Building a $200M Bootstrapped Chess Empire with Chess.com CEO Erik Allebest

Erik Allebest: I wasn't able to raise any money. No one believed in the vision. I asked some classmates if they wanted to like join me on this venture and they're like, 'Nah, we're going to go like do something serious.' And so then my friend and I, you know, he was kind of the CTO. I was the product person. Just the two of us started building it together. Didn't raise any money. Eventually I started putting money in. I had money from a couple previous businesses I had sold. Borrowed like a little bit of money from my friend's mom and then paid it back later. But you know, we just really kind of grew at the speed of cash. And after we launched in 2007, right as I graduated from school and then I think within like 18 months we were starting to charge memberships for like online chess learning and we pretty quickly became profitable and then we just grew, you know, as we had more revenue we would just hire somebody new whether it was a community manager, a developer, a sys admin, you know, eventually designers and it just kind of grew as we had money for it to grow. And we never then again considered raising money. It never crossed our minds.

Erik Allebest: Computers at first made chess a little bit more boring, but then made it so much more exciting. And we're seeing more exciting chess than we ever have. And the players have gotten better. And really computers are now able to help us unlock the game in ways that make our enjoyment of the game better. Whether it's the AI kind of coach on game review that reviews your game and helps you learn from it, or playing against the computer or generating puzzles that are specific for you. So AI has just really helped humans enjoy chess more.

Erik Allebest: One thing that I really love is the concept that if you just take any given day in your life and multiply that by a thousand, that's kind of what your life looks like. So, if you do five chess puzzles a day, multiply that by a thousand, you've done 5,000 chess puzzles. You're going to be much better. Right now, if you want to do a hundred puzzles a day, multiply that by a thousand, right? Or play 10 chess games a day or do yoga every day for 10,000 days. It's not the actual individual one thing that you do on one day, but it's your habits that really compound over time. You can put that into any field, right? Whether you do one sketch a day or you go for one small run every day. There's really not shortcuts to the process. There's shortcuts in the tools. You have to put in the repetitions into your brain. You have to store that. It's the same as when you train a neural net.