Jackie Reses has quietly done what almost no one in finance has pulled off — she's been a Goldman Sachs banker, a private equity partner at Apax, Yahoo's Chief Development Officer, Executive Chairman of Square Financial Services, a board member at Alibaba, Affirm, and Nubank, and now the founder and CEO of Lead Bank, the $1.5B fintech infrastructure company quietly powering Stripe, Ramp, Walmart, Affirm, Revolut, and over 100 crypto companies.

In this episode, Jackie sits down with Molly to share the untold stories behind her improbable career — from sitting in Alibaba board meetings with Jack Ma, Joe Tsai, and Masa Son, to brokering one of the largest value-recovery deals in corporate history for Yahoo, to running Square Capital after a 72-hour hackweek project.

She also gets candid about the hype around "de-banking," what it's really like inside the White House (her brother is VP JD Vance's Chief of Staff), how she built Lead Bank to $280M in revenue with zero sales team, and why the future of financial infrastructure is programmable, on-chain, and AI-native.

Whether you're a founder, operator, investor, or just curious about how the most powerful in American fintech actually work behind the scenes — this conversation is a masterclass.

Jacqueline Reses: https://x.com/jackiereses

Molly O’Shea: https://x.com/MollySOShea

Sourcery: ⁠https://x.com/sourceryy

𝐄𝐏𝐈𝐒𝐎𝐃𝐄 𝐋𝐈𝐍𝐊𝐒

YouTube: https://youtu.be/0rwmXUnn7Tc

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𝐓𝐈𝐌𝐄𝐒𝐓𝐀𝐌𝐏𝐒

(00:00) Jacqueline Reses, CEO of Lead Bank

(01:06) The swiss army knife of Silicon Valley

(02:46) Inside the Alibaba boardroom with Jack Ma and Masa

(05:23) Being one of the only Americans on Alibaba’s board

(10:29) What Jack Ma and Masayoshi Son are really like

(12:32) The biggest lessons Jackie learned from Alibaba

(15:12) From Goldman Sachs to Silicon Valley

(17:44) Why Yahoo hired a PE investor to run HR

(22:53) Yahoo was a hot mess

(25:33) The deal that recovered billions for Yahoo

(26:31) How Jack Dorsey recruited Jackie to Square