Building Chess.com with Jay Severson
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Chess.com started in 2007 and grew steadily in the years following. The platform exploded in popularity during the pandemic, to the point that their servers struggled with the traffic. It was a great problem to have. Chess.com was instrumental in helping to elevate chess to its current height of mainstream popularity.

But how did Chess.com come to be? And how was the platform created? Our guest today is Jay Severson, who co-founded Chess.com and was its CTO. He joins the podcast to talk about the origins of the site, its development, scaling the platform, and what he's working on today.

This episode is hosted by Lee Acheson. Lee Acheson is a software architect, author, and thought leader on cloud computing and application modernization. His best-selling book, Architecting for Scale, is an essential resource for technical teams looking to maintain high availability and manage risk in their cloud environments.

Lee is the host of his podcast, Modern Digital Business, produced for people looking to build and grow their digital business. Listen at mdb.fm. Follow Lee at softwarearchitectureinsights.com and see all his content at leeatchison.com.

Jay, welcome to Software Engineering Daily. Thanks for having me, Lee. So chess.com wasn't your first founding success in the gaming space, right? You created your first internet gaming company, I think, back while you were still in college. Is that correct?

Yeah, back when I was still a computer science major at San Jose State, I started another company called World Gaming Federation. My goal was to provide ladders and tournaments for people that were serious about gaming. So the big games that I was playing back then were things like Warcraft 2 and then even a lot of the Yahoo Classic games, the card games and stuff like that. So I just wanted a tournament system for that. And so I created World Gaming Federation and worked on that kind of out of my dorm room while I was still going to school.

Cool. So now that company you ended up selling, is that correct? Yeah, correct. After about a year, we had some pretty decent tournament technology. We were running tournaments and...

And the other big player in the space at the time was called Cases Ladder or Internet Gaming League, IGL. And they were very big on the ladders and leagues, but had no tournament technology. And so they kind of approached me and said, we'd love to use your technology and integrate it into our platform. I was excited about getting an actual paycheck and some consistent revenue stream while I was going to school to pay for bills.

So I sold it. It wasn't a huge payday, but it was a nice confirmation of an affirmation of what I was building. And so then I ended up working for Cases Ladder for a couple of years, or I think it was three years, and building out their tournament technology there. And then was it after that? Is that when you started chess.com or was there something else in between there?

No, it was a pretty big break. I worked for Cases Ladder, like I said, for a few years, finished up my degree in computer science. Cases Ladder ended up getting bought by a private investor and they wanted to move everybody up to Seattle. I was in San Jose at the time, did not want to make the move. And so I decided to leave Cases Ladder, got a job as a web developer at a mortgage technology company here in San Jose and worked for them for four years. Their name was Myers Internet.

And so it wasn't until quite a number of years later, Myers Internet got purchased. I've got a very small paycheck for my four years of work there on my equity. And so I was pretty disappointed there.

and was kind of motivated to go out and do something on my own. And at the same time, my old friend from college had reached out to me and said, "Hey, I happened to meet the guys, met the guys who own chess.com domain. Let's go meet with them and see if we can do something interesting with that platform." And we had already done a smaller venture together, wholesalechess.com that he had started and wanted me to build the shopping cart system. And so I had already worked with him a little bit and he sold that business, came out here to the Bay Area, was going to Stanford to get his master's degree.

And that's kind of when we reached out at the same time that I was a disgruntled employee at Myers. And so I said, sure, let's do it and started writing some code. Cool. So did you buy the domain or did you partner with the people who owned the domain then?

Yeah, it was kind of a funny story. When he first asked me if I was interested in doing chess.com, I just said, no, I'm not interested. I had seen a lot of chess companies come and go. There was KasparovChess.com that had kind of raised a bunch of money, built a platform, and then gone under. I knew that there was not a lot of money in the space. People want to play chess online, but they don't want to pay any money to do it. There was Yahoo Chess, which was a free place to play. I was

So I wasn't super excited about spending a lot of years of my career building anything in the chess industry. And so I told him I wasn't interested. He said, let's just go meet the guys and see how the meeting goes. We met him in Palo Alto, had some dinner, and he said, Jay, why don't you tell these guys why you're so excited to build the platform? And so it kind of put me on the spot. I talked about the different features we were thinking about adding. They had the domain, but they had built a desktop software and they were using it as a marketing platform and they were

several million dollars, I think, in debt from all the money they had spent building their desktop software. And so they were looking to use the valuable asset that they had, the chess.com domain, and partner with some guys who knew how to build tech, which was my partner, Eric, and I.

And originally, we were just going to lease it from them. It was going to be a co-owned company. They would get some equity, we would get some equity, and there would be certain proof points along the way to make sure we were growing the business. But shortly after we made that deal and we started writing some code, they actually filed for bankruptcy because I think they were trying to get all the debt off their books. And so my partner and his friend went on to the auction phone call and ended up buying the domain and all their assets for a little over $50,000.

Wow. That was relatively cheap for something. Yeah. You know, for chess.com, which is, you know, at that point in time, this was, would have been what about 2010 or something like that? No, no way earlier. This is like 2004, 2005, 2004, 2005. Okay. But still even back then, you know, the well-known domain names like chess.com and those sorts of things would have been very, very, very valuable assets. Yeah.

Yeah, it was definitely a bargain considering the fact that they also got all the tech. Now, the tech wasn't super useful in its current form. We had to kind of retool it to make it more web-ready and all that. But $50,000 for something they had spent $2 million developing, it was definitely pennies on the dollar. We got really fortunate to get those assets. And I don't think we'd be anywhere close to where we are today if we hadn't built this platform on top of chess.com, the domain. I mean, it was a huge...

advantage for us in growing the business as far as SEO, because back then, you know, if you type chess into your browser, the browsers back then would just autofill.com for you. So anybody who was going to their browser and searching for chess kind of naturally ended up on chess.com. So we were able to leverage that advantage in growing traffic and acquiring new users and, you know, eventually kind of getting us to where we are today.

Right, right. I'll tell you, I used to play chess a lot as a kid. I rarely play now. I just don't have the time. But when preparing for this interview, I started fooling around with chess.com. And I'll tell you, one of the things I really like about what you do isn't just the chess games, it's the puzzles.

I'd love going through the puzzles and doing those. I love that sort of a mental stimulation. I don't have to invest in an entire game. I don't have to interact with anyone at the other end either. And so I love the puzzles. What do you find most people are interested in? Are they interested more in the interactive games with a person they don't know and on the other end? Or are they mostly interested in the puzzles or playing the computer? What's the primary interest?

driver for why people use you? I definitely think the majority of people that come to our platform come to play chess. I mean, that's definitely what pulls them in. You know, it's funny you say puzzles because, you know, when we first built the platform, it's not even close to what it looks like today. I mean,

Our goals initially were very, very small. We just wanted to basically route traffic to some other destination and capture eyeballs along the way because we were basically a one dev shop. My partner didn't know how to code. So he was kind of the visionary and I was the builder. And so originally it was like, okay, let's outsource some of this work. Let's find some off the shelf third party software we can use to just get like a forums up and running and get like an email solution. And we'll offer people like an at chess.com domain name,

And so initially when we launched, that's literally what we had. We had like a directory of other chess websites that you could go and find places to play, find places to do tactics, find places to read about chess, to buy books. You know, we were just a directory of other chess websites. You could sign up and create an account and get an at chess.com domain name. So you could have like Lee at chess.com and people loved that.

It wasn't very ambitious. You know, we didn't have like grand plans to becoming like the worldwide chess platform of all things. And it's like the more we built, we were kind of like, all right, instead of sending the people off to this website to go play tactics, what if we built our own tactics trainer, our own puzzle solver? And so I was like, I think I could build that, you know, so then I'd start

putting something together or we would talk to the other websites, see if they were interested in working with us or partnering. And I would say nine times out of 10, we would talk to people and they said they had no interest in working with us. And so we would just be like, all right, we'll just try to build it on our own. And so we spent one day, I mean, literally I spent one day throwing up like a Java applet where people could play against a computer. And it was very simple. It was off the shelf, third party,

kind of open source deal. And then we spent months building this kind of correspondence email chess where you could actually make moves in your browser and it would send the move off to somebody else who would then they would take their turn. You know, so we call daily chess or email chess. Now, we spend a lot of time on different things. And then we kind of came back and we looked at traffic and it was like 80 to 90 percent of the users that came to our platform were just playing on this really terrible play versus the computer Java applet.

And so you're right in that I think a lot of people that come to the platform, I think initially are very intimidated by the idea of playing against other real life people. And so they want to do something that's a little bit more of a solo experience. They want to do a puzzle or they want to just play against the computer.

And so now, you know, chess.com has spent years building out the solo player experience where we have lots of different personalities and you can play against famous people. You can play against Magnus Carlsen when he's 10 or when he's 13. You can, for a while, you could play against Beth Harmon from Queen's Gambit. I'm not sure we still do that because there was some, you know, copyright issues there or whatever with Netflix.

But, you know, I think that's a big draw for people is coming to the platform, play chess, but do it in a way that is a very kind of individual experience and not intimidating where it's like, oh, man, I don't want to go up against some real person and, you know, get killed or for somebody that just feels a little more intimidating.

Right, right. You didn't set out to build a SaaS application. You set out basically to build kind of like a Yahoo for chess. It's kind of what you were trying to do initially, but it evolved over time. And essentially now you're more of a SaaS gaming platform than anything.

Correct. Yeah, that's right. And I think we just kind of went to where the traffic and the users drove us to go. I mean, we just kind of listened to the community. I think initially we were a very content heavy application. So one of the first features we launched was the ability to blog. So you could have chess.com slash blog slash Lee, and it would have like your chess.com blogs and you could write about anything and everything chess.

And so we had a lot of users in the early days who came and they wrote all kinds of amazing chess articles about the history of chess, about famous chess players, famous chess games. They weren't paid contributors. They just wanted to write about chess and they loved that we were giving them an online space to do that.

And what that meant for us was that over the years, we became very SEO heavy for all long tail searching. So no matter what you're searching in chess, like if you want to look up like Bobby Fisher's greatest games, there would be an article about that on chess.com. And so you end up on our platform reading about it.

So being a content platform first really allowed us to win the SEO race against other chess websites that were out there. And then I think we focused on the play features later. And then once we kind of had all that stuff done, we were like, how are we going to monetize this? Because we were getting a lot of traffic. We're getting a lot of users. Ads don't pay that well. And so we knew at some point we needed features that people would be willing to pay for and some sort of freemium service that

so that we would provide, you know, 90% of the stuff was free, but for our power users, they might give us a monthly or yearly subscription paycheck. And so we decided that people were willing to pay for training tools that if we provided all the play tools for free, but said, hey, if you want to get really good,

you can subscribe. And so we took the old desktop software that we had purchased, turned it into lessons because it was basically a database of a lot of different positions with Grandmaster content and comments on top of it.

And we rolled that out into a package that was included as part of the subscription. And so if you subscribe, you got unlimited puzzles and tactics per day, whereas a free user might only get three puzzles per day. You might get access to the first five lessons, but if you wanted more lessons, then you would subscribe. And so

It was kind of like play for free and then subscribe to get better. And so we would hope that people would get the chess bug, have a desire to get better at the game, and then eventually be like, you know what, $100 a year is a pretty good value for the access to all of this amazing content.

So is most of your revenue now coming from those premium experiences versus advertisement? Yes. I don't know the numbers. I mean, just so your listeners know, I was there from the very beginning till 2017 as the CTO. I have not been there since 2017, although I do...

keep in touch with all the guys. They're still good friends with, you know, all the head VPs and the co-founder Eric and all those guys. And I do go to the company meetups every year. I get an update occasionally, but I think that if I was going to throw out a number, I would guess that 80% of Chess's revenue comes from the subscriptions and 20% comes from advertising. And for a site that started with content first, you know, that, that sort of a ratio is really, really good. You know, it's one of the problem with content sites is you're,

very limited on your ability to monetize beyond advertisement, you know, because a lot of people don't really like to pay for premium content that they believe they can get for free. But, you know, it sounds like you found a good niche where it's not just content you're giving away, it's actual training and experience, and that's got a lot more value.

Yeah, and I think, too, for anybody who has gone down the competitive chess road to any degree, meaning you decided to play in a tournament or, you know...

There's tournaments all over the board, over-the-board tournaments that you can go play. And I would say a very small percentage of our users have done that. But for somebody like myself who has gone down that road before, you very quickly find that you're spending a lot of money on books. That was the old traditional way of getting better at chess is you would buy chess books. And one chess book might be $20. And before you know it, you've spent a couple hundred bucks on chess books.

So if you look at our platform in that sense, we're giving away volumes and volumes of Grandmaster content and videos, lessons, tactics, puzzles. They're structured in such a way, I think, that it's much easier to consume them too. Like we're going to look at your games and we're going to say, okay,

He doesn't recognize night forks, or he doesn't recognize bishop pins, or he doesn't recognize pawn structure. And so we'll actually recognize certain patterns in the reasons of why you're losing your games. And we'll recommend certain lessons to you or certain puzzles to you based upon the way that you play. And so it's a much more interactive AI, if you will, approach to actually making a player a better chess player. And so...

I think people see the value. It's like, oh, a hundred bucks for them to analyze my games, tell me what I'm doing wrong, suggest lessons to me, suggest puzzles to me, suggest videos to me. And all those things people realize are not cheap to create. We have grandmasters that work in the chess industry for a living and produce content. And so by them subscribing, they're keeping chess professionals, people who have dedicated their whole lives to the game, employed and

giving them work. So I think people understand it is a virtuous cycle and that they're helping to grow the chess ecosystem and make it a viable living for people that actually have spent their life dedicated to the game. So today, in today's implementation, how much of the strategy and the

training, you know, like you were talking about different ways of seeing what type of training is best for certain individuals, et cetera. How much of that is the traditional database driven approach that, you know, the original, the old style chess AIs used to do versus modern artificial intelligence techniques like, you know, like that are available today, including up to and including generative AI. Yeah.

It's starting to get a little outside. Like I said, I'm five to six years behind where they're at now, but I do know it's changed a lot. I mean, if you were to rewind the clock back to Chess Master and the early chess software that was around, I mean, there was even like Sargon. There was old chess algorithms out there for quite a while. And then you kind of fast forward and then there was like Deep Blue and it could process millions of moves per second.

And then fast forward today, there's completely new algorithms that are figuring out better ways to correctly evaluate chess positions. And our goal is to take chess engines and figure out how to make that interesting to a human being. So it's one thing for a computer to say white is better here by four and a half points.

But for it to actually explain to a human being why it's better is a completely different puzzle to solve. And it's not easy, but that's, I think the key to unlocking a very good computer analysis tool for you and your games. Because if we can actually say the reason why white is better here is because your King is weak and your pawn structure is bad. You know, your pieces aren't developed or whatever, like that actually is meaningful to humans for a long time.

You know, people would say, well, computers just play better. I mean, computers have played better than humans for quite a while now, and it's not even close. I mean, the best players in the world, Magnus Carlsen, cannot beat a computer at all, ever. Not even one game out of 100.

So they've gotten to the point now where they're playing on a much different level. And so unlocking the ability for those top players and even for average players to actually take advantage of what the computer is doing is kind of what we're at the precipice of doing at chess.com. It's like, how can we take computer analysis, computer AI, and make it meaningful to humans so humans can actually get better at the game?

And I think that's where there's a lot of value add. That's part of the reasons why people do go premium is because they see that we have at the end of every game, you can do a game analysis and it'll actually summarize and say, here's how many blunders you made. Here's how many, you know, mistakes, dubious moves, great moves. And some people will just, they get thrilled when they say, oh my gosh, I made in this game, I had four great moves, one brilliancy. People love brilliancies and

And so all of those stats come from our ability to actually pick apart a position and say, like, how hard was it to find this move and to make this move? Were there other equally good moves? If not, then that move qualifies as like a great move. You know, so just trying to pick apart chess positions and figure out how to actually score them and give that feedback to the user is what we've kind of been after. It's definitely kind of the holy grail of chess, I think, going forward is

using computer AI to actually make the game even more interesting to human beings. Because I think when Deep Blue beat Kasparov and it was the beginning of the end for humans and chess, everybody thought the game was going to die.

And what we've seen instead is computers have actually made the game way more interesting because now you almost have like a cheat sheet of perfect moves of like in this position, what was the best move according to a computer? And that's also how our cheating algorithms work as we kind of look at human moves and say, what's the likelihood that they're going to make a perfect move, five, ten moves in a row?

So computers and chess have really made the game very, very interesting. And there's lots of different engines out there that analyze positions differently. So there's a whole computer chess league where engines play against each other all the time, which is fascinating. So, yes, I could ramble on that for a long time. No, no, that's great. And in fact, I was going to ask about the tournament aspect, given your

Initial early background in gaming tournament. Was there ever any thought of bringing a tournament platform into chess.com or was there just enough of that out there and the training aspect was better? That was one of the projects I still built while I was there. I built a tournament system. And so tournaments are hugely popular on chess.com today. It's a big piece of the platform. You can join tournaments of all different levels.

shapes and sizes, different players, different formats. And so that was a big piece that I built while I was still there.

There's amateur kind of user-run tournaments where you as a user can go in and set up a tournament. You can invite all of your friends. You can invite strangers. And there's tournament director status where you get to pick and choose the format. You administer it. You kind of run it yourself. There's official chess.com run tournaments. And then outside of that, there's actually like the professional tournaments where we run tournaments exclusively for the top players in the world.

Speed Chess Championship would be an example of that, where we take the top 16 players and they play a particular format. And they're playing for, I don't know, $10,000 or $25,000. I'm not sure what the stakes are now, but they're playing for pretty decent price pools. So yes, tournaments are a huge part of it, which kind of leads me to talk about there's eSports is a real thing in the chess space now. You have streamers who are playing chess, and we have real-life commentary that's going on.

And so every time we hold these events, it's a big deal on Twitch with a lot of viewership and great commentary, top-notch budgets. So it doesn't just look like it's somebody's YouTube channel. I mean, these are professional events with professional commentary, with big prize funds and lots of viewers, sponsors, the whole deal. So I wasn't a believer that chess would ever be really an esport, but I think with the right format, shorter games, and great commentary...

It's become a real thing. The other thing that's really cool about the way we've done esports is while you're watching two grandmasters play, we have an eval bar, an evaluation bar that shows the viewers exactly like who is winning the game. And I think, you know, rewind 20, 30 years ago, you know, imagine you're watching Gary Kasparov or Bobby Fisher or whatever play a game.

Not only are they six hour games, which are extremely long and boring for a lot of people who aren't in chess, but you would have no idea what's going on in the game. I mean, you can look at a position and if you're not a grand master, you really have no idea who's winning or why.

But now you kind of have this computer eval bar, which is saying, hey, white's better here by a little bit. And then white will make a move. And all of a sudden you'll see the eval bar drop and black's now all of a sudden winning. And so the commentators can react to that and be like, oh, my gosh, white just made a terrible move. He must have missed something. Now black is better. And so the real time computer feedback of any given position makes watching two grandmasters play a lot more interesting from a spectator point of view.

I'm thinking the whole industry of sports commentary, and it was related to chess in particular. What type of skills does it take to be a chess commentator? I mean, you obviously have to be an expert at chess, but it takes a lot more than that to make it interesting to take a chess game and turn it into something where commentary makes it interesting for people to watch, etc. So I imagine finding commentators is probably a hard thing to do.

It is. It's a really unique skill set too because if you think about your average chess grandmaster, somebody who has spent a considerable portion of their life dedicated to the game, they're not typically extroverts. These are people who have had their head buried in a game where you don't talk to your opponent, a game that's played six hours in silence, that you're seeing moves in your head. It's hard to then say to this person who's not used to being –

outwardly social to, Hey, sit in front of this camera and yeah, here's a mic. You're going to talk to, you know, thousands of people, make it interesting, make it exciting somehow, you know, become an extrovert, become a, an announcer, a broadcaster at the same time, be a grandmaster and understand the nuances of this very complex position. And so it has been very tricky finding great commentators in the chess space and

And I think not only that, too, but it's like we have learned that there's a place for the grandmaster and the expert who can accurately break down a position and kind of predict what's about to happen. You need those people commentating on the games. You also need the filler who can just sit there and talk about, you know, what they're thinking, what they're feeling, the.

the history and the backgrounds of the players, any past games that they've played. So you kind of need that personality. But then you almost also need a personality that can relate to the viewer. And so we have found that actually having somebody who is commentating who isn't a grandmaster or an international master, but can ask a question that a novice or an average chess player might ask in a given position, like, why did he put his bishop there? Why hasn't he castled his king yet? Like,

Sometimes a spectator is watching, and even if you're listening to a grandmaster commentate, the grandmaster is commentating, but he's doing it from a completely different viewpoint than your average spectator is. And so it really does take a blend of different personalities on the show to pull off a really successful broadcast. That's actually – this itself is quite interesting. I think that whole space of sports commentary and what works and what doesn't work is itself quite interesting, and seeing it apply to chess –

Like you say, it's not a sport I would have historically thought would have been conducive to esports. Yep, exactly. I agree. I mean, I think when I was first pitched the idea, I think Danny Wrench was our big proponent of it. He's an international master chess player, kind of became the face of chess.com early on doing a bunch of live streaming and things like that. And he was like, you know, pushing esports and chess as a spectator sport very early on.

And I was always like, you know, I don't want to waste time and resources and money doing this because I just don't think people are going to be interested in it. So, you know, I'm glad I was proven wrong because it's actually become a pretty big deal. And it's a big reason why the game and the platform have continued to grow.

And sponsorship is really the thing that keeps that industry going. Is that correct? Yes. Sponsors are big, but really I think it's more about branding recognition and just new user acquisition. I think when you have an e-sports event and it's being streamed on Twitch, you're starting to get cross demographic promotion to other users on Twitch that aren't necessarily chess players or,

So one of the big events that we have run in the past that's been successful is an event called Pog Champs. Now, Pog is like internet slang for like a beginner. And so we had Pog Champs where basically you took a bunch of famous internet celebrities, famous streamers who played things like Fortnite or PogChamp.

pub g or you know other games league of legends and they were well known on twitch already but they weren't chess players and we took all those people put them into a chess tournament and they kind of had grandmasters as their coaches they would go through some training and then we would pit them against another famous celebrity and they would basically play you know two beginner games of chess and so you're watching blunders and horrible moves and mistakes and

but you're also watching their grandmasters kind of facial reactions to the moves they're making. So you're kind of seeing the coaches reactions and you're getting good entertaining commentary because people are like, oh my gosh, these people are terrible chess players, but it's fun to watch normal people play chess and not always grandmasters. And what that did is it really introduced the game to a whole new demographic of people. It made the game more accessible because instead of being a game for geeks, it was now a game for the cool kids because all the cool streamers were playing it.

And so this was right around COVID and also kind of right around Queen's Gambit. And so we kind of had a trifecta of a perfect storm where it was like people are stuck at home. People have nothing to do. They're learning a new language or they're learning how to play chess. And then Queen's Gambit comes out and everybody wants to learn how to play chess because of that show. And then Pogchamps happens. And so everybody's seeing all their famous celebrity personalities playing chess.

And we even had famous football players and athletes and actually real-life Hollywood celebrities playing. I think the Mountain from Game of Thrones was in one of our tournaments, people like that. So all of that happened. And then before I knew it, my son, who was a teenager at the time, and I couldn't get him to even look at a chessboard, all of a sudden, he's coming home and he's playing chess on his phone because all his friends are playing chess on their phones and all the kids on the basketball team and the baseball team are playing chess. And so...

It was a big change culturally, I think almost worldwide, to where all of a sudden it was like chess is now a game for the cool kids. And so that's when we really kind of hockey-sticked in a big way.

Yeah. This would have been 2020, maybe 21 in that time period. Is that correct? Correct. Yep. So that was your big hockey stick. Was that your first big growth spike or did you have other growth spikes earlier on? There was, it's all relative, you know, like a big growth spike to us in the first couple of years would have been like a hiccup today, you know? So I think it's just all very relative. I remember there was one time we were getting, we,

We used to measure things kind of in daily user signups. Like that was our big, exciting metric. And I remember the first time we had like, you know, a thousand people sign up in a single day, we were just like flabbergasted. We're like, I can't believe we had a thousand people join the platform today, you know, in comparison. And we have upwards of 200,000 people signing up per day now. So it's a very big difference. But.

But I remember, I think it was the first year or two after we had launched our iOS application, and there was a whole transition into mobile, which was a whole other story and tech problem to solve. But for a long time, we were just a web platform. And then it was like, okay, I think we need an iOS app. So we had to hire an iOS developer. But a couple of years after we had launched our iOS application for the iPhones, we noticed that

There was like this big spike in users and it just like wasn't going away. It was like, man, every day we're getting like a like double, triple the number of signups. And then finally, I think it was after I felt like four or five days or a week or something. Somebody realized that we had been put onto the app stores, you know, featured apps page.

And nobody told us, nobody warned us, but all of a sudden it was like chess.com was a featured app on the app store. Like the first thing you would see when you go to the app store and just, you know, little things like that that are completely out of your control. And all of a sudden you're getting three to five X, the number of signups that you're used to. And, you know, back then it was like our tools weren't great. So we didn't recognize it right away. And,

And anyway, so there was definitely spikes like that that were just things we didn't even do. There was things like the World Chess Championships would happen. And so all of a sudden, the entire world is tuning in to watch Magnus Carlsen play a big game or Garry Kasparov play a big game. And again, another event completely out of our control. And all of a sudden, our signups would go through the roof.

So they tended to be events that were outside of our control. And we just had to be sure that our platform, our technology was ready and that it was grade A so that when people typed in chess on their browser, ended up at our platform, that we would actually, you know, convert that user to an active user who would come back to the platform because they were impressed with their first time user experience and the tools that we had and the

the games that they could play and things like that. So, you know, same with COVID. COVID was definitely out of our control. Queen's Gambit was out of our control. I would say the majority of our hockey sticks have been accidental and out of our control. And we just happened to be the beneficiaries of a big wave that kind of surged our direction. And it's great that you were able to take advantage of those. You know, a lot of companies will get the opportunity to grow, but their platform won't support the growth because it wasn't planned. Yeah.

And they'll end up struggling because of that. But you were able to keep up with demand. Yeah, exactly. You know, the altar story to that is I've dabbled in lots of different things over the years. But I built a game called Wisecrack for mobile phones. It's basically just like a party game. You know, you write funny questions, you write funny answers. But I didn't spend a lot of time on it. You know, I was like, I hired a couple of people, helped me build it because I just really wanted it during COVID so I could play party games with friends over Zoom.

And all of a sudden I'm getting tons of like literally hundreds of complaints are flooding in about I can't play the game. I really want to play. You know, JB's waiting, JB this and that. And I was like, what is going on? And it was literally probably a month after I put the application into the app store. Justin Bieber found it and tweeted about it, wrote it on his Instagram and said, hey, come play some Wisecrack with me. I mean, literally millions of people were trying to get on my Wisecrack platform and play a game with Justin Bieber online.

And it completely crashed. I mean, my servers weren't working. The app wasn't working. Nothing was working. And so that was a huge missed opportunity, you know? So sometimes a wave comes your way and it literally just crushes you. So that was kind of the other funny story. How was chess.com able to meet that demand? I mean, when you started, you didn't build the application to scale. I mean, you built it using technology you already had, plugging things together, everything.

and going from there. But how did you change it to be a scalable architecture that allowed you to take advantage of those spikes? You know, you can't ever build a platform or an application on day one to support millions and millions of users. It's just, you'll be paralyzed, you know, trying to make it scalable to that degree. And I don't care how much they say, oh, you got, you know, cloud this and cloud that these days. It's just never that simple. There's always going to be things where it's like, okay, I didn't foresee this or that.

So there's sometimes, too, where you just build features that you think are really cool on day one. But if you were to fast forward like five years, you'd be like, that feature is so...

so not scalable. I don't know why we ever built it, you know? So a couple of examples of that is like, we had a map feature in the early days of chest. It would show a pin drop for every single user who was online on chest.com, you know, like an actual map of the globe and you would see pins everywhere. And it was cool when we have like a thousand users, you know, but fast forward is like, this is never going to scale because we're literally calling a Google API with coordinates and trying to figure out where all of our users are. I mean, it's,

It's just like a feature that was cool for like a year. And then it was like, okay, we got to end of life that as soon as possible. That happens a lot. You know, there's lots of times where you think, okay, how can I build this? This is going to work great. And then all of a sudden you're like, wait, this does not work at all for a million users. So I think there isn't really a great answer as far as like, how do you build something to make it scale? It's always going to be the case that you need to refactor and retool and optimize the heck out of your code. It's just, it's always going to be that way.

And the faster you grow, the more nerve wracking, the more painful those retools and refactors are going to be. There was times we were at MySQL, we were a LAMP stack. So it was PHP and MySQL. And there's queries that work great when you're small and queries that don't scale at all once you start to hit that query a lot and when it's trying to scan millions and millions of rows. And so

It was a constant iterative process of like, now this query is our biggest problem. It's taking five seconds. We got to get this query down under a second or down under 100 milliseconds.

And we would just have tools that monitored our slowest code, our slowest requests, our slowest API calls, our slowest queries. And occasionally things would just bubble up and you would be like, okay, now this page is taking nine seconds to load, or this query is taking seven seconds to execute. So it's like, that's now the problem of the day. We've got to figure out why is that query slow? Do we have to refactor? Do we have to re-architect our database? Do we have to denormalize things?

duplicate the data so it's more readable? Do we have to add more indexes? So it was a constant battle. It was just literally a constant battle for years and years and years. I was pulling my hair out. I was screaming expletives in my garage. It was...

Whack-a-mole to the extreme. Yeah, it totally was whack-a-mole. And it's like the nice thing about getting bigger and bigger is that you just have more resources and brains and smart people to rely on. You can hire more brilliant data scientists and better MySQL guys, better DevOps guys. For a couple of years, it was just me. And it was very, very stressful and very nerve-wracking. Yeah.

And we would hire the best and the brightest consultants in the MySQL space. And I swear it felt like we were always doing something for the first time. It was always like, oh, we've never seen that before. We've never seen that before. And I'm like, you know, so many times I felt like, are we the only company in the world that's using MySQL? Because it feels like we're always running up against things they've never seen. And so picking the right tech stack is huge because you want to be on a tech stack where lots of other big companies have already paved the way for you and solved problems and come out with special builds. And

things like that. So picking the right tech stack, I think is a huge deal, picking the right framework, but there isn't really a panacea for it. It's literally just every day is a new problem. Every week is a new problem. Every world chess championship that happens is a new problem because it's going to spike something and that something is going to cause problems. So I'm basically going through that same thing with Landover right now, my new game, where it's like every little day is a new problem and a new fire to put out. And we're constantly trying to figure out what's going on. So.

Let's move on to what you're doing now. You left chess.com and I think you said 2017. And I'm assuming you left it in good hands, obviously, because it's been growing and expanding since then. But you went off to do something else. First, why was that the right time to leave? And what did you go off and start doing? You know, I think like when we started chess.com, Eric and I, we were floor mates in college together. We became very good friends, had a lot of fun adventures our freshman year of college. And then we went off to do something else.

And, you know, we kind of reconnected years later to work on Wholesale Chess together. I left BYU where we were at. So we didn't have four years of college together. He also went off and served a mission for his church. And so he was gone for two years and then I left the school. So we'd kind of like, we weren't super close after our freshman year, but we were definitely good friends. And I think after you work with somebody for a long time in a very heated, stressful environment, it just became apparent after 12 years that it was like,

And CEOs and CTOs, the name of the game is you're going to butt heads a lot. And it's a healthy disagreement process. It's a checks and balances process where the CEO says, let's build this, this, and that. And the CTO says, maybe no and yes. And so there's constant pushback between what we're going to build or what we're not going to build or how we're going to build it or why we can't build it.

you know, and if you don't push back on anything, you're going to over-engineer and you're going to, you know, it's not going to be scalable. It's not going to be feasible. Like if the CEO comes and says, Hey, we want a map of every user on the platform shown on Google maps. You know, like if I had any foresight, I would have been like, look, Eric, when this grows to a million users, this feature is not viable. And so we could have saved ourselves three months of engineering time, never building the map. Right. But

Sometimes you just say, okay, boss, yes, sir, let's do it. Let's build it. You know, so you kind of pick and choose your battles.

But I think after 12 years, it was apparent, one, that it was like we were either going to remain business partners and no longer be friends or let's be friends and let's kind of part ways and do different things. I knew that chess.com was in good hands. Like you said, we had a lot of good engineers and smart guys, and it was no longer a startup. I think when I left, we were right around 100 employees. So there was plenty of guys to pick up where I had left off and carry the tech flag forward.

So it felt like a good time. There was lots of other things happening that I wanted to pursue. Honestly, too, a big part of it was chess.com was growing very linearly in 2017. It was like we would always grow every year, but it was always kind of the same pace every year. There wasn't usually like a big spike. It was just kind of like, OK, yep, you know, we'd have like a little jump here for this event or that event. But it was like this is a solid company. It's growing.

If COVID or Queen's Gambit had happened before I left, I would probably still be there because once those catalysts happen and we really started hockey sticking and growing at a very crazy exponential pace, I probably would have been like, okay, I don't feel good about leaving because there are fires to put out everywhere. And so I'm kind of glad I missed that crazy time, but I'm also a little sad that I wasn't there to actually experience the tidal wave and the tsunami. But

There was a massive rewrite we did in 2014 where we rewrote the entire application of the framework to go from an old framework that I had chosen back in 2005 that was now kind of defunct and unsupported called QCodo. And the main PHP framework of the day was Symfony. And so we were like, we really need to rewrite everything into Symfony. And that was a very painful, dark three-year process that we went through as a company to

And so I think once that was kind of done, I was like, you know, I think that's kind of the end of my tenure and we've got it onto a nice stable platform going forward. It should scale nicely and we can hire talent a lot easier to work on Symphony because it's a very popular framework and platform. And while all that was happening, I was also getting very, very excited about cryptocurrencies. I bought my first Bitcoin right around $100. And so I was really early into the crypto space. I was going to Bitcoin conferences and

And I really want to do something in crypto space and just didn't see any way to do that at chess.com. And so another reason I left was just honestly because I was really excited about going off and exploring crypto. So is that what you're doing now? I tried. I tried for a couple of years. I started two or three companies in the crypto space and realized after a couple of years that I was like, crypto is just not super ready for B2C applications anymore.

You know, it's just everything I built, I was like, you know, this would have been a lot better if it wasn't on the blockchain or it didn't have to do with crypto. I was trying to force, you know, a round peg through a square hole in some ways where I was like, I just really want to build something and I want it to be on the blockchain. I want it to be crypto related. But then I would just be like, why is this even on the blockchain? Why am I doing this with crypto? So, you know, one thing I built was

a Bitcoin betting platform where you could play skill-based games for crypto. That was called Gambit.com. So you could play Backgammon and Monopoly and Domino's and different games and you actually wager Bitcoin while doing it. But again, it was kind of like, why do this with Bitcoin? You could probably just do this with fiat currencies and it'd be the same thing. It'd actually be a lot easier to

And after a year or so doing that, I realized it was a massive legal headache trying to do it in the United States. It's only legal in some states and not all states. And I was like, maybe this would work if I was living offshore. But the legalities behind it and the cheating that runs rampant when there's money involved, it was not super fun after about a year or so.

Eventually kind of closed that down. I tried running a crypto analysis company called Renzi for a little bit. That was actually pretty interesting. But the crypto crash of like 2017, there were some banks that were interested in the technology I was building. But once crypto crashed in a big way, it was like everybody just locked their doors and they're like, we don't want anything to do with crypto. So...

I wasn't quite sure how to monetize that. And then, yeah, there was some other thing I dabbled a little bit. But eventually, after kind of investigating the crypto space, I got burnt out. There was all these altcoins. There was a lot of garbage out there. There was tons of scams. There was tons of pump and dumps. The whole ICO craze happened there.

the initial coin offerings. And there was just so many bad actors in that space that even though like from the beginning, I had been a big believer in cryptocurrency changing the world and being this new awesome global digital currency and all the amazing things that it was going to do, it never materialized. It was always slow. It was always cumbersome. It was expensive. It just never became what I thought it would. And the amount of copycat coins that were out there really kind of polluted everything and made it all just feel

just kind of slimy. And so I eventually just sold all my crypto and got out and was like, let's do something back to where I, you know, I have a lot of passion. And that led me to Settlers of Catan. It's always been one of my favorite games.

And every time I would go online to play, I found myself on these terrible Java applets that were outdated, that I had to update my Java version, or I would end up at a Flash website, and Flash was not supported anymore. So then I went to Katan Universe, and it was riddled with bugs and terrible user experience and paywalls everywhere.

And I just got really frustrated. I'm like, this is such a beautiful game. It's such a great game. I love the basic concept of it all. And I hate the fact that there's nowhere for me to play this game on my phone or on a website that is just awesome. And so I finally was like, that's it. That's my project. That's what I'm going to do. I'm going to try to make the best Catan mobile app there is. And so that's what I've been doing for a little over two years. It's called Landover. We can't call it Catan, obviously. We don't use any of their branding. I also took...

a lot of the mechanics and change them to make the game much more playable. I was very much inspired by Hearthstone, which was basically Magic the Gathering put online and made simpler for the masses. And I was a huge Hearthstone player.

And I loved what they did for this idea of collectible card games. And I was like, I think I can do the same thing for Catan. And so that's what I did. I'm like, I'm going to make Catan better, faster, simpler, make it on my mobile phone, make it so I can play with all my friends. And so now I do. I've got seven or eight games going. All my friends from chess.com play it and they're all addicted. We've got a growing community on Discord and just really excited about it. It's fun. And so in 20 years, it'll be the size of chess.com. That's the hope. That's the hope.

That's great. Well, thank you very much, Jay. This is great. So my guest today has been Jay Severson, who is the founder and CTO of chess.com. Jay, thank you for joining me today on software engineering daily. Thanks for having me. It's been fun.