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Jamie Dimon Reveals A Coffee Table Chat With Jeff Bezos In 1999 That Almost Made Him 'Never Wear A Suit Again…Live On A Houseboat'

Shomik Sen Bhattacharjee
July 20, 2025

JPMorgan Chase CEO Jamie Dimon says a coffee table chat with Jeff Bezos in late 1999 almost pulled him away from Wall Street, but not quite.

What Happened: Dimon recalls hitting it off with the Amazon founder and has "been friends ever since," yet the idea of running the then‑fledgling e‑commerce firm was "just a bridge too far."

During an episode of the Acquired podcast last Wednesday, Dimon said Bezos was hunting for a company president when they met in Seattle. "I'd never wear a suit again… I'd live on a houseboat," he joked, adding that uprooting his young family and abandoning finance felt like an alternate‑universe script.

The banker had reason to hesitate. Amazon's market cap sat near $5 billion at the end of 2000, a far cry from today's $2.4 trillion giant. After flying home, Dimon "got serious" about his job hunt, fielding offers from unnamed global investment banks, insurance titan AIG via a call from Hank Greenberg and even Home Depot's founders, though he admitted he had never stepped foot in one of their stores.

See Also: NYU Professor Warns Companies Against Moving Cash Into Bitcoin -- Unless You’re Strategy, PayPal, Or A Meme Stock: ‘This Is A Bad Idea’

The call that stuck came from a headhunter pitching Chicago's troubled Bank One. Analyst Mike Mayo famously warned that "even Hercules couldn't fix it," yet Dimon saw a chance to rebuild in his natural habitat. He invested $60 million, which was half his net worth into Bank One stock on day one, vowing to "go down with the ship or up with the ship."

Why It Matters: Dimon, over the course of the same podcast, revealed his investment mantra of "don't blow up". It is a guiding principle that has shaped the risk culture at JPMorgan Chase, influencing its approach to financial management and decision-making.

In a separate interview, Jamie Dimon told a crowd at New York's Radio City Music Hall that he bought his first stock at 14 in 1972 only to watch the market plunge 45% within two years. The jolt that, he said, taught him to "always factor the invisible risks."

Read Next:

  • Kevin O’Leary Advocates Entrepreneurship Over Consulting to Students: ‘Why Would Anybody Burn All Those Hours While Someone Else Makes Money?’

Image via Shutterstock

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