Some CEOs love chess; others…not so much

Seth Bannon, the founder of Amicus, a start-up that helps non-profits spread awareness--and raise money--by tapping volunteers' social networks, is in the former category. He likes to boast with a soft humble-braggy smile that during college he spent so much time playing speed rounds of chess (called "blitz") with the hustlers around Harvard Square in Cambridge, Massachusetts, he nearly had to drop out of school. 

Last summer, when Amicus was being incubated at Y Combinator, Bannon was also looking for funding for the company. But so was everyone else. That was evident when Peter Thiel, the Paypal co-founder, audacious-idea advocate, and managing partner at $275 million VC firm Founders Fund, came to speak to the batch of YC founders. As Bannon tells it, as soon as Thiel finished, a throng of young entrepreneurs swarmed him, waiting for their turns to pitch the billionaire their companies.

"He was being pretty brutal. He told one of my batchmates, 'I've got to say, this is a product I'm not at all interested in; I gotta tell you this is a business I'm not at all interested in'," Bannon says. "He was not in a good mood."

Bannon says he cut in anyway, banking on a rumor he'd heard that Thiel was as much of a chess aficionado as himself. In his telling, the conversation went like this:

Bannon: How about a game of blitz?

Thiel: What? 

Bannon: How about a game of blitz?

Thiel: Now?

Bannon: Yeah, I have a table set up over there.

Thiel: Give me five minutes.

Here's what happened next, according to Bannon: 

He came over and the entire batch came to watch, and crowded in all around us. It was five minutes--that's the length of a "blitz" game. He said, "only one game." I said, "no problem." So we played and I beat him. I wasn't nervous. I felt good. I'm like in my element when I'm playing blitz. As soon as he resigned the game, the first thing he said was: "another." 

He won the second one. I think the Founders Fund partner who ended up investing in us probably heard about us thorough that. They ended up putting in for our second seed round.

At some point, I friended Peter Thiel on Facebook, and that was surreal. Once I went to the office, and they showed me around, and showed me all of the cool chess stuff they have. They have a very beautiful chess set.

Bannon didn't even pitch his company. But he got Founders Fund interested--he later met with partner Luke Nosek in New York City. They sealed the deal, and the fund's early-stage-investing arm, FF Angel, invested.

Here's photographic evidence of the match (Thiel left; Bannon right), by Arda Kara.