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Chess.com CEO: Why I Broke Every Startup Rule

No Priors · Aug 18, 2026 · Other Signals

Chess.com CEO built a billion-dollar company by ignoring all conventional startup advice

“People should listen to their heart and listen to like what they want to do and they should think of what do they want to see exist out there in the world and then they just relentlessly go after that.”

Chess.com CEO Erik Allebest shares how he built Chess.com by doing the opposite of conventional startup wisdom: no technical co-founder, no funding, remote work, small market. The content is general entrepreneurship advice with no meaningful AI industry signal.

founder-advice bootstrapping startup-strategy chess-com

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