Jackie Reses: The Most Powerful Woman in Finance; Making $50BN for Yahoo on Alibaba | E996
Jackie Reses (guest), Harry Stebbings (host)
In this episode of The Twenty Minute VC, featuring Jackie Reses and Harry Stebbings, Jackie Reses: The Most Powerful Woman in Finance; Making $50BN for Yahoo on Alibaba | E996 explores jackie Reses on Grit, Fintech Disruption, and Rebuilding Modern Banking Infrastructure Jackie Reses discusses her journey from a chaotic childhood to becoming a leading figure in finance, emphasizing grit, independence, and long-term relationship building as core drivers of her career.
Jackie Reses on Grit, Fintech Disruption, and Rebuilding Modern Banking Infrastructure
Jackie Reses discusses her journey from a chaotic childhood to becoming a leading figure in finance, emphasizing grit, independence, and long-term relationship building as core drivers of her career.
She explains her hiring philosophy, deal-making approach, and lessons from transformative experiences at Yahoo, Alibaba, and Square, including creating tens of billions in value with limited leverage.
Reses analyzes the evolution of fintech, arguing the next decade’s big opportunities lie in expense management and infrastructure, while warning that many neobanks and feature-level products will not endure.
Finally, she outlines her vision for Lead Bank as a deeply compliant, tech-forward infrastructure bank, and reflects on crypto, regulation, macroeconomics, and the cultural foundations of truly high-performance teams.
Key Takeaways
Hire for innate strengths, not resumes or domain experience.
Reses prioritizes raw intelligence, judgment, curiosity, grit, and ability to manage ambiguity over big-brand CVs or narrow domain knowledge, using deep conversations and real-world case studies to uncover what candidates are truly great or terrible at.
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Build long-term followership by optimizing for others’ careers, not your roadmap.
She deliberately sends top performers to business school, other departments, or even other companies when it’s better for their development, believing that genuine, decades-long investment in people builds exceptional loyalty and a network that will repeatedly rejoin her.
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Great deals are created by understanding what the other side really needs.
Reses frames negotiation as non–zero-sum: she probes whether counterparties need optics, timing, or specific economics, and then trades creatively around those needs while holding firm only on the few structural issues that matter most for long-term business health.
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The next fintech frontier is expense management and infrastructure, not just revenue.
While companies like Square, Stripe, and Adyen have streamlined the inbound revenue side, she argues the outbound expense side of the P&L remains fragmented and messy—representing a massive opportunity for new platforms and infra players over the next decade.
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Many consumer neobanks are features, not durable companies.
With debit cards now commodity and digital acquisition costs high, she believes only players with truly differentiated use cases and the right to expand into broader financial products can survive; most narrow, verticalized plays lack enough LTV to stand alone.
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Disruption requires cultures that reward IC excellence and role “resets.”
She warns that equating power with headcount is a “cancer,” and instead elevates top individual contributors and celebrates leaders who leave large teams to start small, entrepreneurial initiatives—anchoring the company around invention, not org charts.
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Modern banks must be equally strong in tech, regulation, and finance.
In building Lead Bank, Reses insists that technology, compliance/regulation, and financial acumen are three co-equal pillars; overweighting any one risks existential failure for both the bank and its fintech clients, especially in what she calls an “anti-network effects” business.
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Notable Quotes
“We built the bank we wanted to see in the world, full stop.”
— Jackie Reses
“I knew enough to know I didn’t know anything, so I started my career at Goldman Sachs.”
— Jackie Reses
“I would rather focus on raw intelligence, judgment, curiosity, grit, and ability to manage ambiguity than domain knowledge or prior scale experience.”
— Jackie Reses
“Equity is good. Equity is good. Equity is good. I have one goal: equity is good.”
— Jackie Reses, on renegotiating Alibaba economics for Yahoo
“Any of our customers can harm another customer… it’s an anti-network effects business.”
— Jackie Reses, on banking infrastructure risk
Questions Answered in This Episode
How can early-stage founders practically adopt Jackie Reses’s approach to hiring for innate strengths when they lack time and brand leverage?
Jackie Reses discusses her journey from a chaotic childhood to becoming a leading figure in finance, emphasizing grit, independence, and long-term relationship building as core drivers of her career.
Get the full analysis with uListen AI
What specific product or market signals would indicate that a fintech aimed at expense management is building a true platform versus just another feature?
She explains her hiring philosophy, deal-making approach, and lessons from transformative experiences at Yahoo, Alibaba, and Square, including creating tens of billions in value with limited leverage.
Get the full analysis with uListen AI
How should founders decide when to disrupt their own successful product lines and move top leaders into smaller, experimental teams without destabilizing the core business?
Reses analyzes the evolution of fintech, arguing the next decade’s big opportunities lie in expense management and infrastructure, while warning that many neobanks and feature-level products will not endure.
Get the full analysis with uListen AI
Given her experience with Alibaba, what frameworks does Reses use today to create leverage in negotiations where she appears to have none?
Finally, she outlines her vision for Lead Bank as a deeply compliant, tech-forward infrastructure bank, and reflects on crypto, regulation, macroeconomics, and the cultural foundations of truly high-performance teams.
Get the full analysis with uListen AI
What are the most critical questions a fintech founder should ask a potential banking partner to avoid being exposed to that bank’s regulatory or operational failures?
Get the full analysis with uListen AI
Transcript Preview
We built the bank we wanted to see in the world, full stop. We built the bank we wanted to see.
(instrumental music) Jackie, I am so excited for this. I loved it when I asked you for people that we had mutual friendships with. You know, you mentioned Mickey, you mentioned Guillaume, you mentioned David Vélez. I- I obviously did my homework. So first, thank you so much for joining me today.
Oh, I'm so happy to be here. I know it's a long time in coming, but I'm happy to be here.
(laughs) We made it happen in the end. But I wanna start with a little bit of an unconventional start, to be honest. Think back to when you were a child. What did you wanna be when you were growing up?
All right, now this sounds terrible because it's so trite, but one of my first memories of playing as a kid is playing bank teller Barbie. I had this pink Barbie convertible and David Cassidy, I'm like a '70s kid so this is like 1976, David Cassidy would, uh, pull up as a customer and I was the bank teller. And so I know that sounds totally ridiculous, but it's in fact true. And so I come from an incredibly entrepreneurial family. Everyone in my family started their own companies. I'm like the only person to have worked for anyone. And so, um, you know, I got lucky in that I knew enough to know I didn't know anything, and so I started my career at Goldman Sachs. But then evolved to pretty entrepreneurial components of any company that I worked at where I was building a team, building a company, building new products. And so I always stuck with financial services because I loved math, I loved the idea of inventing in a really old industry, and I loved building businesses. And so that's the theme that always exists in my life, and- and total entrepreneurialism.
It's funny you say about kind of the- the dreams of being a bank teller there. When I was younger, I always saw like the vaults in movies and they'd open them up and there's like wads of cash. I wanted to be the bank robber. So I- I... we kind of share... I mean, yours is slightly more legitimate than mine, uh, and yours actually became true. Sadly, I haven't had that moment of cash just like hitting me from a vault. But, you know, we'll- we'll get to vaults later. Um-
Well, to be honest, if you, if you come to one of our banks in Kansas City, so I- I run a bank, and we actually have physical locations that are pretty gorgeous in Kansas City, and there is a vault in our Lee's Summit, Missouri location that is absolutely stunning. And so you look at it and say, like, "There should be a movie that happens inside this vault." Because it's pretty cool looking. The door is gigantic and it's old school looking and it's- it's super cool looking. It makes you feel like you're grounded in a lot of history when you go there.
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