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A Chicago Tech Poker Tournament, Started in Chris Gladwin's Basement, Has Now Raised $1M for Charity

And the 'Big Game' Is Coming Back March 28


Christmas Poker
Photo: Getty Images/Andy Kirby

What began as an intimate poker game between some of Chicago's top tech entrepreneurs 15 years ago has grown into an event that brings hundreds of Chicago techies and other business folks together to raise money for charity.

It all started in 2004, when Chicago founder Chris Gladwin held regular poker tournaments in his basement. Gladwin—who at the time was in his early days at Cleversafe, a startup he would later sell to IBM for more than $1 billion—and fellow Chicago entrepreneurs played Texas Hold 'Em, with the winner earning bragging rights and the chance to donate the cash to a charity of their choice.

The group, called Smart Bet Charity, has since raised more than $1 million for charity, and it's organizing one of its largest events yet in hopes of bringing Chicago's tech community together to raise more money for worthy causes.

Smart Bet is holding its next tournament at the Chicago Cultural Center on March 28, where more than 200 players from Chicago’s tech community are expected to compete. The group has held quarterly poker tournaments of smaller sizes in recent years, and hasn't held a large-scale tournament like the one taking place this week since 2012, said Sean Smyth, Smart Bet president and the CEO of PechaKucha.

"We’re bringing back the big game," said Smyth, who also served as a Groupon executive for eight years.

Past winners of Smart Bet’s poker tournaments include a who's who of notable Chicago tech leaders. Shop Runner CEO Sam Yagan, OCA Ventures co-founder Jim Dugan and Grubhub co-founder Mike Evans have all taken home the crown. Gladwin and Smyth have each won it multiple times.

This year's buy-in is $250, and Smyth says he expects the event to generate around $100,000, which will be donated to Future Founders and Chicago Tech Academy, two organizations helping to train the next generation of Chicago tech entrepreneurs.

But the winner of Thursday's tournament will come away with more than just bragging rights and good karma. The top player will earn a seat at the World Series of Poker tournament in Las Vegas this Spring, which is valued at $10,000.

Smyth said Smart Bet is still open for registration, and anyone who comes Thursday will get a chance to play.

You can learn more about the poker tournament here.


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