How I Built This with Guy Raz

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:

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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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Heather Hasson and Trina Spear saw an opportunity nobody else seemed to notice: millions of healthcare workers were spending long days in uncomfortable, ill-fitting scrubs.

So they set out to reinvent them.

Heather was a designer with almost no money. To join her, Trina left a prestigious job at Blackstone and cashed out her retirement. They sold scrubs out of a car, got rejected by hundreds of investors, and eventually built FIGS into a multibillion-dollar public company.

Along the way, they paid $40 million to fight a lawsuit, navigated a pandemic, and watched their company’s valuation swing by billions.

This week, Heather and Trina share how they built the “Lululemon of Scrubs”—and why your net worth is not the same thing as self worth.

What you’ll learn

How a trip to Kenya changed Heather’s view of uniforms–and led her to start her own scarf and tie business

How Heather spotted an opportunity in a stale category: healthcare workers want comfortable clothes, too

How free coffee became a tool for customer growth

How the founders endured hundreds of investor rejections and learned to pursue a quick no

How FIGS built a community that is “diehard obsessed” with their products

How it pays–and what it costs– to defend your company against competitor lawsuits

Why net worth shouldn’t determine self-worth

How Heather and Trina think about resilience, luck, and building a company that lasts

Timestamps:

07:05 - Heather’s dreams to become a surgeon and launch a handbag business fall through, so she takes a life-changing trip to Kenya

13:53 - Heather meets a healthcare friend for coffee: “What are you wearing?... This is garbage.”

20:46 - Trina beats Heather in a tennis match, and the two become business partners

29:38 - Trina walks away from Blackstone to join Heather, and everyone asks, “What are you doing?”

35:05 - FIGS launches: Healthcare workers get it, but investors don’t

47:56 - A big-time investor comes on board—from the movie business

52:17 - A competitor sues for $800 million, and Heather and Trina use anger to their advantage

59:46 - COVID hits… and a year later, FIGS goes public

1:08:22 - No major plans to diversify: FIGS is all-in on scrubs for now

This episode was researched and produced by Katherine Sypher with music by Ramtin Arablouei. It was edited by Neva Grant. Our audio engineer was Robert Rodriguez.

Follow How I Built This:

Instagram → @howibuiltthis

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Website → guyraz.com

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Today’s callers: Kahindo from New York is looking to reboot her African-rooted fashion brand after losing a few key retailers. Then Tara from San Diego considers avenues to educate consumers about the benefits of her wool sauna hats. And Carol from Houston wonders whether to market her collegiate purses and accessories l to students or their gift-giving family members.

Plus, Seth lays out his ambitions to quadruple Insomnia’s locations and become a global chain — without turning to franchising.

Thank you to the founders of Kahindo, Sauna Societé, and Desden for being a part of our show.

Be sure to listen to Insomnia Cookies’ founding story as told by Seth on the show in 2024.

This episode was produced by Casey Herman 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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Loren Castle started baking cookies after surviving cancer in her early twenties. Five years later, Sweet Loren’s refrigerated cookie dough was generating just $350,000 a year. But instead of giving up, she listened to customers, and reinvented the dough without gluten, dairy, eggs or nuts. That transformation turned a small regional business into a national brand sold in more than 30,000 stores.
WHAT YOU'LL LEARN

How surviving cancer at 22 inspired Loren to rethink her career and develop a passion for healthier food.

What working at New York’s Levain Bakery taught her about the enormous appeal—and profitability—of cookies.

Why Loren decided to sell ready-made cookie dough instead of cookies

Why she was totally unprepared for her first Whole Foods meeting—but went anyway

Why raising her first $1 million from friends and family was much harder than she expected.

Why hundreds of customer requests revealed an unmet need for allergen-free cookie dough.

Why growing slowly may have saved the company.

Why Loren isn't rushing to sell Sweet Loren’s

TIMESTAMPS:
8:40 – After her mother's leukemia diagnosis, Loren is diagnosed with Hodgkin's Lymphoma at 22.
13:12 – Watching people line up for cookies at Levain Bakery: “I think this is America’s favorite food.”
14:54 – Selling baked goods at Smorgasburg: customers ask if they can just buy the dough
26:52 – Just as Whole Foods agrees to carry her cookie dough, Loren loses her mom
37:41 – What happens after Sweet Loren’s gets on The Today Show: “The whole country is excited by this.”
50:19 – Loren reconsiders her recipes after customers ask for dough without gluten, dairy, eggs.
56:24 – Loren takes the leap: discontinuing her original product line and going allergen-free for all.
1:05:41 – From one Whole Foods to 30,000 stores–the company expands nationally.
1:07:46 – After years of struggle, Loren explains why she wants to keep building the company instead of pursuing an exit.

This episode was produced by Carla Esteves, with music composed by Ramtin Arablouei. It was edited by Neva Grant. Our audio engineer was Jimmy Keeley.

Follow How I Built This:
Instagram → @howibuiltthis
X → @HowIBuiltThis
Facebook → How I Built This
Follow Guy Raz:
Instagram → @guy.raz
Youtube → guy_raz

X → @guyraz
Substack → guyraz.substack.com
Website → guyraz.com


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