The Exchanges

Q Um, alright, do you have an example of a company that didn't build something useful and just got tired before they could, before they could iterate their way towards usefulness?

A Um, there's, I, I can think of, uh, in, in the, in our first batch of Y Combinator, there was a company called, um, they went through a couple names. They started off as a dating site. The, the, the site that I think went public was called Brain Guppy. And the idea was they would, it was kind of this question answer site for building up kind of unique profiles. Almost like a, a really trimmed down OkCupid. And they, they went through a couple iterations of the site. The guys were really clever and smart. Um, the site was kind of fun, but they weren't really getting a whole lot of traction. And then at the end of the summer, they, they all went back to school. And, and so they had this kind of, you know, They, they, they were faced with this decision of, do we continue pushing the site that isn't getting, you know, isn't getting a lot of traction, or do we just go back to school? And so they ended up going back to school, and the site foundered, and, and the rest is history. Now, for that reason, Y Combinator has a rule where they don't generally bring in students who, ah, can go back to school. You either have to drop out or graduate before doing Y Combinator.

AI assessment note: “in our first batch of Y Combinator, there was a company called... Brain Guppy”

Q Do you remember the day when you signed the paperwork, when it was done? What was that like?

A Yes. Uh, I remember actually the day before, much better. The day before was when all, all the lawyers had agreed, and we basically said, tomorrow we're gonna sign the papers. And I remember I got really emotional that day. I was, I was sitting there at my desk in, uh, in Boston, and I just cried. I was just so, uh, I don't know if I was excited or relieved. It was a stressful time trying to sell Reddit, and there was lots of times when we thought, oh, it's not going to work out. We just wasted the last month negotiating with these guys. And that was, uh, that was, that was a pretty emotional time. And then when we actually signed Reddit, it was like, uh, or when we signed those papers, uh, it was almost just like, uh, any other day. I felt like I had already gone through the, uh, The, the, the big, ah, breakthrough the day prior.

AI assessment note: “when we actually signed those papers, uh, it was almost just like, uh, any other day.”

Q Who were the first moderators that you brought into Reddit?

A Hmm. That's a good question. Um, I know one of the first outside moderators that sticks in my mind is QGYH too. Um, he, he was, uh, this insane Reddit user. I shouldn't say he was insane. He spent insane amounts of time on the site and we always thought he was a bot for, for a long time because we would look at his, his usage and there was never, there was like never an hour during the day where he didn't check Reddit. We're like, this guy like never sleeps. He's just always on Reddit. And so, in my mind, he's one of the first. Uh, Alexis would be the, would probably have a better answer to that. Um, but, but I know we brought him in to, uh, just keep an eye on things because we, we, he was spending more time on the site than we were at that point.

AI assessment note: “one of the first outside moderators that sticks in my mind is QGYH too”

Q When I asked Paul Graham about how, about Hacker News, he said that it takes a lot of time for him to manage that community. Here you guys have a much bigger community with Reddit, and I see that you interact with people via email, you're active on the, on the site itself. How do you do that?

A You know, we, we started off, when, when we launched, Alexis and I would just answer every single feedback email we got. And, and for a while that was sustainable. It, it, unfortunately, is no longer sustainable. But, ah, the community also, ah, one of the, there's, there's kind of an interesting backstory between Hacker News and Reddit. And one of the decisions that we made on Reddit is that we don't want to be moderators. It's, it, it doesn't scale very well. And, and, and on Reddit, a lot of the users are moderators. And especially on all of the smaller subreddits, you know, The vast majority of which I've probably never even seen, or neither have any of the other Reddit, you know, administrators. And the community, Reddit's been very good about self-policing itself, and appointing other moderators and keeping things together. And also, I should say the bigger issue is that there's a distinct lack of moderation on Reddit. To a large extent, it's anything goes. As long as it's not spam, most content will survive. And so that was one of the big philosophical differences between Reddit and Hacker News is, is we didn't want to remove content or we didn't want to tailor, uh, the site to any particular type of content.

AI assessment note: “one of the decisions that we made on Reddit is that we don't want to be moderators”

Q Were your parents the kind of people, well, how would your parents have reacted if it failed, and you looked silly in front of them?

A You know, my, my, ah, you know, they would have been supportive. Like, they, they, they would never, like, tease me or anything, but my mom was kind of, especially in the early days of writing, was always calling me, being like, hey, you know, when are you gonna get a real job? Ah, and, and it was like, you know, never. And, And, and I just, I, I really wanted to, you know, demonstrate to them that, you know, this was a real job, and we were building a real thing, and while, and while, uh, you know, they can't relate to the content on Reddit, or, or, or, you know, any of the things that, I shouldn't say any, but many of the things that make Reddit kind of magical, you know, might not appeal to them, uh, but that we were actually doing something real, and making an impact.

AI assessment note: “they would have been supportive. Like, they, they, they would never, like, tease me”

Q if there was a system out there that anyone can go and use than to say there's one person Who's Paul Graham, and if you could get his year, and you could get his time, then your site will be user friendly, and if you can't, then there's no answer here. I want to understand why, why he does it, or how he does it, sorry. What do you think?

A I think Paul's a good product guy. Um, you know, there are lots of good product people out there. Um, they're not always working on the right things, but Paul is, I think he's an exceptionally good product guy. He has a really good eye for what's useful and what isn't. Um, and, and he's also completely stateless and has no social filter. So it, it, it helps that you can go to this guy who will just be like, this is stupid. And it doesn't matter whether you've been friends with him for five years or you just met him or, or what, you'll just, he'll say that to anybody. Like if Larry and Sergey showed him like a new version of some Google product, Paul would have no problem being like, this is stupid. Nobody will use this. And, and you might be right. It's the thing. And so I, Paul, Paul, I think the combination of his being good at products Being completely honest and having no social expectations, uh, makes, um, a very useful source of feedback.

AI assessment note: “combination of his being good at products Being completely honest and having no social expectations”

Q No, you weren't. I had, I had Alexis on here. You talked about how the, how the idea for Reddit came about. No question in my mind that you guys were not copycats, but how do you grow a community the way that you guys do? You have an incredible community. I'd like to be able to do that.

A It was, it was all word of mouth. We, we didn't, all of our users came, uh, you know, organically. And so we have a lot of genuine users and, and, and, and Reddit can be a little off putting at first, either from, you know, the, the, The, the tone of, of the, you know, the headlines, or the comments, or the design of the site, it doesn't appeal to everybody, and so the users who stuck around, stuck around for the right reasons, right? They really liked the content, or they liked the way things work, or they appreciated what we were trying to build, which is just a simple, easy to use thing for, you know, consuming large amounts of content. And so, in that regard, every user we had was really valuable.

AI assessment note: “It was, it was all word of mouth. We, we didn't, all of our users came”

Q I see. Um, well, had, how is, Now you're in a situation where you don't need it so much. You're not a poor college student. You're now in a situation where you've got a wife. How's when you need to spend time with her. How's, how's this different?

A Uh, it's different in a lot of ways. Um, you know, our, our hours are different. I work more reasonable hours now. Um, but I also know a lot more now than I did five years ago. So, uh, you know, I don't have to learn, you know, I don't have to learn how to build web apps again. I, uh, I know a lot more this time. So in that regard, I get a decent amount of work done. And, and, and Adam is also a technical founder, so we had two programmers when we started this summer, which made building the first product go a lot quicker. Um, but one of the things I learned on Reddit was, uh, how to not burn out, or I, I should say, like, on Reddit, I burned out a couple times. I just wouldn't get any work done for a while, because I just didn't feel like working on the same thing. And, and, and, you know, one of the experiences is, or one of the lessons is, have a, have a life, you know. So now I'm much more Uh, cognizant of, like, having hobbies and spending time with my wife and spending time with my friends, because those are the things that kind of keep you happy and make life worth living.

AI assessment note: “our hours are different. I work more reasonable hours now.”

Q So Alexis told me the initial, the initial audience came from Paul Graham's community, that he emailed the people in his address book, he said check out this site, and they came in, and they were active. Was there another, another burst of, of members, more people, was there another source that brought in a lot of people?

A So Paul brought us the first maybe thousand or so uniques. And then after that, I don't remember any specific huge waves. Um, there, there were times when we, we would be surprised like, Hey, look, we spiked again, but it was, it wasn't always clear why. Uh, kids going back to college in the fall is generally a big, a big boost of users for us. There's not generally one event that's tied to it, but we found ourselves always chasing spikes that happened in August and September. Um, The last big spike they had, I think, was this big redesign. But that, you know, that was, that's relatively recent. Uh, Reddit and Dig both being five years old now.

AI assessment note: “And then after that, I don't remember any specific huge waves.”

Q around Y Combinator. You've talked to new startups. You've given them advice. You've also seen some succeed and some, and some fail. The ones who don't make it, we don't really get to hear much about them. I'd love to interview any Y Combinator company that didn't make it to find out what, what happened. Short of that, since you're here and you've seen them, what do you think happened?

A I think a lot of them have a common story in that they weren't building something. They weren't building something inherently useful or, and, and they didn't, they didn't recognize that soon enough, or they didn't have the stamina to change ideas. And so when they weren't getting traction with their idea, they were going to have to either do something radical to convince people that what they were doing is useful or do something radical or even more radical and build something completely Completely new. And, and a lot of people just don't have the stamina to do so, uh, that, that other things are calling them, you know, jobs, stable salaries, or going back to school, or, you know, it's easy to say, I think it's easy to make an excuse to, to, to go do something else. And, and I think that's kind of the common story, right? And, and there's a lot of cases where founders just didn't gel. They didn't know each other beforehand well enough, or they, they, they weren't the right, they weren't the right mix, or they weren't the right type of people, um, But I, I think the fundamental issue is not building something useful and not, you know, not really committing for the long haul. Just quitting too soon is a common issue.

AI assessment note: “they weren't building something inherently useful or, and, and they didn't, they didn't recognize that soon enough”

Q I mean, personally, I think on, on Calacanis' show, you guys, uh, you said that you became a millionaire afterwards. Here you're telling me that you were a poor college kid when you started out. So, personally, away from work, how did life change?

A Ah, things, uh, having money takes a lot of stress out of life. Um, it's, it's funny, I, I, I, I'm in this weird position now where I don't remember quite how, uh, my, my thinking about money has changed. I know it obviously has because I don't really think about money a whole lot these days, but also don't, um, live a, a, a demonstrably different life. Uh, I still hang out with the same friends and we still, you know, like my, my favorite memories are still, Uh, are, are basically the same things that I used to do in college or, you know, that summer with Reddit before we sold, which is hanging out with my friends, you know, playing video games or playing cards or, you know, whatever we do together. Um, so day to day life hasn't changed a whole lot. I feel like I'm a little less, uh, stressed out or like, I, I don't think so much about what I'm going to spend money on, but I also don't spend a whole lot of money. So it's, um, it's, it's, it's hard to say it to be honest.

AI assessment note: “having money takes a lot of stress out of life.”

Q Alright, let's talk about Hipmunk. What's the idea behind your new site, Hipmunk?

A So, Hipmunk, the, the, the idea behind it is really simple. That buying plane tickets or, or traveling, uh, planning traveling is, is a very painful experience. And we can do better. Uh, and, and so that, that's, that's the simple, uh, The simple motivating factor behind it. Uh, when, when my co-founder Adam called me this past spring and said, Hey, I want to do this travel thing. Uh, my only objection was, are you sure we want to be in this space? Um, you know, it's an easy sell that yes, there should be a better travel thing. You should be able to buy tickets easier. You should be, you know, plane tickets easier or hotels easier. Um, that was not the thing we talked about because that was obvious. Buying plane in hotels sucks.

AI assessment note: “the idea behind it is really simple. That buying plane tickets... is a very painful experience”

Q Okay. Um, did you ever disagree with him? Did you ever say, no, you're wrong, and how did that go? What did you disagree with him about?

A Oh, our, our name, the logo, he hated the logo. He thought we should put the logo down in the lower right of the screen so people would, you know, it's, there was a lot of branding things that he cared about. It was like, you know, we've got this. Um, Over the years, you know, the kind of Reddit hacker news schism, where he wanted his own, you know, Reddit so he could, you know, have that community. And we agreed with him quite vehemently there, and, and to the extent where he, that, that he built his own version of Reddit. Um, uh, but, but, you know, once we knew we were onto something, or, or we had, once we had the philosophy behind something that was working, we would generally stick with it. And Paul doesn't take things personally when you disagree with them, which is also.

AI assessment note: “Oh, our, our name, the logo, he hated the logo.”

Q What was the decision like inside to allow moderators to come in and to figure out who the right moderators would be?

A Uh, it was mostly out of necessity. We just didn't have time to, to do it ourselves anymore. I was doing development stuff. Alexis was doing his, Marketing stuff and flittering around the country like he does. And so we, we just needed help. And fortunately, and it took a lot of convincing to be honest, because we felt very, uh, strongly about the direction of the site, how it should be maintained. And we knew if we had gotten like a bad moderator who just banned everybody for silly reasons, that would be a bad story for us. And But we didn't have a choice. You know, we just needed somebody to, to watch things and take care of things. And we've had those bad. Go ahead.

AI assessment note: “it was mostly out of necessity. We just didn't have time”