quit Hewlett-Packard to go work for a couple of lame ass guys, you know, one of whom is like this hippy guy who wears Birkenstocks and torn jeans and dropped out of school and had to sell a beaten up VW van to just afford to get started on this. Why would you go work for these jokers when you’ve got a job at Hewlett-Packard?”

The short way of saying this, I guess, is there was no startup culture.

Craig : Yeah, that’s kinda what I was leading at before when you were explaining the ecosystem, because it both seems like the ground was incredibly fertile, like there were all these places to get the components but without the media environment you’re still kind of on your own, you know?

Bill : Right, completely on your own.

Craig : Yeah. So did that notion precipitate you leaving Apple in the beginning?

Bill : Well, when I was working at Hewlett-Packard I thought that working with my friends on making it possible for people to have their own personal computers was really exciting. And as I said, there was basically no risk in my mind. I could easily find another job if it didn’t work.

Now, after a year and a half of all these people being hired in and other people growing and me going nowhere professionally and getting really bored, I had some people I’d worked with previously at a job just out of high school who wanted to hire me as a product engineer for their little company. I thought that that was a lot better because I’d actually be able to do engineering.

So I jumped shipped and I went to work for them, and then after them I went off to Japan for a couple of years.

Craig : Why did you end up leaving them so quickly and going to Japan?

Bill : Let’s see, those are actually two separate things. I worked with them for several months and they, instead of having me design things which is what I wanted to do, they had me doing a lot of technician work because their product line needed a lot of technician work.

Craig : Which is what you were doing at Apple.

Bill : Yeah, so it was boring again and therefore I wasn’t performing to their expectations and so they laid me off.

Craig : Ah, okay.

Bill : I had been thinking of going to another country to teach my religion, the Baha’i Faith, and so I decided to do that in Japan for a couple of years. I also got my black belt in Aikido while I was there.

Then when I came back I worked for a friend who was working on a TV project and I was doing engineering and technicianing for that project, and then Jobs hired me to be like the 15th person on the Mac project.

Craig : So then you’re back in the fold. How did you view the work at that point?

Bill : Well you know, Apple had changed a lot and it was really a different company. But I wanted a job and Jobs hired me into the Mac group and the Mac group turned out to be pretty cool.

Craig : Agreed. You stayed there until the 90s, right?

Bill : Yeah, let’s see. I went back in 1981. I think October of 1981, and was there until what, ’94? Something like that. I think including my first year and a half it was about 12 years total.

Craig : Okay, and you were doing a lot of interface stuff at that point, right?

Bill : Well my job morphed a number of times over the years. I did facilities planning, laying out our two new Mac buildings as we moved from one building to another and grew. I did general engineering support. I was the lab manager and managed the technician and kept the engineering lab running and stocked with parts. I did some programming. Ultimately I migrated into user interface design for my last years at Apple and actually was quite good at it.

Craig : That’s so funny. The 90s seems like fairly early days for that field. Are there any vestiges of your work still around in the interface?

Bill : Yeah, you know in the Macintosh finder when you’re showing a list of folders and there is the column of triangles along the left side?

Craig : Yup.

Bill : And then if you click on a triangle then it expands an indented list of subfolders and so forth?

Craig : Yup.

Bill : I had a hand in that. The system software people came to me with this new feature they wanted and I suggested they put a line of controls down there and the icon I suggested was a circle which could be empty or grey or black. And someone else changed it into the triangles, which I thought was brilliant, but having the column of controls to open and close folders, that was my idea.

Craig : That’s really cool.

Bill : Yeah, and there are few other vestiges but that’s the easiest one to point to.

Craig : It’s been a while now since you were there. How do you think about Apple? Do you even think about it much anymore?

Bill : I use Apple products all the time and yeah, of course I follow it, I had so much invested in it, you know?

Craig : Yeah. You left in the 90s. What was the public opinion of Apple when you left?

Bill : It’s hard to tell because Apple’s fortunes in the media and public eye have been up and down so much but I think we were up at that point. I think we had done the Mac II and brought color to the Mac. We had the Mac II and the Mac IIcx which was a smaller Mac II. We had slots and color. And we had started using hard drives instead of just floppy drives. So those had been around for a while but we put those in and we had recently introduced the first sort of widely available CD-ROM drive so that people could start using CDs. That enabled everyone who do things on CDs whether it was multimedia presentations or just distributing software. All of that was enabled by Apple biting the bullet to build a CD drive when there really weren’t any CDs available.

Craig : Man, that’s wild. So when you think back on Apple, are your memories fond?

Bill : Well, they’re complicated but fundamentally fond, yes.

I mean, there were times when morale was so low that people were putting this poster all over saying, “Life is hard and then you die.” And that was kinda how people felt at that time.

But there were also very wonderful and exciting times, you know. A lot of those, so…

Craig : How did you feel through all that tumult as a non-founder but someone who was there in the beginning?

Bill : Well, to succeed early on you have to be a self-starter. You have to be self-empowered. You have to have a sense that, “I can do whatever needs to be done even if it’s never been done before. Even if you’ve never done it before or it’s never been done before.” You have to have that belief that, “I can do it.”

Now, Jobs as a founder had a lot of drive. He also had a lot of hustle. He was moving all the time. It takes that and I was always being presented with new challenges saying, “Well, you know, we need to build a burn-in box.” I’ve never done that before. “We need to provide reliable power to like, a dozen things.” Well, I’ve never done that before. “We need to figure out a fixture for doing this.” Well, I’ve never done that before. You know?

Craig : And now that you’re running your own thing, have you learned lessons about being the head person?

Bill : Oh yeah, I’ve learned a lot of lessons. One of them is that over the years, by being observant, I have seen all the pieces it takes to put together a company. And you may not have them all on the table at the beginning, but it’s easier for me to look ahead and see where the company is going to have to grow.

When I was designing software for people I would always think, “Where is this product going to grow, and let me design it so that you could add features that would look like natural extensions of the product, you know, rather than tacked on stupid things.” So as I build a company I’m thinking about all those things too. How do I anticipate the growth?

Another thing that I learned is that you’ve got to hustle and you’ve got to be everywhere and do everything. There are a million jobs to be done and when you’re one guy, you have to do all million. And when you have two people you only have to do half a million and when you have four people you have to do a quarter million, okay? But you still have to be very versatile.

Craig : For sure. So do you have any advice for someone who is thinking about joining an early company?

Bill : Yeah. Be prepared to do anything and everything that’s needed. You need to be cool with that. Whether it’s taking out the garbage or clipping the bushes or cleaning up vomit or going to a meeting and pretending you’re the marketing manager, whatever it is, be ready to do anything that needs to be done. And if you’re not up for that, don’t sign on.

Another thing about being an employee is that it is entirely unpredictable. Is the company going to be successful or not? Is it going to go places or not? Are the founders going to be happy or sad or anxious or angry or whatever? All of it could change from moment to moment.

So be a person who can survive with chaos and uncertainty and realize that you know, it’s not because of you and that that’s life. This is part of the deal.

Also, be prepared as either a founder or an employee to spend your life on it. Be prepared to give your life to the enterprise. Forget about family, forget about children, forget about your pets or your garden. It is going to be all-consuming and that’s one reason why I’m starting my startup so late. I waited until I could neglect my children without harm to them.

Craig : [Laughter] How so?

Bill : They’re out of the house now so I figured, “Okay, now I can do what I want.”

Another thing is that as a startup founder you figure that there are 1,000 things that are going to have to be done that require 1,000 different specialties and you’re only going to be good at 5 of them. Then you’re really only going to be interested in doing 10 of them and there are going to be 200 of them that you absolutely hate and cannot stand. But you have to do them all.

For example, many people, many engineers are really great at designing a product but absolutely terrified to actually tell anyone about it or to promote themselves or to say it’s good. So marketing and sales are complete anathema to them. But you’re going to have to step up to the plate and do some of it.

Craig : And so how do you prioritize?

Bill : It helps if you can plan ahead and plot a trajectory for things. It helps if you’re savvy enough to plan ahead and say, “What does it take to build a business?” And that will tell you at what stages things need to be done.

For example, at a very early stage you have to figure out, “What do I want to do?” Right after that, you’re going to have to choose a name, you’re going to have to incorporate, you’re going to have to get a checking account and so forth. The priority is built into the sequence to some extent. So, if you understand the stages of building a business, to a large extent you can predict when certain things are going to become priorities.

And you might find that, “Okay, I can put off marketing for a while and maybe while I’m putting it off, while I’m developing my product, I will search for a marketing firm or a marketing person so that when marketing becomes the priority I won’t have to do it myself.”

Understanding as well as possible what you’re getting into so that you can plan effectively is a really good strategy. Otherwise everything is going to be a surprise, everything is going to be immediately urgent, and everything is going to be a new learning experience. You’re going to be clueless. So you know, it’s a long answer to your short question but it’s the real answer. The better you can predict your growth path and the sequence of the challenges you face, the better you can plan for them. And the fewer emergencies you’ll have, the fewer unexpected obstacles you have, the better able you’ll be able to face them with grace and efficiency at a low cost and a low stress level in a timely manner. And to a large extent the priorities will unfold with the plan.

One thing that’s wonderful is that there’s a lot of information available. There are a lot of books, there are a lot of incubators, there are lot of blogs and so forth that there never were before. And of course, information gleaned off the internet is, you know, hugely unreliable. But given you’re good at dealing with that — and that’s something everyone ought to be good at — there’s a huge amount of free information out there that’s really useful. And you’re going to have to be — here’s another way of putting being a founder — you’re going to have to be a student.

You’re going to have to be a self-learning student, a self-taught student. You’re going to have to teach yourself marketing and sales and accounting and cash-flow and engineering and testing for regulatory certifications. You’re going to have to become knowledgeable about a huge number of things. So being effective at self-study and self-learning is a huge part of it.

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craigrcannon · 5 years

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The YC Podcast Equipment

The best gear is what you already have.

Bill Burr made a hugely popular podcast from his phone for years.

But, if you’re curious about what we use at YC, here’s the list. Audio Mics: Shure SM7B Recorder: Sound Devices MixPre-6 Recorder Accessory: Anker USB Type C Wall Charger Mic Arm: Rode PSA1

Video Cameras: Canon 70D Camera Accessory: AC Adapter Camera Software: Magic Lantern Lenses: Canon EF 50mm f/1.4; Tokina at-X 14-20mm f/2; Canon EF-S 18-55mm f/3.5-5.6. Tripod: Manfrotto Compact Action Tripod

Software Editing Software: Adobe Premiere, Adobe Audition, Adobe Media Encoder Podcast Chapter Software: Forecast Podcast Host: Backtracks

#podcasting #podcast #yc #y combinator

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craigrcannon · 8 years

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Japan, One Convenience Store At A Time

Heads up! Below is a long post about bike stuff. If you like this sort of thing you can subscribe to my newsletter about bike trips.

I land in Tokyo and catch a bus to the city center. Pulling my bike box out from the bus, a station attendant gives me a look as if to say, “And now what?”

I’m going to set this thing up on the sidewalk.

It takes a while before the pieces, now all over the ground, resemble a bike. Everyone looks. Only the kids maintain eye contact. A couple of them wave.

When the bike’s ready I break down the box, surveying street corners for a trash can. I find none. If Japan is the future, the future is too clean.

Eventually I find a bin outside 7–11. This marks the beginning of my dependence on Japanese convenience stores.

My first few days disappear in a haze of ramen shops and grilled meats. I linger in a basement bar where salarymen stand around drinking and eating oily food before falling asleep on their train home. When the bar closes I get on the bike and start riding. Tokyo’s enormity is most apparent at night; each district has a hub that’s larger and more illuminated than the central hub in most US cities.

Eventually I turn onto a quieter road and pass beneath train tracks. Right alongside the tracks are two short alleys, crammed with miniature bars. Finding one bar that’s just loud enough, I push back the flags outside and slide open the frosted door. Then the entire bar, 6 people, turns to greet me. They let out a cheer and make room in the corner.

Several rounds of sake later I learn that the woman I’m sitting next to is a professional Keirin rider. She’s racing in two days in Utsunomiya. I have no idea where that is but agree to go.

I catch a train to Utsunomiya the next morning and camp outside Nikko. The days are short and I’m inside my tent by 6PM. Usually I spend a couple hours reading or wasting time on my phone before falling asleep. One way I like to waste time on my phone is searching Google for photos of the area where I’m staying, which is how I come across this:

I’m looking at the Irohazaka, a famous climb just a few miles away. In the morning I shake the ice off my tent, pack up, and give it a go. What’s particularly cool about the Irohazaka is that it’s actually two roads: one up (above), one down (below).

After the climb I turn around and make my way back to Utsunomiya for the race. As I’m buying my ticket an ancient Japanese man points at the pink rain cover on my backpack and starts talking shit. I don’t know Japanese but his tone makes it obvious. He points, says something to the ticket taker, and they both laugh before he starts in on me again. I like this place.

Keirin’s one of four sports you can legally gamble on in Japan, which means it’s just as fun to watch the race as it is to observe the guys — and it’s all guys — trying to pick a winner. Many of them sit inside and watch the race from what looks like a lecture hall, shuffling slips of paper on tiny desks as they stare at the screen then back down, checking their luck.

I walk over to the betting machine but can’t figure it out. I lean over to see what the guy next to me is doing though he quickly indicates that what I’m doing is not cool. I give up and loiter around the tea machines, waiting for the next race to start.

I leave for Hokkaido later that night. The entire trip will take over a day and involve substantial schlepping because, to take a bike on a Japanese train, it has to be partially disassembled and in a bike bag. 😑🔫

Breaking a bike down and attaching frame bags to a backpack takes practice. Finding a place on the train to stash it while avoiding a conductor temper tantrum is mostly luck. Lashing the bike to a pole in the train’s vestibule usually works.

Once in Hokkaido I catch a local train to Niseko, where I make camp in the woods. It snows overnight. I wake up to single digit temperatures. This was a dumb idea.

I pack up, go snowboarding for a few hours, and catch a train south. As much as I like arbitrary challenges, dragging my bike through snowfields feels like overkill. I look up a temperature map of Japan and pair it with my advanced research tactic: Google Images. Shikoku looks interesting. Done.

Shikoku is Japan’s smallest major island. It’s home to a 1,200 km coastal pilgrimage route but I want elevation and decide to cross it right up the middle. Inspired by Andrew Skurka, I’m hoping to create a sort of Shikoku High Route. Unfortunately, despite being warmer than Hokkaido, Shikoku also has “winter” and many of the roads I hope to take are closed. Instead, I’ll spend five days traversing north along river valleys and ridges.

Uwajima To A Park Under A Bridge 69.1 mi, 7,884 ft I camp on a hill looking west over Uwajima. I wake up at 5:30, condensation dripping off my tent onto the down sleeping bag I bought off Craigslist in Tokyo. Staying dry will be a constant battle on this trip.

I follow a river out of the city to my first convenience store stop of the day. I didn’t know this before visiting Japan but their convenience stores are amazing. They have very edible prepared food and really good diner coffee. Apparently many Japanese salarymen don’t even cook at home anymore, they just eat from convenience stores. Another thing these guys no longer do at home is browse softcore porn magazines — watch out for that aisle.

I buy a coffee and sit outside, wasting time on my phone when something odd happens. A construction worker walks over to me and hands me what looks like a hotdog. Before I can compute what’s happened he’s in his truck and driving away. This will happen three more times on the trip. Some of my friends think it’s because I haven’t shaved in several months and look like a homeless bike person. I prefer to think Japanese people are just kind to travelers. We’re probably both right.

I eat the hotdog thing (weird) and start along a road that quickly narrows to one lane. The snow’s melting off the ground and forming a dense mist. I go hours without seeing a car.

About 40 miles in I start climbing and keep climbing, for 18 miles. Near the top I get a lesson in bike pushing, inching my way along several hundred meters of black ice. Once on the ridgeline, I follow it into a tiny town with a general store (closed) and public bathroom (open) where I stop to wring the cold sweat from my shirt and hat and gloves and arm warmers and jacket and socks.

Back on the bike I get ready to descend from the ridge, shifting onto the big ring. Then, trying to shift across the cassette, I hear the distinct sound of plastic cracking. A piece inside my right shifter has snapped. I pull over, laughing. The exact reason I shouldn’t have used STI shifters on this trip has come to pass. They’re full of tiny, proprietary parts. Good luck fixing one on the road.

Thankfully, the rear derailleur’s still holding tension so, even though I’m stuck with one gear, I can pick it. I pull the cable through the derailleur until the chain is in the middle of the cassette. Looks like I’m finishing the trip on a two speed.

I find a small park along a river to set up camp just before dark, hoping my stuff will be kind of dry in the morning.

A Park Under A Bridge To Ochi 43.2 mi, 3,563 ft Nothing is dry. Some things are frozen. The sky is clearing and it looks like today might be sunny. I take longer than usual to pack up, making coffee and trying to shake the moisture off the tent. I climb out of the valley through an evergreen forest. A few miles up the climb there’s a “road closed” sign, which I casually pass. Unfortunately there’s a work crew ahead. One of the guys informs me that the road isn’t pretend closed and that the snow on it is above my head. I don’t completely believe him but take the message.

I drop back into the valley and follow another route north. Passing a lake, I cut up a ridge on a deserted road covered in loose pine needles and rockslide debris. After topping out I enter another river valley before reaching Ochi in the early afternoon. It’s been an easy day but the daylight hours are short and honestly, I’m totally content to just hang out on this trip.

Ochi To Motoyama 71.9 mi, 6,348 ft 20 easy miles take me to my convenience store stop of the day. With only two speeds on the bike, there’s no need to think about how to ride. I’m either spinning or standing.

After Ino I follow a single lane road through the hills. I take a wrong turn at a fork, assuming what looks like an old driveway can’t be a numbered road, and cruise down a hill. While climbing back up the ridge I stumble into the most impressive shrine (and staircase) of the trip.

At around 32 miles there’s a small town where I stop at a vending machine, trying out a hot canned coffee (not bad). Just before leaving I realize that my front brake’s been rubbing on the wheel all morning. The handlebar bag is pressing against the brake cable. Laughing at my bike’s sorry state, I sort of fix it and just keep going. Friction is character building, right?

The next ten miles form a steady climb to about 2,600 feet. I cross a small saddle before 20 miles of downhill, first through tight switchbacks then along a deep, clear river. The road slopes just enough to make my gearing useless so I just coast, hoping I don’t launch over a guardrail when not paying attention to the road.

I make camp along the river in Motoyama though Tosa has a better convenience store.

Motoyama To The Iya Valley 54.8 mi, 4,721 ft I wake to ice all over my tent. I do my best to shake it off but only get about half of it before admitting defeat and packing up.

I see a few possible routes out of Motoyama, some more remote than others. Several of them might be closed so I stop by the police station to ask for directions. Once one guy figures out what I’m after, four dudes surround the table and produce paper topo maps to consult on the project. Without any language in common, we spend ten minutes pointing at roads, eventually concluding that two of the three options are closed, I think. As I’m walking out I hear, “be careful” and look back to see the dad-ish cop smiling. What an odd expression to know.

I ride north to Oboke, where I stop for an early lunch. I find what looks like a noodle shop but the owner points me across the street to a small grocery store. I assume that means they’re closed. I ask the woman running the grocery store if I can find ramen nearby. She points back across the street and says “Soba. Udon.” I’m completely lost as to what’s happening. She steps out from behind the register, walks over to a refrigerator and grabs two packages of noodles. Still not really sure what’s happening, I pick one and pay for it. She hands them to me with a piece of paper and points me back across the street. I walk over and show the shop owner the paper, then the noodles. She takes both, smiles, and points at a small table inside. I’ve cracked the code. I sit down with a dumb look of accomplishment on my face.

The meal is excellent but poorly timed. I leave town and am immediately standing on the pedals, climbing 1,000 ft before entering the Iya Valley. My main objective for the day is to visit the Iya Onsen, which I do and it’s great. I haven’t showered in almost a week so this is a welcome stop.

I hang out in the hot pool for a while then spend probably 30 minutes standing under a heater in the locker room wasting time on my phone as my clothes dry. Thankfully it’s a weekday and the locker room is empty so I don’t look like a total creep.

Leaving the onsen I backtrack a few miles then go north up the valley. Gradually clouds fill the sky. Just before it’s too dark to ride without lights I pass through a truly eery place.

I’m riding down a deserted road when I see what looks like a scarecrow in a field. Then I see another outside a house. Then two sitting outside a store. It’s an entire village without people, just life-size dolls. I don’t stop to take pictures.

Postscript: Turns out there’s at least one person in the village––the woman who makes the dolls. She makes them in the image of locals that have moved away… or died. Here’s a video about it.

I ride another ten miles to what’s marked as a campsite on my map. Unfortunately it’s across a river and the bridge is closed. It’s nearly dark so I climb up a hill and pitch my tent in the woods. From my sleeping bag I stare at the tent wall, unable to shake the village off.

Iya Valley to Tokushima 50.6 mi, 3,307 ft Within one mile of leaving camp I might be screwed. A crane is taking up the entire road. There’s been a landslide and crew is working to rebuild the road’s edge. I decide to try my luck and slip the bike under one of the support legs, hoping the route north isn’t totally destroyed. The work crew notices me but doesn’t freak out so I just wave, hop on my bike, and start riding.

As I continue the road turns icier and icier. First it’s just in the shaded corners, then it’s across the entire surface. Eventually I make it to the top where I pass through a small tunnel. Immediately there’s a shift in road surface–now it’s ice plus rockslide debris. I’m ecstatic though. There’s no one up here.

I’m flying down empty switchbacks until I take a tight corner and nearly flatten some Japanese wildlife. Just hanging out in the middle of the road are a macaque and a serow. I barely avoid them and slide to a stop. Having never seen a serow before, I try to take a photo but it gets away. I determine that it must have been a tuna.

Once I reach the valley floor it’s an easy ride into Tokushima. I find a ramen shop and order a bowl, then another. Eventually I have to admit that I’m full and have run out of ways to procrastinate. Time to take the bike apart, the next train leaves in 30 minutes.

Thanks for reading! If you like this sort of thing you can subscribe to my newsletter about bike trips.

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craigrcannon · 8 years

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Biking The Ho Chi Minh Highway

Heads up! Below is a super long post about bike stuff. If you like this sort of thing you can subscribe to my newsletter about bike rides.

I arrive in Vietnam with a vague plan: bike from Saigon to Hanoi.

At a Czech bar in Saigon an English expat tells me there are two possible routes: Route 1A, which follows the coast and is Vietnam’s main artery, and the Ho Chi Minh Highway, which runs up the center of the country and through the mountains.

Leaning over a row of empty Saigon beers, his friend makes the choice for me. “1A is terrible, don’t take it. All trucks, construction, and dust.” Looks like I’m taking the Ho Chi Minh Highway.

[Craig Googles “Ho Chi Minh Highway”]

As I dig around online it becomes clear that the HCMH is a fairly popular motorbike trip for tourists looking to take this picture.

This is going to be easy. Let’s go.

Leaving Saigon Vietnam is shaped much like Italy–it’s wide at the top then narrows and hooks west as it goes south. To its west, Laos and Cambodia. To its north, China’s Yunnan and Guanxi regions. And to the east, the South China Sea.

Saigon, also known as Ho Chi Minh City, is in the south. It’s about 8M people i.e. almost the same size as New York. Saigon’s population density is reported as 1/3 of NY’s but you wouldn’t guess it. The streets are absolutely packed with scooters, which, if you forget the incessant honking, flow quite peacefully through the city. As a cyclist the scooter density is intimidating but actually it’s fairly safe. Nobody can pick up speed with all the traffic.

My route out of the city would be straightforward–Ho Chi Minh Highway all the way to Hanoi. I plot my path with Strava and chose daily endpoints based on motorbike guides such as Tom’s, which is excellent.

Day 1: Saigon to Bao Loc 117.6mi, 6,493ft Saigon boots me out with 40 of the trip’s dustiest miles on the infamous Highway 1A. About 25 miles in I stop for a gigantic egg banh mi, my go-to road food, and while I wait for the sandwich one of the old men hanging around the stand decides to investigate my setup, squeezing both my tires and then my legs, which is a bit awkward. He approves and lets me continue on.

After mile 40 I cut north and follow better roads though the fun part doesn’t really start until mile 100 when, without much notice, the road pitches up and all of a sudden I’m weaving through mountains. Traffic slows and thins out. The clouds open up and soak everything, offering a small taste of what’s in store for me several hundred miles ahead.

In Bao Loc I stay in the Memories Hotel, which is fine. Tip: most “beds” in Vietnam are comically hard. The default firmness is “yoga mat on cement”, so a sleeping pad wouldn’t be a bad idea if you want a bed-like surface.

Day 2: Bao Loc to Buon Ma Thuot 162.4mi, 9,541ft Leaving Bao Loc I roll through 65 miles of unmemorable highway before climbing up to about 4,000ft then descending for 15 miles on a stretch of road that is fun in a “this entire country is an incomplete construction project” kind of way.

Tip: I very, very rarely open up the brakes and fly down hills in Vietnam. Each presents new hazards —rockslides, buses overtaking trucks on blind corners, algae on wet cement, a monkey in the lane (seriously) — and launching myself over a goat into an oncoming bus directly conflicts with my plan to finish the ride on two wheels.

Around mile 135 I catch about 30 minutes of golden light as I cut between rice fields on a flat and windy stretch. It’s one of the moments on the trip when I wish I’d not just brought my phone to take photos. But, as the sun sets and the fields lose their saturation, I switch my focus to making Buon Ma Thuot before a truck forces me off the road into a pile of burning trash.

After the day��s ride I’m wiped. I picked up a cold in Saigon and after a couple days of dusty riding it catches up to me. I decide to take an easier day tomorrow.

I stay in the Ngọc Mai Guesthouse, which is a bit dirty though the owner is a cyclist and makes energetic conversation as I pack my bike up in the morning. He invites me on a ride with his club if I stay an extra day and finds a spare bar end plug to replace the one that popped out of my bars the day before.

Day 3: Buon Ma Thuot to Ea Drang 49.2mi, 3,435ft I start late after a breakfast of egg banh mi and a pineapple, another staple. The ride passes quickly and I end at Nhà Hàng Khách Sạn Hoa Dao, the shoddiest hotel of the trip. My room is on the third floor and there’s no elevator — just an elevator shaft with furniture blocking the hole — so I have to walk through the second floor, which is both a construction site and a laundry facility, it seems. Like many of the hotels on my trip, I’m definitely the only person paying to stay here. Wouldn’t recommend this one unless you design Call of Duty maps and need some inspiration.

Tip: Before giving a hotel your passport, confirm the price of the room — usually around 200,000 VND — then ask to see it, checking if the AC and Wi-Fi actually work.

Day 4: Ea Drang to Kon Tum 94.2mi, 5,269ft

Today is uneventful. Pleiku is miserable but Kon Tum is surprisingly lively and brimming with egg banh mis. I’ve now also added nuoc mia, fresh sugar cane juice, to my ride diet. It’s made with a cart-sized juicer and can be found in almost any town. Be forewarned, the variability in nuoc mia taste and quality is wider than any food I’ve ever consumed. If you get a good batch with ice and a bit of salt it’s the perfect ride drink. If, however, you get a slightly warm batch from a bad cane it tastes like lawn trimmings steeped in greywater. And never ever accept pre-made nuoc mia no matter how much you want it. Trust me.

I stay in the Thinh Vuong Hotel, home of the trip’s hardest beds.

Day 5: Kon Tum to Kham Duc 108.4mi, 8,983ft If given the option to do Saigon to Hanoi again, any way I’d like, I’d arrange a shuttle from Saigon to 70 miles into this leg. A lot of the riding up until this point has been hard in a not fun, feels like punishment way. Around mile 70 things shift.

Traffic has been steadily decreasing since Kon Tum. Mountains appear on both sides around mile 45. The vegetation grows more dense with each mile. Then the road surface switches to a corduroyed cement, a harbinger of the little used, often damp, terrain ahead.

I climb from 2k to 3k feet fairly quickly, dropping down into a small saddle before climbing up over 3k feet again. Then, without much warning, there’s a 2k foot descent on jungle switchbacks. I see a runaway truck ramp for the first time of the trip and know that I’m in the good stuff.

By the end of the descent it’s pouring rain and I take an easy spin into Kham Duc, which is the only place on the trip where I feel unwelcome. I fear I’ve crossed a cultural dividing line between south and north Vietnam and that all future interactions will be uncomfortable. This won’t be the case at all. Kham Duc just sucks.

I stay in the Be Chau Giang Hotel, which is unwelcoming though I hear it’s the best place in town.

Day 6: Kham Duc to A Luoi 135.5mi, 11,342ft I have no qualms about rolling out of Kham Duc before anyone wakes up. Today’s ride contains some of the trip’s longest stretches without any towns so yesterday I loaded up on food and water. I grabbed packs of peanut brittle, one of Vietnam’s only pocketable snacks with decent fat and calorie density. It’s usually available in towns, especially if you have some already and can show a shop owner what you want.

I ride alongside the Thu Bon River for 40 miles. The roads are damp from yesterday’s downpours but the sky is clear as the sun rises and burns off the fog between the mountains. At mile 40 I reach Thanh My and stop for two bottle fills of nuoc mia.

In Thanh My my route forks onto a quieter road, crosses the Thu Bon River, and punches up. I climb 1,000 feet then lose it all before climbing right back up to 1,700 feet. It’s about 30 miles to Prao, which is the last stop before 50 miles of uninhabited jungle. With no banh mi in sight, I grab more peanut candy and load up on water, filling my two water bottles and jamming two 1.5L bottles in my backpack. I also have a Sawyer water filter, which, in hindsight, I should have used during remote sections instead of schlepping water.

Heading out of Prao the road just climbs and climbs. The grade is gradual and undulating so I don’t go very high but with a loaded bike it sure feels like work. At this point I really wish I could throw my gear into a SAG wagon and pick up the pace. Since I can’t, I take it easy and gratuitously stop to shoot photos that glamorize the trip for my millions of followers.

23 miles into the section I start descending and wonder if I’ve hit the top, which I haven’t. 6 miles later the road pitches up and the rain starts. It’s the kind of rain that saturates everything in 30 seconds. August thunderstorm rain. I make sure my electronics are bundled up and continue riding. On several occasions I find myself laughing at just how bad the conditions are.

I pass through a tunnel and think I’ve hit the top. I haven’t. Eventually I ride through another tunnel where motorbikers are playing cards, waiting for the rain to subside. They give me a once-over, laugh, and keep playing. The descent starts and is over much sooner than I expect. After dipping in and out of a village, I’m on a plateau. If I turn left I’ll be in Laos after just a few kilometers. Instead, I turn right and head north, following an oddly straight road into A Luoi, where I’ll spend the night.

I stay at the Thanh Quang Guest House, which has a corrugated roof that is pitched in such a way that it amplifies the downpours to apocalyptic levels of noise. It’s shockingly loud but kind of soothing.

Day 7: A Luoi to Khe Sanh 65.8mi, 4,993ft Khe Sanh is as far as I can go today before another remote stretch so I take a slow morning. I poke around the town’s covered market, picking up any baked goods that seem appetizing. I try to buy bananas though after asking for just a couple the woman selling them laughs at me and hands me an entire bunch for free. I’m walking back to the guest house in the pouring rain when an elderly woman approaches me with an umbrella and insists on shielding me from the rain. We don’t speak each other’s language but both laugh at the image of her, at 4’6”, holding an umbrella over us while we walk down the street.

Back at the guest house I meet Kong, a Malaysian who grew up in Holland and is now teaching English in Da Nang. He’s making a visa run, taking a quick trip to Laos where he’ll have his passport stamped so he can return to work in Vietnam. He’s brought a friend along who wants to see the countryside. We sit on a stoop waiting for the rain to subside, which it sort of does, so we part ways.

At mile 13 I begin a 40 mile descent that starts with steep, misty turns before mellowing out and following a river valley north. Around mile 57 I cross a bridge and join up with a fairly major road that links Laos and Vietnam. I turn left toward Laos and climb for about 5 miles before I reach Khe Sanh where I stay in the Khanh Phuong Hotel, which is surprisingly comfortable.

During my nightly egg banh mi hunt I meet Mitch and Dave, who are traveling south by motorbike and have developed the same addiction. Laughing, they show me photos of Mitch’s scooter in pieces while it was being rebuilt at a roadside mechanic. I share my chocolate racecars as we swap info on each other’s upcoming sections. They tip me off to a hotel in Long Son, about halfway between Khe Sanh and Phong Nha. This info takes a huge stress off as I’d been mentally preparing to ride the entire 150 mile leg to Phong Nha in one day. It’s remote and I have no idea if I can get food or water on the way. More importantly, the Strava route claims 301 feet of elevation change, which is clearly wrong but I don’t know by how much. Turns out it’s off by about 13,000 feet.

Day 8: Khe Sanh to Long Son 83.3mi, 6,572ft I leave Khe Sanh loaded up with water and food for the 80 mile ride. 16 miles in I hit an unexpected town and grab two banh mis of the non-egg varietal. Obvious mistake. I continue riding but feel off for about 30 minutes.

As I leave town the road drops through farmland then climbs for about 10 miles, reaching 3,500 feet before descending into a valley. Around mile 43 the road kicks up and I’m back in the jungle, riding one switchback after the next for 40 miles. Aside from the animals and viruses that want to kill me, there ain’t much out here.

I stay in Long Son at the hotel, which looks like it could have been a car dealership in a past life. It has a huge front room with absolutely nothing in it. I can’t find anyone working or staying there so I go back onto the village’s tiny main stretch and buy a pineapple at a small shack. After sloppily peeling and eating it on the hotel stoop I investigate the single floor building again. Turns out the proprietor is sleeping in one of the rooms. I wake him up and he seems to have trouble understanding what I’m after, which is a bit odd. Eventually we sort the room out though he never seems to leave his sleepy, probably intoxicated, haze for the remainder of my stay. Also, he’s one of those Vietnamese dudes that regularly and loudly hawks up phlegm, which is particularly gross in an echoey building. Anyway, the room is fine.

Based on a comment in Tom’s guide, I eat dinner at a home near the hotel. Two huge plates of eggs, greens, and rice covered in chilis. A group of men working next door stop to investigate my bike. Throughout Vietnam people insist on grabbing the tires and knowing the price of my bike. They never approve of the 28mm tire width and are always shocked at the price, which I eventually decide is $800, an inaccurate number that’s high enough to trigger their desired response of “wow, that’s a lot” without making me look like a total moron for owning a bike worth more than their scooters.

Walking back to the hotel I’m glad to have split the trip to Phong Nha in two. It is possible to do the leg in one go but it’d be a long day with touring gear and mean passing stunning scenery in the dark.

Day 9: Long Son to Xuan Son 71.7mi, 7,067ft Today is very, very damp. Around mile 20 the day’s climb begins, about 13 miles and 2,000 feet. It’s never difficult riding but the corduroy cement on worn tires proves to be a grippy, slow combination. On several occasions I get off the bike and inspect it for brake rub, hub issues, or a trailer I didn’t realize I’m pulling. Turns out the road is just slow and after days of loaded touring and horrendous nutrition my legs don’t have much gas. I continue on, so slowly.

At mile 41 the most grin-inducing descent of the entire trip begins. It’s only 6 miles and 1,500 feet but after miles and miles of sticky cement it’s perfect. When I reach the end I can either turn right and go into Xuan Son or continue straight and visit one of Phong Nha’s famous caves. I opt to check out Thien Duong aka Paradise Cave. I’m not sure if something called Paradise Cave will be the worst thing I’ve ever experienced or actually cool. Turns out it’s really neat. I’m there on a weekday during the off season so it’s nearly empty. After an hour or so inside the cave I hop back on the bike and ride the 15 miles into town.

I stay in the Heritage by Night Hotel, which is overpriced (350,000 VND vs the normal 200–250k) and has terrible Wi-Fi. That said, it is distinctly without any of the backpackers that seem to fuel Xuan Son’s downtown of overpriced food and loud hostels. I heard the Phong Nha Farmstay is a nice option but their only available rooms were over 1M VND so I decide to pass.

Day 10: Xuan Son to Pho Chau 113.2mi, 4,770ft Before seeing the backpacker wasteland of Xuan Son I considered spending a second day around Phong Nha so I could check out another cave. I can’t stomach another day near that town so I hit the road.

After about 10 miles the day’s only climb starts, ascending 1,500 feet over 10 miles. During the descent my Revelate Sweetroll slips and starts lightly rubbing on my front wheel. I have headphones in and can’t hear it. By the end of the hill there’s a quarter-sized hole in the bag and a tire-shaped divot in the plastic coating on my u-lock inside the bag. Exasperated, I curse the thing for the 50th time of the trip and cinch things up as best I can.

Around mile 63 the road turns left and straightens out. I have the distinct sense that the fun, scenic part of the trip is over. I am right.

I reach Pho Chau and enter the only hotel of the trip that’s too dirty for even me, Khach san Ngan Pho. On seeing the cell they graciously allow me to pay for, I turn around and walk out. I find a perfectly nice room at the Ly Ha Hotel down the block. At the time I have no clue how fortunate that choice will be. I’ll be spending a few nights in Pho Chau after an unwise dinner decision.

Once I finish cleaning off my bike, a mandatory daily task to prevent drivetrain implosion, I set out to find food. My banh mi search is unsuccessful but I see a restaurant with people eating it, which is a good sign. I order the plainest thing I can with some nutritional value: rice and eggs. After my first plateful I order a second, doubling down on my demise. I pay my bill, walk back to the hotel, and go to sleep.

Day 11: Pho Chau to Toilet 0.0mi, 0ft Around midnight I wake up. Things are not well. I have a stomachache unlike one I’ve had in years. I think I’m going to throw up. Yup, I’m throwing up… now. My ungraceful and complete purge will continue for the next nine hours. I won’t be riding bikes today.

Around noon I trudge downstairs in zombie mode and show the hotel owner’s daughter a picture of Pedialyte. She laughs. I will not be getting Pedialyte in Pho Chau.

But I’m determined to not die. My day will end in a better state than it began. I throw a leg over my bike and head toward the central market. Surely someone has to sell some kind of concoction that will help me not die. Where are the elixirs made from endangered species I’ve heard about?

I find a window that looks like a pharmacy thing. I show the women inside a picture of Pedialyte. They take my phone, look at more pictures of Pedialyte, then say no without offering any other information. Dealing with people in Vietnam often unfolds this way. It’s like interacting with your computer terminal. “Do you have this?” “No.” And that’s it. No suggestions as to alternatives. No ideas as to where you might find it. It’s annoying.

Anyway, I see another pharmacy window thing and show the pharmacist the same photo. I get the same response, a hand gesture that means “I don’t have the thing you want.” At this point I’ve reached the edge of town so I’m ready to be a bit more creative. After a dozen translations via Google Translate — tip: only use it to translate nouns, full sentences seem to come out as incomprehensible — she decides to dig around her stores and unearths something called Oresol, which upon shaking the tube sounds like tablets. Maybe it’s similar to Alka-Seltzer? Good enough. I buy two tubes.

Feeling like I’m on a roll, I wonder if she has anything like Emergen-C, which might mix nicely with whatever this Oresol is. No luck with Google Translate. I start to point at stuff behind the counter. We find some packets that have pictures of oranges on them, they feel hard but look good enough. I’ll take ten. Back at the hotel I discover I’ve purchased ten packets of Flintstone-like vitamins. One out of two ain’t bad though.

The Oresol mix goes down fairly well and I slowly eat some bread, which also goes down ok. I feel pretty exhausted but desperately want to leave Pho Chau. I’ll head out tomorrow.

Day 12: Pho Chau to Thai Hoa 89.0mi, 3,399ft This is not a fun ride. I throw up once and don’t want to eat at all, which compounds my fatigue. The highlight of the day is reaching the end and seeing a kid power washing a bus. I pull over and ask if we can clean my bike. We take turns blasting the hell out of it, which is fun. I should end more rides with power tools.

I stay in the Ngoc Ha Hotel. It’s fine.

Day 13: Thai Hoa to Hanoi 157.4mi, 4,173ft Today I have to make a choice: buckle down and make Hanoi or split the leg in two days. I leave early and punt the decision to mile 82, where there’s a homestay option. There are some scenic-ish bits along the way but I’ve lost interest.

At mile 82 I feel tired but know I can finish the ride without much trouble so I make the call for Hanoi. Entering the city isn’t fun but not nearly as bad as leaving Saigon.

I end the ride at the Nova Hotel, an expensive (600,000 VND) though very pleasant option with a comfortable bed and great shower.

I’m tired and the bike is in rough shape but we made it. 2,000km of occasionally scenic roads in the books. Now for some cultural meat and a beer.

Thanks for reading! If you like this sort of thing you can subscribe to my newsletter about bike rides.

Here are the tips that didn’t make it into the report.

1. I wouldn’t recommend someone else do this ride. However, a very fun trip would be from Day 5, Mile 70 to Day 10, Mile 64. Better still would be doing that stretch with a SAG wagon carrying all your stuff and plenty of high quality food. Nutrition was a big problem for me.

2. You must be able to fix everything on your bike. I got zero, yes zero, flats on this ride but did have to deal with a loosening rear hub, a left crank trying to unscrew itself, and a front derailleur shifting horribly from unending dirt exposure.

3. These roads are very dirty. You’ll need to clean your bike every day to keep it moderately functional.

4. The Kryptonite U-Lock I brought was totally overkill. In Vietnamese cities there are security guards to watch over scooters and bikes at almost every shop. In the countryside my bike never left my sight. Also, people here want scooters more than your silly bicycle. A simple cable lock would be fine.

5. When planning daily miles, be conservative. Keep in mind that you’ll need to do the miles even when it’s pouring rain and you have several mechanicals.

6. I didn’t bring camping gear because I knew hotels would be super cheap. It’s obviously possible to camp but I wouldn’t recommend it. I saw very few attractive roadside options and think the language barrier with farmers would prove to be a real challenge. There’s also unexploded ordnance littered all over Vietnam from the war so…

Selected Gear Notes Highlights: Rapha Classic Jersey — Mine’s seen a ton of use and is ready to be retired but I’ll be replacing it with the same thing. This is the only jersey I brought.

Shimano SH-M163 Shoes — These were the perfect choice. Stiff enough to ride long days but totally comfortable when walking. They’re the only shoes I brought.

Cuben Fiber Electronics Sleeves — I had extra CF lying around so I made sleeves for my phone and laptop. They were a nice precaution when the rain was really coming down.

Clement Strada LGG 28mm Tires — Great choice for questionably-paved roads. That said, they aren’t the longest lasting tire so you might want to consider alternatives for touring.

Meh: Revelate Tangle Frame Bag — Got the job done but it’s not great. One thing in particular is super annoying. The lefthand pocket has an internal sleeve whose top is at the exact height of the outer zipper. It gets caught in the zipper often enough for it to be an issue.

Revelate Viscacha Saddle Bag — Works but wiggles when you’re out of the saddle. I’d recommend buying one with a support like the Porcelain Rocket version.

Lezyne Road Drive Pump — Works but also ripped the valve out of the stem on two occasions. It’s probable that this was user error but in my mind that’s a bad design.

Rapha Backpack — I decided to bring my laptop so that meant either panniers or a backpack. I opted for the backpack. This bag’s build materials, especially the zippers, aren’t nearly as nice as what I’ve come to expect from Rapha.

iPhone 6S — Great GPS with a mediocre camera.

Garmin 510 —Buggy routing and clumsy touchscreen but good ride tracking with a long battery life.

Bad: Revelate Sweet Roll — Doesn’t work well on a road bike with any substantial weight. Always slipping down into the tire. Would not recommend.

ProLink Chain Lube— Lube works but the bottle is prone to leaking so it’s a poor choice for touring.

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craigrcannon · 9 years

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Biking up a Hill for Two Days

Heads up! This is a super long post about bike stuff.

If you enjoy stuff like this, I’m starting a newsletter where I’ll report back on awesome rides people have taken. You can subscribe here.

3:00 AM, Sunday, Hour 34 I rotate my left foot and unclip from the pedal. My cleat clumsily finds level ground among the gravel on the road’s shoulder. Hunched over, forearms on the bars, I know what’s happened. Sleep deprivation is sinking its teeth in and the longer I’m at a standstill, the harder it’ll be to restart.

I have to make a choice. Rest or push through?

Up to this point sugar and caffeine have kept me going but as I lift myself off the bars and put my right foot on the pavement, the choice is clear – my legs are wobbling and my head is heavy, so heavy – I have to take a break.

We open the hatchback’s rear door, throw the bags out of the way, and I crawl in, barely finding the energy to swallow a couple painkillers and drink water before I curl up between a track pump and what looks to be a refrigerated tote bag. Instantly I’m asleep.

29k In June I heard about a challenge: 29,028.9 feet of elevation in one ride. People call it Everesting and as with all niche activities, there are plenty of rules. The most important rule is that you pick one hill and ride laps of it until you break 29k.

Yes, you literally ride up and down a hill until your reach the height of Everest. I know, it’s crazy.

But the thing is, when I started road biking last year I found myself drawn to climbs. They stir up a meditative state in me. I love riding big climbs for the first time, never knowing what’s around the next corner, hoping they’ll never end. Even now as I write this I’m imagining my current fascination, the Dolomites. I see them, the remote single lane roads. I feel their well-worn pavement. All I’m left to wonder is just how high they’ll go. And oh the post-ride pizza!

On June 21 I climbed the 29k and ended the ride feeling great in spite of the fact that my “nutrition” consisted of a pizza I left in my car at the bottom of the hill. Thankfully there was one slice left so I could snag that Garmin Instagram at the end. 🏄

Immediately I started looking for something bigger. I came across the 48 hour record, 94,452 feet, and felt pretty confident that I could top it. So, I composed an email about the attempt to my bike group, the Knackered Tyres, then let it sit in my drafts folder for a couple days. Once I overcame my fear of looking like a doofus if I didn’t break the record, I sent the email, and the dates were set: August 7-9.

3:20 AM, Sunday, Hour 34 I’m woken up having slept 20 minutes. Time to get back on the bike. I push aside the spare wheelset leaning on the door and crawl out of the hatchback. I stand up. I feel alert. I feel strong. Sleeping worked! Wait, maybe it was the painkillers. No, it was definitely the sleeping.

I look over at Hank Field who has generously and perhaps insanely volunteered to ride with me from 1:30AM-6:30AM. He looks to be in great spirits. He’s ready to roll. I slide my shoes back on, take a sip of tea, and we’re off.

“Training” I put training in quotes because I wouldn’t go so far as to call what I do training. There’s no real rhyme or reason to my riding. I ride 100-200 miles per week with a good amount of climbing thrown in. I don’t have a power meter or heart rate monitor though maybe I will someday. Up until now it’s just been about riding hard when I feel good then still putting in miles when I feel slow.

That said, going into the 48 hour ride confidently was important so I ran two tests.

1. Can I stay awake for 48 hours? I woke up on a Friday morning at 5:30AM and went through my day as I normally would. Then for the remainder of the weekend I went on short 10-25 mile rides every few hours, testing to see how I performed without sleep. After about 20 hours of awake time I found I was pretty much useless for anything but eating, watching Netflix, and riding bikes.

On Saturday one of the KTs, Eric House, invited me to ride Mt. Diablo the following morning. As you might know, Sunday at 8AM is more than 48 hours after 5:30AM on Friday. I thought it’d be a good test of my abilities so I slept 90 minutes and went for it.

During that ride I realized I needed to use an electrolyte mix with protein or else my legs would start to feel mushy. All the little things you can get away with on a short (less than 6 hour) ride, like drinking just sugary electrolyte supplements, don’t fly on longer rides. They tend to create exponentially larger problems as the hours increase.

2. What does a 24 hour ride feel like and how much elevation can I get during it? I hadn’t ridden anything close to 24 hours before so I needed to know what I could expect from my body and also from the course throughout the day.

I started at 7:30AM on Saturday with a car full of food and water. Many KTs joined throughout that ride, cheering me on while plying me with carbs. On that ride I got into the mid-40s and though I’d hoped to hit 50k, I felt that when the day came, my learnings from the test ride in addition to the excitement of the attempt would be enough to push me past the record.

On that ride it became clear that I’d burn a ton of time if I tried to self-support. Ernst Schmidt told me this before the ride but I didn’t fully believe him until I experienced it firsthand. All your breaks add up and are much longer than you think when you’re sleep deprived. So, my mom ended up flying out from Boston for the record attempt and running support for the entire 48 hours. She’s awesome.

After those two tests I felt confident that the record was doable so I focused on getting in miles without taking risks - no super long rides or fast descents. I have no idea how tapering works.

4:00 AM, Sunday, Hour 35 Sleeping 20 minutes changed everything. Right before the break I was taking about 13 minutes per lap; I need to be under 12 minutes to break the record. Now I’m feeling strong and knocking down one 10 minute lap after the next.

With that sleep break I burned the extra time I had from riding quickly on Friday night, but it doesn’t matter. I don’t need any more breaks. It sounds insane but with 14 hours to go, I can see the light at the end of the tunnel.

10 minute lap. Then another. Then another. We have it.

The Bike I ride a steel bike made by Jeremy Sycip in Santa Rosa, CA. It’s super smooth and with the 36 spoke wheels I have (not pictured) I can pretty much ride any road, paved or dirt, and not worry about it. Yes, there are lighter bikes in existence but I’m also 170 lbs so worrying about a couple pounds on the bike is sort of like weighing a car without the engine.

Weight aside, the bike has a story and it’s neat to have a connection to the person that made it. Jeremy heard about the ride and emailed congratulating me, which was pretty awesome.

Here’s the setup I used for the ride if you’re interested: Sycip Roadster, Shimano 105 11 speed, 50/34 crankset, 11-32 cassette, ENVE Road 1.0 fork, Velocity A23 36 spoke wheels with 105 hubs, and 25mm Continental Grand Prix 4000 S II tires at 110 PSI.

2:00PM, Sunday, Hour 45 Damn, it got hot. I wasn’t expecting heat.

Yesterday was 65 and cloudy. Today’s sunny and 80. I feel like I’m riding in a sauna. My breathing is short. The road’s radiating heat. I take a break and water’s dumped down my jersey–too much water. My chamois is soaked. I run behind a car and drop my shorts, replacing the wet ones with others that are sweaty but not soaked.

Each minute is ticking by faster. We’re on target but it’s going to be close.

We pass 90,000 feet.

The parking lot at the bottom of South Park is filling up with friends.

91,000 feet.

People are literally watching us ride up and down a hill. We joke about having created the NASCAR of cycling.

92,000 feet.

From here on out I’d like to talk about how tire pressure relates to rolling resistance on endurance rides.

Just kidding.

3:30 PM, Sunday, Hour 46 93,000 feet.

One more rider joins the pack. Then another, then another.

I’m committing the cardinal sin of staring at my Garmin. I’m watching the feet climb. Everyone knows we’re close but I’m the only one who has the live numbers.

93,500 feet.

Three laps to break the record.

94,000 feet. I let the group know. Everyone’s looking lighter on their pedals.

We hit the bottom of the hill. There’s a crowd. I call out, “this is it!”

Friends start clapping and shouting. We’re all smiling as we turn around and point uphill.

We start the climb, the numbers tick away on the Garmin, which I’ve come to accept doesn’t care how far I’ve climbed. Then it happens.

94,452 feet. “Got it!” “Woohoo!” We’re exchanging fist bumps, back pats. I laugh as I nearly crash with another rider while giving them a high five.

We hit the top of the climb. We have more than 20 minutes left. I look at Ernst, “two more laps?” “I was hoping you’d say that.”

What’s next Two weeks ago I was just some dude who biked a lot. Now people are asking me what’s next. It’s kind of wild.

I’d like to devote more time to planning, riding, and documenting endurance rides. While taking time off the bike this week I’ve started to look for new rides. Long miles, tons of elevation, and plenty of gravel. These are rides that don’t offer bailout options and could leave me slumped over at a remote general store asking for a bed and a pizza IV. I’m super excited.

If you’d like to follow along, I’m starting a newsletter to share ride reports from awesome people. You can subscribe here.

Last thing. I’m thinking about taking on a sponsor to help make more rides possible. If your company is interested, my email is [email protected].

Thank you for reading this. Now go ride a bike!

See the ride on Strava.

Thanks to all the people that made this record possible: Ernst Schmidt, Hank Field, Paul McKenzie (he rode 10k!), Bernard Demai (he’s 68 and rode 6 hours on a single speed mountain bike!), Kelly Keller, Matt Raimi, Laurence Witschi, Phorest Bateson, Gabor Torok, Eric House, Mike Wachter, Kristen Anderson, William Holzapfel, Peter Repetti, Charlie Huizenga, Bridgette Anderson, Luke Iseman, Adam Peterson, Brian Janosch, Allie Townsend, Knackered Tyres, East Bay Velo Club, and of course, Jeanmarie Cannon.

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