We didn't hit 10 million uniques per month until 2010. One story we've heard over and over again for users that end up sticking around and becoming Redditors is, I noticed Reddit kept coming up in search results or I started seeing it in here or I'd ask a question and it would come up. I casually used it for some period of time, usually like months to years. Then I found this thing, and then I discovered I was coming back every day. The first summer, all of the content that was on Reddit was either being submitted by Steve and Alexis or it was being submitted by a bunch of YC and associated.
Pablo:What's crazy to me as an outsider is just that a company that today does nearly a billion dollars in revenue, five years in had trivial amounts of revenue. It is just crazy how long some of these things can take until you I guess get the balance right and can really start monetizing.
Chris:A hundred percent and I think the flip side of it though is that what we didn't appreciate at that point was that the product had, again, to use modern terms, it had immediate product market fit. The magic of Reddit was there was never any question about we never even thought about marketing. There wasn't any need to market. There wasn't any need to do any lead gen.
Pablo:People listening right now, they just hate you. Welcome to the product Market Fit Show brought to you by Mistral, a seed stage firm based in Canada. I'm Pablo. I'm a founder turned VC. My goal is to help early stage founders like you find product market fit. Chris, welcome to the show.
Chris:It's nice to be here. Thanks for having me.
Pablo:Reddit is a world known brand now. It's a $9 billion company, nearly a billion in revenue, over a billion MAUs. You're not just a CTO. I mean, you were the founding engineer. You were there from day one. I mean, it's a long story. We're 2024 now. This is 2005. We're going back almost 20 years. I'm excited to dive into those early days, just what it was like to start. The world was so different. You were in YCs first batch, right?
Chris:Yeah, so actually I was probably – I wasn't there quite first day but I was definitely there within the first six months. Yeah, quick version of me is I was actually in grad school at that point, mid 2005. I had gotten roped into working on a startup with a friend, which at that point, to set the stage, nobody was doing startups in 2004, 2005 really. It was still pretty deep in the hangover from the original dotcom bust, which honestly, to go back even further, so I was actually class of 2000. I was in that boat of, I decided to go to grad school that fall. I had all these friends that were coming out to California and getting these great signing bonuses and these fantastic jobs. And then by September I always started grad school and none of those jobs actually existed anymore . <laugh> , hopefully I did crater. And I was like, so all summer I'm like kicking myself like, oh man, I should have like, I should joined , joined that startup and it's like, oh, that startup is no longer there because the market no longer exists. But yeah, fi four years later, I was kind of like halfway through grad school , um, hit that point of burnout that I think everyone goes through at some point in grad school school and did like a side project that turned into a startup. The nice results of that summer , um, was , uh, I learned how hard it is to start a company. Uh, my my company , uh, created that summer, but I had two free bedrooms in my apartment and , um, Steve and Alexis from Reddit , um, moved in. They were friends from that batch. And then I think it was probably two months or so before Steve kind of coaxed me to, to, to help out , um, and help out, turn it into first employee. And the rest, as they say is history
Pablo:It's history. Yeah, that's right. The other 20 years just that's easy stuff.
Chris:Yeah, the next 19 years, whatever, things happened. It's mostly seen deleted like in The Simpsons. It's like, oh, I don't really know what happened in that intervening time stage.
Pablo:I have to ask, do you remember – I mean, this was a long time ago. Do you remember what the vibe was in YC back then because now Paul Graham is a legend, YC is within the world of startups the number one most well-known thing, not just accelerator, just brand I would say in general. Maybe Sequoia's up there, but that first batch, why did people even join? You know what I mean? Was Paul Graham a big deal? What was the idea?
Chris:I mean, Paul Graham had a big cult following at that point. He was, I don't know if notorious is the right word. He had a a tech blog, he still has that I still have been reading all his years. He was also very big in the Lisp community. He wrote the two textbooks on Lisp. In fact, it was one of those things that I actually found out like I discovered after I met Paul and knew him for a while that the Lisp book that I had on my shelf was actually his and those moments I'm like, "Oh, my freshman year Lisp book from '96. This is actually Paul's. That's pretty funny." I'd say that the defining characteristics of YC in the early days was they actually would oftentimes chafe at the idea of calling them an accelerator because they were trying to do something that was much more straightforward of just – Paul's thesis was to use modern terms. If there was liquidity available for smart founders to go and start a company and if you could just set them loose, give them a little bit of seed funding and set them on their way, then that would create this rich ecosystem of startups that would actually thrive. I think that if any bet has been proven to be true, it's that one which is that we now know in Retrospect that startups have a 90 plus percent failure rate. It's an ensemble situation where you have to have a couple of successes pay off the long trail of failures. Like many things in life, the only way to become a good successful startup founder is to do it a couple times and learn how to learn the NOx live. It feels like the first time I read a management book when I was middle of my career, I remember reading it, being I don't understand what one of this stuff means. Then you go and you manage for a while and you get a couple scars and you come back and you read the book and it's like, oh, now I understand what this toolkit contains. It's similar with startups, like you start a company and it's like, oh, how hard could it be to start a company? Then you're like, apparently payroll's a thing. Who knew? Managing investors, like managing a board, you have to do all that stuff live before you really can appreciate what parts are are complicated and what parts just require some skill.
Pablo:Yeah, I mean, there's so many pieces of the puzzle when it comes – that's one of the frustrations almost is you start, you have this idea, you just want to deliver a product, and then you just find out all the little friction, all the little things you got to do to just build, get that idea into reality. Yeah, you only learn that by going through it.
Chris:Definitely, yeah. On top of it all, one of the signs of successful company is you have to go through the phase of growing the team and then you discover that you – speaking from experience here, I spent my entire career as a software engineer effectively. When you go through that shift of having to actually – your output is not the software, it's the people who are building the software now and you become more and more removed from the actual day-to-day software development. At this point in my career, I've got 1,000 people in my org, which every time I say it, I just shut a little bit. It's like, that's a lot of people who are up looking at me for some guidance on what's going on. It's like, I'm just some guy who likes to write code but don't get to do that as much anymore. I threaten. I mostly threatened to write code.
Pablo:Take me back. I'm really curious because you're working on this other startup, you're in the same batch as Reddit, but how do you actually end up joining Steve and Alexis?
Chris:I mean, it wasn't much more complicated than what I mentioned. Legitimately that batch was very small. There's 10 startups that batch. The first company FlameOut happened within the first literal three or four weeks of the batch. I think we actually were down to nine within a few weeks. It was like tell us all this time. It was like the disagreement about equity division between the team or something, which again, in Retrospect, it just seems so silly. It's like you're divvying up a company that doesn't exist yet and arguing how much you own.
Pablo:It's a bad sign.
Chris:It's a really bad sign. It's a sign of immediate lack of trust. It's like they don't actually trust each other enough, but that was a while first batch. I mean some of the folks in that batch, besides Reddit, there was Justin Khan and Emmett Cheer at the company. Right, Twitch, yeah.
Pablo:At the time the company was called Kiko and it was a calendar startup but they went on to do just TV shortly thereafter which got also got into a later YC batch and then Twitch. Sam Altman was in that batch doing his startup looped, if I remember right. It was a social location app, like basically the snap map but back in 2005 on feature phones. It had some pretty good solid bones in there or at least a bunch of people who were, I don't know, in Retrospect, all roughly the same crazy maybe is the way to describe it. pretty good at picking people. Paul Graham's pretty good at picking people.
Chris:I think he did a pretty good job on the first on the first batch. I think the best way to describe the actual experience was the shared context of – there was no other room you could be in than that room where everyone was literally going through the same thing that summer. Everyone had just established a company. We were all learning how to build basically web apps live at a point when web two was just becoming a thing that was being talked about. No one knew how to build scaled web products or at least there wasn't a kit to do it. You're learning live and then being able to once a week at dinner, have a chat with some other people who were doing the same thing and being like, oh, I literally just solved that problem this week, here's what I did; first discoveries of some of the new things that come along with CSS, which to this day remains one of the worst toolkits imaginable. I'm sorry, I went back in engineering mostly by training. I got out of that early. I mostly have completely uninformed opinions on it at this point, which still are funny. From my standpoint, we were working on, sounds really mundane but desktop search. Me and my co-founder at the time were a couple of physicists who just couldn't find PDFs on our fricking hard drives that we had downloaded because the search toolkit that existed on a computer was pretty terrible at that point. We ended up trying to solve the general problem with search on desktop. This is about, I don't know, I think it was that fall that Mac OS shipped an update where they actually gave you the search bar. That's how far back in the past it was. I think we were competing with that stupid dog in Windows. It would appear and like, oh, you look like you're trying to run a search. It's like, yeah, this is completely useless.
Pablo:My life changed when I stopped clicking on files and I just open up the search and pull up a document.
Chris:Yeah, it's like command, space, bar. Everything is command, space, bar at this point. Yeah, that was still a relatively new new idea. Of course, now at this point files locally really? Everything's in a browser window and it's probably stored somewhere else that you just have to find it.
Pablo:I guess my question is, when you joined, what was the MVP of Reddit? I mean, in Reddit it was actually almost known for not changing or at least not changing all that much, and so how similar was the first version of Reddit to what we see today?
Chris:I think a lot. A lot of the basics existed all the way back to that year. I'd say for that summer and for the first version of Reddit, it really was just a front page with a bunch of links. You could submit content, you could give it a title, and you could vote on it, and that was it. There was no conversations. There was no discussions. If I remember right, the first comments appeared later that year in December of '05, give or take, after I had started. It was a major addition. I remember also really clearly setting the tone for Reddit's culture literally one of the first comments that appeared was something like, "Reddit has comments now. I guess it's now just slash dot. We should all move on to the next thing." It was great while it lasted. It's like, oh yeah. I mean it's like eternal September all the way down. Voting plus comments goes back to 2005, basically. I think the next major edition we did was when we added subreddits closer to 2007, 2008. I would say that was one of those things that actually slowly started appearing where initially we had created a set of – we just started finding that the amount of content being submitted was so large, we had to have some an organizational principle around it and the original idea, we started breaking down topics. We curated in the first crack about 10 or so, now we call them communities but at the time we just called them subreddits because they're a chunk of Reddit around a given topic and that was things like science, politics, basically clear delineations that the community wanted to separate out.
Pablo:When I look at Reddit, at least I think the most powerful asset you have is this incredibly strong community, and more so than maybe any other social network frankly is the defining feature to the point that communities now subreddits can move markets. It's pretty incredible. How did you get that going? Everybody wants to build a community, but it's so hard to do. I'm just curious in those early days, I remember stories of seeding the threads and stuff, putting things there to get conversation started, but do you remember how you guys got that going in 2005, 2006 because it's easy once there's content but it's hard when it's a blank page?
Chris:Yeah, 2005 was – I remember really clear this is right before I started where for that first summer, all of the content that was on Reddit was either being submitted by Steve and Alexis or it was being submitted by a bunch of YC and associated because we were the first users as a group. There was a point that Steve likes to talk about where he finally took a day off on the weekend. He just decided I'm taking Saturday off and then he went back to Reddit. I mean, I'm going to butcher his story but he can yell at me later. He comes back to it the next morning and he is like, "It's going to be stale. I'm going to go submit it. I have to dig up a bunch of content and post it." He opened up Reddit and there were 25 fresh links on the front page and he had nothing to do with any of them and it was just like this like, oh, the system seems to be working. From that point on there's no need to start creating this – that particular community, that very first community, which was just reddit.com, started to run itself and it just started becoming this place where interesting content would just appear and bubble up. I think one of the things we got right really early on was the underlying math of just how content became popular on Reddit and how long it stayed up there was very simple. It was optimized for being able to index it on statically so you could actually render really fast. We had it publicly in the open source version of Reddit from about 2008 till 2017. Honestly, that algorithm didn't change markedly for most of the first 15 years of Reddit. It was a very straightforward setup just based on age of the content and the number of votes it got. A lot of the work went into just making sure that the votes that we had good anti cheating logic to make sure people weren't doing things that were inorganic. The core of it was very well established. Later on, that same process worked for communities where we noticed up front that there were a bunch of topical areas that were starting to form, and so starting to peel those off of a front page made sense. There wasn't any real work to seed them because the content was already present. The real change was in 2008 when we actually opened up the floodgates and just said like, "Hey, if you think you have a good idea for community, go make one." Then that was the initial burst of just all sorts of random stuff that users started coming up with. I mean, that's where actually AMAs, which are a cornerstone of Reddit right now, were primarily something that formed on its own. IEMA was formed around then. Most of the major communities that came later were ones that were just organically created by users and that's actually the best result.
Pablo:That was almost like adding fuel to the file. There was already momentum and you're just feeding and feeding and feeding it.
Chris:Yeah, a hundred percent. Then to get to the other secret sauce that we have since that beginning moderators, to start with the first version of moderation was we just basically allowed the creator of those communities to have a similar toolkit that we had for keeping track of content. That wasn't much more than just being able to remove content or see reports. Subsequently we discovered as communities got larger, they needed to be able to add more people to the moderation team and so we basically added that permission. The feature that no one really notices that I think had the biggest impact was we gave mods the ability to edit the content on the side of the page where you could actually explain the community and just say what it's about, because you had to be able to say – you come to ran a community, what am I supposed to be doing here? What we found happened very quickly is that they started using that space to start to create rules of how to use the community. You can think of it in the same way that we originally created a politics community because we wanted to get politics off the front page because people were complaining. You wanted to have the opposite of happen where it was actually – because we've been through multiple elections at that point. 2008 was the election that actually kicked it over where people were tired of politics and they're like, "Okay, no more politics here, put it over there." We had the opposite happen where it's like, yeah, only post content to peer reviewed scientific articles in our slash science. Starting to have those be a list of actual rules started creating more structure for communities to create their own culture effectively.
Pablo:Is that the key thing that hooks people and keeps them coming back where they just find themselves so identified I guess in these and there's just something for everyone?
Chris:Yeah, I think that with hindsight, one story we've heard over and over again for users that end up sticking around and becoming Redditors is there's this particular arc that usually goes something like, "Yeah, I noticed Reddit." It kept coming up in search results or I started seeing it in here or I'd ask a question and it would come up. I casually used it for some period of time, usually months to years. Then I found this thing, and then I discovered I was coming back every day. That thing is always very specific to the person. It's like you're a botanist or you're a hobby gardener, and you find a community that's dedicated to your particular variety of gardening and it's like, "Oh my God! I'm going to just going to stick with this forever." Another one that comes up that's also not talked about as much is we actually have really good support communities; so for people who have wanted to stop drinking, for people who have substance abuse, for people going through divorces, those can be very sticky because there's not really a place anywhere else where you can go in and be honest and talk about your actual problems and not worry about it coming back to you as a person. I mean, that's the magical model that we picked early on was we decided that we didn't want to have real names, we didn't want to have association with you. We just relied on the fact that if you're going to waste a bunch of time creating a fake user and a fake persona, if it's entertaining, great, otherwise there's no motivation to go and create a fake persona because it doesn't come back to you. It actually cuts both ways. Even though we are pseudo anonymous, the incentives are such that authenticity is what comes out of that because there's no reason to try to be an influencer.
Pablo:That's right. I mean, unless you're trying to troll like that, that's always the only reason I can think of to, to create like a fake, fake persona. Yeah.
Chris:Yeah, that seems a big waste of time for very little return. The other standard approaches, of course like an opera, we deal with, and again this is a tales of time on Reddit, spam. Trying to spam, trying to sell, pushing pills, that's the cornerstone of the internet. You can either be identified as spam or you can go through the front door and pay for advertising, but there's that in between. It was just like, yeah, you're just wasting everyone's time and efforts. We'll just get rid of that content.
Pablo:In those early days, like 2005, 2006, how much was it just straight organic word of mouth, and how much did Google and Google results play a role in growth?
Chris:Very early on it was almost entirely word of mouth. In fact, in the early days, we have a lot less insight into how things spread at that point because keep in mind, we're older than Google Analytics. We used to run our own analytics toolkit. Actually that was my first jobs was doing our traffic was we used to see a bump in traffic in those days in September and what we figured was probably happening was when people would go back, like people would go to college or go back to school, there was an opportunity for word of mouth on campus because the 18 through 20 was always – 20s range was always very large on Reddit. We had a suspicion that it was just like, yeah, you come back from the summer and now you tell all your friends about this place you found and then it just spreads that way, but it was definitely very organic. It wasn't until much later where, probably the last five or 10 years where Google's played such a large role.
Pablo:I'm trying to get a sense of magnitude. I know it's a long time ago, but do you remember that first year, that second year, we're talking about 10,000 users a month, 100,000, a million, what scale were you operating at
Chris:I looked this up because I figured you were going to ask this question. Let me actually find it. I just was complaining about it somewhere. Okay, so we didn't hit 10 million uniques per month until 2010. We hit about a million a month in mid to late '06, but at that point we also were on a pretty good three to six month doubling curve. If anything, the rate that we were growing was about the same pace where we could actually keep the site perky. When the load's going to be twice as much in three months, it really focuses the mind to like, okay, what's the current bottleneck that we're going to hit and what's the next bottleneck we're going to hit and how do we make sure we're at least a couple bottlenecks away from the actual major outage?
Pablo:How often were there big outages in those first days, like just didn't work?
Chris:I think that the outages were in the early days, very early days, not particularly often and always something that ended up being like we don't know how to use this technology yet. Also, oh man, without failure we would have outages whenever – the team was always very small. If the team decided to go out to dinner collectively, if all four of us were in the same place, somebody's phone was going to go off. It's a guaranteed thing. I remember very clearly being out to dinner and Steve's phone went off and we had to run back to the apartment which doubled as the office, hopped on, and that was the first time we discovered that – We've used PostgreSQL as our database forever, and that was the first time we actually discovered that PostgreSQL had a configuration file we should look at. The tuned version of PostgreSQL back in 2005 was optimized for a 486 with eight megabytes of Ram. It was probably the first time we had an index fall out of memory where it was like, oh wow, we can just add two zeros to this setting and all of a sudden it works. The AI was like, yeah, let's figure out what all these settings do in this particular file, and just that compounded across a bunch of things. By the way, the impression I want to leave here isn't that we didn't know what we were doing. It was like nobody knew what they were doing at that point and we're all discovering it live.
Pablo:Walk me through, so the acquisition was when, in 2006?
Chris:It was Halloween '06, October 31st.
Pablo:At that time, Facebook started 2004. I don't know exactly how big they were, but I'm sure things were flying off. I don't know what you guys were looking at if you were comparing yourself to them or other social networks, but I'm curious, what was the logic for taking that exit especially when you had that growth. Those numbers were pretty big, especially back then, right?
Chris:Yeah, no, I mean, I think that the breakout successes that were at the same time like, yeah, Facebook was 2004, but Facebook also was still – I think at that point – I can't remember when they rebranded from the Facebook to Facebook. The original domain was even different because it was hard to get facebook.com even then. They were mostly limited to college campuses until a little later. The breakout success summer of '05 was actually YouTube. Youtube came out of nowhere and exploded, and they got bought very quickly that year by Google. I mean, for us it was like – again, this is still at a point where there really wasn't much of an acquisition path available. Companies were still just waking up to the idea of startups again. The pitch at the time from Conde was actually very good, which was Conde is this premium content generator that understands monetization and then we are an engine for getting you to content that doesn't have a monetization path.
Pablo:Pre-revenue, at the time you guys were making –
Chris:Advertising was a side thought at that point. We barely had advertisement on Reddit. It was one of those pitches that was almost like, with our powers combined, we could take over the world. At that point it's like, what do we know? We're all in our mid to late 20s. It's like somebody comes at you and you're like, "We'd like to buy this for more than you've ever seen, tell me more . It sounds like a good idea."
Pablo:The world's changed. I think now many first time founders, I mean, honestly at the end of the day, they'd probably take it too but at least they would pretend like they shouldn't. They're going for the unicorn, you know?
Chris:Yeah, it was a different funding world. I don't think the word unicorn was coined until at least 10 years later. The idea of talking about series A, B, C, D, that wasn't even really back – it was in the lexicon from the late 90s but it really hadn't come back. It just wasn't really like an offer on the table sounds like a good way to do it and then, hey, we can always go start at their startup.
Pablo:What was it like after acquisition? Did they let you run things more or less the way you used to or did things get a lot more annoying?
Chris:No, the nice parts about working inside of Conde Nast is they did leave us to our own devices. Actually there was a couple nice parts. A fun fact, Reddit was actually started in Somerville, Massachusetts not too far from where YC was based, which was in Cambridge. A lot of that first summer batch was actually all in Massachusetts, not in California. It wasn't until that winter when YC decided to do a second batch. They decided to do the winter down at Trevor Blackwell's office in Palo Alto, I want to say; definitely down the peninsula, because why would you purposely inflict east coast winters on your startup plus doubles the surface area for like, oh, if you can tap the east coast for some knowledge, you can also tap Stanford in that area. The side effect to that though was that when we got acquired, Conde wasn't sure where to put us and the nearest property they had they could stick us next to was going to be wired which is based in San Francisco. The side effects of getting acquired are like, "And we want you all to move out to California." I'm like, okay. We all moved out; worked out of the wired office for four or five years. If anything, that was probably more fun than anything else was just getting to talk to folks who have been reading their articles for like the last five, 10 years being in the bay where the center of the tech universe even then and just generally being left to own devices because of course Conde's mothership is really in New York.
Pablo:I think we were talking about this before, you guys kept the team pretty small even after the acquisition for a while, right?
Chris:We never had more than 10 employees up until 2011. I left in 2010; late '10. At that point the company was four engineers and some support. They had one sales person who was actually Conde asked employee. We saw other folks who were on the business side but it was one community manager just to start.
Pablo:How come? These days, if you're the next clubhouse, you think you're the next clubhouse, let's say, you raise a lot of money and you hire a lot of people. How did you do it with tent?
Chris:That's the side effect of also being acquired at that point is that we did have a P&L and we were very heavy on the L because it was very hard to get the P. It turns out that where the logic of the acquisition was a little wrong was trying to get people to advertise on style.com is not difficult. Trying to get the same advertisers to advertise on Reddit is extremely difficult. Let's just say the vibe is very different. It's like high class style publication versus a bunch of -- It was actually very difficult to get even – to get to even cover our own costs was actually very difficult, and so hiring was also difficult. One thing that also hit us was you might recall 2008 was a big economic downturn; another reason where actually the acquisition was really great because we would've ended up in a pretty tough spot trying to get funding 2008, 2009. That period of time there was a company-wide hiring phrase at Conde because they were worried about the downturn. That meant if we were growing or not, we couldn't hire. If anything, it taught us to be fairly lean and fairly efficient with our tech. That's also the year where we migrated into the cloud. We actually were very early AWS users mostly because it was a lot easier to get servers by putting them on a corp card than it was to actually have to deal with procurement and getting them shipped out and having to rack them up ourselves.
Pablo:By the time you leave in 2010, do you remember the size of Reddit? Was there meaningful revenue or were we at 10 million users a month or so?
Chris:Yeah, when I left, it was in the vicinity of 10 million users a month and the revenue was not large enough to be worth mentioning on this podcast. I do remember in 2010 we launched Reddit Gold, which was our first attempt at doing some something like a subscription model on Reddit. I think in that first week, we raked in the, at the time eye watering number of a hundred thousand dollars from users just donating to Reddit. That was a completely insanely large number in the scheme of things like. That was larger than the last couple months of ad sales, if I remember right at the time.
Pablo:What's crazy to me as an outsider is just that a company that today does nearly a billion dollars in revenue, revenue five years in had trivial amounts of revenue. It's just crazy how long some of these things can take until you I guess get the balance right and can really start monetizing.
Chris:A hundred percent, and I think the flip side of it though is that what we didn't appreciate at that point was that the product had, again, to use modern terms, it had immediate product market fit. The magic of Reddit was there was never any question about we never even thought about marketing. There wasn't any need to market. There wasn't any need to do any lead gen.
Pablo:People listening right now, they just hate you.
Chris:I know, but it's again, it's one of those things where we didn't realize the time that was an unusual thing. The fact that we had to work really hard on the revenue side, it wasn't until the modern era where we really started doubling down in revenue and the last basically 2015, 2016 on was a really had to go hard at it and figure out how to solve that particular problem. For the early days, the problem was never the users. If anything, there were days where we're like, "Oh, cut, can they just stop coming for one day so we can clean up this database?" I mean, great. I just want to take the whole site down time; I need to run a full vacuum, like just let the vacuum finish.
Pablo:Tell me the – so then you shift. In 2010, you and Steve decide to go off and do Hipmunk. What's the story there?
Chris:Similar story, which was that I never come immediately but I come eventually. I come quickly. It took a little away time. Steve left in end of 2009 and then went off and came with an idea with a friend of ours, Adam Goldstein, to build a travel meta search site called Hipmunk and I ended up joining about a year later end of 2010. I would say that to go back to my point about product market fit, part of the design choice around Hipmunk was let's make a very nicely designed site and product that has immediate ways to get to revenue and that we just have to deal with – let's find a path where we don't have to deal with complaining users and we can get to revenue and really nice product. We succeeded in all directions and then realized that of course that the hard part is getting people to actually come to your site is very difficult. Steve and I talked about this in Retrospect, it's like we just had this notion that we were going to turn it on and people would just come. That has been the story with Reddit. If anything, we built it with notions of scale that are just hilarious in Retrospect of like, oh yeah, we like a couple of architects who are used to dealing with huge scale in Reddit. We'll just make this thing fast and really scalable and easy to scale up, and scaling was never the problem. It was getting users to come. If you could get somebody to come back twice in a year, that was a rampant success.
Pablo:It's so funny how life does that to you. You learn all these things, like this time I'm going to get it right and then you forget that. What do you say?
Chris:Yeah, and the side effect even was we ended up building a lot of systems that looked very similar to the shape of the technology at Reddit because same architects were building it, which meant that when I eventually came back or we both came back, Steve came back in in '15 and I came back to Reddit in '16, it was almost like coming back to an alternate history where they had chosen a slightly different path because we had actually diverged in our direction. Came back and found that it's like, "Oh, wow, they're still using the first version of this thing that we wrote. We've already written three other versions but that was a different company. Crap." How does this work again?
Pablo:What was Hipmunk? Was it like a hotels.com, like a booking.com thing or something else?
Chris:I think that the closer analogy would be it turns out that there's two different – oh God! These are things that I didn't know I'd ever have to learn about. It turns out that there are two things that exist for searching across multiple flight or hotel providers. There's something called an OTA, which is an online travel agent, and then there's something called Meta Search. OTA actually legitimately has a travel agent's license. That industry is weirdly regulated. There's actually a whole classification system. Meta Search is you're built as a search provider on top of other providers. We built Hipmunk initially as Meta Search. We made our own deals with airlines, made our deals with Meta Search providers, and the idea was to become effectively an aggregator. I think that the clearest analogy I would give would be, if you go to Google now and you search for flights, they'll give you that overview. It's basically Google Flights, which came out again, came a couple years into Hipmunk existing where they decided to start making a foray into that. After they bought one of the large data providers for for flight data called ITA, they started building out that product. We initially started with flights, and then we moved into hotels because that's the path that everyone takes. The reason why everyone takes that path is because it turns out that hotels are much easier to monetize than flights. Flights you're making maybe a few dollars a ticket, whereas hotels usually get a percentage.
Pablo:How did you end up solving it, the core user problem, which by the way is frankly, demand is most startups problems. That is just how to get users until you get product market fit and then you have other problems, but that's usually the zero to one issue.
Chris:Yeah, I think that Hipmunk's real differentiator was its flight product where we really started. We wanted to provide a way to solve our own problem first which was, it's just a pain to figure out which flight to take. I have a couple of very simple requirements most of the time for looking for a flight, even to this day. I travel a lot now and I miss Hipmunk's UI. We showed flights as a bunch of Gantt charts effectively, like here's a time bar that shows you when the flight is and you can go through and you can basically say like, "I want to leave after 9:00 in the morning and I want to arrive before this time. Show me everything that fits that and they're like, oh look, this one has a really stupid eight hour layover. Kick that out." We created a simple sort called agony, which was you could start by lowest agony and we give you effectively direct flights and flights that had reasonable layovers. Reasonable layovers is what you would expect. 30 minute layover, that's not a real layover because the flight's going to probably be you have to run between terminals, as opposed to, yeah, about two hours about the sweet spot. We built out a quick little bit of mass that showed that with an ICUI. The product really was the UI. It was quickly being able to get to a flight that's reasonable and be able to pick your return path, be able to break down by price, just all the things you'd expect in a product with a very simple visual aesthetic.
Pablo:Did you and Steve have an aura at that point coming out of Reddit? Was it easier to hire, easy to fundraise the way that it would be now if you had a Reddit exit?
Chris:I think it definitely helped. I mean, what actually did help there too was Hipmunk was also an YC company. Getting back into YC was also easier having already done it once. Part of doing startups is doing startups or doing startups well is you have to be able to get your knocks at some point. Already having had a startup behind your belt and an acquisition behind your belt helps a lot. I think also the other things that came up were like, yeah, we had to exist as architects, set a pretty decent sized product with a decent user base. Therefore, we were pretty good engineers at that point and we knew web development really well. If anything, the learning curve for Hipmunk was that was the time when app stores really starting to take off and so we had to start learning how different the requirements are of dealing with the Play Store and with the App Store on iOS. That was a new muscle, but it wasn't a difficult thing to hire for. It was difficult to do well at that point in history.
Pablo:At that point, I mean like you said, Reddit, you had to do no marketing, it was all word of mouth this time. Did you get into paid ads or what do you remember? What was your big acquisition channel?
Chris:Some of the early hires we had to do at Hipmunk that never even came to mind at Reddit, we had to hire a BD lead extremely early. That was because that was entirely to make deals with airlines and hotels and larger companies just required attention and it required somebody who had some experience doing BD as a profession. Marketing was also extremely early. I remember actually even at the time back in 2010, 2011, we hired our first social media manager, which having just been at Reddit for so long, the idea of a person whose job it is to manage social media, what the hell was this? How is that a job? Also another thing that came up around that year 2010, 2011 was also the first time I heard the word data scientist. I'm like, data scientist? You mean that has a name now? You just dig through the logs and you get the answer. I didn't know that was a full-time job. The earliest part of the team, the first 12 employees give or take, included at least two people working on BD and at least one person doing marketing and the rest of it was mostly software engineers but there was a customer service element as well where we actually had to have – we were dealing with money and the side effect dealing with money is you have to pay to have a CS team around to answer questions because the last thing you want to do is have some person stuck in limbo with their money.
Pablo:With Hipmunk, did you guys get to product market fit, would you say?
Chris:What we learned most with Hipmunk was we definitely solved a set of user problems really well and we had some really rampant support, users who really loved using the product. I think what we learned though was economies of scale are a bitch. Having a small product like Hipmunk meant that we couldn't take advantage of just the bulk discounts you start getting when you have volume. Originally we went into it with a bunch of disdain for the large players, because it's like look at how crappy their product is. Yeah, their product is crappy but they're booking a billion dollars in revenue. You can afford a lot of crappiness if you can actually get that much lead gen, because you can spend a ton of money on marketing to get more users. I mean, you can buy a Super Bowl ad and be completely reasonable.
Pablo:Talking about flights, this is different, but always most flights customer service, when you're in it's just terrible. Sometimes I talk to people about this and I'm like the problem is when it comes down to it, I'm cheap as shit and I'm going to take the cheapest flight that gets me fastest and I don't care if they – they might have yelled at me when I was on the plane but if it's the cheapest flight that gets me fastest, I'm going again.
Chris:That's the thing too is the flight is the means to the end. You're on the flight because you have to be and you don't have a lot of choice. It's like a temporary purgatory before you're doing the thing you actually want to do. No one takes a flight because they're like, "Oh yeah, I want to spend six hours in this metal tube with a bunch of humanity." It's like, no, you do it because you're going to go to fricking Maui and you have to get in the plane to get to Maui, which is also why we found that it's straight -- that's actually why we chose agony as our sort because everyone hates – there's very few people who are like, oh, I love flying. Even people who have -- at this point in my life, I have 1K status, which as we all know isn't a good thing. It just means I fly enough that I actually got status. It's like the mark of the beast. It's like, oh, I'm sorry, you have 1K. I remember I was in a plane at one point recently and the guy behind me hit his 3 million mile mark, and everyone around him was like, congrats, whoa. It's like, are you okay?
Pablo:It's like, are you okay, dude?
Chris:He wasn't old. He was younger than I was. I was like, "Oh man, you've spent a lot of time in planes."
Pablo:That's rough . Yeah, that's rough.
Chris:It's like that George Clooney movie from 20 years ago. He was up in the air and it was like he realized he spent his entire life on planes. Yeah.
Pablo:No, good. Walk me through, did you guys end up selling that? I'm interested obviously in the transition back in Reddit. Did you end up selling Hipmunk or how do you come back to Reddit? How does that happen?
Chris:I think by about 2015, Hipmunk was in a good steady state. From my standpoint, a lot of the technical problems were solved or were just a matter of playing an existing playbook. There wasn't a lot of difficult work to be done there. What happened for me was I ended up consulting for Reddit mid '15, because at that point they were starting, starting to scale up a little bit more. The company was up to around 70 employees. They were looking at actually building a mobile app. They were looking at doing something that – some of the stuff that I had originally specialized in Retrospect was I became an infrastructure generalist. I became probably one of the first SREs in the team just as nature of the beast. I also ended up being one of the first people to work on what amounts to being – we eventually called anti ego, which is our user safety stuff. I was secondary to another guy, Mike Aldi, who is a good friend of mine now, who was the first – I don't know. At the time he was more the troll poker. He would help to fend off the trolls and put them back under their bridges and got really good at building out the toolkit for making sure the users actually had some amount of safety. Coming back the things that were top of the list for me were working on that safety toolkit, and so I ended up doing some consulting along those lines; talking about mobile usage; talking actually about data science, which wasn't really a function that existed much at Reddit that point, which again, my title at Hipmunk was actually chief scientist, which most of my titles historically was a joke but at the same time actually it was accurate. I was a scientist but also data science had come on the scene around that time, and so it made sense to say, well, Chris can work in analytics. Then by the end of that year, it was – I've made this analogy a bunch of times, but I have to repeat it. It's like it had the same feeling as dating your ex-girlfriend where it's like you dated a long time ago and you broke up for very good reason, but that was like five years ago.
Pablo:Have you changed?
Chris:You both changed as people, so let's just see what happens. That was actually exactly how it felt where I had thought that I had emotionally separated myself from Reddit and then actually by about midyear in '15 Reddit was going through some tough times. They had a major blackout that was infamous, the first real modern blackout, and there was this possibility that Reddit would cease to exist and that hurt in a way that I wasn't expecting. It was almost like, oh God – I'm twisting metaphors in a bad way here but I'm going to do it. It was like seeing your kid in tough times. We worked really hard to get you going and then you find out that later on they're leading a rough life, so maybe it's time to swoop back in and see if you can actually help.
Pablo:Especially when it was a known brand, real brand with real users, a real community, the thought that that could go away, I could see that being not easy to accept, not easy to swallow.
Chris:Yeah, and I think to some extent too, we just had a different model for how to approach Reddit, the community as well of – I remember historically there's always been pitchforks and torches on Reddit. That's the nature of the product. Prior to 2010, some of the ways to solve the problem would be the community would get ahead of Steve about something and then Steve would appear and just Spez would just comment, no. I remember there was one case where it happened in 2008, 2009, where he just replied no, and then the response he got was, "Okay, guys, let's just call it clearance from the advents. They're not into it, so let's just move on."
Pablo:It's crazy the persona of Reddit. It's pretty wild. It's just pretty wild to look from the outside. It's so unique.
Chris:It's very much so
Pablo:I was going to ask, you mentioned the mobile app, what took so long? App Store comes out in '08, '09. I just have to ask that. It's nothing to do with product market fit but you would think –
Chris:I know. I mean, that's a fantastic question. Actually, we had a couple of early forays into it. I think that I can start off with saying the first answer is honestly capacity. We had a very small team at that point. Like I said, we had four or five engineers tops. Rather than spending time learning a new new kit, we initially decided to just build like a mobile experience that was actually not bad. Early on there was actually – I wonder if it still works. I'm going to really quickly just check and see if this thing is still in existence. No, it's not anymore. Okay, good. We used to have a particular view of Reddit that was optimized for mobile browsers. At this point 2008, we weren't just targeting iPhones, we were targeting Blackberry, Research in Motion and Palm OS and all those features where we didn't know what was going to be the clear winner, so we just picked that. Second, we actually did at one point bring in a contract firm to build us a first version of a Reddit app. Then subsequently after about 2008 when we open sourced, we started having more of an ecosystem of third party usage of Reddit appearing and early on there was a whole set of third party apps that developed. In fact to the point where I believe in 2013, 2014 it's after I left, but Reddit bought one of the major iOS apps called Alien Blue and then relied on that as the iOS solution for a while with no equivalent solution for Android. By about 2016, the idea was that we were looking to probably do a bit of the look of Reddit and do some cleanup, and at the same time it was worth actually investing in some first party clients that really were taken from the ground up that had a particular more modern style.
Pablo:The other thing I wanted to touch on is the monetization piece. I mean, you mentioned it wasn't really a focus I guess until about you guys came back in 2015, 2016. I'm curious just what worked? Fundamentally, what were some of the big things that you did? I mean, you think, okay, you're going to make money on ads, but what were some of the key things that you implemented that really drove the real revenue that you have now?
Chris:Okay, well, two things. One of them is going to sound like a cop out but I'm going to say it anyway. One of the things that actually had the most impact for revenue was just fricking grit. The reason I say grit is because trying to bootstrap an ads business – it really was bootstrapping at that point because we're talking about very low numbers even in 2015. Trying to bootstrap an ads product on top of a "social media platform" was extremely difficult given the fact that we had made a bunch of different choices from the rest of social media. We had no real user data. We have basically interest data. Everything is in the public and in the clear. You go to the front page, you're going to see the good and the bad of Reddit based on popularity. That's the value proposition of the product is that it's going to be an unvarnished view of what people are talking about. No wild gardens, no fancy look and feel. It really was educating advertisers over a very long time and really kudos to our ads team and our sales team then to now of just having to continue that path of saying like, "No, we're differentiated. We have a different value proposition than what you got off the social media. We're not really social media but we'll pretend to be, or at least we'll call ourselves that." It's the cleanest bucket. The second thing that actually came up early on we actually did do a self-serve product in 2008. The first version was my build where we wanted to actually have users be able to basically buy screen real estate on Reddit directly with the credit card. From about 2016 on, it was rebuilding that into a modern auction, actually doing it in a CPC model as opposed to a CPM model which was a lot harder to explain, building out things like tracking pixels; really building the whole kit and caboodle of what is expected on a modern ads platform but again, with a start date of 2016 as opposed to everyone else who had started in the early 18s. Lots of catch up, but also the nice thing about catch up is that you do get a chance to take advantage of the modern toolkit. We made it all the way into the 55 minute mark or so without me saying LOMs. This is a tech podcast. Somebody has to say LOM at some point. I think it's on the screen. There's a certain advantage of being a startup now and being able to take advantage of the full kit of kitchen sink ML technology is actually ridiculously powerful for especially building the first version. You can save yourself some amount of ashla just doing it using the modern toolkit of just simple experience asking a bot to help you build it and getting moderation for free or at least getting some amount of content understanding kind of comes for free these days which is a really nice and powerful.
Pablo:Listen Chris, we'll stop it there. I'll ask the two questions that that we always end up on. The first one for Reddit, you touched on this but I'll ask it anyways. When did you feel like Reddit had true product market fit?
Chris:In hindsight, it was pretty clear that it immediately solved the need that we didn't know was unmet. If we're going to pick a date, I would say probably when we launched subreddits, it was pretty clear that that was a thing that meant that Reddit could continue to grow and scale past a relatively small community of nerds, frankly.
Pablo:The other question I have is having gone through this journey over the last 20 years and especially since you're an angel and certainly a mentor and advisor to a lot of early stage founders, what are some of the most common pieces of advice that you find yourself giving early stage founders or if you could give yourself back then, however you want to think about it?
Chris:Yeah, I mean, I think that some of the things – actually, at this point in my career, I have entire mental frameworks about scaling orgs, which I find terrifying to say out loud. Again, having 1,000 people on my team right now means that I don't think in terms of individuals; I think in terms of teams and org shapes. The evolution of a startup, there's a point usually that happens around the series B phase, which is almost like the startup adolescence phase where it's like nothing quite fits. You don't really know what you're doing anymore because you've had enough success to get a couple of rounds of VC. Usually that's when they you try to expand the product portfolio and you discover that things aren't sticking as well as they were on your mainline product, and you're also going through the team growth phase of – there's a switchover that happens at around 50 people where you go from effectively a small tightly knit family almost, not to abuse the term, into more of like, no, there are just people who are your coworkers who you don't necessarily know very well. That can be very tough for startups to go through because there's so much initial work that is based on implicit distributed trust across the entire company. Those two things tend to hit about the same point, which is usually around the series B and that's a fun problem where you start to think about things – you think about teams rather than individual people. That's usually the point also where you have to hire a real manager, hire somebody who's been a director before to actually start laying out processes that actually help you scale your business. I think that was actually the place where that's where I feel like I learned the most at Hipmunk was actually building a company up to 100 people and then also got a chance to start deploying that toolkit, coming back to Reddit when it was roughly the same size.
Pablo:Chris, it was great having you on the show.
Chris:Thanks for having me. I really appreciate it.
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