Jamie Dimon’s 1998 firing shocked Wall Street. Then he took a meeting with Jeff Bezos in Seattle

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SEE FULL BIO JPMorgan CEO Jamie Dimon

That path abruptly collapsed when Dimon was unceremoniously fired, as Dimon recalled in a recent podcast appearance

Conversely, Speaking to Acquired, the JPMorgan Chase CEO said the shock was not just fessional but deeply personal; Dimon recalls fielding nervous questions from his children the family’s future as 50 colleagues gathered at his apartment for “a wake” that night (noteworthy indeed)

Dimon said he told his guests that he was doing alright, it was his “net worth, not his self worth” that had been shaken (something worth watching)

Dimon said he spent the next 18 months considering his next step, out of an office in the Seagram Building

He said he dabbled in teaching, considered starting his own merchant bank, and even contemplated retirement, being 42 years old at the time

But he also called various connections, keeping an open-mind (this bears monitoring)

One of these led to a visit to Seattle to meet Amazon founder Jeff Bezos, who was seeking a president for his fast-growing company, and they had a particularly consequential conversation

The Amazon what-if and the road not taken Dimon and Bezos hit it off, saying they’ve “been friends ever since. ” Yet he also says it was just “a bridge too far,” not just to move to Seattle, but to leave finance for the world, and running Amazon full-time

Dimon said he would have been stepping into a radically different industry and life, joking that it would have been a “When Harry Met Sally” scenario or an alternate universe: “I’ll never wear a suit again (noteworthy indeed)

Nevertheless, 4 trillion colossus it is today

On the other hand, After the Amazon visit, Dimon said he “got serious” and considered other positions

Other offers included running other global investment banks, which Dimon declined to name, and even insurance giant AIG, as he fielded a call from Hank Greenberg

On the other hand, Another offer he declined was from Ken Langone, Bernie Marcus and Arthur Blank, and Dimon said he had good conversations, but eventually confessed that he had never actually stepped foot in a Depot before

But what stuck was a headhunter’s call Bank One—a large but beleaguered Chicago bank

It had recently merged with other regional banks and was beset by infighting, brand confusion, and mounting losses (which is quite significant)

Dimon recalled that analyst Mike Mayo had a great line at the time the bank’s blems: “Even Hercules couldn’t fix it (quite telling) (which is quite significant). ” How Dimon became the captain of the ship Undeterred by the daunting turnaround task, Dimon saw potential where others saw wreckage

He described the idea of another banking job as “my habitat”—and he described Bank One as a place where his operational style and relentless focus on risk management could make an impact

Moreover, He uoted his young family, moved to Chicago, and signaled ultimate commitment by half his net worth—$60 million—directly into Bank One’s stock the day he took the job. “I was going to go down with the ship or up with the ship,” he said, determined to demonstrate to holders and his new team that he was “alock, stock, and barrel. ” He also talked generally why he made this particular career decision instead of a New York-based investment banking job (fascinating analysis)

He was in charge at Bank One as the CEO, he said, whereas he expressed doubts whether he could fully trust people in the investment banking world, after his bruising experience with his mentor Sandy Weill and Citigroup

Meanwhile, Within days, he confronted the scale of the challenge: management discord, disjointed IT systems, failing credit card operations, and a 21-member board split by tribal rivalries, in today's financial world

Rather than seek short-term wins, Dimon insisted on honest reporting, transparent communication, and building a long-term strategy—traits that would later crystallize at JPMorgan Chase and Dimon’s belief in having a “fortress balance sheet. ” He explained on the podcast that Bank One’s tolerance for risk was far too excessive and the bank wasn’t being honest with itself

By owning up to its own blems, it could set course for a stronger balance sheet that would be a fortress when the market turned

Captain of the ship or the houseboat, in this volatile climate

Dimon’s wager on Bank One—and the leadership apach he honed there—set the stage for his stewardship of JPMorgan Chase

As JPMorgan has gone from strength to strength, Dimon has matured into a senior voice in American society itself, weighing in on and central banking a, and wielding substantial influence

American finance might look foundly different if Dimon had taken Bezos’ offer and chosen to join Amazon

On the other hand, Instead, he could have been a executive living on the verbial houseboat, considering recent developments

Moreover, JPMorgan declined to further for this report

However, For this story, Fortune used generative AI to help with an initial draft

Conversely, An editor verified the accuracy of the information before publishing

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