How I Built This with Guy Raz

In the early 1980s, Ron Shaich took over Au Bon Pain, a struggling group of Boston bakeries, and helped grow it into a national chain with 250 locations. But Ron saw an even bigger opportunity in a small bakery chain in St. Louis. So he made a remarkable gamble: he sold Au Bon Pain to focus entirely on what would become Panera Bread. That bet helped transform the way Americans eat—and turned Panera into a multibillion-dollar business.

What You’ll Learn

How customers asking for sliced baguettes helped Ron discover a bigger business in sandwiches

What he saw in a 19-store bakery chain with surprisingly low real estate costs

Why Ron sold Au Bon Pain after building it into a national chain to concentrate on Panera

How Panera used falling real estate and construction costs to expand during the Great Recession

Why Ron believed staying on Wall Street could threaten the long-term bets that made Panera successful

Production Credits

How I Built This is produced by Podcast Pointman and part of the Vox Media Podcast Network.

Follow How I Built This:

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Jack Haldrup didn’t set out to build a billion-dollar company. He just wanted a way out of consulting and a bar of soap he actually liked.

After developing psoriasis, Jack started paying closer attention to the products he used on his skin. A chance purchase at a farmers market introduced him to handmade soap and sparked a business idea. With just $1,500, he launched an online soap company, shipping orders from his closet. Eventually, his mom took over fulfillment from his childhood bedroom.

But growing the company meant navigating a trademark dispute, a painful split with a lifelong friend and business partner, and rising expenses that forced Jack to cut staff and rethink the business.

Then, in 2018, a video ad made on a small budget went viral and transformed Dr. Squatch into a rocket ship. By 2020, annual sales had reached $113 million, and Unilever acquired the company in 2025 in a deal reportedly worth $1.5 billion.

In this episode, Jack explains why spending most of his remaining savings on a marketing class became a turning point, how Dr. Squatch found its voice through funny ads, and why he eventually stepped down as CEO of the company he’d built.

What You’ll Learn

Why Jack saw an untapped opportunity in a product that had been around for centuries

How subscription boxes helped Dr. Squatch find its first customers

Why Jack made a $3,500 bet on a marketing class when money was running low

How Facebook ads helped Dr. Squatch grow before its viral video breakthrough

What Jack learned about hiring, managing costs, and scaling a fast-growing business

How Jack navigated the transition from founder to CEO—and eventually stepped away

Production Credits

How I Built This is produced by Podcast Pointman and part of the Vox Media Podcast Network.

Follow How I Built This:

YouTube → @HowIBuiltThis

Instagram → @howibuiltthis

X → @HowIBuiltThis

Facebook → How I Built This

Follow Guy Raz:

Instagram → @guy.raz

X → @guyraz

Substack → guyraz.substack.com

Website → guyraz.com
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Michael Dell was building a tech business in his dorm room long before it became a familiar startup story. In 1983, the UT Austin student began selling PC upgrade kits. Within months, he left college to devote himself to the business. When Dell entered the Fortune 500 in 1992, Michael was just 27—the youngest CEO on the list.

In this episode, Michael explains how a teenage job selling newspaper subscriptions taught him to find customers, why he abandoned plans to become a doctor, and how Dell became a global powerhouse in computing technology.

He also shares what he learned from the mistakes that came with building a business so quickly.

What You'll Learn

How Dell sold computers for half the price of IBM's and still made a profit

Why a customer visit led Michael to rethink his entire business

How Michael scaled his startup to $66 million in annual sales by age 21

Why he returned as Dell's CEO in 2007—and how he navigated a changing PC industry

What Michael learned from Dell's early missteps, and why he prioritized customers over competitors

Production Credits

How I Built This is produced by Podcast Pointman and part of the Vox Media Podcast Network.

Follow How I Built This:

YouTube → @HowIBuiltThis

Instagram → @howibuiltthis

X → @HowIBuiltThis

Facebook → How I Built This

Follow Guy Raz:

Instagram → @guy.raz

X → @guyraz

Substack → guyraz.substack.com

Website → guyraz.com
Learn more about your ad choices. Visit podcastchoices.com/adchoices

This episode is available on Youtube: https://youtu.be/ZYf-DfxJg1c

Brian Chesky was 26 when he and his co-founders launched Airbnb, turning a few air mattresses in a San Francisco apartment into one of the most successful startups of all time.

But as Airbnb grew into a company worth more than $100 billion, Brian struggled to keep up. He hired experienced executives, trusted them to make decisions, and watched the company become increasingly chaotic. Looking back, he says Airbnb succeeded in spite of his leadership, not because of it.

Then COVID hit, and Airbnb lost 80% of its business in a matter of weeks. Facing the possibility of losing everything he'd built, Brian completely reinvented the way he ran the company—and soon after, much of his life outside work, too.

In this episode, Brian explains why some of the most common leadership advice can be disastrous for startups, what he learned from Steve Jobs and Barack Obama, and why the day after Airbnb’s IPO was one of the loneliest of his life. Plus, how Airbnb.org is providing free housing to people in crisis—and why Brian wants to expand that effort to one million nights a year.

What You'll Learn

How an art school graduate with no business experience became the CEO of Airbnb

Why Brian describes himself as “naturally a great founder but naturally a terrible CEO”

How following conventional leadership advice created chaos inside Airbnb

Why Brian believes "hire great people and get out of their way" can be a death sentence for startups

How losing 80% of Airbnb's business during COVID forced Brian to reinvent his leadership style

What studying Steve Jobs taught Brian about getting into the details

How Barack Obama helped Brian understand and confront his loneliness

Why reaching a $100 billion valuation left Brian feeling empty

How Airbnb.org grew from helping people displaced by Hurricane Sandy into a global nonprofit—and an ambitious plan to provide one million nights of free housing annually

How Brian thinks about Airbnb's future—and why he has no plans to stop building

Timestamps:

(00:03:23) - Airbnb goes public at a $100 billion valuation, but Brian wakes up feeling empty

(00:06:05) - From art school to Silicon Valley: How Brian became an unlikely tech founder

(00:10:37) - "I was a great founder and a terrible CEO": Brian's early leadership mistakes

(00:13:21) - Why hiring experienced executives and getting out of their way didn't work

(00:17:59) - The self-doubt and chaos of running a fast-growing company

(00:23:41) - How Barack Obama helped Brian confront his loneliness and reconnect with old friends

(00:33:55) - Why Airbnb's early success led to overconfidence and costly distractions

(00:38:10) - COVID wipes out 80% of Airbnb's business—and forces Brian to change

(00:40:05) - What Brian learned from Steve Jobs about hands-on leadership

(00:47:44) - Why Airbnb's leadership overhaul drove away much of its executive team

(00:50:54) - The 70 revisions of a single press release that helped Brian redefine excellence

(00:52:12) - How Brian gets honest feedback from employees who might be afraid to disagree

(00:57:38) - Why Airbnb is reconsidering some of its long-held beliefs about its business

(01:00:48) - Airbnb's plans to provide free housing for people in crisis

(01:05:09) - Why Brian hopes to keep building for the rest of his life

Production Credits

Our production is handled by Podcast Pointman.

Follow How I Built This:

YouTube → @HowIBuiltThis

Instagram → @howibuiltthis

X → @HowIBuiltThis

Facebook → How I Built This

Follow Guy Raz:

Instagram → @guy.raz

X → @guyraz

Substack → guyraz.substack.com

Website → guyraz.com
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Today’s callers: Dominic in London faces challenges with profitability and scaling for his foldable bike helmet. Then, Ivana in Vancouver wonders how to maintain the momentum of her pet gear brand as she prepares for the arrival of her first child. Danny in South Carolina wants to expand her nail salon concept without making major trade-offs in her family life. And Justin in Boston grapples with prioritizing the many channels in which he sells his customized footwear.

Plus, Tope discusses Calendly’s new AI-powered scheduling assistant and how advances in technology are making it easier than ever to get new software applications off the ground.

Thank you to the founders of Newlane, Playfield, the Nail Room, and ISlide for being a part of our show.

Be sure to listen to Calendly's founding story as told by Tope on the show in 2020.

Some news: This is the final episode of the Advice Line. Thanks to all of the callers and returning guests who were a part of its run, and to all of you who tuned in — you make How I Built This great.

This episode was produced by Alex Cheng with music by Ramtin Arablouei. It was edited by John Isabella. Our audio engineer was Annlie Huang.

You can follow HIBT on X & Instagram and sign up for Guy's free newsletter at guyraz.com and on Substack.
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