Stay ConnectedGuy Raz interviews the world’s best-known entrepreneurs to learn how they built their iconic brands. In each episode, founders reveal deep, intimate moments of doubt and failure, and share insights on their eventual success. How I Built This is a master-class on innovation, creativity, leadership and how to navigate challenges of all kinds.
How I Built This is part of the Vox Media Podcast Network.
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
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
Learn more about your ad choices. Visit podcastchoices.com/adchoices
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.
Learn more about your ad choices. Visit podcastchoices.com/adchoices
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
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
Learn more about your ad choices. Visit podcastchoices.com/adchoices
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.
Learn more about your ad choices. Visit podcastchoices.com/adchoices
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
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
Learn more about your ad choices. Visit podcastchoices.com/adchoices
Today’s callers: Lindzi from Chicago wants to expand her gourmet marshmallow brand into retail without cannibalizing her high-margin DTC sales. Then, Vivi from Hawaii considers how to best tell her sustainable swimwear brand’s story to a digital audience. And Aly from Los Angeles wonders whether a subscription model is best for her whimsical curated experiences.
Plus, Tara talks about her latest entrepreneurial venture, Snackish, and how starting a new company feels different the second time around...
Thank you to the founders of XO Marshmallows, Vivi’s Vacation, and Romanticize Collective for being a part of our show.
Be sure to listen to SmartSweets’ founding story as told by Tara on the show in 2024.
This episode was produced by Chris Maccini 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.
Learn more about your ad choices. Visit podcastchoices.com/adchoices
In the early 1990’s, Tim League spent $50,000 in savings to lease an abandoned movie theater on the wrong side of the tracks—a shaky experiment that eventually grew into a thriving national chain. As Tim and his wife Karrie built theaters in Austin and beyond, they made a name for themselves by offering dinner with the movie, creative pairings (like sake with Godzilla), and roadshows where movie-goers could watch Deliverance in canoes, or Rocky on the famous steps in Philly. Alamo Drafthouse Cinema now has dozens of locations across the country, but there have been plenty of bruises along the way: a failed first theater, a fractious lawsuit with business partners, and a swan dive into the red during the pandemic.
This episode was produced by Carla Esteves, with music by Ramtin Arablouei.
Edited by Neva Grant, with research help from Carla Esteves.
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
Learn more about your ad choices. Visit podcastchoices.com/adchoices
Today’s callers: Mercedes in Utah tries to find harmony between quality and speed as she scales her concert attire brand for musicians. Then Danny in Colorado grapples with the tradeoffs of growing his sustainable and functional coffee brand. And Riya in Illinois wonders how to build awareness for her app that aids people affected by speech loss.
Plus, Nick’s insights on how AI is changing the way we fill our grocery carts — and how grocers respond to food and nutrition trends.
Thank you to the founders of Blackstrad Concert Attire, Peak State Coffee, and Voice Back for being a part of our show.
And be sure to listen to Thrive Market’s founding story as told by Nick in 2024.
This episode was produced by Sam Paulson 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 or on Substack.
Learn more about your ad choices. Visit podcastchoices.com/adchoices
Stories about starting a business are almost always full of drama. They’re about ambition, loss, triumph, catastrophe, resilience. And they’re also full of life lessons – which is why Guy Raz launched How I Built This 10 years ago: He wanted to host a free master class in entrepreneurship, one conversation at a time. Ten years on, he’s conducted over 600 interviews with some of the world’s most successful founders, and on today’s show, he replays some of the most memorable moments and lessons. Joining him is Jamie Siminoff, the founder of RING and a former guest on the show. Why Jamie? He’s a friend, a fan, and – as you may remember from his first interview - he doesn’t hide his emotions.
Timestamps:
5:10 A lightbulb switches on at an NYC bodega: “Oh my God, look at all those cherries!”
9:33 The moment Stitch Fix founder Katrina Lake realized she should start her own business.
12:04 The difference between scary and dangerous, and why it matters for founders
19:35 Eileen Fisher’s first, terrifying trade show: “I couldn’t speak. I just stood there.”
22:59 “Everything was on one computer?” The chaotic launch of Instagram
27:32 How Sara Blakely sold her first Spanx
31:16 The marketing genius behind Liquid Death
39:40 Why 2008 was the worst year of Joe Gebbia’s life
44:51 How the co-founder of Banana Republic fell asleep at the wheel—literally
53:40 Makeup mogul Bobbi Brown on selling to Estee Lauder: “I am not a follow-the- leader-kind of person.”
1:01:59 Luck, skill, and staying on the surfboard
This episode was produced by Casey Herman, with music by Ramtin Arablouei.
Edited by Neva Grant. Our audio engineer was Robert Rodriguez.
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
Learn more about your ad choices. Visit podcastchoices.com/adchoices
CEO and co-founder of Boll & Branch, Scott Tannen joins Ring founder Jamie Siminoff and Guy on the Advice Line to answer questions from three early-stage entrepreneurs. Plus, Jamie and Guy talk about how creating repeat customers often comes from creating social good.
First, we hear from Melita in Toronto who's wondering whether to continue bootstrapping her organic clothing business. Then Eric in the Sunshine State asks which direction to take to grow his sunscreen apparel lines. And Chris in Alpine Meadows, California, is trying to figure out how to get his sleek binoculars into the hands of more people.
Thank you to the founders of Q for Quinn, L Cubed Lifestyle, and Nocs Provisions.
If you’d like to be featured on a future Advice Line episode, leave us a one-minute message that tells us about your business and a specific question you’d like answered. Send a voice memo to hibt@id.wondery.com or call 1-800-433-1298.
And be sure to listen to the story of how Jamie founded Ring from our episode back in 2020, as well as his appearance on the Advice Line in 2024.. And how Scott and his wife Missy started Boll & Branch, a story they told on the show in 2024.
This episode was produced by J.C. Howard with music by Ramtin Arablouei.
It was edited by Andrea Bruce. 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
Learn more about your ad choices. Visit podcastchoices.com/adchoices
Our TOPPODCAST Picks 
