How Reddit Was Born, Sold, Broken…and Rebuilt: Steve Huffman & first employee Chris Slowe

[00:00:00] The major shakeup in Silicon Valley this weekend, Ellen Powell 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 made a decision that broke the camel's back. She abruptly fired someone who was 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.

[00:00:31] Over 2,000 subreddits, many of the most popular ones, went completely dark. Now Ellen Powell did respond to this. She says, Today, Reddit is the sixth most visited website in the world, and is a public company worth over $30 billion. But a decade ago, the media started to be launched in the community. The media started to be launched in the community, and the media started to be launched in the community. Today, Reddit is the sixth most visited website in the world, and is a public company worth over $30 billion.

[00:00:59] But a decade ago, it almost stopped existing. Welcome to Leap Forward. I'm David Orsenko. Today on the show, Steve Huffman, Reddit's founder who came back as CEO to rescue the site and turn things around. And Chris Slo, 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.

[00:01:27] 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. Are you ready to get started? Yeah, let's go. Steve, thanks for coming on the show. My pleasure. Great to see you. So, to kick us off, actually, we already talked to Slo, and we have a few clips to play for you here.

[00:01:56] Steven Ladd Huffman, first of his name. How can I describe him? He is kind of the spirit of Reddit as an embodiment. He is snarky. He is funny. He is a warm, gooey center surrounded by a prickly surrounding that is a total distraction on purpose to protect his warm, gooey center. He cares a lot about people, fantastic technologists. There's a couple of engineers that I've known over my career who I usually refer to as inferiorly correct, and he is in that category.

[00:02:24] So, it's funny because I'd also describe you as Reddit in human form. Like, which direction do you think that went? Do you think you influenced Reddit or Reddit influenced you? You know, 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 of the early internet. I think I was shaped by growing up online.

[00:02:53] 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 in the public library. And so, that's where I became like enmeshed in the kind of early internet culture.

[00:03:20] 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 enmeshed on the early internet. Do you remember any, it was post-BBS, right? So, it would have been like forums or? So, it was a little post-BBS. So, PBS's were still around. So, I did do BBS's as well. There was a couple local ones.

[00:03:45] But then, on the internet, so the webpage 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, which I loved reading those. Ted the Tool's 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?

[00:04:15] Did you guys play pranks? Like, what was kind of the vibe at home? So, 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. And my home with my mom, that was also like school and sports. And that kind of routine and rigor. And then I'd spend primarily my summers with my dad. Which was basically not school.

[00:04:42] And so, that would be like all sports, all fun, all games. And so, it was like a little bit of a mix. And then, both sets of parents had two sons themselves. So, they were very, very busy with the young kids. And so, my sister and I, as a result, I think became very close. Did you ever get in trouble at school for any like trolling or pranks or? Well, so, the lock picking, which I learned on the internet. Yeah, I got in trouble for that.

[00:05:10] 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. 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.

[00:05:39] And then, the headmaster, 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 use to get in. Like, you literally, you 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 930. Finally, one of my friends goes to Mr. Quinn and says, Mr. Quinn, there was no key. We picked the doors. And Mr. Quinn's like, that's not true. Like, that's only in movies.

[00:06:09] So, standoff continued. And then finally, Mr. Quinn said, okay, if you can pick the door in front of me, I will believe you and then you can graduate. 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. And then we got to graduate.

[00:06:38] 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, the original idea for Reddit, it was like two ideas. Paul loved this website called Delicious.

[00:07:06] 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 slash 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.

[00:07:37] 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.

[00:08:04] 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, even. Do you remember, like 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 there's a very distinct laugh. He laughs a lot. And that's a loud laugh.

[00:08:34] 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. Now, he was there with a different company called Mamap that he started with one of his college buddies, Zach. But yes, meeting Chris and hearing Chris was probably my first memory, actually. And then, at some point, Steve and Alexis moved into your apartment, right? Was that before or after you had started working on Reddit? So, that was before.

[00:09:02] So, the way that it ended up was, 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 with 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 paint a picture for us for 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? Oh, okay. So, we're dealing with a three-bedroom apartment.

[00:09:32] And the whole building was probably slowly imploding. And so, we're all sitting around in a circle, all facing the wall. And legitimately, we all had to tape up the wheels on our chairs. Because if you let go from your desk, you would just slowly, by gravity, fall back towards the center of the room. And then, of course, Steve, being the CEO, he's the one who had the window, which looked out three-creet across an alley two-way wall. You know, top-notch startup living 2005. Yeah, it was as messy as it sounds.

[00:10:00] I think every day we'd 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. 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.

[00:10:30] Yep. That was true for the first year. So, I would start work at around like 7 o'clock, 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? 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.

[00:11:00] 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, fascinating project at night. With honestly 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 Condé Nast.

[00:11:27] Like what did Reddit look like when you decided to sell the company? We started in June 2005. I think we started talking to Condé around maybe March 2006. So, not even a year. Mm-hmm. Reddit was a handful of communities then. So, users couldn't make subreddits quite yet. But we had made a few ourselves. But there was a vibrant community there. And this was part of Condé's push to digitize.

[00:11:55] The original pitch for why Reddit made so much sense with Condé Nast was that Condé 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. 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?

[00:12:23] 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. Mm-hmm. Where I was very emotional. Because it just, it felt like a dream come true.

[00:12:50] 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. I loved programming and 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 we 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.

[00:13:18] I remember crying with kind of relief and happiness. And, you know, then we actually closed it. It was less, it felt mostly like a non-event. Mm-hmm. I remember being in the room signing the papers. I had already kind of gotten my emotions out. And then later, I moved to San Francisco to work on Reddit at Wired's office. And so, it was basically, it's like we had this nice moment, but I loved working on Reddit. And so, it was just like back to work. Yeah.

[00:13:47] I mean, you moved to San Francisco in late 2006. I moved there in early 2007. You know, we lived in like North Beach and 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? It certainly, I mean, changed my life financially in a major way.

[00:14:12] 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, I was making $25,000 a year as a grad student. And then, you know, we all did the same thing, which is like, we all literally went to the ATM that day as soon as everything cleared. And like, you know, kept the receipt.

[00:14:42] Because 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. We went to the Kong, which is a notorious Chinese place in Harvard Square. I 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.

[00:15:08] 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 a tech company, strikes at rich, then I don't know, day trades or something. Like, you know, but I didn't know the next step. 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 maybe a midlife crisis.

[00:15:38] And then, actually, the funny thing was that, 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 he's just, his response was, I'm in San Francisco. He'd 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.

[00:16:07] It was like me, the Twitch guys, Justin Emmett, Michael Kyle, 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, continued 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.

[00:16:33] Was there a moment when, like, the gloss wore off and the excitement kind of faded and the realities 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 on a 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?

[00:17:10] I was, like, unmanageable, like, completely unmanageable. So, my boss was Coro. She was the corp dev guy who executed that deal. I had a great relationship with them, but I was just, like, such a little turd, you know? And so, yeah, I had a hard time conforming to the big company bureaucracy. But I had a, 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.

[00:17:38] When you did decide to leave, the most common outcome, like, when a founder leaves acquired company is, like, that that thing just kind of withers and dies. Like, did it feel like that's what was going to happen to Reddit? Or, like, what did it, what did you think was going to happen to Reddit when you left? I didn't feel like that would happen. I don't know if I gave much thought to it, to be honest. Like, it wasn't a big team to begin with, but the majority of the team was staying. And so, no, I didn't really worry about it dying. I think the other founders left in, like, around 2009.

[00:18:09] What was the office like after they were gone? Um, yeah. So, Steve and Alexis both left in 09. And at that point, I decided to stick around for a year. But it was a tough year. One thing that made it very difficult was that just because you can sell ads on the September issue of Vogue doesn't mean you can sell ads on a product like Reddit, which at that point was described as dystopian Craigslist as far as a user experience. And so, it was very difficult actually for the sales team to sell Reddit. Mm-hmm.

[00:18:38] We weren't making money compared to the rest of Condé. They were happy to include our traffic numbers in their totals for how big of a media company they were. But it was very difficult to actually make enough money to even cover costs. But credit to them, like, they kind of kept arm's length. They didn't squish us. Typical startup destruction is like the parent company comes in and just kind of sucks the marrow out of the bones and just, like, leaves the husk of the company behind. We were kind of left to our own devices for good or for bad. And that was actually, I think, what kind of saved Reddit. And at this point also, Reddit was still growing pretty rapidly.

[00:19:07] So, 2010 was the year where we definitely passed through a billion impressions a month. And we're still scaling up pretty rapidly. Wow. It was a tough combination. So, yeah, I mean, you're a skeleton crew. You know, you're serving a billion impressions a month. I mean, did you, like, did you think about leaving? Like, why did you stick around? I ended up leaving. I ended up making it just about a year and then ended up jumping ship and joining Hipmunk. There was probably a last straw, which was mostly that we couldn't hire.

[00:19:32] In fact, the negotiation that I had on my own departure was, when I leave, you can't destroy my seat. Can you, like, can we hire somebody in my seat? And that person that we hired actually ended up being pretty important. And also at one point was the only employee working at Reddit. I still used Reddit every day. It's such a funny decision in hindsight to leave, but I had no perspective. You know, I started another company about six months later called Hipmunk. And we sold plane tickets. We were competing with Kayak.

[00:20:03] It was my time at Hipmunk that allowed me to appreciate how special Reddit was. Because Hipmunk was not magical. It was impossible to grow. We built a nice product that was always dying. And that's when I realized, oh, like this Reddit, this thing that just kind of grows on its own and we don't fully understand it. That is the exceptional case. Hipmunk, decent product, naive team, is very low organic retention. That's actually the norm.

[00:20:32] Start company worked really hard and it still dies anyway. So Reddit kept growing. And, you know, and just absolutely insane to think, you know, even four people could go down to just one person. I mean, you know, what do you think it was about Reddit? Like, what was that lightning in a bottle where it kept growing even though it had the skeleton crew maintaining it? Like people genuinely loved Reddit. It was almost like patriotism. It was like this undying love for the product. You know, it seems like almost everything else is built around this kind of like FOMO as a service.

[00:20:59] And here you've got Reddit where it's like, I'm going to go in there and I'm going to find something like find people and things that are like funny and entertaining and just like just like very human. It's kind of been in the DNA of the company and the product since the very beginning. And it's the one thing that after now, what is it? It's 21 years later. It's still there. And it's still kind of part of the core bones of the experience. I mean, you kind of alluded to other platforms don't have that. You know, I would totally agree. What do you think it is about Reddit that brings that experience that's very different than talking online and other places?

[00:21:29] I think there's a couple of there's a couple of choices that we made in the early days that we just got right. And I think the two I would highlight would be comments. We just kind of got the comment sort algorithm right. And I know that's like a minor thing, but like it means you go into a comment thread and like because you have a this kind of combination of like the whole thread sorted up votes and down votes.

[00:21:51] The trolls get kind of pushed to the bottom and like it just kind of means that everything is up at the top is just kind of like genuinely interesting or funny or a complete takedown of the post. That's very comprehensively researched and thought about. We just put a lot of emphasis on this kind of like long form intelligent discourse as part of the culture. And it's sort of stuck. And the comment threads made sure that there was actually a good, healthy discussion happening attached to them. The second thing was actually the subreddit model.

[00:22:19] We built an engine for people to be able to create communities around a topic or interest that was important to them. And that meant that we weren't building a single product. We were building almost like a factory for products that were going to be meaningful for people. You know, you can come into Reddit. You can find a bunch of stuff you don't like, but you can also find a bunch of stuff you do. The work is to make sure that we get the humans to the stuff that they like. The engine of Reddit was at first, then still is now today. People.

[00:22:50] Reddit is a digital version of a natural phenomenon, which is when people are together, they create community. It's like a libertarian point of view of just like let the creative energy through. The communities are natural. It's how do you build a product that lets the creativity flow through, but doesn't constrain it so much that the communities and the magic that comes from them, you know, suffer.

[00:23:19] After the break, the indestructible Reddit self-destructs. Welcome back. You leave to start, Hipmunk. I know you've told me before that Hipmunk was like your proving grounds, your training grounds where you got like really good at startups, even though it was like it was a slog, it was hard. But I also really kind of want to focus on what it was like watching Reddit from the outside at that point in time.

[00:23:48] Was there any moment where you're looking at it saying, this is this isn't good? Right. I didn't work at Reddit. Eventually, not immediately, but eventually I'd lose access to the code base and I'd lost contact with the company. So I didn't have any real day-to-day contact with the people who are working at Reddit. So I was really on the outside. And yeah, there was moments big and small where users were getting the best of Reddit, but we had bad users, bad people doing bad things on Reddit. It was a minority.

[00:24:17] It was a very small minority, but they were getting all of the attention. I remember this very frustrating to watch. And I think Reddit, the company was really struggling with dealing with that because the ethos of Reddit, the company was, it was we don't ban things. This came from a position of humility. Like who are we to judge what consenting adults talk about? But in the first years of Reddit, there wasn't much to ban. There just wasn't a lot of bad behavior.

[00:24:47] And so the company didn't know how to do it. There's no tools for doing it. You couldn't remove a subreddit. And so watching that from the outside, watching the company struggle with that, I mean, I didn't have an answer for them either. Because that was where I came from. It's like, well, we don't ban things. The side effect of those years was oftentimes I would describe the problems as the inmates started running the asylum. And that's where, you know, if you've got good moderators running communities, they can kind of keep the trolls at bay. If you have trolls as the moderators, that's when you start having a problem.

[00:25:16] And that's really what we started seeing in those interim years of just this kind of like blanket. Reddit is an open platform where anything should be allowed was the ethos that was being perpetuated. And that unfortunately is not the way it's supposed to work. For better or for worse, I wasn't there and I could think about it with a little more distance just from the outside. Like I think Reddit should do something.

[00:25:36] Like I had a little more conviction about, hey, if we don't draw a line here and start taking action, then this thing is actually going to die because it's dying. And so if the choice is death, then the alternatives become easier to accept. Yeah, there was kind of this moment, right? Where there's like a progression of CEOs. There was this one week where things were, you know, things really took a nosedive. What was going on for you in that week? So prior to that week, I had been communicating with Reddit about potentially coming back.

[00:26:07] But I told them, I was like, I'm not coming back. Like I'm at Hitmonk. Like I can't. This team is really important to me. This company is in a really formative time itself. We were in the middle of an M&A process. I talked to Adam about us. Like I'm having these conversations. Like I'm not going back to Reddit while we're in this sale process. And then that like totally chaotic week at Reddit happened. But the platform was basically completely shut down. I remember it was days of drama where just like, it looked like Reddit was probably going to die.

[00:26:37] And I remember that weekend I texted Steve just kind of like, hey, you know, if everyone wants to stay in Jakku and take Reddit back over, now's your chance. And he just wrote back, stand by. Chris texted me. And so did every other person I know. Like literally every person I know called or texted that week and said, what is going on at Reddit? You have to go back.

[00:27:05] And the hard part then was like, he was the co-founder at Hitmonk. And we were doing like, you know, that startup was fun. And then we scaled the company up to 100 people. And it was kind of a big deal to consider jumping ship from your baby to go back to your other baby, who is now in trouble. I remember, so at my friend's 30th birthday at dinner, sitting next to Michael Seibel, like just weighing this over. I was like, I can't go back. But I have to go back. So that was like maybe a Friday.

[00:27:33] And so it was like Saturday or Sunday. I called Bob Sauerberg on Reddit's board and Sam Altman, who was on Reddit's board and told him, hey, I'll do it. I'll come back. And they're like, OK, great. You start Monday. And I had to call Adam. I called Adam that weekend, my Hitmonk co-founder and told him, I was like, I'm really, really sorry. I know I promised I wouldn't do this, but I have to do this.

[00:27:53] That at the time, I think, was the hardest decision I had to make in life because it broke my heart to have to break that promise to Adam. Because I knew on one hand, I was like, it's screwing Hitmonk. And it's screwing those people who work there because they're trying to sell the company. And if I leave, I was the CTO. I was also the more notable founder. So if I leave that really F's them. I promised Adam I wouldn't do that.

[00:28:23] And I did. To Adam's credit, he was mad at me for like three days. Because, you know, it was the obvious thing to do. Yeah, it was such a crazy time leaving Hitmonk and going back to Reddit, just into the chaos of that situation. That was an intense moment. Yeah, I mean, I remember at the time thinking like this is, like on the one hand, it was obvious. But on the other hand, it kind of seemed like Reddit maybe was going to die.

[00:28:53] And this was going to be a tough job to take on for sure. You know, what was your first day like walking? Do you remember walking back, you know, into the Reddit office at the old company? Oh my. Yeah, that was tough. That was tough. It was awkward. The employees were not happy. One, they didn't know me. So there's about 70 or so people at Reddit. I don't think I had worked with any of them. They were just getting crushed. Like I think they were just embarrassed to be in the press for all this like terrible content. Reddit had terrible reputation.

[00:29:21] I was the third CEO in six months. And then they were just watching the platform they love just crumble. And, you know, they didn't know me. You know, I led Reddit with six friends. Mm-hmm. And then I was the CTO at Hitmonk. So I wasn't the CEO at Hitmonk. And so coming into Reddit, all of a sudden it was all on me and I knew Reddit better than anybody. But I didn't know how to run a company that size with that spotlight. It was tough.

[00:29:50] But I think sometimes in moments like that where things are so intense and so chaotic and so hard, there's nothing you can do but just, you know, take one step at a time. One of my favorite sayings is, how does a mouse eat an elephant? One bite at a time. And so you just kind of have to go in every day and just take your bite, take your bite and just know eventually you're gonna, you know, get through it.

[00:30:18] I remember a story you told me at the time, like you said, it was chaotic. You know, there's decisions being made left and right. And you were like, hey man, this is like not like running a normal startup. This is a turnaround. And I remember you telling me that like you had to put in a decision making freeze to basically figure out what was going on at the company. Tell me a little bit more about that story. And then just like what was different about running a turnaround versus running a growth mode startup? Oh, the company just had no compass at the time.

[00:30:48] It just had no way of making decisions consistently. The crises were centered around those bad content on Reddit. The previous team was trying to remove it, but they didn't have any policies. They were afraid to create policies. You know, they were banning content that was like medium bad while content that was really bad was allowed to stay. But that was kind of the core of the crisis. It's like, oh, once you start banning stuff, now you're taking on the moral burden for what's on the platform. Oh, you're going to ban that, but not that.

[00:31:16] But the problem is the company had no way of making these decisions. It's like, what's bad? What's not bad? So it was just like, okay, let's think this through for a second. What is Reddit for? Like, why do we work here? And then maybe we have a chance of making decisions that get us there. But actually, there's some amount of gratitude I have for those moments when it's so crazy. All you can like, all of a sudden, everybody's got conflicting advice.

[00:31:42] There's nobody you can know where you can turn because everybody you respect has different opinions. And so in those moments, all I can do is just go back to what I kind of feel is right. And actually, I think those have been some of the most productive times in my career or we've made some of the most important decisions was just like, okay, I have no place to get advice from, or rather, I have too many places to get advice from and none of it makes sense. So I'm just going to kind of go with my gut on what I think is right for Reddit. And that was what was going on in that moment.

[00:32:10] So I remember Steve came in and the first thing he did was like, he basically just like, of course, we're gonna have to figure out how to ban communities. Like, of course, we're gonna have to get these communities under control. Of course, we're going to have policies that actually are like reasonable. And that was a kind of a record screech for that, that company at that point, because, you know, the ethos was, oh, no, you can't upset the user base. Like, look what happens when you set them. They're gonna revolt. Just to give you an example of this. You know, we hadn't banned a subreddit before. We didn't know how to ban a subreddit. We had it like really nasty. I can't say the name.

[00:32:40] And we created this in between process called like quarantining. It's like, we don't want to ban people from talking, but I also don't want to promote us on Reddit. So we're going to quarantine it. And that meant this community would not be on Reddit's front page. It would be hard to join in this and that. And so I remember going in front of the company and just saying, raise your hand if you think we should ban this subreddit. Some people raised their hand. Raise your hand if you think this quarantining is the right approach. That ended up being the majority opinion. So I was like, okay, we'll do that.

[00:33:07] And then that night I was writing the post, the Reddit post explaining our decision. And I'm reading the post. I'm like, this sounds stupid. Like this. I don't know. Like, I'm just reading my own words here and I can't get behind it. And so I told the team, I was like, I'm going to ban it. It's the only decision I can actually explain that's in harmony with, you know, my values. And so we just banned it. And I think my post actually said something to this effect, which is like at the end of the day, you can't break Reddit. So like, why are we going to quarantine this?

[00:33:36] Like the point is like to kill us. They're not having a real conversation. They're having conversations designed to destroy Reddit by compromising its values. And then it felt like such an agonizing decision because we talked about for weeks. I did this whole voting thing. We built all this technology. And then at the 11th hour, I was like, this is stupid. Just ban it. And that was like the beginning of the moral, like moral, moral clarity for Reddit for like what we will allow and what we won't. And then all of a sudden the decision to highlight didn't seem that difficult.

[00:34:07] That's the funny thing about hard decisions is once you make them, if they were right, they don't seem that hard at all. And you wonder why you agonized about it. When did you realize that Reddit was probably going to make it through? So when I came back, I was doing user safety as my first kind of major job. At that point, we called it anti-evil. I always liked that title better. And every time we do a band wave, there would be this like pitchforks and torches on the platform for a couple of days. And then I remember we made it, it was like late 17, early 18. And we banned this group of communities that were kind of now getting to more on the borderline.

[00:34:38] And the response we got was like, oh, about fucking time, guys. What took you so long? And there was no drama. And it was just kind of this like, this like fresh air of, you got them finally. Good job. Why did you wait? And like, oh, okay, something has drastically changed. And from that point, it just became like the problems were the exceptions. It went from actively putting out the fires to now it was like starting to build systems that prevent the fires from happening in the first place. So then you kind of go from this moment just like absolutely agonizing.

[00:35:09] You know, over the next few years, and I say this as a compliment, you bring Reddit back to boring. You know, you built this stable business, you know, hired this team that you trusted. You know, when you look back, is there anything from like those times that you take away that you feel like other founders could learn from? There were things I think we did well, which was really working back from our mission. Like what's the point of Reddit? What's it for? We've changed the words over the years.

[00:35:37] But the average set of words over the years is Reddit's for community and belonging. Like does this create community or does this hurt community? I think that sort of discipline and stubbornness really helped us. We make good decisions by listening to the voices in our heads. And I think I made some bad decisions by not listening to the voice in my head. It's tough when you're young, though. I was insecure in the role.

[00:36:02] And so I didn't feel confident in always trusting my gut, even though in hindsight, I think it was it was right more than it was wrong. But I don't know if there's any advice I could give around that, because every company is different and people are messy. Like you just have to walk the path. There's something almost absurd about first selling Reddit for 10 million in 2006 and then 18 years later taking the same company public.

[00:36:31] When Reddit did finally go public, like what did what did that feel like having been through that whole process? You know, it felt similar to selling it the first time. By the way, going public took forever. I think we started that process maybe in the end of 21. Oh, wow. But the stock market was very topsy-turvy. And we ended up delaying it for two years. So by the time we went out, on one hand, yes, there was this sense of relief. Ten times greater than when we had sold the company the first time.

[00:36:58] But I also knew there's going to be a moment where you're really happy and you're going to have this sense of relief because you finally crossed the finish line. And then you're going to realize that it wasn't the finish line. It was the starting line again. And then you're going to go back to work. And so I knew that was going to happen because I'd been through that now enough times. And so by the time we IPO'd, I remember saying, okay, this is great. You know, back to work. Like we still have a lot of work to do. And I still struggle with this at Reddit.

[00:37:26] Like I'm not a great celebrator because it's kind of like, okay, good. Now, you know, back to work. Because I know the work never ends and we're here for the journey. You know, I'm here for the journey. The journey never ends. But seeing employees happy, that was probably one of the happiest moments of my career. After the break, Reddit discovers their data is being used to train AI and needs to decide what to do about it.

[00:37:57] Welcome back. So I want to shift gears just a little bit here and talk a little bit about Reddit plus LLMs and AI. When did you first kind of become aware that like LLMs were reading Reddit and training on Reddit and that it was impacting their understanding of the world? So I would say that it's a little tricky to pin down.

[00:38:20] So for a very long time, there was an unofficial big query export of Reddit comments that was being regularly snapshotted. There's a whole ecosystem of tools that were around that would basically give you searchable indexes to Reddit content. And we didn't pay a lot of attention to them because they were annoying, but they weren't as annoying as everything else we were having to deal with. And then I remember like playing with some of the earlier LLMs and there was kind of like a, I don't know how to put it.

[00:38:46] There's a particular tone on Reddit of like this kind of like insightful, snarky kind of actually that started to bleed through on the models. And I think that was the moment where we kind of were like, this feels like if you put two and two together, it's like easy access to our data. And it sounds like our data, I bet a lot of our data is in, is actually baked into these models. We were born of the open internet. Information wants to be free. That was our philosophy.

[00:39:14] It was important to me that anybody who wants to see the knowledge of humanity that's on Reddit can do so. But that was before these AI projects were like these massive commercial companies with really huge negative externalities as well, right? So in the beginning of 23, we realized, oh, it's not just a part of the open internet. We're actually being stolen from and used to create these companies and technologies that in some cases are actually not even helping Reddit, not even helping humanity. That's when our point of view changed.

[00:39:43] You know, it's become like really core. I mean, a lot of times you go to Chachipiti or Claude or whatever LLM, you ask it a question, you realize later on that like a lot of that content is coming directly from Reddit. What is it about Reddit that's so valuable to LLM's learning? Reddit is, I think, the only place on the internet that has a couple of key characteristics that make it useful for this. The incentives on Reddit are different.

[00:40:10] So on social media, the currency is attention. So it causes people to behave unnaturally. They contort themselves to get attention. So you try to be funny or you try to be offensive or you have to be pretty, but it's not real. And so Reddit is much more real because if you're good at Reddit, you can't take it with you. You can't get rich and famous in the real world for being good at Reddit. You can just be good at Reddit. And so what do people do in the absence?

[00:40:38] Well, they're just kind of interesting and helpful and funny. They just speak their mind, right? They're not going to get in trouble for it, but they're also not going to get paid for it. So what else are you going to do? So the incentives are different. The scale is different. All right, it's just big. There's nothing at that scale that is as authentic that is also open. The other platforms where people talk about stuff are largely closed. You know, social media is basically all behind log and walls.

[00:41:04] So, yeah, we have this combination of authenticity, of scale, of openness that has turned it into a legitimate place where you can see what people actually think about just about everything. Reddit is like the one place on the internet where you read the comments. You go to Reddit for the comments. The comments are the product. Mm-hmm. Like everywhere else, it's a cesspool. And so training conversational model, you want to kind of emulate that. So you would expect that it would be very compatible.

[00:41:33] How do you think about AI and agents specifically on Reddit? I mean, do you imagine a future where AI agents become their own constituency and they have their own subreddits? Or like, do they have a parallel Reddit? Or like, how do you imagine that like co-engagement working? Okay, the shortest version of my answer is I don't know. But I can tell you the shape of where I think things will go. We're not anti-agent. But I think labeling that sort of usage is really important.

[00:42:02] I think it's really important. I think it's really important. I think it's really important. I think it's really important to understand that. Mm-hmm. Mm-hmm. That are API integrations that, you know, basically go all the way from novelty accounts through to like bots that help with moderation, bots that actually help to like manage Reddit itself.

[00:42:28] And those interactions, like we're requiring that they label themselves as apps. And that, we think, kind of strikes the right balance of, look, you should be able to interact with an LLM on Reddit, but you should know you're interacting with an LLM on Reddit. I think that sort of transparency is really important. What we don't know is just where this whole space is going. You know, if you're under the age of five now, you're never going to exist in a world without LLMs.

[00:42:55] And who knows what that technology is going to look like three months from now, let alone five years from now. So I don't think we can just say, never, never, never. And now we're running into what is the gray area for me, which is it's a human user of Reddit who uses AI to write. It's annoying right now because the writing is so bad. But how long is AI going to be a garbage writer for? Another couple of months? I'll finish where I started, which is, I don't know. You know, we'll take it one step at a time.

[00:43:25] Have you guys thought about creating like a, you know, a shadow Reddit specifically for bots to chat with each other? Like, wasn't there a, wasn't there like a, oh man, wasn't like an open claw? Didn't somebody do that? It was open. It was like open claw. It got pretty weird actually. It got pretty weird. I mean, I, we could actually create like an entire community models that are just based around like everyone here has to be an app. That'd be a fun one. I'll show you that as a feature request, David. So paint us a picture for like maybe 10 years from now.

[00:43:55] Like what does the world look like? What does Reddit look like? I think Reddit runs on these timeless primitives, human connection, community conversation. So that as its core is what Reddit will be. Communities created by our users, people talking about stuff they're interested in. I don't think that's going to change. Now the content types going to change. Like when we created Reddit, it was all links and then text posts and then images. Now Reddit has lots of video.

[00:44:23] I think there'll be content formats that we can't conceive of yet. I think the UI for computers is going to be completely different. My guess is we'll still have screens and keyboards, but we'll also have other UIs. You know, like AirPods or whatever, whatever brain implant, you know, will exist in a couple of years. So anything, everything will be different and everything will be the same. At the end of the day, people want to talk to other people about stuff they care about. That is not going away. The mechanism through which they do that may evolve.

[00:44:50] But I think as, as long as people are doing it, I think Reddit has a place in this world. I do think that like one of the things we've done a really good job at has been keeping Reddit human and we still want to keep Reddit human. Like people want to talk to people. People want to be social. It's in our nature. You know, I consider it our job to make sure that we can at least guard that for as long as possible. And then like you, then you can choose like, how do you set your filter up? How do you talk to your agent? When do you talk to your agent, but still have a place to actually go to talk to people. Reddit's not magic. People are magic.

[00:45:20] And I think, I think it's a really powerful, exciting thing. And I still think we haven't, not think, we have not fully realized our vision for Reddit. But those primitives from the early days of people created communities, the conversations, the joy, the fun, the magic. That is at the end of the day, what we are working on.

[00:45:49] This podcast is brought to you by Leap Forward Ventures, an investor in early stage startups. If you liked this episode, we'd love your help spreading the word. Forward it to a friend or give us a rating wherever you're listening. This episode was produced by Kim Naderfei-Petersa, Craig Ely is our engineer, Rhys Laudano made our cover art, music is by Jim Brunberg and Ben Landsberg of Wonderly. I'm David Rusenko, and this is the Leap Forward podcast. See you next episode.

[00:46:24] Do you have any kind of memories from those really early interviews? Well, I do. I mean, I remember with Steve and Alexis, they had come up from UVA. Paul had met them at the How to Start a Startup talk at Harvard. They had like taken the train up to see him give that talk and then applied to Y Combinator. And they were doing this idea, it was ordering food on your cell phone. Go figure.

[00:46:53] But it was like, you know, 10 years too early. Or maybe not 10 years, but you know, it was a few years too early for that idea. Because this is before smartphones were even around. And they of course had no connections to any food companies. They're like, you can walk into McDonald's having ordered your food and just pick it up. And we thought, great idea, but we just don't see this happening. So we rejected them. But I remember I loved them. I just thought that they were just so earnest.

[00:47:23] And she was bummed that we turned them down. She really liked those guys. And so I thought, oh, Jessica's sad. I need to figure out how to make Jessica not sad. Maybe there's some way we can accept them after all. I know, I'll call them and say, we'll fund them if they'll do this other thing. And then the next Monday, Paul reached out to them and was like, we really liked you guys. Do you think we could maybe brainstorm a new idea? And they literally got off the train that they were taking back to Virginia.

[00:47:51] They got off the train in Connecticut and got back on a train to Boston. And they came up with the idea for Reddit then. And they were in our batch. But how did you expect that if they didn't get off the train? That Kenny, you can do that with the ability to bring back to college. The more fun family and you can do it, I guess, will it be a decent chance. Then you can go to the future.