Insider Today: The unstoppable Sam Altman

OpenAI CEO Sam Altman.

Welcome back to our Sunday edition, a roundup of some of our top stories. If you’re sick of me running the Sunday edition for Matt Turner, I have good news: He’s back next week. (However, you’re still stuck with me on the weekdays.)

On the agenda today:

Middle managers are getting fed up with their jobs.
Inside a self-help retreat for some of America’s most hard-charging female executives.
Wall Street says it’s going to rein in 100-hour workweeks. Junior bankers aren’t buying it.
Not even Sam Altman can stop Sam Altman from winning.

But first: A look back at Harris vs. Trump.

This week’s dispatch

Up for debate

As volatile as the US presidential election has already been, Tuesday’s debate still provided more twists and turns.

The first in-person meeting between Vice President Kamala Harris and former President Donald Trump had plenty of fireworks. Most notable was Harris’ jab about the size of Trump’s rallies.

The comment clearly got under Trump’s skin, somewhat throwing the former president off his game. And even one of Trump’s biggest supporters — Elon Musk — acknowledged that Harris “exceeded most people’s expectations.” (He’s still backing Trump, though.)

In the end, most signs pointed to Harris winning the debate. But how impactful that is come November remains to be seen. Polls showed Trump lost all three debates to Hillary Clinton in 2016.

Trump, meanwhile, has maintained he performed well on Tuesday, and his allies have blamed ABC debate moderators David Muir and Linsey Davis of tipping the scales in Harris’ favor.

One undeniable win Harris can claim is the support of Taylor Swift, who officially endorsed the vice president. (JD Vance, Trump’s running mate, isn’t worried.)

But the ultimate losers might have been American voters. For all the back-and-forth, neither candidate provided many details about how they plan to fix the economy. Lucky for you, we did our own analysis based on their past records and campaign promises.

And don’t get your hopes up for a rematch. Despite a push from Harris’ camp for round two in October, Trump put the kibosh on running it back.

Middle managers are over it

Burnout rates among middle managers have risen in the past few years — and it’s no wonder why. They’ve been the target of layoffs, had to enforce unpopular RTO policies, and they’re often the bearer of bad news as raises get smaller and less frequent.

B-17 spoke to some middle managers who said the stress was enough for them to consider asking for a demotion. Others are looking for a way out altogether.

How they’re trying to cope.

Did we girlboss too close to the sun?

It’s not easy being a successful woman in business. Female executives can feel especially trapped between the demands of career and home, and some can’t figure out how to achieve a better work-life balance.

Fortunately for the overworked girlboss, a self-help retreat for women in charge purports to have the answer. B-17 writer went behind the scenes.

Here’s what she found.

The more things “change”…

After the death of an investment banking associate and former Green Beret in May, JPMorgan and Bank of America pledged to cap junior bankers’ hours at 80 per week “in most cases.”

But the juniors aren’t convinced. At all. “In reality, nothing is going to change,” one incoming analyst told B-17. And their skepticism is more than just a feeling: History is on their side.

Can IB really change?

Sam Altman’s rise, fall, and rise again

About a year ago, OpenAI CEO Sam Altman was at the top of his game, with one VC partner telling B-17 at the time that he was “bigger than Taylor Swift.” But soon after, Altman’s pristine image started to crack.

In May, he made enemies with Scarlett Johansson, and around the same time, some of OpenAI’s top talent began leaving. But on the business front, the chaos doesn’t seem to matter. From a landmark Apple deal to reportedly raising money at a sky-high valuation, OpenAI just keeps winning.

Why no one cares about Altman’s villain arc.

This week’s quote:

“It’s God or the universe or source energy or the Great Pumpkin or whatever telling me I don’t need to have a job.”

— Kevin Cash, a Navy veteran with five degrees, describes his frustrating experience applying for nearly 2,200 jobs since getting laid off in late 2022.

More of this week’s top reads:

Apple’s new iPhone 16 with AI seems … kind of boring. That could actually be a good thing.
Why everyone from meme lords to stock traders is obsessed with Nvidia.
44 of the most promising AI startups of 2024, according to top VCs.
Millions of people are about to get free HBO, thanks to WBD’s new cable deal.
Why MrBeast could face big business problems and become “BuzzFeed 2.0,” according to a prominent VC.
Jensen Huang says if “anything were to happen” in Taiwan, Nvidia could have GPUs made somewhere else.
San Francisco gave Twitter a massive tax break to stay put. What went wrong?
AI startups are pitching a new passive-income side hustle: automated videos for YouTube and TikTok.
Private equity firms made billions off of higher education. Students paid the price.
The Insider Today team: Dan DeFrancesco, deputy editor and anchor, in New York. Grace Lett, editor, in Chicago. Amanda Yen, fellow, in New York.