When Jeff Bezos was drumming up his early visions of Amazon while working as a hedge fund manager, his Wall Street boss questioned if he could achieve success and financial security by selling books on the internet. And when Howard Schultz was looking for money to back his coffee business, called Starbucks, more than 200 investors believed no one would pay $3 for a cup of joe. 

The same goes for two of Chess.com’s founders, Danny Rensch and Erik Allebest, when they were shopping out their platform to potential investors. Rensch tells Fortune they were routinely overlooked and disregarded.

“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. 

No investor, no problem: Chess.com founder had his own back

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?”

It was the ‘laughingstock’ of the chess community before amassing 225 million users

When Chess.com was still on its business bambi legs, it not only had to take heat from the VC world, but also from its own community. Players were doubtful; the internet was still in its relative infancy in 2009. Plus, there were other niche chess gaming sites like ChessPark (which became a part of Chess.com), Chess Tempo, and Red Hot Pawn. 

“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.