Chess.com

“Totally. Every day. Every day I think about it. I have so few regrets in life, but that is one.”

“What we're trying to do is push people toward not playing a person first, but knowingly playing a coach bot personality where they will win and feel good But not to just throw them in the pool of players against other people where there's a fifty-fifty chance …”

“Chess.com is my third chess business, which is totally absurd to say.”

“When our PokerStars investor, you know, the Sheinberg family, when they exited to GA, I said, I am going to block this transaction as hard as I can, unless We set aside a huge percentage comparatively of the sale. Everybody is going to pay. I think it was seve…”

“56,000 dollars.”

“We tried for like the first Five years to raise money. We tried many times. We tried angels. We tried, I met Peter Thiel. I went, I met a bunch of different angels. I went up and down. I used all my connections up and down Silicon, you know, Sand Hill road to …”

“I would just say to them, Hey, how much money do you need to do this job? And if we can make that, we'll do it. And if not, I'll let you know, but really, what do you need to do this? Because I'm not going to make you an offer. Cause I don't know your life. I …”

“We were doing live streaming back when it was justin.tv long before it was Twitch.”

“We are, we have not historically been a metrics-driven business. We are, we've been a heart and mission and chess-driven business.”

“We are nobody's highest paying job. We immediately filter for highest pay. Like if you are looking for your highest paying job, it will not be chess.com.”

“Our most recent wave was Completely driven off of short forms, whether it's YouTube shorts, Instagram, you know stuff or reels or, you know, TikTok. It is totally driven.”

“But now you have a whole bunch of high school kids and junior high kids and younger people getting into chess, and they subscribe at a way lower rate. And so registration numbers went through the roof, but our subscriber numbers didn't follow.”

“We are not out there trying to have a stand on any particular issues, but our belief is that chess is for everyone, and that's an inclusive message.”

“Everything I saw going on in Silicon Valley was like spend, spend, spend. We did the opposite. We thought about monetizing immediately.”

“His name is Esai Scheinberg, founder of PokerStars. He loves chess. He wants to meet you. I meet with him. He's like, hey, I want to buy in. I want 50% of the company. We're like, get out of here. We're like, no chance, no way. And so, and he's like, okay, I'l…”

“So just, we could say we've got about a 150, a little over a 150, a hundred and sixty million registered members. We have Take a weekly active users is probably around 10% of that. Around fifteen million. About 10% of that are active subscribers.”

“The majority of people pay yearly. And most people do tend toward our highest paid product because they get the most access and our retention on paid users is really good.”

“When COVID came and the Queen's Gambit hit and our numbers like five X overnight, it grew the game of chess five X.”

“First of all, talent is all over the world. And if you are geographically confined on talent, you have a smaller hiring pool and you are now competing in ways, you know, that are hard. It's hard to compete against these massive dangled comp packages in certain…”

“That's when we met GA, but again, it was to buy out existing equity. It was not to raise money. There was no primary money put in whatsoever. It was all just buying founders' equity and equal ownership.”

“Our business is funded by learners. Playing is free. Learning is Behind the paywall.”

“It pains me to say this, but somebody who wins their first game of chess is two to three times more likely to stay around than someone who loses their first game.”

“You know, it's actually a strangely low number, but it's like, 60% of our active users come in on a day and play. Half of them will do a, will do puzzles. So half of that number will do puzzles, and then half of that number again will do lessons. Game review i…”

“We'd totally been burned on, on paid acquisition, and we pretty much made You know, a very firm rule that we weren't going to do paid acquisition. And so instead we said, we're going to take any money that we have and we're going to put it into content because…”

“I probably hired the first. 300 to 400 people myself who worked at the company.”

“They subscribed at a higher rate, but then retained at a lower rate, to your point. And that kind of, we swallowed that, but it's not like it went up and back down. It went up and stayed up significantly. So yes, it was net massive growth, but yes, they later …”

“People go back to the classics and for a little bit of just like safety. I mean, my kids listen to music from generations past because there's something that's like just classic about that. And I think that chess will be the fallback Of the greatest strategy g…”

“Ridiculously large role, especially at the beginning and the beginning sets the tone for later. Now, I mean, in today's world, if we hadn't done it, if you, would you have to start on chess.com? Probably not, but given the time that we started and how it worke…”