Sezzle Founder/CEO Charlie Youakim

Perhaps you’ve noticed when you hit the checkout button on your online purchases there’s often an option to buy now, pay later. It’s reverse layaway—you get the goods now, and you pay them off in a four or six interest free installments. No fees, no need for credit. Young consumers seem to love it and so buy now pay later is being embraced by more and more retailers, from small indie shops to the big direct to consumer brands like Peloton and Warby Parker. The pandemic only accelerated adoption rates and analysts project buy now pay later solutions could rack up $680 billion in transaction volume worldwide by 2025. There are several big players in the field, like Afterpay and Affirm, which hit a $24 billion valuation after going public in January. But that hasn’t deterred Sezzle, a Minneapolis-based buy now pay later platform that went public on the Australian securities exchange in 2019 and continues to gain traction in the U.S. “I want to win,” says Sezzle founder/CEO Charlie Youakim, who was featured on TCB's Tech 20 in 2020. “We’re still in last place in the payment space, even though we’re having success. That’s what drives me. I know we can beat them. We just have to keep on innovating and listening to our stakeholders.” Yoaukim didn’t set out to create a payment platform. His is a winding founder’s tale that includes many startup signatures: sleeping on a couch, a fallout with a co-founder, a failure that eventually led to the big idea. "Start small," he advises other founders. "Find that first customers. Make it work great. Listen to that customer. When they have issues, fix them. When they have ideas, do them. Keep on walking forward." Sezzle launched in 2017 as a payment processing platform. Retailers liked the model because it was less expensive than credit card fees, but consumers didn’t latch on. “We ran with the idea that [a digital payment option] was a preference," Youakim says. "But what if it’s not a preference? What if it’s a lack of access? We flipped the hypothesis. We had to build a cr