Erik Allebest
Co-founder and CEO, Chess.com. On 3 shows, 3 appearances. The Shows tab opens the full record on each.
founderexecutiveinvestor@erikallebest ↗LinkedIn ↗chess.com ↗
Erik Allebest co-founded Chess.com with Jay Severson in 2005, famously bootstrapping the business to over $100M ARR and scaling it into the world’s leading online chess community. Before Chess.com, he founded other chess enterprises, including the after-school program Schoolhouse Chess and the e-commerce equipment supplier Wholesale Chess.
3shows
3appearances
88statements
14resolved
11supported
0contradicted
79%fully supported
Everything Erik Allebest said on any show that made the record, most notable first. Each card names its show and opens the statement there.
Allebest: Founders are naive about the friction of forced VC exits
“I think people are a little bit Naive about the downsides of raising money. Ultimately your investors will want an exit and it may not be at the same time as you. And for a business that's as mission driven as chess.com is, it's, it has at times been irritatin…”
Allebest: We tell every hire that Chess.com will never be their highest-paying job
“One thing we tell people who work at chess.com, every single person who gets hired,
They hear the same thing, which is chess.com will never be your highest paying job. We're just economically not set up for it.”
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 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 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: Pure software businesses without big tech rivals can avoid venture capital
“For a pure software and content business like ours you know, and one where we didn't have like, you know, no major tech company was bearing down on us. We were able to kind of take a little bit of the slower, a slower road there which was great developed a gre…”
Chess.com remains bootstrapped as private equity investments were entirely secondary
“Well, I'll tell you, we're still a bootstrap business because CBC came in, but they still, you know they came in and bought secondary.”
The abundance of startup advice today is a founder's curse
“I think one of the curses of being a founder today is just how much like founder advice there is out there.”
Poker players will eventually care about skill ratings as much as money
“But I think that as people get used to like, wait, I actually care about my poker rating and I treat this as like something important. I think people are gonna care about it as much as money because it's a reflection of like the value and their skill as a play…”
Allebest: Running Chess.com today is much more stressful than his earlier ventures
“I, you know, in, in many ways I was happier than I am today because the stress of chess.com today is so much more than it was back then. So, you know, I don't wish a huge success on anyone. It can be quite a burden at times to be totally honest.”
Allebest: Pure executive leadership makes no sense for startups under 20 people
“There's not really a role for a leader in a startup that's, you know, you got to get your hands dirty. You got to roll up your sleeves. You have to have vision. You have to be directive. You know, and so I think, you know, being a CEO leader at an, you know, a…”
Allebest: Chess.com will have single-digit revenue growth in 2024
“I think a lot of people would look at, you know, single digit growth, like we're going to have this year and say, ah, well, you're not ready to be a public company.”
Allebest: Severe online criticism reflects deep community passion for chess
“And, you know, I take all the criticism, including death threats, I take it as a sign of how much people love chess and how passionate they are.”
Allebest: Raising venture capital psychologically feels like earning revenue for founders
“I think raising money feels a lot like earning money. It's a self-validation.”
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: 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: 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: Silicon Valley wrongly believed the chess market was capped at $10M
“Well, I mean, now knowing what I know, I mean, chess is a much bigger market. I don't think I did anything wrong. I think everybody was wrong. I think consensus, including from me, was that chess was too small, and so why would you invest in a business that yo…”
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: 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: 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: 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 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: 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…”
One line per show, most statements first. The link opens Erik's full record on that show: the calibration, argument clarity, speaking style and every statement made there.
| Show | Role there | Eps | Statements | Record | |
|---|---|---|---|---|---|
 20VCLEDGER | Co-founder and CEO, Chess.com | 1 | 39 | 89% 8/9 | full record on 20VC → |
 NEON SHOWLEDGER | Co-founder and CEO, Chess.com | 1 | 26 | 100% 1/1 | full record on the Neon Show → |
 NO PRIORSLEDGER | Co-founder and CEO, Chess.com | 1 | 23 | 50% 2/4 | full record on No Priors → |