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Solo Student Entrepreneur to Over $50M Revenue: Chess.com CEO Erik Allebest (Part 3)

Posted on Wednesday, Dec 1st 2021

Sramana Mitra: What happens next?

Erik Allebest: I had an internship at a big tech company. I wasn’t that interested in it. Frankly, I did a bunch of internships while I was at Stanford. Pretty much every person I met with at every big company wanted to talk about entrepreneurship. None of them love their jobs. That’s the honest truth. They want to talk about what I had done as an entrepreneur, which I thought was weird. It made me realize I’m not cut out for big companies.

I was wireframing out my vision for Chess.com. At that time, I didn’t have a wireframing program. I was using Microsoft Word. I built a 150-page wireframe of Chess.com in Microsoft Word. Then I went back to my college Chess Club President friend and said, “Let’s build this thing.”

Sramana Mitra: What was he doing?

Erik Allebest: He was working at another internet company doing mortgages. He started doing it on the side with me. I was doing frontend while he was doing backend. He would get off work at 6PM and we’d work till three in the morning. Finally, he quit his job. We just did this full-time. We just built it for months.

Sramana Mitra: Where were you based at this point?

Erik Allebest: We were still in the Bay Area.

Sramana Mitra: What was the capability that you focused on?

Erik Allebest: This was a community. Back then, Myspace was a big thing. We basically built Myspace for chess. You could talk in the forum and find resources. We didn’t have Play or Lessons. People liked it. They liked the News feature. They liked having a profile. We even gave them vanity email addresses. At that time, it was a big deal. When we launched, everyone said, “I just want to play chess.”

Sramana Mitra: Was there any other site at that point where you could play against people from the community?

Erik Allebest: There were several, but none of them had the experience we wanted. We were scratching our own itch. A lot of them had to download something on the computer. Others weren’t well-designed. There were one or two that were pretty good but didn’t want to partner with us.

Sramana Mitra: What was the experience that you wanted?

Erik Allebest: I wanted a place that felt like home for me as a chess player where I could have friendships and enjoy the content. We envisioned a home for the game of chess online. One that felt open to anybody including people who were new to the game. That’s the reason why we chose the chess pawn as our logo. Most people are pawns. Beginners are pawns. We’re not taking this as an elitist thing. This is chess for everybody.

Sramana Mitra: Did you have a way to match levels?

Erik Allebest: Chess has a naturally built-in rating system. Everybody starts out in the middle. You then get rated down or up.

Sramana Mitra: That was available early on in the feature set.

Erik Allebest: Yes.

This segment is part 3 in the series : Solo Student Entrepreneur to Over $50M Revenue: Chess.com CEO Erik Allebest
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