A major shakeup in Silicon Valley this weekend. Ellen Pao forced to resign after a very nasty and very public revolt by Reddit users.
In July of 2015, the struggling CEO of Reddit at the time, Ellen Pao, made a decision that broke the camel's back. She abruptly fired someone who's loved by the moderator community, and they pulled the biggest lever they had.
A lot of people visiting the popular social sharing website Reddit hit a wall. Volunteer moderators of many subreddits, forums for topics from history to video games, had locked out users.
Over 2,000 subreddits, many of the most popular ones, went completely dark.
Now, we haven't communicated well, and we have surprised moderators and the community with big changes. The mods in the community have lost trust in me and in us, the administrators on Reddit.
Today, Reddit is the sixth most visited website in the world and is a public company worth over $30 billion. But a decade ago, it almost stopped existing. Welcome to Leap Forward. I'm David Rossenko. Today on the show, Steve Huffman, Reddit's founder, who came back as CEO to rescue the site and turn things around. And Chris Slow, Reddit's first employee and later its CTO.
I heard it was going to be a radical expose on Steve. And you know, after 20 years, I'm here for it.
In today's episode, how a couple college kids built one of the most important places online for human conversation that is now also becoming the next training ground for AI. Here's Steve Huffman. Uh, you ready to get started?
Steve, thanks for coming on the show.
My pleasure. Great to see you.
So, to kick us off, actually, we already talked to Slow and we have a few clips to play for you. Steven Lad Huffman, first of his name. How can I describe him? He is kind of the spirit of Reddit as an embodiment. Uh, he is snarky, he is funny, he is a warm gooey center surrounded by a prickly surrounding that is a total uh distraction on purpose uh to protect his warm gooey center. Cares a lot about people. Uh, fantastic technologist. There's a couple of engineers that I've known over my career who I usually refer to as infuriatingly correct, and he is in that category. So, it's funny because I'd also describe you as Reddit in human form. Like, which direction do you think that went? You think you influenced Reddit or Reddit influenced you?
I think it goes in both directions for sure in that I submitted most of the content in the early days. And so, yeah, there was a lot of tone setting there. But I was also both me and Reddit are, you know, of the early internet. I think I was shaped by growing up online. So when I went to public school and middle school in Virginia and school got out at like 2:30, but it was walking distance from where my mom worked as a lawyer. And so I would walk over to her office which was next door to the public library and they had the internet. And so I would spend basically two, three hours a day every day after school on the internet at the public library. And so that's where I became like immersed in the kind of early internet culture when the internet was this like kind of wide open, free, funny, unregulated space.
You said when you went to the library you kind of like immersed on the early internet. It was post BBS, right? So it would have been like forums or...
So it was a little post BBS. So BBSs were still around. So I did do BBSs as well. Uh, there was a couple local ones. Um, but then on the internet, so the web page I went to the most often, I think it was a website for a European college, but it had the Hacker Manifesto. It had the Bastard Operator from Hell, uh, which I loved reading those. The Tools Guide to Lockpicking. So it had kind of all this like early internet culture stuff. That's the culture that I really kind of grew up in.
What was home like? Like was it a funny household? Did you guys play pranks? Like what was kind of the vibe at home?
My parents divorced when I was young, when I was like four. And so I kind of had two homes. So I primarily lived with my mom and my stepdad. I didn't have internet at home. On the internet, the web page I went to the most often, I think it was a web page for a European college. It was like this university web page, but it had the Hacker Manifesto. It had the Bastard Operator from Hell, which I loved reading those. It had, I think, the Tools Guide to Lockpicking. So, it had kind of all this like early internet culture stuff, kind of all of this stuff. And so, that's what I grew up reading. Now, I was a kid though, so all that content was probably created by, you know, 20, 30, 40 year olds. So, I was like a little young for that. But that's the culture that I really kind of grew up in online.
Did you ever get in trouble at school for any like trolling or pranks or...
Well, so the lockpicking which I learned on the internet. Yeah, I got in trouble for that. So, uh, so I went to this small private school in Virginia. And so the night before we graduated, we picked our way into one of the classrooms that I knew had a trapdoor to the roof and we climbed up there and we just kind of spent the night hanging out up there. Um, but then we'd also got into the office of the school and like looked at our files and next morning all of our families come into the gymnasium for graduation and they have us in this classroom and then our headmaster, um, Mr. Quinn comes in and he says, 'Some of you broke into the school last night. We're not going to let you graduate until you give us the key that you used to get in.' Like you literally are not graduating until you give me this key. And so our families and friends are all waiting. I think by now it's like 9:30. Finally, one of my friends, um, goes to Mr. Quinn and says, 'Uh, Mr. Quinn, there was no key. Uh, we picked the doors.' And Mr. Quinn's like, 'That's not true.' Like that's only in movies. The standoff continued and then finally Mr. Quinn said, 'Okay, um, if you can pick the door in front of me, I will believe you and then you can graduate.' And so I just had to pick a classroom door in front of all of my friends and Mr. Quinn so that we could graduate. Now, I was like super nervous, so like my hands were shaking. So, it took me a few minutes, but finally the lock popped open and Mr. Quinn goes, 'Well, shit.' Uh, and then we got to graduate.
So, um, that's awesome. So, moving on to how Reddit was started. You know, you famously attended Paul Graham's How to Start a Startup talk at Harvard. Then you apply to YC, you get rejected, Paul calls you back, you know, you get off the train, you come back and you brainstorm and come up with the idea for Reddit there at that point. Like, what was that idea for Reddit?
So, uh, the original idea for Reddit, it was like two ideas. So Paul loved this website called Delicious. And Delicious was a social bookmarking website. So if you found a website you liked, you could bookmark it on this website, Delicious. There was this page on Delicious called Delicious/popular, which was showing the most popular things that had been bookmarked. But Paul Graham pointed out that why do you bookmark things? You bookmark things because you can't read them in one sitting or maybe you want to come back and reference them later. So it was this dynamic list of the most popular boring pages on the internet. And so Paul was like, 'Well, what if that was good content? What if that was interesting things?' So that was half the idea for Reddit. The other half was Slashdot. So I was a Slashdot user. The title was Slashdot: News for Nerds, Stuff That Matters. But within each of these posts, there were comments, and that's where the Slashdot community lived was in the comments. And it was a really vibrant, interesting, funny community. And so the first idea for Reddit was basically Delicious plus Slashdot. The user-powered nature of Delicious, but the community that lives in the comments of Slashdot. Those are the primitives for Reddit still today.
That was the very first YC batch ever. Do you remember meeting Chris and what your first impression of him was?
My first impression of Chris, you hear him before you see him because he has a very distinct laugh. He laughs a lot and it's a loud laugh. And as you were asking that question, I heard Chris laugh. I'm at the office right now and so I heard him laugh through the wall. Um, now he was there with a different company, uh, called Mam that he started with one of his college buddies, Zach. But yes, meeting Chris, uh, and hearing Chris was probably my first memory actually.
Um, and then at some point Steve and Alexis moved into your apartment, right? Was that before or after you had started working on Reddit?
Um, so, uh, that was before. So, the way that it ended up was, uh, at the end of the summer, I had a failed startup. We just couldn't get it off the ground. They quickly needed a place to stay. And here I was with two free bedrooms in my apartment, um, with, uh, no co-founder left. And so, they moved in as roommates actually originally. So, I think they moved in in September. And in October, I officially started at Reddit as first employee.
Just painting a picture for us, like what was that apartment like? Like, where was it in the city? Like was it small, big, like you know, clean, messy, like what are we dealing with here?
Um, so it was a three-bedroom apartment and the whole building was probably slowly imploding. And so we're all sitting around in a circle all facing the wall. Uh, and legitimately we all had to tape up the wheels on our chairs cuz if you let go from your desk, you would just slowly by gravity fall back towards the center of the room. Um, and then of course Steve being the CEO, he's the one who had the window which looked out three feet across an alley to a wall. You know, top-notch startup living, uh, 2005.
Yeah, it was as messy as it sounds. I think every day we just wake up and think about what would be cool to make on Reddit that day and then make it. I think our planning horizon was max a day or two and Chris was doing double duty. He was finishing his PhD at Harvard. So he would wake up before we did, go to work at Harvard. Uh, we would get up and work and then Chris would get home when it was dark out and then we'd go to bed and he would stay up working on Reddit.
Grind till probably 1 or 2 in the morning, go to bed, restart the next day.
Why didn't you drop out of your PhD? Like, why do both at the same time?
Um, honestly, it was just a heck of a lot of fun. The reason I had started doing startups in the first place was because after about four years in grad school, I started actually getting a little burnt out. You'd think that the way to get around burnout wouldn't be to like stack a startup on top of it. But the side effect of the startup was like it was an entirely separate interesting creative outlet. So it was almost like I could put my energy into grad school by day and kind of get that work done and then switch gears and have like a totally interesting, like fascinating project at night. Um, with honestly a lot of like, a lot of just kind of like, the camaraderie was great. Like, you know, if you want your startup to succeed the team has to work well together and at that point 2006 like everyone got along really well and like we just were kind of grinding away trying to make it succeed.
So kind of through those early days, you know, Reddit keeps growing, it keeps growing. You know, at some point you get approached by Conde Nast. Like, what did Reddit look like when you decided to sell the company?
We started in June 2005. I think we started talking to Conde Nast around maybe March 2006, so not even a year. Reddit was a handful of communities then, so users couldn't make subreddits quite yet. Um, but we had made a few ourselves but there was a vibrant community there. Um, and this was part of Conde Nast's push to digitize Reddit. The original pitch for why Reddit made so much sense in Conde Nast was that Conde Nast was this kind of like media powerhouse and this ad sales powerhouse, right? Like people come to them with sacks of money and just like want to buy advertising. And then Reddit is this traffic engine where not only can we send traffic around, but like it was growing like gangbusters. Like we were doubling every three months at that point. Um, but we weren't sure we wanted to sell the company. We were open to it because it seemed like that was the prophecy, right? Join YC, create company, sell company, right? That was the kind of Paul Graham school of business. And the deal took a long time. And so there was a moment I remember a couple days before we closed where like we knew it would actually get there. You know, I think we had walked away a couple of times along the way as you should do I think in any deal.
Where I was very emotional because it just felt like a dream come true. Like, started a company under the tutelage of Paul Graham who was a big part of the internet culture I grew up with. So we talked about all that internet culture. A big part of that I forgot to mention was actually Paul loved programming in Lisp. He was probably the most famous Lisp programmer. He wrote a couple books on it. He was very popular on Slashdot, his essays, and that's how I met Paul is through his essays which I learned about through Slashdot. So Paul is a big character in my life. So when that came true, I was very emotional. Um, I remember crying with kind of relief and happiness. And, you know, then we actually closed it. It felt mostly like a non-event. I think I remember being in the room signing the papers. I had already kind of gotten my emotions out. And then I moved to San Francisco to work on Reddit at Wired's office and so it was basically like we had this nice moment but I loved working on Reddit and so it was just like back to work.
I remember, um, yeah, I mean you moved to San Francisco in late 2006, I moved there in early 2007. You know, we lived in like North Beach in the Y Scraper, a couple floors away from each other. I mean, I was straight out of college, right? Like, we had no money. And I remember heading out to the bar and thinking, 'Man, Steve's rich. He's buying drinks tonight.' How did the sale change your life at the time? Or like, was it just back to normal and back to working on Reddit?
Um, it certainly, I mean, changed my life financially in a major way. Prior to the sale of Reddit, I probably had maybe $1,000 in my checking account, maybe. And so all of a sudden, going from that to like a million when you're 21 was a huge change. I mean, life-changing. At that point, uh, I was making $25,000 a year as a grad student. Um, and then, you know, we all did the same thing, which is like we all literally like went to the ATM that day as soon as everything cleared and like, you know, kept the receipt. Um, cuz it's like, oh, look, that's a comma that I've not seen before. That's kind of cool. That was actually Halloween. And so, we ended up having what I would call the world's lamest Halloween celebration party. We all dressed up. Uh, we went to the Kong, which is a notorious Chinese place in Harvard Square, drank scorpion bowls and just kind of hung out for the night. And so it was like very exciting. It was an unfathomable amount of money. Um, but I had this conflict which is I was like, am I supposed to quit? Like am I supposed to retire? I love working on Reddit. Like what do I do? Because the prophecy, right, is like, oh, kid moves out west, starts tech company, strikes it rich, uh, then I don't know, day trades or something like that. You know, but I didn't know the next step and so all of a sudden I was 21 and had checked off everything that I conceived of on my life plan at that point and so it was a little bit of a maybe a midlife crisis.
And then actually, um, funny thing was that, um, so literally the next day, it's November 1st, I call up Steve for dinner and I'm like, hey, Kristen and I are making pizza, do you want to come over? And his response was, I'm in San Francisco. He literally like taken the first flight out the next day and just like moved to San Francisco. And so that's when I, you know, met you and kind of the next crew of YC founders. I'm actually looking back really grateful to have been in that building. Um, it was like me, uh, the Twitch guys, Justin Kan, Michael Seibel, uh, you guys, the Weebly guys. I think there was 13 companies in that apartment building in San Francisco at its peak. So I'm so grateful to have been continue to be that deep in the early startup culture so that I didn't like accidentally escape. I remember seeing everybody starting these companies like, oh yeah, like not only is the story not over, it's like just barely beginning.
Was there a moment when like the gloss wore off and the excitement kind of faded and the reality of working at a big company, you know, kind of took over?
Yeah. So, when I showed up to work at Wired on my first day, they gave me an iBook, which was like the cheap entry-level Apple student computer that was like supposed to be my work computer. And I was like, are you guys like, it's like I just sold you my tech company and you're giving me this like plastic laptop. Like, is this a joke? Um, so there's a lot of moments like that where I was just like a little young, arrogant, salty kid. And so I was like, I'm going to put this in a drawer and I'm just going to work on Reddit. I was like unmanageable, like completely unmanageable. Uh, so my boss was Caro. He was the corp dev guy who executed that deal. I had a great relationship with him, but I was just like such a little turd. You know, uh, and so yeah, I had a hard time conforming to the big company bureaucracy. But we had contracts from the acquisition for three years and so I would leave at the end of the three years just because I felt like I was supposed to and I wanted to own my own company again.
