Jackie Less got off to an early start in the life of an entrepreneur.
In what she describes as “a rather rough childhood” in Atlantic City, she and her siblings ran a carnival game on the boardwalk.
“What really drove me was my own desire to make sure I was successful and had the security I could create for myself, so I felt that my independence and my entrepreneurial background really drove me.”
RES was named to the first CNBC Changemaker list of 2024.
From the success of the first, quick, easy to set up “all cash” game, Rest ran a custom t-shirt and taxi business in college.
The business planning became more complicated after that, but also increased success, starting with his early career at Wharton and Goldman Sachs.
She helped Square grow into what the tech sector has ever had to real banks, and built it “from scratch, first line of code, first policy.”
That experience hopes to own the bank she achieved in 2022 when she purchased a Kansas City, Missouri-based community bank and converted it to her current lead bank.
“One of the issues I saw is that over the last 10-15 years, Fintech has put a beautiful gloss on the front end of its apps to facilitate financial services. And I think we all feel the infrastructure is terrible with the fintech apps we use,” Reses said.
A big test of how fintech infrastructure has improved during Covid.
“Square, like other Fintechs, had a way of supporting food trucks, barbershops and restaurants, and getting them things that most of the big banks didn’t actually do.
“This was probably one of the most intense life experiences I’ve ever had. I had to build a product in two weeks.
Rest never escaped from the tough mission. It also paid off in a very great way in her fintech era, where she was entrusted with serving the Alibaba committee by her then employer Yahoo.
She hammerted a deal that gave Yahoo a 15% stake in the Chinese internet giant. “It was a very intense relationship between Yahoo’s leadership and Alibaba’s ownership,” she recalled.
Building trust between Alibaba co-founder Jack Ma and the rest of the Alibaba executive team, Joe Tsai and the Yahoo Board and Management team, was not easy amid toxic relationships and mistrust. “There were no personal animus there that was there before appearing on Alibaba’s board, and I think I could have said with a fresh eye, ‘Let’s get started.’ ”
Les has started many times since her independent life began, she says, at the age of 14 when she was sent to boarding school. And she learned a lot of lessons along the way about getting into the company, big companies and moving on to the next big idea.
You can watch a full interview with Reses about her life and career on CNBC Changemaker and CNBC’s YouTube channel.
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