Bill Clerico is an unassuming bachelor. Slight, friendly, and coder-pale, he doesn’t appear to be the sort who’d revel in the ritual humiliations of a TV dating show. But for 44 minutes in 2011, you could find Clerico on Bravo, submitting his looks (“a little, nerdy redhead”), his three-year-old startup (“Nobody cares about a software company”), and his makeout game (“Do you really know how to kiss?”) to some derision on The Millionaire Matchmake “I was single then, and figured I would mortgage a little person dignity for awareness,” Clerico says. “Did not find love.”
That was only his latest effort to get people to notice his payments software company, WePay. He’d tried recruiting financial startup royalty, but a request to meet with PayPal co-founder Peter Thiel went nowhere. Then WePay hijacked some publicity at a PayPal developer conference, dropping a 600-pound block of ice—with dollar bills encased within and a message about PayPal “freezing your accounts”—at the entrance. Awkwardly flirting on reality TV was just the next step in Clerico’s campaign to make his payments-processing company sound more attractive than, well, a payments processing company.
“It wasn’t an interesting space to be in when we got started,” Clerico recalls. “The view was that there are just such strong monopolies there in terms of the existing banks … and no one’s built a successful payments company since PayPal.”
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