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Aman Narang says Toast's revenue fell over 90 percent during COVID before it cut 55 percent of staff
How I Built This with Guy Raz·Money

Aman Narang says Toast's revenue fell over 90 percent during COVID before it cut 55 percent of staff

The Toast CEO's survival story is a reminder that being essential software for restaurants is fantastic right up until restaurants are legally unable to be restaurants.

Jul 20, 2026
Elizabeth Stone says Netflix needs fewer narrow specialists and more systems thinkers in the AI era
Money

Elizabeth Stone says Netflix needs fewer narrow specialists and more systems thinkers in the AI era

Netflix’s CPTO argues that AI makes cross-functional judgment more valuable than one-lane expertise, though she’s not ready to throw engineering, design, or data science craft into the volcano.

Jul 19, 2026
The Twenty Minute VC hosts say Britain’s £300 million elite tennis pipeline has produced almost no champions
Money

The Twenty Minute VC hosts say Britain’s £300 million elite tennis pipeline has produced almost no champions

The episode’s best point is not that Jannik Sinner is ruthless, it’s that Italy’s club-heavy tennis system makes Britain’s expensive elite pipeline look weirdly barren.

Jul 18, 2026
Tom Ellsworth says IBM has 135,000 employees in India and only 40,000 in the U.S.
Money

Tom Ellsworth says IBM has 135,000 employees in India and only 40,000 in the U.S.

The PBD panel treated IBM’s brutal earnings reaction less like a bad quarter and more like a warning light for a company that may have outsourced its identity.

Jul 17, 2026
Kenneth Cole says wholesale won't build your brand if you don't own the customer relationship
How I Built This with Guy Raz·Money

Kenneth Cole says wholesale won't build your brand if you don't own the customer relationship

On How I Built This, Cole gave a very department-store-era warning to modern founders: revenue through retailers can look like momentum while quietly leaving the brand in someone else's hands.

Jul 16, 2026
Tom Rinks says he would have settled the Taco Bell Chihuahua lawsuit for $200,000 before a $30.1 million jury award
How I Built This with Guy Raz·Money

Tom Rinks says he would have settled the Taco Bell Chihuahua lawsuit for $200,000 before a $30.1 million jury award

Before Sun Bum became a sunscreen juggernaut, Rinks says Taco Bell could have ended the Chihuahua fight for a fraction of what a jury later awarded.

Jul 13, 2026
Noam Segal says tech workers fear doing more for the same pay more than losing their jobs to AI
Money

Noam Segal says tech workers fear doing more for the same pay more than losing their jobs to AI

The AI job panic has been sold as a robot replacement story, but Segal's survey says the more immediate fear is much more office Slack: congratulations, your output just became your new quota.

Jul 12, 2026
Jeni Britton says seed oil panic is too fad-like to build a frozen-fry brand around
How I Built This with Guy Raz·Money

Jeni Britton says seed oil panic is too fad-like to build a frozen-fry brand around

The Jeni's Splendid Ice Creams founder told a beef-tallow fries startup to sell taste first, not online wellness panic.

Jul 9, 2026
Caleb Hammer says Gen Z is doom spending because algorithms make the future feel hopeless
Money

Caleb Hammer says Gen Z is doom spending because algorithms make the future feel hopeless

The personal-finance YouTuber argues that young people are spending like the apocalypse is already on layaway, and he’s mostly right, with one big caveat.

Jul 7, 2026
Mike Rowe says China built 1,000 ships last year while America built three
The Shawn Ryan Show·Money

Mike Rowe says China built 1,000 ships last year while America built three

The Dirty Jobs host turns a shipbuilding stat into a warning about welders, electricians, student debt, and America’s bad habit of treating trade work like a consolation prize.

Jul 7, 2026
Krishna Kaliannan says he first coated Catalina Crunch cereal in a washing machine
How I Built This with Guy Raz·Money

Krishna Kaliannan says he first coated Catalina Crunch cereal in a washing machine

The Catalina Crunch founder's weirdest manufacturing hack is also the cleanest explanation of why making a modern keto cereal is much harder than making a pitch deck.

Jul 6, 2026
Ben Felix says young people saving money in their 20s is probably a financial mistake
The Diary of a CEO·Money

Ben Felix says young people saving money in their 20s is probably a financial mistake

The Canadian portfolio manager and YouTuber has the research to back it up, and a caveat that could save you from using it as an excuse.

Jul 3, 2026
Ronnen Harary says Spin Master became too rigid after he stopped being co-CEO
How I Built This with Guy Raz·Money

Ronnen Harary says Spin Master became too rigid after he stopped being co-CEO

The PAW Patrol co-founder’s most revealing advice was not for a caller, it was the quiet admission that a hit-making toy company can get housebroken.

Jul 2, 2026
Jeremy Grantham says investors should wish SpaceX fails because success would supercharge AI robots
The Diary of a CEO·Money

Jeremy Grantham says investors should wish SpaceX fails because success would supercharge AI robots

The billionaire investor gives Steven Bartlett the rare anti-hype SpaceX take, then tells him his own stake may be sitting on a bubble story.

Jun 30, 2026
Jeremy Grantham says US stocks may not recover for 20 years and Wall Street knows it
The Diary of a CEO·Money

Jeremy Grantham says US stocks may not recover for 20 years and Wall Street knows it

The veteran investor who called the 2000 and 2008 crashes says a 70% decline in US tech stocks would not be unexpected, and your financial advisor will never warn you.

Jun 25, 2026
Nick Hanauer Comes to Yell About Neoliberalism and He's Not Wrong
The Diary of a CEO·Money

Nick Hanauer Comes to Yell About Neoliberalism and He's Not Wrong

The venture capitalist and self-described 'pitchfork-avoider' spends an hour telling a table of entrepreneurs that everything they believe about small business is right, and everything they believe about how to get there is wrong.

Jun 10, 2026
Tara LaFerrara Built a Million-Dollar Fitness Business by Refusing to Be Perfect
Young and Profiting·Money

Tara LaFerrara Built a Million-Dollar Fitness Business by Refusing to Be Perfect

The Broads founder on coaching funnels, a $130,000 app failure, and why 'do the cringe thing' is actually a business strategy.

Jun 10, 2026
Ex-Google Insider Mo Gawdat Says Your Job Has About Three Years
The Diary of a CEO·Money

Ex-Google Insider Mo Gawdat Says Your Job Has About Three Years

The former Google X chief business officer comes to The Diary of a CEO with a countdown clock and a dim view of Sam Altman's recent pivot to optimism.

Jun 1, 2026
Jessie Inchauspé Says Your Breakfast Is Why You Feel Terrible by 10 a.m.
Young and Profiting·Money

Jessie Inchauspé Says Your Breakfast Is Why You Feel Terrible by 10 a.m.

The Glucose Goddess on sugar crashes, aging like a chicken in an oven, and why orange juice is basically a can of Coke.

Jun 1, 2026
Benjamin Hardy Says You're Measuring Yourself Wrong, and He Has the Viktor Frankl Story to Prove It
Young and Profiting·Money

Benjamin Hardy Says You're Measuring Yourself Wrong, and He Has the Viktor Frankl Story to Prove It

The organizational psychologist behind 'The Gap and the Gain' explains why hitting your goals might make you feel worse, and what Mr. Beast figured out at 17 that most adults never do.

May 29, 2026
David Bach's $27.40 Sermon Is Both Simple and Incomplete, Which Is Exactly the Point
The Diary of a CEO·Money

David Bach's $27.40 Sermon Is Both Simple and Incomplete, Which Is Exactly the Point

The 'Automatic Millionaire' guy brought a brick of cash to London and made a very clean argument for a very messy reality.

May 28, 2026
Natalie Dawson says you should not think about passive income until you have $1 million in the bank
The Diary of a CEO·Money

Natalie Dawson says you should not think about passive income until you have $1 million in the bank

The business operator’s blunt advice on The Diary of a CEO is useful, if a little too clean for the messy reality of getting rich.

May 21, 2026