In any entrepreneur’s journey, there are bound to be naysayers and doors slammed in their face.
“We were laughed out of VC rooms who said that chess would never be anything. Nobody invested early on, and it became the biggest blessing in disguise,” Rensch recalls.
Instead of relying on the pockets of investors, the Chess.com founders dipped into their own. They bootstrapped the online business in 2009 with money from Allebest’s former chess ventures, also borrowing $70,000 from a mother’s friend, which Rensch says they paid back very quickly. Soon, the entrepreneurs proved that VC investors missed out on a huge win; today, Chess.com is one of the largest online chess platforms in the world with more than 225 million registered members and 40 million active monthly users. Chess.com says it even surpassed a $1 billion valuation back in 2023.
Despite having to keep his day job for years while his bootstrapped company was clawing its way to profitability, Rensch says he wouldn’t have it any other way. It’s a part of Chess.com’s underdog story as the platform concept was not only mocked by venture capitalists, but also by the chess community at large. Now, the website has become essential for anyone who’s interested in, or serious about, chess—from novices to grandmasters.
“That is a really important part of the story—there was no money raised. We were completely bootstrapped,” Rensch continues. “And given where chess went, I think it’s funny and adds to the magic of ‘Wow, what happened here?”
“Chess.com was the laughingstock of the online chess community,” Rensch says. “It sounds so funny to say now, but it really is important to reflect and understand that the internet—at its earliest inception—was not web two or let alone web three. Your website was just a place with a phone number for a lot of people.”
“There were niche communities and there were the main ones, but Chess.com itself, and the idea that it would become such an amazing home for every level of the chess playing community…was kind of ridiculous for most,” Rensch continues.
Rensch says he sees his website as a skill-sharpener that enriches people’s lives. In looking at Chess.com like a subscription service—like a Duolingo, Strava, or Spotify—the platform is a “lifestyle” ritual that users feel adds value to their well-being. And in the 16 years since the website’s inception, more than 225 million chess lovers have flocked to the platform to sharpen their gameplay and be in community.
