Episode summary
Eight Bosses Share the Biggest Money Regrets in Their Careers | Bloomberg Businessweek
Bloomberg Businessweek Daily
· · 9 min · Hosts: Carol Massar, Tim Stenovec · Guests: Kate Krader
Summary
Kate Krader discusses her Bloomberg Businessweek series on how executives spend, prepare, and regret money decisions. The conversation ranges from the surprisingly personal details CEOs share about their routines to the practical lessons those stories reveal about career timing, confidence, and discipline.
Krader says the recurring appeal of the series is that high-powered leaders are willing to admit habits and anxieties that sound ordinary: some use AI to save time, some psych themselves up with ritual, and some even rely on exercise or grooming before big moments. She also says the most memorable stories are often the early-career experiences that shaped later judgment, like David Solomon’s first job scooping ice cream and another executive learning to count money quickly.
The sharpest part of the segment is about money regrets. Krader highlights missed opportunities such as selling California Pizza Kitchen to PepsiCo, failing to buy Tesla stock in 2010, and getting out of major investments too early. The executives’ regrets are presented as reminders that hesitation, vague plans, and premature exits can matter as much as bold moves.
Key takeaways
- Krader says executives are unusually candid when asked how they prepare for major moments, from mushrooms to blowouts to gym time.
- David Solomon’s first job scooping ice cream in Westchester County taught him to listen carefully and get orders right, Krader says.
- One CEO’s biggest regret was not buying Tesla stock in 2010, while another regretted selling a large chunk of California Pizza Kitchen too soon.
- Krader argues that some of the most useful regret stories are about delayed decisions, like buying a house or refinancing a mortgage after waiting too long.
- Matt Navaro of Stanley 1913 regrets not studying abroad, a choice Krader says many listeners can relate to.
Notable quotes
“Some of them are taking mushrooms. That's what I like. I had to Google those mushrooms, Kate”
“I think what was that? That was like how what was that? His meditation”
“he has the number down like he would be several million dollars richer right now if um he's the CEO of Red Savannah”
“what he said people should focus on is the kind of things you talk about doing but don't do, like buying a house”
“I need to stay here. I need to build up my bank account”
How the episode opens
Bloomberg Audio Studios, podcasts, radio, news. — You're listening to Bloomberg Business Week with Carol Masser and Tim Stenc on Bloomberg Radio. — Maybe I'm just kind of excited because we have um a super favorite person uh in town. She's normally in London. Uh she is known all over the world um for her coverage of food, beverage, and restaurants. Um knows that space. So, well, but now CEOs are also dishing it out to her.
We're talking about Kate Crater. She's Bloomberg Pursuits Food Editor. She's behind the CEO diet. It's a monthly series in Bloomberg Business Week in which executives from around the world tell Kate how they manage their time in out of the office.
Is this fun? It's become really fun. You feel like they're you feel like a CEO therapist psychiatrist like telling you, you know, they're telling you like how they get through their day, what their AI — Some of them are taking mushrooms. That's what I like. I had to Google those mushrooms, Kate. Those are the legal kind of mushrooms that you wrote about with this one CEO.
Yeah, he was um — The true true med pay payments or true payments CEO. — I think that's right. Yeah, that's exactly right. And I think what was that? That was like how what was that? His meditation. — Yeah, that was how he pyes up for a big like he py for a big moment. Oh my god, Tim, I'm you're going to have to become the editor of CEO Diet now. Where do you
That one just really stuck with me because — Some of them you — They get pretty candid. You know which one um was a big like it was it was actually kind of fun also because it came with a picture.
From the episode’s captions: roughly the first two minutes, lightly cleaned. Keep watching on YouTube →
Topics
- career regrets
- ceo motivation
- business news roundup
- technology stories
- economics and politics
Watch the episode
Summary, takeaways and quote selection by Octagon. Quotes are short excerpts; the full conversation is in the episode.
More from Bloomberg Businessweek Daily
-
Bloomberg Businessweek Weekend - November 13th, 2026 | Bloomberg Businessweek -
Inside Jensen Huang’s Final Hours as Nvidia CEO | Bloomberg Businessweek -
Jensen Huang's Exit Kicks Off Nvidia Strategy Reset | Bloomberg Businessweek -
Special Episode: Bobby Jain on Why He Chose Millennium Again | Bloomberg Businessweek -
Bloomberg Businessweek Daily Podcast: Jensen’s Nvidia Departure -
Take-Two Releasing Long-Awaited Grand Theft Auto VI Next Week | Bloomberg Businessweek
Bloomberg Businessweek Daily, this episode and its artwork belong to Bloomberg. Octagon is not affiliated with the show; this page is an independent summary.
