Jackie Reses got an early start on the entrepreneurial life.
During what she describes as a “pretty gritty childhood” in Atlantic City, she and her brother ran carnival games on the boardwalk, one of which (flukey ball) she said, “I think is now illegal.”
“I think the thing that really drove me was my own desire to succeed and make sure that I had the security that I could create for myself, and so I felt that self-reliance and that entrepreneurial background really is what drove me,” Reses told CNBC’s Julia Boorstin in a Changemakers Spotlight video interview.
Reses was named to the inaugural CNBC Changemakers list in 2024.
From those first, quick, easy-to-set-up “all cash” game successes, Reses went on to run custom t-shirt and taxi businesses in college.
The business plans got more complicated after that, but the successes got bigger also, starting with Wharton and an early career at Goldman Sachs, where Reses says many of her leadership principles were set.
She helped Square to grow into the closest thing the tech sector has ever had to an actual bank, building it “from the ground up, first line of code, first policy,” she said.
That experience led Reses to want to own a bank, a goal she accomplished in 2022 when she bought a community bank based in Kansas City, Missouri, and transformed it into the current Lead Bank, which now also provides infrastructure to fintech companies.
“One of the problems I’ve seen is that fintechs, over the last 10 to 15 years, have put a beautiful sheen on the front end of an app to make financial services easier. And I think we’ve all felt that with fintech apps that we use; the infrastructure, however, is terrible,” Reses said.
A big test for how good that fintech infrastructure could become arose during Covid, when Reses reached out on behalf of Square to then-Treasury Secretary Steve Mnuchin to recommend a role for fintechs in disbursing emergency government funds to small businesses, just as the Treasury and Small Business Administration were putting in place the initial ideas for what would become the Paycheck Protection Program — an experience she now describes as “stressful but incredible.”
“Square helps the food trucks, the barber shops, the restaurants, as do other fintechs, and we had a way to get to them that most large banks really didn’t. And so at that point in time, I had this idea that we should call the Treasury Secretary,” she recalled.
“It was probably one of the most intense life experiences I’ve ever had. We had to build a product in two weeks that was one of the biggest lending programs ever created to serve Main Street America,” she added.
Reses has never shied away from a tough assignment, and that paid off in a very big way before her fintech years when she was tasked by then-employer Yahoo to serve on the Alibaba board, in an effort to repair what she describes as “a toxic relationship” mired in “mistrust.”
She ended up hammering out a deal that gave Yahoo a 15% stake in the Chinese internet giant that would ultimately be worth $40 billion after the company’s IPO. “It was an extremely acrimonious relationship between the leadership of Yahoo and the ownership of Alibaba,” she recalled.
Building trust between Alibaba co-founders Jack Ma and Joe Tsai, the rest of the executive team at Alibaba, and the Yahoo board and management team, was not easy amid a toxic relationship and mistrust. “I didn’t have any of the personal animus that was there prior to my showing up on the board of Alibaba. And I think with a fresh pair of eyes, I was able to say, ‘Let’s start over.'”
Reses has started over many times since her independent life began, she says, at the age of 14, when she was sent to boarding school. And she has learned many lessons along the way about starting companies, leading companies, and moving on to the next big idea.
You can watch the full interview with Reses on her life and career at CNBC Changemakers or on CNBC’s YouTube channel.
