Jay Severson on how to succeed as a business-minded chess player

Jay Severson story starts with programming, which he studied both in high school and in college. Then he worked as a software engineer for several years, before his friend from college decided to start chess.com.

Then it all took off: a long journey with its ups and downs, risks and working all nights long. So what the two friends achieved, and which new idea Jay’s working on right now: let him speak for himself.

“When my friend, Eric, came up with his idea about chess.com, I was quite reluctant. I love chess, I was a chess club president in college, I played it in high school, but I was also sure there wasn't a lot of money to be made", says Jay.

"People don't like to pay money for playing chess. But he convinced me to do it properly, with a great domain and capitalizing on a lot of missing facets of online chess. So we started.

We moonlighted while we had other jobs: I had a lot of contract work, I had a day job. I worked on it when I could, and it took us a couple of years to launch our first real version and get members coming in.

It's grown today to be the number one chess site in the world, with over 300 employees and 60-70 million users.

I don't check the count every day, but it goes up every day. And it's great. We're almost close to 10 million monthly active users now. And there are millions of games played every day. It's a fantastic company, a fantastic team, I was proud to be a part of it from 2006 to 2018, when I finally left as a full-time CTO position there.

The beginning was very hard. My partner, Eric, and I were working in my bedroom, at my house in San Jose, that was the office. There were a lot of very long hours when we tried to get stuff done. Initially, we had a very small product scope.

We wanted to have an email solution, so people could come to the chess site and get "chess.com" email address, which everybody wanted then as a cool flavor for email addresses. We wanted a directory listing of other chess sites, like forums. And we wanted some basic articles about learning how to play chess.

So it was very content oriented. A lot of people came to write blogs, so user-created content became an early piece of our business model. Our site grew very quickly on the content side, which allowed us to SEO very well, especially with the domain name. So traffic grew fairly quickly in those first couple of years.

But as the CTO at the time, my main job was just to write the code. I had to architect the MySQL database, I had to build the API's. In the beginning, our team grew very slowly, because we didn't have any funds. For five years I was just coding, and then assigning tasks out at a very slow pace to two or three developers who joined us in the early days.

And then once the team grew to a certain size, and the company really started to snowball, I found myself mainly focused on database growing pains.

I was up 24 hours a day, trying to make sure that our MySQL database wasn't crashing all the time. I hated it, it was painful, it was not making a lot of money, it was consuming all of my time.

And having a fast-growing site is what you always want. But be careful what you wish for, because it's extremely stressful and extremely tiring to support, especially when you have a very small team and very little funds. You're kind of the last line of defense.

After a few years, we turned on our subscriptions, and money started coming in the door. So we were able to start hiring people, we were profitable. It was nice, we could finally take a salary for ourselves as the founders.

The business mind of Jay Severson

The great thing about Eric and me is that we were business-minded first, and chess players second.

And I think one of the reasons why people failed in the space was because they were chess players first and business-minded second.

They were so enamored by anything they could possibly do in the chess space, that they weren't really careful enough on the business side of things to make sure they didn't overspend, or didn't overpromise, didn’t overarchitect or whatever. We started very small, and we didn't hire until we actually had revenue coming in the doors. We never outspent what we had. And I think that was a big reason for our success.

After over 10 years of working together, Eric and I decided to follow our separate ways. We had many (healthy) clashes, and at some point we decided to save our friendship. Also, I wanted to go off and try new things. At that time, cryptocurrency had come along, I was very much into it and I had some startup ideas in the cryptocurrency space that I wanted to explore as well.

I tried an online skill-based betting platform on Bitcoin and cryptocurrencies, where you could bet on games of Backgammon or the games of skill. But there were many legal issues and together with lots of cheating that people do in skill based betting, it turned out to be not a fun space to be in.

I love to play games in general, and I've always been a big gamer.

I have much more passion for anything I do, if it's gaming-related.

Some cryptocurrency companies that I had started were not gaming related. And I noticed that I burned out pretty early on. Now, I'm working on a Landover app, which is basically a Settlers of Catan style of game that's playable mostly on your mobile phone.

I love the basic concept of it, I love the hexagon board, I love the resource gathering, I love trying to choose a decision tree of where you want to build and scale up technology, or culture, or whatever. I sat down and thought about all the different things that we could do to Catan to speed the game up and to make it simpler.

So I came up with a bunch of ideas. Now we've got a team of five developers who are working on it full-time, with a couple of designers who have been helping us along the way. And I think the game looks amazing. It's beautiful.”

Here are Jay’s three tips for people who start building their own digital product:

       
1.        Ideas are very cheap, it's all about execution. The idea is not a big deal. The hard part, the 99.9%, of what makes a company successful, is the execution, the operation and the team. Spend your time on preparing before you start running with your concept.        
       
2.        Scratch your own itch (or, as they also say, “eat your own dog’s food”). Make sure that whatever you're building, it's something that you would use, it makes it a lot easier to build it the correct way.        
       
3.        Be ready that the world of startups and being an entrepreneur will not be easier than having a normal job where you have a boss.        

“I am jealous of the people that go to work from nine to five and come home and get to do whatever they want and forget about their day job.”

If you want to hear the full story of Jay Severson, where he tells how he dropped coding even though he didn’t want to, how he started and stopped at exercise.com, what other games he made and which piece of advice he would give to all the startupers, listen to our new podcast. Also, you may check Jay’s new project, Landover, here.