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Charlie Youakim Is on a Mission to Financially Empower Gen Z

‘Buy now, pay later’ installments-based fintech companies are all the rage right now. But for Sezzle’s cofounder Charlie Youakim, his business is about much more than generating profits.

Photo courtesy of Sezzle

It’s seven o’clock in the morning, and Charlie Youakim is already into his second meeting of the day, this one a video ‘meet and greet’ with the Sezzle team in Brazil—a new market where the Minneapolis-based fintech company recently announced expansion plans for its ‘buy now, pay later’ installments-based payments platform. After a few perfunctory welcome comments, Youakim launches into the topic of Sezzle’s mission of financially empowering Gen Z, a subject that, no matter how many times he has talked about it in the past, is still delivered with all the gusto and optimism you might expect of a young entrepreneur in his first investor pitch, painting a vision for how his new idea will solve a problem that will change the world. But unlike so many leaders in the era of so-called woke capitalism, in which companies riff endlessly about their high profile ESG and DEI initiatives—oftentimes with not much to show for it—Youakim has staked his reputation and, indeed the success of Sezzle, on his ability to deliver not only profits but also pay out meaningful social dividends as well. And for a company that is adroitly positioning itself as a nimbler and more virtuous successor to the global consumer banking industry, that is no small undertaking. 

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At 44, Youakim is not exactly young by Silicon Valley standards, but then again Sezzle isn’t this son of a Palestinian immigrant’s first rodeo either. Youakim built his first company, Passport, into one of the nation’s leading mobile parking apps, later using the bulk of his share of the proceeds from its sale in 2015 to fund Sezzle. And although it took some time for Youakim and fellow co-founder Paul Paradis to finally land on the idea of offering consumers the option to purchase goods from retailers with interest-free installments, they haven’t looked back since. 

In 2019, Sezzle went public on the Australian ASX, and according to the company’s recent SEC filings, a U.S. public offering is imminent. The company now has over three million active users and over 40,000 merchants on its platform. Like many of its closest competitors that offer similar zero percent financing for everyday items, such as Sweden-based Klarna and Australia-based Afterpay, Sezzle’s bread and butter had traditionally been focused on helping boost sales for small and medium-sized sellers, but in June this year, retail juggernaut Target announced that it had selected Sezzle as its exclusive ‘buy now, pay later’ partner, becoming the first top 10 retailer in the U.S. to offer such a solution to their customers. 

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What undoubtedly set Sezzle apart from its competitors and caught the attention of Target was the company’s steadfast commitment to democratizing financial freedom for a user base that skews much younger than that of a typical financial institution. Youakim’s stroke of brilliance was realizing early on that younger consumers want more out of their brands—particularly when it comes to their banking partners. This market segment—best known as Gen Z—is a cohort that is eager to start credit-building but is also very weary of big banks, hidden fees and predatory credit card lending. For these teens and 20-somethings, trust, transparency and doing right by society are highly valued. Youakim knew that being extremely transparent with Sezzle users about how the company makes its money and providing its users with an array of financial education and budgeting tools was not only the right thing to do, but it was also aligned with the overall worldview of conscientious consumerism held so deeply by this youngest generation of consumer. 

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For Youakim, the most important date in the company’s short but consequential history isn’t its founding date nor its IPO on the ASX—it’s the day Sezzle became a certified B-Corp, a testament to its commitment to the so-called “triple bottom line” approach to business: people, planet and profits. And with Sezzle launching local operations in Canada, Europe, India and now Brazil, Youakim is taking his vision for a better, more just way of approaching payments and financial services to the entire world.

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