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Jackie Reses: The Most Powerful Woman in Finance; Making $50BN for Yahoo on Alibaba | E996

Jackie Reses is the Chair and CEO of Lead Bank, a community bank in Kansas City. Previously, she was the Executive Chairman of Square Financial Services and Capital Lead and Head of the People Team at Block Inc (Square). Prior, she had leadership positions at Yahoo! and was a Partner at Apax Partners Worldwide. Jackie also spent seven years at Goldman Sachs in mergers and acquisitions and the principal investment area. Jackie is on the board of directors of Endeavor, Affirm and Nubank. Previously, she served on the Board of Directors of Alibaba Group. She has been named one of Forbes’ “Self Made Women”, Fast Company’s “Most Creative People in Business,” and American Banker “Most Powerful Woman in Finance”. ---------------------------------------------------------------------- Timestamps: 0:00 Intro 0:34 Who is Jackie Reses? 7:38 What is high performance? 12:39 Hiring Mistakes 20:51 Successful Deal Making 25:05 Best and Worst Investments 31:16 Fintech Winners and Losers of the Future 38:46 Defensibility in Banking 43:01 Crypto Winter and Central Banking 47:29 Jackie’s Insight into the Fed 50:48 Wave of M&As in Fintech? 56:56 Fintech Superapp 1:09:02 Quick Fire Round 1:12:38 Does Crypto do more harm than good? 1:16:47 Biggest Lesson Working With Jack Dorsey ---------------------------------------------------------------------- In Today’s Episode with Jackie Reses We Discuss: 1. From Humble Beginnings to “Most Powerful Woman in Finance”: What is Jackie running from? How did Jackie’s upbringing impact her approach to business and management today? What does jackie know now that she wishes she had known when she started her career? 2. Building the Best Teams: Lessons from Square and Yahoo Why does Jackie believe that past experience is BS in hiring candidates for a role? Why does Jackie deliberately not look for domain knowledge when hiring? Why does Jackie believe employers should tell candidates what they suck at in hiring? What does Jackie mean when she says, “you have to invest in people for 20 years”? 3. The Best Deal-Maker in the Business: Secret to Negotiating: What does Jackie believe is the secret to successful negotiations? How did Jackie do the Alibaba deal for Yahoo and make $50BN for them? Why does Jackie believe the Laffonts and Coatue are the best risk managers? What are the biggest mistakes people make in deal-making today? 4. The Next Wave of Fintech: Who wins and who loses in the next wave of fintech? What will happen to the crypto industry? How will crypto be regulated? Why does Jackie believe that financial super apps are BS? Why does Jackie believe that Goldman tried and failed to innovate? Will we see a wave of M&A in fintech over the coming years? ---------------------------------------------------------------------- Subscribe on Spotify: https://open.spotify.com/show/3j2KMcZTtgTNBKwtZBMHvl?si=85bc9196860e4466 Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/the-twenty-minute-vc-20vc-venture-capital-startup/id958230465 Follow Harry Stebbings on Twitter: https://twitter.com/HarryStebbings Follow Jackie Reses on Twitter: https://twitter.com/jackiereses Follow 20VC on Instagram: https://www.instagram.com/20vc_reels Follow 20VC on TikTok: https://www.tiktok.com/@20vc_tok Visit our Website: https://www.20vc.com Subscribe to our Newsletter: https://www.thetwentyminutevc.com/contact ------------------------------ #JackieReses #LeadBank #HarryStebbings #fintech

Jackie ResesguestHarry Stebbingshost
Mar 30, 20231h 19mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

Jackie Reses on Grit, Fintech Disruption, and Rebuilding Modern Banking Infrastructure

  1. 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.
  2. 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.
  3. 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.
  4. 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.

IDEAS WORTH REMEMBERING

5 ideas

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.

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.

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.

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.

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.

WORDS WORTH SAVING

5 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

Personal background, grit, and early independence shaping career ambitionHiring, talent evaluation, and building high-performance, loyal teamsDeal-making philosophy, Alibaba–Yahoo transactions, and risk managementFintech evolution: revenue vs. expenses, infrastructure, and neobanksCrypto markets, regulation, and the role of central banks and the FedBuilding Lead Bank and reinventing banking infrastructure and cultureMacro environment, M&A in fintech, and the future of super apps

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