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South Florida entrepreneur challenges PayPal co-founder Peter Thiel to million-dollar game of chess

A.J. Steigman is used to being the scrappy startup sort. He launched his company in the Parkland home of his parents, who would feed his team and sometimes let the group crash overnight. He's now raised an impressive $550,000 in capital, but that's far short of the millions he believes he needs to grow his business.

So the 27-year-old entrepreneur put on his best game face for his next move.

Soletron-White-in-black-with-White-TextLast week, Steigman, who founded Soletron,  an ecommerce and social networking site for street wear, challenged PayPal co-founder and billionaire venture capitalist Peter Thiel to a game of chess. Both are chess "lifetime masters" at the game, rated nearly identically in the top 1 percent of the U.S., Steigman says.

The stakes? As Steigman proposes, if Steigman wins, Thiel would invest a cool million of Series A funding in his company. If Steigman loses, he would give Thiel a stake in Soletron -- the size to be negotiated.

"I have the utmost respect for Peter, both on and off the board. I think this could be a postive, fun, entertaining event and I hope he accepts," Steigman says.

No word yet from Thiel, but either way, the publicity received from Steigman's chess challenge, picked up by dozens of entrepreneurship and chess blogs and blasted on social media, is already a win. And it illustrates the creativity some entrepreneurs are deploying to seek the all-important funding for their companies.

Steigman grew up in Coral Springs and attended The University School at Nova Southeastern since kindergarten. After graduating from Emory University he worked as an investment banker at Merrill Lynch in New York for awhile. But the itch to run his own business proved too strong, so he founded and ran a sneaker store at the Seminole Hard Rock Casino in Hollywood -- one of the top performing stores for Nike accounts, he said. There he also saw the limitations of that concept. Designers would come in to pitch cool new brands and he had no room to promote or display them. That's when he had the idea for Soletron, an Etsy for street wear, sneakers and skateboards.

Santonio HolmesHe soon sold his store to focus "150 percent" on Soletron, which he launched in 2010. "We're a platform for designers without holding inventory," he says. Shane Robinson, another investment banker he had become friends with at Merrill Lynch, would become his co-founder, and Soletron quickly gained customers in its key demographic, males aged 15 to 25. Today, Soletron's site includes 100 brands and about 2,000 products, Steigman says. 

Along the way he has added an impressive board of advisors, including  professional football player and Superbowl MVP Santonio Holmes, Tom Austin, the co-founder of AND1 basketball, Bruce Chizen, former CEO of Adobe, John Friedman, founder of Easton Capital, and Bob Rice, founder of Tangent Capital. (Photo shows Steigman with Holmes)

Soletron Earbuds"Starting a business is kind of like a step-level video game," says Steigman, explaining that the co-founders had to first prove why two non-tech investment bankers could start this company and then prove themselves at every step by reaching milestones.  "You have to believe in yourself and your concept."

Diversitile_Bumble Bee DunksSteigman has employed other creative tricks of the entrepreneur trade to make his limited resources go further. He has employed interns from several universities to work on code and develop apps for him. This summer, Steigman temporalily moved his company operations up to Philadelphia, where he is working with a team of interns from University of Pennsylvania's Wharton School. About five of his 10 employees went with him, where they are staying in a rented six-bedroom house, ala Facebook style, Steigman says.

He's even considering moving his company headquarters there, he said, because it is closer to his lawyers, board members and some of his team in New York City. Yet, he said he would always have a presence in South Florida and has local partnerships with the Opium nightclub at Hard Rock and others. "As long as I have my laptop I can be anywhere I need to be. It's not like goodbye Florida."

Gary KasparovSteigman played in his first chess tournament at the age of 5, and he became a national master  at 13. If the game becomes a reality, Steigman says that all sponsorship  proceeds would go to charity.

Steigman  sees a lot of similarities between the game of chess and entrepreneurship. "Chess takes a great deal of mental focus... You can be in a very bad position for a long period of time... You can also be overconfident and blow the game. ... It's a game of persistence, absolutely. And you have to think moves ahead." 

  (Photos above, all from A.J. Steigman, show some of Soletron's products, and a young A.J. Steigman with former World Chess Champion Gary Kasparov in New York City in 1995 at the Intel Grand Prix and playing chess with former World Chess Champion Anatoly Karpov  in 1995 at the World Youth Chess Championships in San Lorenzo, Brazil)