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Chess.com Cofounder Defies Doubters to Build a 225 Million-User Empire

Chess.com Cofounder Defies Doubters to Build a 225 Million-User Empire

Photo: Fortune · Stuart Isett/Fortune

When Erik Allebest co-founded Chess.com in 2007, few could have predicted the massive digital empire he would build. Like tech titans Jeff Bezos and Starbucks founder Howard Schultz, Allebest faced skepticism, raised eyebrows, and outright doubt from investors, peers, and even friends. Yet today, with over 225 million registered users worldwide, Chess.com stands as the definitive online platform for chess enthusiasts, competitive players, and casual fans alike.

“People thought chess was a dying game, that no one would pay attention online. Now, I get the last laugh,” Allebest said in a recent interview.


The Vision: Making Chess Global

From the start, Allebest envisioned a platform that would democratize chess, making it accessible to anyone, anywhere. While traditional chess clubs were limited by geography, and tournament play often exclusive, Chess.com aimed to bring chess online with social features, lessons, and live tournaments.

Key innovations that set Chess.com apart:

  • Real-time multiplayer chess with global matchmaking
  • Tactics trainers and interactive lessons for all skill levels
  • Live streams of grandmaster games and commentary
  • Mobile apps to make chess accessible on the go
  • A robust community forum and social networking features

Allebest recognized early that technology could bridge barriers between casual players and professionals, creating an inclusive ecosystem that had never existed before.


Overcoming Skepticism: “They Said It Wouldn’t Work”

In the early days, Allebest recalls being told repeatedly that online chess would never gain traction. Skeptics argued:

  • Chess was too niche for mass-market appeal
  • People wouldn’t pay for premium memberships
  • Traditional chess organizations would resist digital disruption

Allebest drew inspiration from pioneers like Bezos, who famously persisted despite skepticism about selling books online, and Schultz, who had to convince investors that Americans would embrace a European-style coffee culture. Chess.com, like Amazon and Starbucks, relied on long-term vision over short-term validation.

“When people doubt your vision, it’s often a sign you’re onto something big,” he said. “I just kept building.”


Growth Explosion: From Hundreds to Millions

Chess.com’s user growth was gradual at first, but accelerated dramatically during the COVID-19 pandemic, when global lockdowns fueled a surge in online gaming. Several factors contributed:

  • Pandemic-induced boredom drove millions to pick up chess
  • Popular culture, including shows like The Queen’s Gambit, spurred interest
  • Free-to-play models with optional paid subscriptions attracted casual and serious players alike

By 2023, Chess.com surpassed 200 million users, with active monthly users numbering in the tens of millions. Paid memberships provide access to advanced lessons, ad-free experiences, and tournament entry, generating significant revenue that supports platform development and global expansion.


Transforming Chess Culture

Beyond numbers, Chess.com has transformed chess culture itself, making it more inclusive and globally accessible:

  • Hosting international online tournaments with cash prizes
  • Offering platforms for women, juniors, and amateurs to compete
  • Partnering with schools to introduce chess as an educational tool
  • Broadcasting professional matches with commentary to engage casual audiences

Allebest believes that making chess fun and approachable is just as important as technical innovation. His platform combines gaming, education, and social networking in a way that has reshaped the perception of chess worldwide.


Monetization and Strategic Growth

Chess.com’s business model combines freemium subscriptions, advertising, tournament sponsorships, and merchandise, mirroring strategies used by successful tech platforms. The company has also invested heavily in AI-powered tools, including:

  • Game analysis engines
  • Personalized training plans
  • Matchmaking algorithms
  • Cheating detection systems

These innovations not only enhance user experience but reinforce Chess.com’s position as the gold standard in online chess.


The Legacy of Persistence

Allebest’s journey underscores a broader lesson for entrepreneurs: persistence often beats early criticism. Like Bezos and Schultz, his vision required resilience, patience, and a willingness to challenge the status quo. Today, Chess.com is not just a platform—it’s a global community, an educational hub, and a cultural phenomenon.

“When people laughed at the idea, we just kept building. Now we’re connecting millions of people around the world through chess. That’s the reward,” Allebest said.


The Future: Expanding the Digital Board

Looking ahead, Chess.com plans to:

  • Expand AI-driven coaching tools
  • Launch new competitive leagues and tournaments
  • Enhance mobile and social integration
  • Explore collaborations with esports and gaming platforms
  • Continue global expansion, reaching underserved markets

Allebest emphasizes that the platform’s success is tied not just to technology, but to community, engagement, and a vision of chess as a universal pastime.


Conclusion

Erik Allebest’s story is a reminder that big ideas often face early ridicule, but persistence and vision can transform a niche concept into a global powerhouse. Chess.com now stands as a testament to what can be achieved when technology, strategy, and ambition intersect.

From a humble startup to a 225 million-user empire, Allebest proves that even in the most traditional industries, innovation and bold thinking can change the game—literally and figuratively.

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Jamie Heart (Editor)
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