A banker fuelling fintech’s rise

Jackie Reses: People don’t appreciate how operationally rigorous it is to open a bank.

JACKIE Reses, after decades of financial-services experience at the likes of Goldman Sachs Group Inc, Yahoo Inc and Jack Dorsey’s Block Inc, became one of a handful of billionaires to buy a bank – and one that’s growing exponentially.

Using mostly her own money, she became the largest shareholder four years ago in Lead Bank, which now powers some of the world’s best-known financial-technology (fintech) companies, including Nubank, Stripe and Affirm. 

Her Kansas City, Missouri-based firm has helped fuel the rise of those fintechs, many of which can’t provide most of their trademark services without working with a bank.

Now, some of Lead’s fintech clients are becoming banks themselves, raising the question of how critical Reses’ company will continue to be to their operations in the years ahead. 

Lead is also navigating a tricky landscape as she partners with fintechs that are often intertwining new finance and digital assets with a traditionally staid system.

“We’ve made a deliberate choice to have this area be a strength when other banks have chosen to be just good enough,” said Reses, 56.

Lead’s trajectory – and the decisions now being made by the fintechs it works with – are hardly unfamiliar territory to Reses, who built a bank from scratch once before.

She worked with Jack Dorsey and early executives at Block Inc – then called Square – to help that firm become a US bank in 2020 to support its lending business. It was one of the earliest fintechs to do so, which helped build Reses’ reputation in the space – and made her a billionaire.

“We have no regrets with the charter and, frankly, the investment we made in the foundation of building controls, doing it in the right way, being regulated as a feature, now sets us up in a place where we can move very quickly,” Richard Rosenthal, chief executive officer (CEO) of Square Financial Services, said during a panel discussion in Philadelphia on Sept 25.

During the process, Reses experienced the build-or-buy conundrum that many fintechs are facing today.

After consultants showed Reses a potential acquisition and she met with federal regulators, she decided that building from scratch – applying for what’s known as a de novo charter – would be more efficient.

That didn’t make it easy, though – especially for a tech company. 

It’s a similar conundrum faced by her clients.

In January, Nubank received conditional approval for a national bank charter, but said that it would team up with Lead in the meantime to launch US banking operations.

That’ll help the startup get a foothold in the market even sooner.

“People don’t appreciate how operationally rigorous it is to open a bank,” given that US taxpayers are on the hook if a lender fails, Reses said.

“It requires so much work to bring a tech company up to that level of execution.

“At the time, it makes you question whether it’s worth it.”

A little over a year after receiving conditional approval for Block’s charter in March 2020, Reses decided to buy Lead while she was visiting hedge fund billionaire Bill Ackman at his home in Bridgehampton, Long Island.

Reses also once sat on the board of Ackman’s Pershing Square Tontine Holdings and currently serves on the Pershing Square SPARC Holdings advisory board.

Reses is Lead’s largest shareholder, controlling 40% of the bank, and would have paid for it entirely herself if not for the intervention of serial venture capitalist Micky Malka, a friend through the fintech industry, who convinced her to bring on external money and invested himself as well.

The US$56mil deal was completed in August 2022.

“Jackie, by going through the process at Square, knew what banks had to do and what these fintech startups needed as banking infrastructure,” said venture capitalist Vinod Khosla, who met Reses after she joined Block.

He served on that company’s board before stepping down in 2015 ahead of it going public.

Lead has been on a growth trajectory in recent years.

The company was most recently valued at US$1.5bil after a US$70mil capital raise last year, with the backing of Ribbit Capital, Khosla Ventures, Andreessen Horowitz and a slew of other prominent venture-capital firms.

Lead is also on track to top US$600mil in revenue by the end of this year, more than double the 2025 figure.

Rivals Column, Coastal Financial Corp and Cross River Bank work similarly, though some have stumbled.

Everett, Washington-based Coastal recently took a charge of almost US$70mil to cover potential losses from a loan portfolio tied to one of its fintech partners.

Some of Lead’s competitors are also owned by wealthy individuals.

An early Stripe employee, Darragh Buckley, bought  Longview, Washington-based Twin City Bank last year to expand his work with fintech clients. 

Plaid Inc co-founder William Hockey bought a California bank in 2021 and rebranded it Column.

BlackRock Inc CEO Larry Fink, an investor in Lead Bank, said he sees very few executives trying to substantively link artificial intelligence and other nascent technologies to financial services – connections that must be taken very seriously, given the risk that could be introduced to the broader financial system.

Reses understands that, he said. 

“She’s paranoid,” Fink said. “That is a great thing.”

Boardwalk, pharmacy

Reses had a start in life unlike most bank CEOs.

At 16, she rented two stalls on a Jersey Shore boardwalk, one for a milk-can toss, the other for flukey ball.

Running the carnival games paid her way through the University of Pennsylvania’s Wharton School – sometimes night classes, because they were cheaper – and was her first job after helping her parents at their pharmaceutical businesses as a kid.

“I didn’t know that people worked five days a week until I went to Goldman Sachs,” she said.

“I just assumed everyone worked on Christmas because that’s what my family did my entire life.”

Reses said that some of her fondest early recollections are of working – with her mother behind the counter at her pharmacy, and with her father on deliveries for his medical-supply business. 

“There were so many formidable memories built around a family-owned business with people who lived and breathed work and their own entrepreneurial business, and so I didn’t know any better,” she said. 

Her parents’ marriage ended when she was in her mid-teens, and her entrepreneurialism was born of a need for independence, including financial.

“I was caught as a bowling ball in the middle of a family crisis between the two of them, and had to survive,” she said.

Reses used Wharton as a springboard to Goldman, joining in 1992, before the Wall Street heavyweight was a public company – as far from a small-town small business as she could get.

She spent seven years at the firm, including time in the mergers-and-acquisitions (M&A) group, where she began building a network that now reaches across the finance industry.

Years later, for example, Reses reconnected with the mentee Goldman formally assigned her, Sarah Levy, who is now CEO of the fintech Betterment.

At a party Reses hosted, Levy said she connected with Sallie Krawcheck, the former head of Bank of America Corp’s global-wealth and investment-management unit.

That encounter led to conversations resulting in Betterment’s acquisition last year of Ellevest, the woman-focused wealth-management tool that Krawcheck founded.

“What she’s accomplished, she’s one of very few, and it’s really impressive,” Levy said of Reses.

Reses also persuaded then-Treasury secretary Steve Mnuchin – a one-time Goldman colleague – to allow fintechs to distribute Covid-era Paycheck Protection Programme funds, since many were already lending to small businesses.

“It doesn’t take too far to trace connections back to Wharton or Goldman,” Reses said.

“I was fascinated with how they thought about business on a global scale, and I sought them out because I wanted to learn, because I had to dig myself out of ‘the kid from Atlantic City’.”

Before joining Block, Reses found her way to California’s tech scene via Yahoo after around a decade of working for a private equity firm.

At Yahoo, she served as chief development officer, where she oversaw the firm’s workforce, acquisitions, the company’s search-affiliate business and its Asian assets.

It was her highest-profile role up until that point, and she worked closely with then-CEO Marissa Mayer through the tumultuous process of bringing Yahoo-backed Chinese eCommerce site Alibaba public and then ultimately divesting its stake in what had been one of the firm’s crown jewels.

Mayer and Reses held differing views on M&A strategy, sometimes leading to disagreement, Reses said, but the two are on good terms and see each other occasionally.

Mayer didn’t respond to a request for comment.

“I was responsible for the tax structure, and for the assets, and the initial public offering (IPO), and that was a once-in-a-lifetime opportunity to have,” she said.

Dorsey had tried to poach her before the Alibaba IPO, she said, but it wasn’t until 2015, when they workshopped how Square could take on financial services, that she agreed to make the move.

Washington regular

Reses now splits her time among Silicon Valley, New York and Kansas City.

She also travels to Washington around every other month, given how much time she spends on regulation.

Reses served as chair of the economic development council at the Federal Reserve (Fed) Bank of San Francisco from 2015 to 2023, and still serves on the Kansas City Fed’s Community Depository Institutions Advisory Committee, a role that will end this year.

She was a key player helping the White House craft the Genius Act, which provides regulatory clarity around stablecoins and US President Donald Trump signed into law in July 2025.

Part of Reses’ deep ties to Washington are also familial: until the end of the summer, her brother Jacob was chief of staff to US vice-president JD Vance.

“I don’t abuse that privilege, but I certainly enjoy opportunities to lend my expertise or get feedback from relevant people in his network that are related to what I do,” Reses said.

“There’s not a politician in the country that doesn’t drive me crazy in some way, shape or form, and for better or for worse, I usually tell them that while I’m meeting with them – in a kind way.”

As CEOs of the largest US banks are actively blocking artificial intelligence-driven personal agents and thorny liability questions arise, Reses has again turned to Washington.

This time, she’s urging elected officials to consider the implications of artificial intelligence’s effects on financial services and recommended a specific policy framework for how to move forward.

“No one’s had the conversation before we put this forward, and we wanted to make sure that it started, and it started with substance,” she said.

“There is no established framework for it, and everything is on the table.”

As for the fintechs, Reses also recognises that while there are many becoming banks, many aren’t, and she aims to be there for those startups.

“You actually have partners who could achieve what you need to achieve without all of the costs and burdens on your business,” she said.

“I think the trade-off has become harder for people, because they don’t have to do it.” — Bloomberg