Climbing That Mountain
Photo by Eliesa Johnson

Climbing That Mountain

On the path to breakthroughs

Just as we were wrapping up our spring issue of StartMN, Zip Co., an Australian buy now, pay later company, acquired Sezzle, a Minneapolis-based competitor. 

“I want to win,” Sezzle founder and CEO Charlie Youakim told me last year in a conversation on By All Means, TCB’s podcast on leadership and innovation. Sezzle may not yet be the leader in a field that didn’t even exist just a handful of years ago—and is still seeking its path to profitability in the face of mounting regulatory scrutiny—but this merger puts it in the running. Sezzle moves into a new chapter, and Youakim will become president and CEO of Zip’s operations in the U.S., Mexico, and Canada and executive director and president of Sezzle. So it sure feels like a win.

Just two years ago, Sezzle was featured on our annual Tech 20 list as a promising fintech innovation. This year’s  entrants (see “Tech 20,”) can take Sezzle’s fast rise as proof of how quickly business can scale up when you hit on the right idea at the right moment. Also worth noting: Sezzle launched as a payment processing platform in 2017. When it failed to catch on, Youakim flipped the model to buy now, pay later, and stuck with it, even when investors expressed doubts. 

“Know where the pinnacle is and keep picking a path with the goal that you want to get to the top.” 

—Charlie Youakim, founder, Sezzle

When it comes to building a business, “you just keep on pushing ahead,” Youakim has said. “It’s like mountain climbing. Know where the pinnacle is and keep picking a path with the goal that you want to get to the top.”

For our fourth annual Tech 20 list, which we’re migrating from Twin Cities Business, we introduce you to founders on the fast track, along with innovations and advances coming out of large companies in 2022. Get ready for robots delivering your ice cream, electric motorhomes, software solutions for talent retention, and medical breakthroughs. We live among some brilliant problem solvers here in Minnesota. As individuals, they shine brightly; presented as a group, they’re dazzling. (Our wealth of innovators is even more impressive when you consider we easily could have doubled the list.) 

In this issue you’ll also meet a trio of founders likely headed to a Tech 20 list soon. Because starting up isn’t all mergers and paydays, we’ve created the Founder’s Journal to follow early-stage entrepreneurs through the ups, downs, and zigzags that come with every new venture. The three we selected will have some big decisions, challenges, and opportunities in the year ahead, and they’ll share it all at 

Read more from this issue

Big thanks go to Connie Rutledge, who introduced me to a couple of our Founder’s Journal participants. “I think one of the biggest challenges founders face is the numerous critical decisions they have to make when it’s hard to know with any certainty which answer is the right answer,” says Rutledge, CEO of the Finnovation Lab, which provides funding, mentorship, and workspace for early-stage founders in Minneapolis. “A series like [the Founder’s Journal] has the potential to share great insights about how leaders grapple with ambiguity, how they recover from mistakes, and how they learn to trust themselves.” 

We hope the series becomes a catalyst for honest conversation, and meaningful connections—both for the founders and for those inspired by them. As Yasameen Sajady, Maazah founder, says, “Sometimes you reach a mental block or see the daunting mountain ahead, and having someone to call is everything—the reminder of the discomfort and ambiguity of doing something new is normal and to keep pushing ahead until you get to the other side.”

This sort of dialogue is why we created StartMN and why we’re so encouraged by your early support, enthusiasm, and ideas. Many of the stories you’ll read in this issue were sparked by conversations with stakeholders in our entrepreneurial community who lead from a place of collaboration and a desire to make Minnesota a national destination for problem solvers.

We’re here for it. Let’s keep talking.   

Related Stories