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Chess.com launched a poker site and is planning even more classic games. Chess.com has done one thing, and one thing very well, for almost 20 years, but now it's going beyond its domain name. The biggest name in online chess quietly launched its first companion site in beta back in May: Gambit, a free online poker website where players can learn the game without risking any real money. Now Gambit's ready to really get the ball rolling with its first livestreamed event and collaborations with content creators, and Chess.com is planning to branch out into even more games from here. Ordering Custom Maps Chess.com's chief growth officer, Albert Cheng, told The Verge the company chose poker for its first companion site because, like chess, it has learning and social elements on top of just playing the game. He also promised there will never be real-money gambling on Gambit, saying, "Real money is the problem we built Gambit to get away from, the whole industry makes money when beginners lose. We'd rather build a place where people can actually learn." Gambit will look familiar to anyone who's used Chess.com. It borrows the same design style and includes similar play modes, like bot matches, games with friends, tournaments, a review mode for studying your past games, and a learning mode. Gambit even includes Chess.com's bot characters, with matching skill levels - I immediately recognized "Martin," the lowest skill level bot from Chess.com, who is also the lowest skill level bot on Gambit. Image: Gambit Chess.com also developed its own Elo-style rating system for Gambit. Cheng explained in an interview with The Verge that the rating system serves as the main motivator for players to improve: "You're not gambling your own hard-earned money necessarily, so the stakes are lower from that standpoint, but you need something to counterbalance it that you care about, and that keeps the ecosystem in play, and keeps the poker that's on Gambit reasonably high-quality." The rating system is also the backbone of Gambit's paid subscription for access to premium learning features, following the same model Chess.com uses. "Our primary business model of Chess.com is a subscription, but most people play Chess.com for free," Cheng said. "They subscribe to get unlimited access to review their games and to get unlimited puzzles, lessons, et cetera." A reliable rating system allows players to track their improvement, potentially motivating them to pay for those premium features. Image: Gambit Rating systems are also at the heart of Chess's next move. Chess.com is now looking to expand into even more classic games, including go, backgammon, and mahjong. Like Gambit, Chess.com is developing Elo-style rating systems for these games, as well. Cheng didn't say when the new sites will launch but that "development is moving quite rapidly" on them, using the same playbook he used for Gambit. AI is a key reason Chess.com was finally able to expand into other games after nearly 20 years, according to Cheng. He and one other employee took Gambit from prototype to launch within a year, partly with help from AI, mainly for coding tasks. "I think the biggest advantage that it's provided is essentially being able to read our existing codebase and our design system and apply consistent patterns to how we develop Chess.com over to a different platform and do so quickly," Cheng said. Discover more Following Political News He went on to add that there were also a lot of areas where AI struggles, such as brand and feature design. "I think that's the best ultimate use of AI is that ultimately it's going to be a blend, right?" Cheng said, adding, "Just because code is easier to write doesn't mean that you just let it run on its own, but it certainly is a superpower in getting things off the ground." Cheng also said the version of Gambit that's live at the time of writing has "zero or close to zero" AI-created assets, which were used in early prototypes. According to Cheng, without help from AI, getting another site up and running would have required a bigger team or "would have been a lot more disruptive to the status quo of building and growing Chess." Now that a "small, scrappy" team can get a new platform off the ground much faster, it's opened the door for Chess.com to dip into more games, starting with poker. As Chess.com plans its next move, Cheng says they're focusing on games with "both that classic durability plus the community around it," like chess. Now that Gambit has launched, Cheng's leaning into the community and social side of the platform more, following Chess.com's lead, and getting content creators more involved. On August 31st at 12PM ET / 9AM PT, Gambit's livestreaming its Gambit Cup for the first time on Twitch and YouTube with Chess.com co-founder Danny Rensch and chess content creator Alexandra Botez. 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Chess.com launched a poker site and is planning even more classic games. by bleffel | Aug 30, 2026 Chess.com has done one thing, and one thing very well, for almost 20 years, but now it's going beyond its domain name. The biggest name in online chess quietly launched its first companion site in beta back in May: Gambit, a free online poker website where players can learn the game without risking any real money. Now Gambit's ready to really get the ball rolling with its first livestreamed event and collaborations with content creators, and Chess.com is planning to branch out into even more games from here. Chess.com's chief growth officer, Albert Cheng, told The Verge the company chose poker for its first companion site because, like ches... This post was originally published on this site

How Chess.com bootstrapped to $200M revenue and 250M users. Chess.com CEO Erik Allebest explains how he built a $200M bootstrapped platform with 250M users and how AI is elevating human skill. Visual TL;DR When Erik Allebest bought the Chess.com domain out of a bankruptcy auction for $56,000 in 2005, almost every Silicon Valley investor told him he was wasting his time. Venture capitalists on Sand Hill Road wrote off the project as an uninvestable niche hobby. Two decades later, Allebest has built Chess.com into a bootstrapped online powerhouse with over 250 million registered members, 10 million daily active users, and more than $200 million in annual revenue. In a recent episode of the No Priors podcast hosted by Sarah Guo, Allebest shared the key milestones behind the platform's unexpected rise, the impact of cultural moments like Netflix's The Queen's Gambit, and how artificial intelligence continues to reshape human skill in competitive games. Who is Erik Allebest. Erik Allebest is the co-founder and Chief Executive Officer of Chess.com. While attending Stanford Business School, Allebest sought to build an online community where chess enthusiasts could learn, share, and play directly in their web browsers. After failing to secure venture financing, Allebest and his co-founder built the company slowly using cash flow from paid subscriptions. Today, Allebest oversees a fully remote team of 650 employees dedicated to expanding chess worldwide. Building a bootstrapped empire. Chess.com did not follow the standard Silicon Valley playbook of raising massive early-stage capital. Instead, the team grew strictly at the speed of cash flow. Within 18 months of launching in 2007, the site introduced paid memberships for online learning tools and achieved profitability. "We never then again considered raising money. It never crossed our minds. We just thought, hey, we're profitable, let's just keep growing.", Erik Allebest The company sustained steady organic growth for years, but recent cultural shifts created massive user expansion. The combination of pandemic stay-at-home measures, the release of The Queen's Gambit, viral short-form video content, and viral novelties like the Mittens AI bot drove multiple massive waves of new players. Each time usage normalized after a spike, the platform established a significantly higher baseline of daily active users. How AI transformed chess practice. When IBM's Deep Blue defeated Garry Kasparov 30 years ago, critics predicted that superhuman computer chess engines would destroy human interest in the game. Allebest notes that the opposite occurred. Early chess engines like Stockfish initially made high-level play rigid, as grandmasters tried to copy computer precision. However, the arrival of neural network engines like Leela Chess Zero introduced creative and aggressive styles of play that inspired human players. Rather than replacing human players, modern AI tools on Chess.com serve as personal coaches, analyze blunders, and generate tailored puzzles. Today, ten-year-old prodigies are reaching elite master ratings faster than ever before because AI tools democratize access to world-class feedback. Applying the Chess playbook to poker. Chess.com is also exploring how to adapt its rating systems and skill tracking models to other traditional games, including poker. In traditional online poker, success is often measured purely by chip counts or bankrolls, which can be distorted by re-buys or bot activity. Allebest envisions a skill rating system for poker similar to the chess Elo rating. "As people get used to like, wait, I actually care about my poker rating, people are going to care about it as much as money because it's a reflection of the value and their skill as a player.", Erik Allebest By evaluating actual strategic decisions rather than financial totals alone, a standardized skill rating could create a fresh competitive metric for casual and professional poker players alike. (C) 2026 StartupHub.ai. All rights reserved. You may not republish this article in full without a license. Search engines and AI research tools may crawl and summarize for reference. Bulk reproduction or model training requires a license. See our terms. 1 comment. Matthew LaCrosse 18d ago The success isn't just about bootstrapping or AI; it's the community-first mindset. Most platforms fail because they treat users as numbers. Chess.com thrives because it built a culture, making each player feel part of something bigger.