Money Mover

Sezzle CEO Charlie Youakim (shown in a lounge above his Minneapolis office) takes phone calls on his treadmill to get in 10 miles a day.

The future looked grim in mid-2022 for Minneapolis-based Sezzle, an also-ran in the fast-growing buy-now, pay-later fintech business. It had burned through most of the $115 million it had raised in a 2019 initial public offering on the Australian stock market and two subsequent offerings. A rescue deal it had struck to be acquired by a competitor was collapsing, along with both companies' stock prices. And when tiny Sezzle tried to sign up big retailers, it had to make too many concessions to ever turn a profit—a problem because the typical buy-now, pay-later transaction, which allows online shoppers to pay for purchases in four installments at 0% interest, relies on subsidies from merchants.

Meanwhile, investor enthusiasm for money-losing fintechs, which surged during the early days of the pandemic, was evaporating. Venture capital funding for the sector fell from a record $141 billion worldwide in 2021 to $39 billion in 2023, per CB Insights.

"We were reaching a tech-pocalypse with interest rates rising, and [investors were] thinking 'We've got to look at the fundamentals of companies, and our fundamentals were not great,' remembers Charlie Youakim, Sezzle's 47-year-old CEO and cofounder.

To survive, he started chopping. He shuttered the company's operations in Europe, India and Brazil, cut worldwide staff from 580 to 240 and began shedding unfavorable partnerships. He even trimmed headcount in the U.S.—the heart of Sezzle's business—by 10% and made symbolic changes like canceling the $500-a-month contract for a fancy Bevi machine that dispensed carbonated and flavored water at headquarters.