Ep. 79: Rookly, The Power of Chess, and Building a Fun Future of Education with Matt Zeitlin, Co-Founder of Rookly

(upbeat music) Hello everybody and welcome to Straight To It. I'm Charlie Sightland. Today, I was fortunate to have a conversation with Matt Sightland. Matt is the co-founder of Rookley, along with Amir Moizami. Rookley makes school chess more fun and accessible by offering easy online competition. Students can see their opponents, play together with friends, connect with other schools without even leaving their respective campuses. Matt and Amir have been playing chess together since they were six years old. They believe in the power of chess for education while at the same time understanding the difficulties of competing in person firsthand. We discuss how the company came to be, chess and its transformative power for education and much more. Enjoy the interview. - I'm wondering if we could start by you telling us a little bit about the origin story of Rookley. Knowing that you've known Amir since you were young, how did you guys come to work together? - I grew up playing chess. Amir was a year younger than me. And we were both super serious chess players, chess classes together, et cetera, went to nationals. We both ended up winning national championships. But then I think for both of us around middle school, high school, just life, school got in the way. And we both stopped playing chess as seriously, went to colleges on opposite coasts. And I actually hadn't heard from him for a few years. When at some point he asked to talk to me, he's like, hey, I got an idea. I'd love to hear your thoughts about it. And so he pitches me this idea for online chess lessons, basically under the view that teaching chess, and this was right at the tail end of COVID. So it was a very practical issue where he'd been doing some chess teaching. And teaching chess is very hard. You have to schlep a bunch of pieces, a bunch of boards to places, long travel time. So it is not great for the instructor. And it's also very hard for schools because there just aren't that many great chess instructors, especially in more rural areas. So someone might have to travel like two hours if you want in person instruction. So he reached out to me with this idea. The extra thought I was a chemistry major at the time, but turned out I was a computer science major. So I was like, hey, I'd be interested in working on this part time. I thought it seemed cool. It was nothing I'd ever done before. So I was like, hey, I'll work on this part time and just fell in love doing it. And was full time off to the races like a month later. - And how did the idea evolve originally from lessons? - Yeah, it's a great question. So yeah, we went through different iterations. We actually started with lessons for adults because things with children have lots more regulations, compliance, we had to find lawyers and deal with all that first. So we ran some lessons with adults, but all went well. People seem to enjoy it, but it's hard to get adults to want to commit to something for a long extended period of time. So then we always naturally wanted to do which was teach lessons in schools. Under the view that beyond just the benefit of not needing a person chest instructor, remote chest is a lot of benefits where you can easily pair people up to play. You can control what moves people are making, making sure students are making legal moves. You can watch all the games at once. You can have different fun teaching mechanisms where students can make moves. You can see them, they can see each other's moves. And so that was super successful. We worked with a bunch of schools doing that, but then the refrain we always heard was, our kids won competition. And it was one of those ideas that made a ton of sense in hindsight. This was actually a mere idea. It was a very brilliant idea, because basically what we remembered was that, as a kid, chest competition was going on the weekend to some crazy place, like Prussia, New Jersey, some playing and some tournament for a whole weekend. You have matches that might be five hours long. You'd be there a whole weekend, middle of nowhere. And so along with school and just life, it just wasn't feasible. And I think we found that's the experience for a lot of places. This is when Amir and I grew up in New York City, which is probably like the best place in the world to learn and compete in chess. And even that was painful, but so our schools that we have an Arkansas and such just couldn't do that at all. So when we heard enough ideas for this league idea, we basically said, okay, let's build and see what happens. And it ended up being super popular. So right now we work with about 250 schools all across the country. And we basically provide a platform where school chess teams can compete against each other at different designated times. So right now we run, I think nine leagues at different days and times throughout the US, so the ideas you might have 30 schools at Monday at four that are all gonna have their chess teams compete against each other. And I think what's fun about it is that it gives chess this experience that's a lot more like, I plan on the basketball team in middle school. And part of that is just the fun camaraderie being on a team, having rivals working together. And this I think really allows chess to do that in a much more fun way than if you just have a student playing an anonymous person online. And for someone who isn't familiar, would you tell us more about how your product works from each perspective? For example, if you're a student, you're a teacher and you're administrator, what does it look like? - I guess the student perspective is the most interesting since you know, as you always say, that's the one that really matters. But we try to make it easy to join as possible. You just have a school-specific link. You put it in, put in your username, you're good to go, you jump right in the room, then the ideas. You see everybody else that's gonna be competing along with your teammates. And then once it's time to start, the proctor will pair students. And then throughout the match, you finish games, you win, you get a point, you continually play games all the way to the end of the hour. And at the end, team with the most wins is the winner. But what's fun about it is that because of the structure, the pairings get better and better as time goes on because you can better see student records how good different students are. So you end up with better matchups of best players versus best players. And the other fun thing is from a school admin perspective, you can actually spectate all the games at once in like a bird's eye view. And then also if you're a student waiting in between games, you can also spectate games. And then from the proctor, it's a similar bird's eye view where you can essentially see everything going on. So you can jump in if there's any games with issues. But then the main job is just trying to pair people smartly in subsequent games. Gotcha. And when you were growing up and you had the opportunity to play chess, what do you think playing chess as a kid? What type of effect did that have on your life? - I think at a very positive effect, I think the unfun answer, but one that's increasing the relevant today is it really helped develop just patience and ability to just sit and think because when I played chess you'd have matches that were two hours in the clock, both sides. If you reach 40 moves, you get another hour. So you could have a match that would go five, six hours. And you're basically just sitting there you in an opponent in a board. And so I think that really just helped build a lot of resilience, perseverance, ability to just think through a situation that I think has certainly well in life both in academically and then in the work world. And I think that's a pretty similar experience what a lot of chess players have had. - How do you see this with your students? Have you heard me testimonials or customer stories that have really stood out to you? - Yes, so I think what's most heartening to me is actually something different where when Amir and I played chess, there was some team aspect, not really. Chess was not popular, but we've actually heard a ton of really nice testimonials about how being part of a chess team has helped kids who might have had trouble finding a good friend group or fitting in to basically find some activity that they could both strive in and improve in but also just find other people they could hang out with and have fun on a day and work toward a common goal. So I think that's almost the most heartening one for me because there's plenty of time to improve and learn and work on critical thinking skills but just the quicker effective helping kids have more fun at school, this is really meaningful to us. And then, I think the whole academic side of it is really, really interesting. And I think there are a ton of studies of different merits that try to show how much playing chess might improve your academics or not, improve your math skills or whatever. That's a very hard thing to quantify. Nothing that we've quantified yet but it's something we'd be very interested in looking at in the long run. - Gotcha. Gotcha. And you talked about how when you played as a kid, chess wasn't quite as popular. And I know that there were a few moments, I think, one during the pandemic when chess got a lot more popular and that sort of era. Was that something that surprised you and has that trend kept up? - Yes, I always say to people, I talk about Rookly and they're like, why is Rookly good idea? I always start with the popularity of chess and I always joke that I'm shocked by it. it, because it still doesn't make that much sense to me. I love chess, but it's a game that hasn't really changed much. And I think during COVID people saw it could be fun to watch online, they saw streamers compete, and I think that really helps. But what's cool is that the popularity of chess has, if anything, just continued to grow since the pandemic. To the point that, you know, part of the reason teachers like Rookley as they say, "Okay, my kids are already playing chess.com games in class during lunch, so let me actually give them a proper outlet for this instead of them having to do it in some clandestine way." But honestly, I couldn't tell you why. My favorite thing, my favorite chess memory, since a kid has been playing Bug House, two-person chess with friends in college. You know, I like different kinds of chess. I have no idea why chess has taken off and just continued to take off, but I am happy for it, because I think it's a great game. Working with schools and administrators, seeing how education operates through Rookley, how is this informed, how you view education? I think it's really showed me how hard the educators drop is, because, you know, it's always really easy from the outside to say, you know, "Why can't teacher X put on this club or do this or that?" But the reality is a lot of the teachers who've helped run Rookley or build chess clubs at these schools are doing it on their own time. They're not compensating any extra for it. They have other responsibilities. So I think that's kind of been the most, you know, telling and sad thing to me that, you know, I wish there were better extracurricular systems where teachers could be rewarded for taking time out of their day to build these great programs. With respect to education, one of the trickiest parts is, you know, how do you motivate kids to actually want to learn and want to enjoy? And I think that's, you know, increasingly relevant in the age of AI and such. But, you know, something we've seen is you can offer chess, you can offer anything. If the kids don't engage, you don't really want to do it. You know, it doesn't really work. So at the end of the day, you also just really benefit from having teacher, some kind of faculty person who's just exciting, can help get kids excited. And I think that's one of the other reasons why we really like this idea of a league because, you know, it really does seem that having competition some way to measure yourself, some way to motivate for progress really helps motivate kids to actually also just want to sit and learn. Yeah, and if this is something that Rookley's done for chess, is this, is that model of taking something like chess and making it easier and making it more fun? Do you envision that for other, other things that Rookley could do? Yeah, great business instincts. That's something we've definitely thought about. You know, I think our plan is we have a ton of plans and chess, and that would continue for at least the next year. But I think in the long run, our view is that chess has a great niche where it has both academic benefits, but students kind of see it like a game. But, you know, one of the phrases we love is to say, we want to celebrate chess players like their athletes, give them similar mechanisms, similar ways to stand out and shine. And I think that's true for academics across the board, where, you know, example I give as I was, I loved chemistry in high school. And there was like a small chemistry Olympiad club at my school. I didn't even know it existed. It might have been fun, but if you could have some kind of fun chemistry competition on Rookley for like top chemistry students at schools to compete in, I would have loved to do that. And I think there are a ton of students who would. And I think that, you know, that similar idea of just fun, but easy competition could be spread to, you know, pretty much any academic subject. Got it. Got it. And now getting into running Rookley, and the journey it's been on, could you take us through some of the, you know, more pivotal or difficult points that you've come across while running Rookley, and how you've navigated them? It's a great question. You know, it's funny. I think that, you know, my co-founder may have a better answer for this question. I'm a very even keeled, consistent person. I've always believed in Rookley and the vision through ups and downs. You know, it's tough. I mean, we've probably been doing Rookley for like three plus years now. And so I think a big part of it is just having the perseverance to say I'm just going to keep taking another step day after day. And I think for, you know, I'm always on the engineering side of the business. So it's a little easier for me because I always have control. I can see, you know, the product of what I do each and every day. But then for someone in sales, it's like, okay, I spent all this time trying to get this big sale. And then for some silly reason, some school bureaucracy, it doesn't work out. And I think, you know, moments of that could be disheartening. But that's why, you know, I think we always say the most important thing in a business is the co-founder relationship. And I'm here and I've always been great at, you know, lifting each other up when the other's down and just saying, you know, we're going to keep grinding, keep trying to figure things out. And I think that's part of the reason why even if, you know, I always say, oh, man, you know, I wish I could have built this twice, three times as fast if I knew I did today. But still day after day, you know, the business grows, the product improves. And that's what's, you know, important to us. And I think I have to ask about this given, given recent news and your, your focus on the engineering side of the business AI. So how have you deployed it so far? And how do you see the company benefiting your facing challenges from it? That's another great question. You know, AI holds, I guess I can, you know, from an engineering side, I can start with that. I have always thought it has been incredibly overhyped. And I still think it is recently in the last three months with different improvements. I actually do use it and find use for it, particularly for tasks that have been done before, more automated translation type coding tasks. You know, I could go on the AI topic for a long time. I have many opinions about it, none of it positive. I would sum it up as I do not enjoy using it because it's basically telling someone else what to do. It's just constant task switching, going back and forth. And my real concern is just that, you know, if AI code ever is as good as it's promised, it will mean that as a society, we have many more issues than just AI code because the AI is too good and can do many things. But I won't go too long on that tangent. I do think AI has a very interesting role in chess. Something that's different about chess is that, you know, chess engines have been way better than any human player for a long time. And the way those engines are designed, you could call it AI, but it's, you know, completely dissimilar from how large language models work. And so these engines will always be better than any kind of AI ever will be. But AI still could play a role in theory because one of the challenges of chess is that if you're trying to learn chess to play game on chess.com and on move 15, it says your position got worse by one pawn's worth. There's not easy answers to why that happened. It's a super complicated game. So having some AI that could say, hey, you know, I'm going to take the engine output that says, here's some information about this position. You know, can you basically interpret why something might have happened? I think that could be a very useful teaching tool because, you know, what's most valuable is not the engine output. It's saying, why? Because that's how you learn. So I think, you know, there are definite benefits toward learning and being able to generate learning content over time. Yeah. Yeah. And so it's overhyped. What is it? What do you think specifically like about its functions are overexaggerated? You know, I think part of the issue is that most, you know, demos, examples are showing what I'd call toy problems. You know, small, well-contained, you know, build this app from the specification, build this or that. Recently, they've gotten more interesting. You know, it's built a browser, built a C compiler. And those are legitimately impressive. They're useful. And they could have serious benefit. But, you know, the actual software engineering work on a day-to-day basis generally falls much more on the system engineering side where it's the question of how do all the parts of the system link together? So, you know, I've started to find AI more valuable and kind of doing quick boilerplate-type tasks. But that still might be, you know, 25% of my time directing I had to do that. And just the way it currently works, you know, we've kept hearing. All software engineering will be automated within six months. People say that two years ago. They'll say it again. They're still saying it. But, you know, there's been no evidence basically that AI can solve problems that hasn't seen before. Or even, you know, a better way to describe it would be problems with very bespoke constraints. You know, the reason software is so complicated is that it's a very highly-dimensional problem because you have all these different constraints, all this different business logic, all this different user needs. And you just can't encode all that. It'll remember some, it'll forget others, and then you'll be left with issues. So, you know, I think my main frustration with AI is, comes down to the fact that if you watch it, you manage it, you give it feedback, you edit its work. That takes a lot of your time to do that you could be doing it yourself. If you don't do that, it might produce a good output or it might produce an output that if you let it keep going long enough, it produces a ton of code that you don't understand and then might have a bunch of latent bugs that you then can't debug. So, you know, it's one of those trade-offs where it's something I want to learn to do better and I do think it'll be a part of future software engineering. I just don't like the way it's been over-hyped and try to, you know, basically dissuade people for programming. And I've read about how recent studies in just in general for its efficiency, it hasn't improved efficiency. First of the reasons that you're talking about how it takes so much time just to like, you know, the errors and the, you know, prompting it, it just takes time away from you. Oh, exactly. I think it's funny. Like, I can see the appeal where I type something and then I kind of sit back and relax for one or two minutes because I know that's long it'll take to do it. And then I kind of feel productive. But then, you know, if I think about it, I'm like, was that really the best use of two minutes? It was relaxing. Well, you need to get the Instagram Reels integration in there, right? Yeah. So that's the other problem. Like, it's definitely, you know, we talked about attention span before, you know, it's definitely hurt my attention span because when I start working on a hard task, I'm like, oh, maybe I could just ask AI to start framing this out for me and then I can easily see how continuing to do that just makes it harder and harder to kind of buckle down and solve hard problems. Gotcha. Overall, and you're, you know, experience building. Rookly, what have been the most meaningful lessons you've learned? I think the most meaningful lessons I've learned is a good question. I mean, at the end of the day, business is about people. And, you know, I think I was talking about it a year before. I'm just blessed to have such a great relationship with the co-founder, but also our employees. Our employees are wonderful. And I think that's what makes the business fun day to day. And I think, you know, it's basically super meaningful to us to be able to work on a problem that helps people with a bunch of people who we all like. But I think, you know, for us at the end of the day, what's most meaningful is just thinking, hey, you know, we're building something that ideally will just make a few cuts happier. And, you know, that's kind of enough for us. And that's always like the important thing we try to fall back on. We think of the frustration of business and thinking, oh, are we growing fast enough? Are we building fast enough? It's just like, okay, hey, at the end of the day, people are using the product. They're enjoying it, you know, and that's that's important in itself. Gotcha. Gotcha. And for the next year or two, what should fans and customers really expect to see? Yes. So I think, you know, one goal is just to continue to grow the number of schools. Right now, we've around 250, the goals to hit a thousand. And really, the idea is, you know, the more schools and league, the better the league becomes because you can much better match quality of player match age, which just makes matches better. We have a ton of ideas in the product front, primarily around how can we build different fun learning or gaming experiences around roughly? So, you know, that might be different personalized learning that helps you focus on specific mistakes you might have made during a league. So the idea is that you can basically have a student profile that's integrated across lessons, leagues, something you just do at home. And you can really start to see more progress as a chess player and be recognized for it. And, you know, we're not sure what form this will take. We think there are lots of fun, more multiplayer, ask things you can apply to chess. And so some of these are more quieter ideas. We're working on a background. I think there's a lot of fun things you can do with bots, different customizations. That'll be fun product ideas. But, you know, I think in the short term, one of the biggest challenges we're trying to tackle is just hiring. You know, primarily, I'm the only engineer. An increasing time gets spent on other parts of business and, you know, just random operation stuff. And so, you know, we're really looking for someone who's just really passionate about education, programming, product design to come along and help build a lot of these cool features. Matt, thank you so much for being here. I have final question of, in a decade, where do you see Rookly? I think Argo for Rookly is that it's basically the predominant chess competition platform in the world, at least at a scholastic level where the idea is if you want to compete in chess, you compete on Rookly because that's where all the best players are that can compete. So, you basically remove the bearish entry and you can really have anyone who wants to show that the best of chess, come play on Rookly. And then beyond that, just build out a whole ecosystem where if you want to go from nothing to being a great chess player, you can learn to do it on Rookly. And then, similar fashion to play it, you know, across all academics so that, you know, anyone who has an academic passion can really feel like they could be celebrated.