Jamie Dimon might finally be ready to call it quits

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Hello! If you had a billion dollars, you'd probably buy a few silly things. (For me, it's a ski mountain.) But what about a boat designed specifically for Navy SEAL missions and a Black Hawk helicopter? This billionaire defense entrepreneur did exactly that.

In today's big story, we're looking at Jamie Dimon's update on his eventual retirement. (For real this time.)

What's on deck:

• Markets: A former Goldman Sachs VP gives a firsthand account of the "boys only" culture that drove her out.
• Tech: Microsoft just gave us a look at AI-powered computers.
• Business: Millennials are throwing some cold water on the FIRE movement.

But first, JPM - JD = ?

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The big story

A retirement looms

The world's most recognizable banker might finally be ready to call it quits.

JPMorgan CEO Jamie Dimon, who has led the bank for almost two decades, said the plan to find his successor is "well on its way," at the bank's annual investor day, writes Business Insider's Paul Squire.

Dimon, who is 68 and has an incentive package to stay through at least 2026, had joked for years that he was five years away from retirement whenever the topic came up. But this time he nodded to his long-running joke, saying it's "not five years anymore."

The comings and goings of Wall Street executives are common, even at the highest levels. Two of the biggest US banks, Citi and Morgan Stanley, have named new CEOs over the past three years.

But Dimon and JPMorgan are a different story.

The bank's CEO since 2006 and chairman since 2007, Dimon's legacy has grown with JPMorgan's size. He helped the banking industry weather the 2008 financial crisis, growing JPMorgan into the largest US bank by assets.

There have been challenges, too, including a $6 billion trading loss thanks to the London Whale. But JPMorgan's continued success in recent years, including its help during the Silicon Valley Bank crisis, has only strengthened Dimon's position atop Wall Street.

As big as Dimon's shoes will be to fill, JPMorgan has been preparing for a while. 

Wall Street has long speculated about who will ultimately succeed Dimon. Earlier this year, the bank offered some clues with a leadership shuffle that saw Jennifer Piepszak, Marianne Lake, and Troy Rohrbaugh take on new roles.

But speculating where Dimon will end up is just as interesting an exercise.

Politics has long been viewed as Dimon's potential post-banking career. His most recent annual letter to shareholders reads like something a politician could build a campaign around.

He certainly seems to have a hang of the whole lobbying thing. A report from The Wall Street Journal this weekend identified Dimon as the key person organizing bank CEOs' fight against proposed regulations requiring lenders to hold more cash on their balance sheets.

Dimon's work paid off, with the Fed now looking to loosen its restrictions, according to the WSJ's report, which cited people familiar with the matter.

In the meantime, JPMorgan continues to push forward with Dimon at the helm. The bank's investor day included slides highlighting plans for its growth in areas like investment banking, AI, and tech spending, writes BI's Reed Alexander.

Dimon and other executives also addressed questions about the untimely death of a Bank of America banker and the impact within their firm, writes Reed.

However, with or without Dimon, investors didn't necessarily seem sold on the bank's vision. JPMorgan's stock finished down 4.5% on Monday.

3 things in markets

1. What Goldman Sachs is getting wrong with its women employees. Lindsay MacMillan was named vice president at the bank by the time she was 28, but left feeling burnt out. The work wasn't the issue — it was feeling like she had to keep her feminine side tucked away on the job.
2. More than a third of US states are showing signs of real economic trouble. Nancy Lazar, Piper Sandler's chief global economist, highlighted the recent uptick in average unemployment in 19 states as a sign a recession could be looming. The fact the wealthy are still sitting pretty highlights our "very bifurcated economy, unstable economy," she added.
3. FDIC boss resigns. Martin Gruenberg has told staff he'll stand down as chairman once a replacement has been found, per The Wall Street Journal. Gruenberg's resignation comes after an independent report described the FDIC's work culture as "patriarchal," "misogynistic," and "insular."

3 things in tech

1. More AI is coming. This time, it's for our PCs. Microsoft just unveiled its Copilot+ PCs, which start at $999. The announcement came ahead of Build, Microsoft's annual developer conference, where it's expected to reveal more of its AI innovations.
2. Neuralink is making some changes. After getting the FDA go-ahead for a second implant, Neuralink will embed the wires deeper into the brain to fix problems it encountered with its first patient. A report from the Wall Street Journal says the company hopes to conduct its next implant in June.
3. OpenAI angers Scarlett Johansson. The "Her" actor said in a statement on Monday that she had previously turned down Sam Altman's request to voice GPT-4o — and so was "shocked" and "angered" after OpenAI released a voice for its new model that sounded "eerily similar" to her own.

3 things in business

1. Millennials' take on the FIRE movement is more about financial independence than slowing down from work. For a certain group of millennials, the FIRE movement — or financial independence, retire early — isn't all about an easy retirement. Instead, they're busy creating their own versions of life after work.
2. Hims & Hers is getting into the weight-loss drug game. The online pharmacy said it will sell weight-loss injectables starting at $200 a month — far less than competitors like Ozempic. The company's stock surged more than 30% on Monday in response to the news.
3. Red Lobster goes bankrupt. The troubled restaurant chain — best known for its all-you-can-eat shrimp promotion — said in a statement on Sunday that it had filed for Chapter 11 bankruptcy, although its restaurants will stay open for now.

In other news

• Former Iranian official partly blames US sanctions for the helicopter crash that killed its president.
• What Donald Trump might do if he wins a second term in 2024.
• Diddy's downfall: Sean Combs' career looks bleak after leaked tape, entertainment lawyer says.
• OpenAI pulls ChatGPT's 'Sky' voice after users compared it to Scarlett Johansson.
• Here's how much money you need to make to be middle class in each US state.
• Bill Gates thinks you should read this new book to get smarter on how AI will transform education.
• How Khaby Lame, the world's most-followed TikToker, built his business and where he's headed next.

What's happening today

• Today's earnings: Lowe's, Macy's, and other companies are reporting.
• Microsoft's BUILD developer conference starts today.

The Insider Today team: Dan DeFrancesco, deputy editor and anchor, in New York. Jordan Parker Erb, editor, in New York. Hallam Bullock, senior editor, in London. George Glover, reporter, in London.