How I Built This with Guy Raz

Guy Raz | Vox Media

Guy 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.

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Thursday · 40 min
Panera: Ron Shaich. The Big Bet That Changed Fast Food (2018)
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: 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
Monday · 1 hr 20 min
Dr. Squatch: Jack Haldrup. From a Closet Full of Soap to a $1.5 Billion Brand
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 Learn more about your ad choices. Visit podcastchoices.com/adchoices
November 5 · 46 min
Dell Computers: Michael Dell. The College Dropout Who Took on IBM (2018)
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
November 2 · 1 hr 15 min
Airbnb CEO Brian Chesky: “I Was a Great Founder and a Terrible CEO”
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 Learn more about your ad choices. Visit podcastchoices.com/adchoices
October 29 · 1 hr
Advice Line with Tope Awotona of Calendly
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
October 26 · 1 hr 11 min
FIGS: Trina Spear and Heather Hasson. The $2.5 Billion Scrubs Brand That Investors Said Would Never Work
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
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October 23 · 43 min
Advice Line with Seth Berkowitz of Insomnia Cookies
Today’s callers: Kohindo 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.T
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October 19 · 1 hr 8 min
Sweet Loren’s: Loren Castle. How A Recipe Makeover Built a National Cookie Brand
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 LEARNHow surviving cancer at 22 inspired Loren to rethink her career and develop a passi
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October 15 · 47 min
Advice Line with Tara Bosch of SmartSweets
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 aro
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October 12 · 1 hr 21 min
Alamo Drafthouse Cinema: Tim and Karrie League (2023)
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 Cin
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October 8 · 45 min
Advice Line with Nick Green of Thrive Market
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 fo
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October 5 · 1 hr 15 min
10 Years of How I Built This: A Decade of Innovation, Risk and Reinvention
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. J
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October 1 · 47 min
Advice Line with Scott Tannen of Boll & Branch and Jamie Siminoff of Ring (2025)
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
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September 28 · 1 hr 35 min
Seventh Generation: Alan Newman and Jeffrey Hollender. A Partnership that Flourished—until it Failed. (2021)
With its eco-friendly paper towels, diapers, and cleansers, Seventh Generation was one of the first—and most successful—green household brands to hit the market. But in the early 1990s, its two founders had a bitter falling out.Alan Newman and Jeffrey Hollender have barely spoken since that time, but they both agreed to come on the show to talk about the business they were both passionate about, and the delicate nature of partnership.What you'll learn: Why Alan says his great strength—and his gr
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September 24 · 44 min
Advice Line with Danny Meyer of Shake Shack
Today’s callers: Janell from Kentucky wonders how to build a sense of hospitality into her canned bourbon cocktail brand. Jade from South Carolina considers the upsides and risks of shipping her smoked salmon directly to customers. And Bar from Colorado considers strategies for bringing his protein-packed cous cous to quick service restaurants.Plus Danny talks about the elements of a strong company culture as described in his new book, What Could Possibly Go Right?Thank you to the founders of Po
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September 21 · 1 hr 2 min
Banza: Brian Rudolph. The Chickpea Pasta That Nearly Turned to Mush
Brian Rudolph started making chickpea pasta in his Detroit apartment because wheat made him feel sick. A decade later, Banza was in more than 25,000 stores, and today, it’s one of the most popular pasta brands in the country. Success was not automatic: The business barely got off the ground because the cooked pasta was turning to mush—and as Banza became known for its health benefits, a food-safety scare sent sales plunging by 30%.In this episode, Brian explains why he was inspired to create a w
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September 10 · 43 min
Advice Line with Michelle Wahler of Beyond Yoga
Today's callers: Carrie from Paris wants to turn interest into bookings for her boutique study-abroad programs for adults. Then, Grace from Nashville considers how to re-build relationships with interior designers she may have let down early on in her furniture upholstery business. And Angel from Indiana explores how to translate the emotional appeal of her self-care soap kits into stronger online sales.Plus, Michelle explains why founders don't always need to raise outside capital, and why they
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September 7 · 52 min
Thrive Causemetics: Karissa Bodnar. How a Beauty Business Made Millions for a Mission
Karissa Bodnar had a dream job at L'Oréal when a close friend died from cancer at age 24. It shook her up and made her reassess what she really wanted to do with her life. The answer? Build her own beauty business with a mission of “giving back.”The problem? Nobody seemed to want to carry her products. She pitched Sephora, Nordstrom, Ulta, and others—and kept hearing no.She stuck it out, pouring tens of thousands of dollars of her own savings into it, and worked a full-time job to fund the formu
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September 3 · 43 min
Advice Line with Kip Tindell of The Container Store
Today’s callers: Juliette in France wonders how to raise awareness of her “magical” cooling device—without a costly ad campaign. Then David in North Carolina looks to grow the wholesale channel of his engraved gifts business in light of thinning retail margins. And Kaitlin in California wants to leverage the virality of her supportive, bordered sheets and create an enduring sleep brand.Plus, Kip reflects on The Container Store’s bankruptcy and acquisition, and plugs patience and persistence as t
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August 31 · 1 hr 27 min
Bogg Bag: Kim Vaccarella. The $100 Million Business She Almost Abandoned
Kim’s inspiration to launch a business came from an unlikely source: Her son’s Crocs. She thought the durable, washable material would make a great beach bag. So she designed one. But after investing her savings—inlcuding some of her kids’ college fund—Kim was crushed when her first major shipment of Bogg bags was defective. It knocked her so off balance, that she put the entire business on hold. Then something unexpected happened.The few thousand customers who already had a bag….clamored for mo

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