Employee #1: Reddit

by Craig Cannon7/7/2016

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!


  • Craig Cannon

    Craig is the Director of Content at YC.