The silly $50K bet that got Venmo’s founders in hot water with PayPal

Three years ago at the Northside Festival, Venmo founders Iqram Magdon-Ismail and Andrew Kortina were high with excitement following a fireside chat. In their post-festival fervor, they bet employee Mike Linshi $50,000 that he wouldn’t buy and wear a fitted colorful T-shirt with an abstract design they found at a nearby store. But Linshi was up to the challenge. The shirt was donned—and the money was exchanged on Venmo. 

Venmo’s parent company, PayPal, didn’t think it was so funny. Three months later, it launched an investigation into the sizable transaction

That anecdote represents Venmo’s early disregard for the rules that businesses (especially financial ones) have to abide by. In my new feature on Venmo, I write about how it went from obstreperous startup to disciplined corporate player with a plan for the future. Read all about it here.

[Photo: courtesy of Venmo]RR