Tech entrepreneur challenges billionaire investor to million-dollar chess match

If I win, you invest $1 million in my startup. If I lose, you get a free stake in the company.

That’s the chess match challenge issued by one A.J. Steigman, founder and CEO of

“It’s kind of like Apollo Creed versus Rocky here,” Steigman said. “Will he allow the underdog the opportunity?”

The Apollo Creed in this case is Peter Thiel — a founder of PayPal, the first outside investor in Facebook and a high-profile venture capitalist based in San Francisco.

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And chess is both men’s strong suit.

Steigman, 27, and Thiel, 44, were both child prodigies in their day.

They’re both officially ranked as “chess masters.”

Steigman says the idea behind the chess match is to encourage entrepreneurs to think creatively when it comes to raising capital in today’s tight market.

“I think it will be inspirational,” Steigman said. “Peter and I can be a vehicle to inspire other entrepreneurs who just can’t raise capital to try unconventional tactics, to not give up and to go after their dreams.”

Steigman says the year-and-half-old Soletron, which is basically Etsy for streetwear, has so far raised $550,000.

The company is spending the summer in Philadelphia, tapping the expertise of interns from Penn’s Wharton School.

“We rented a six-bedroom house, Facebook style, right on 34th and Market,” said Steigman. “It’s pretty cool. We have all the interns working and sleeping out of there. It’s very start-upy.”

Steigman, a Florida native, says he’s thinking about keeping Soletron HQ in Philadelphia for good.

As for the million-dollar chess match, it’s been about a week, and Steigman’s yet to receive word from the Thiel camp.

“He really is a legend, he’s really a hero, if he does accept — jokingly here — just make sure that he brings his PayPal account,” said Steigman.

A representative from Peter Thiel’s Founders Fund declined to comment after several requests were made.

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