The Ledger
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Allebest forced exiting investors to pool tens of millions for staff
“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…”
Allebest set early salaries by asking candidates what they needed to live
“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 …”
Allebest: Chess.com instituted a firm rule against paid user acquisition
“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…”
Allebest regrets selling equity to Chess.com's first investor
“Totally. Every day. Every day I think about it. I have so few regrets in life, but that is one.”
Allebest: VCs including Peter Thiel rejected Chess.com for five years
“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 …”
Allebest: Short-form video completely drove Chess.com's latest growth wave
“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.”
Allebest: PokerStars founder Esai Scheinberg acquired over 20% of Chess.com
“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…”
Allebest: COVID and The Queen's Gambit 5xed Chess.com overnight
“When COVID came and the Queen's Gambit hit and our numbers like five X overnight, it grew the game of chess five X.”
Allebest: Geographic hiring constraints shrink talent pools and inflate compensation
“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…”
Allebest: Chess.com's General Atlantic deal was 100% secondary equity
“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.”
Allebest: Queen's Gambit subscribers converted at higher rates but retained worse
“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 …”
Allebest: Exact-match domains were essential for web startups, unlike today
“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…”
Allebest: Chess.com pushes new users to play coach bots first
“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 …”
Allebest: Chess.com historically operated without metrics-driven management
“We are, we have not historically been a metrics-driven business. We are, we've been a heart and mission and chess-driven business.”
Allebest: Chess.com intentionally filters out applicants seeking top market salary
“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.”
Allebest: Chess.com avoids taking corporate stances on political issues
“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.”
Allebest: Chess.com prioritized immediate monetization over typical Silicon Valley spending
“Everything I saw going on in Silicon Valley was like spend, spend, spend. We did the opposite. We thought about monetizing immediately.”
Allebest: Chess.com has 150M+ registered members and 15M weekly active users
“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.”
Allebest: Winning first chess game doubles or triples user retention
“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.”
Allebest outlines Chess.com daily user engagement across playing, puzzles, and lessons
“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…”
Allebest: Chess will remain the preeminent strategy game as media proliferates
“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…”
Allebest: Chess.com was live streaming on Justin.tv before Twitch existed
“We were doing live streaming back when it was justin.tv long before it was Twitch.”
Allebest: Younger Chess.com users convert to paid subscriptions at lower rates
“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.”
Allebest: Most Chess.com paid users choose annual billing and highest tier
“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.”
Allebest: Chess.com offers free play while monetizing educational features
“Our business is funded by learners. Playing is free. Learning is Behind the paywall.”