How I Built This with Guy Raz
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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Recent Episodes
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Michael Dell shares the remarkable story of building Dell Computer Corporation from his University of Texas dorm room in 1984. Starting at age 18 with a simple business of upgrading IBM PCs, Dell scaled to a $66 million company by age 21 and eventually became the world's number one PC seller. He discusses his early entrepreneurial ventures, including a highly successful newspaper subscription business in high school, his precocious understanding of market inefficiencies, and how he revolutionized computer sales through direct-to-consumer models and just-in-time supply chains.
- Early Entrepreneurial Ventures and the Newspaper Business
- The Dorm Room Computer Upgrade Business
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Advice Line with Tope Awotona of Calendly
Oct 29, 2026Summary Preview
Guy Raz and Tope Awatonna, founder of Calendly, field questions from three entrepreneurs seeking guidance on scaling their businesses. The callers include Dom from New Lane (a UK-based folding bike helmet company), Ivana from Playfield (a dog walking accessories brand), and Justin from iSlide (a custom footwear company). Topics covered include product differentiation, operational delegation during life transitions, and strategic channel focus for growth.
- Introduction and Tope's Journey Update
- Dom's New Lane Folding Helmet Challenge
FIGS: Trina Spear and Heather Hasson. The $2.5 Billion Scrubs Brand That Investors Said Would Never Work
Oct 26, 2026Summary Preview
This episode features Heather Hassan and Trina Speer, co-founders of Figs, who transformed the medical scrubs industry into a $2.5 billion publicly traded company. Despite having minimal healthcare backgrounds, they identified an overlooked market of 24 million U.S. healthcare workers buying their own ill-fitting, unfashionable scrubs. Through direct-to-consumer sales, technical innovation, and community building, they disrupted an industry controlled by distributors and faced hundreds of investor rejections before finally achieving success.
- Heather's Journey from Failed Dreams to Fashion
- The Scrubs Epiphany and Early Validation
Advice Line with Seth Berkowitz of Insomnia Cookies
Oct 22, 2026Summary Preview
Seth Berkowitz, founder and CEO of Insomnia Cookies, joins Guy Raz to advise three entrepreneurs on growing their businesses. The callers seek guidance on customer acquisition strategies, marketing channels, and navigating split buyer-user dynamics. Seth draws on his experience scaling Insomnia Cookies from a dorm room operation to nearly 400 locations, emphasizing the importance of earning growth through consumer love, maintaining quality control, and staying close to customer data.
- Introduction and Seth's Growth Philosophy
- Kahindo's Luxury Fashion Brand Challenge
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Lauren Castle built Sweet Lauren's from a personal health journey into a $100M+ allergen-free cookie dough brand. After battling cancer at 22, she became obsessed with healthy baking and spent years perfecting natural cookie recipes. What started as a tiny farmer's market business in 2011 grew slowly through regional Whole Foods stores before a pivotal 2017 decision to go completely allergen-free transformed the company. Today, Sweet Lauren's is sold in over 30,000 stores and has made the Inc. 5000 list eight consecutive years.
- Personal Transformation Through Cancer
- Recipe Development and Farmer's Market Testing
Advice Line with Tara Bosch of SmartSweets
Oct 15, 2026Summary Preview
On this episode of the Advice Line, Guy Raz is joined by Tara Bosch, founder of SmartSweets and her new venture Snackish, to advise three entrepreneurs: Lindsay of XO Marshmallow on transitioning from DTC to grocery retail, Vivi of Vivi's Vacation on translating brand essence into marketing, and Allie of Romanticize Collective on evolving her experience-based subscription model. The conversations center on customer validation, niche marketing, maintaining authenticity, and knowing when to pivot business models.
- Introduction to Guest Tara Bosch and Snackish
- Lindsay's XO Marshmallow: Transitioning from DTC to Grocery
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Tim and Carrie League share the wild journey of building Alamo Drafthouse Cinema from a failing art house theater in Bakersfield to a national chain that revolutionized moviegoing by combining full-service dining with film. Their story includes living behind a movie screen, installing sheetrock backwards, bankruptcy during COVID, and ultimately selling to Sony Pictures Entertainment.
- From Shell Engineer to Movie Theater Owner
- The Bakersfield Struggle and a Tragic End
Advice Line with Nick Green of Thrive Market
Oct 08, 2026Summary Preview
In this Advice Line episode, Guy Raz and Nick Green, co-founder of Thrive Market, help three entrepreneurs navigate challenges in their growing businesses. They discuss balancing product quality with speed to market for a concert attire brand, fundraising strategies for a mission-driven coffee company, and scaling awareness for an AI-powered voice cloning app for people with speech loss. The conversation emphasizes the importance of focus, data-driven decisions, and sustainable growth strategies.
- Concert Attire for Musicians: Balancing Quality and Speed
- Peak State Coffee: Mission-Driven Growth Without Compromise
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Guy Raz celebrates the 10-year anniversary of How I Built This by revisiting memorable moments from 600+ founder interviews. Joined by Jamie Siminoff (founder of Ring), they explore recurring themes of entrepreneurship: fear and vulnerability, the lightbulb moment, scrappy beginnings, inevitable failures, raising capital challenges, and the balance between luck and skill that defines startup success.
- Fear as a Driving Force in Entrepreneurship
- The Lightbulb Moment: Finding Problems Worth Solving
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Jamie Siminoff (Ring founder) and Scott Tannen (Bull & Branch co-founder), who attended high school together, reunite to offer advice to entrepreneurs. They tackle questions about raising capital versus bootstrapping, market positioning, and expanding beyond traditional customer bases. The episode showcases how two seemingly different businesses—home security and organic bedding—share common challenges in building consumer brands.
- The Founders' Reunion and Updates
- Organic Cotton Socks: To Bootstrap or Raise Capital
Seventh Generation: Alan Newman and Jeffrey Hollender. A Partnership that Flourished—until it Failed. (2021)
Sep 28, 2026Summary Preview
Jeffrey Hollander and Alan Newman co-founded Seventh Generation in 1988, turning a struggling mail-order catalog selling eco-friendly products into a pioneering brand of green cleaning supplies sold nationwide. This episode explores their complementary partnership, bitter falling out in 1992 when Alan took a sabbatical, and their subsequent successes and failures. Unilever acquired the company for $600-700 million in 2016, marking the transformation of a small hippie business into a mainstream eco-friendly powerhouse. The two founders reunite on the show to discuss their relationship, what went wrong, and lessons learned about partnerships.
- The Founders' Early Years and Paths to Business
- Alan Inherits Seventh Generation and Jeffrey Joins
Advice Line with Danny Meyer of Shake Shack
Sep 24, 2026Summary Preview
Danny Meyer, legendary restaurateur and founder of Union Square Hospitality Group, shares insights on building enduring culture, scaling hospitality businesses, and navigating challenges. The episode features three entrepreneurs seeking advice: Janelle Bass from Ponyboy Slings (bourbon-based canned cocktails), Jade Taylor from Angel Oak Smokehouse (premium smoked salmon), and Barb Ruhis from Booskus (high-protein, high-fiber couscous). Meyer discusses transitioning to executive chairman, the evolution from family values to expected behaviors, and the importance of maintaining hope through business cycles.
- Building Culture Through Expected Behaviors
- Recognizing Genuine Hospitality
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Advice Line with Michelle Wahler of Beyond Yoga
Sep 17, 2026Summary Preview
Guy Raz hosts the Advice Line on How I Built This Lab, joined by Michelle Whaler, co-founder and former CEO of Beyond Yoga. Michelle shares insights from building her yoga apparel company over 20+ years before selling to Levi's for $400 million in 2021. Three entrepreneurs call in seeking advice: Carrie Angoff with Elective Study Abroad (adult education travel experiences), Grace Reth with Grace Ann Upholstery (custom furniture reupholstery), and Angel Raymer with Sacred Paws Soap Company (self-care soap kits with crystals). Michelle and Guy provide strategic guidance on converting interested customers, rebuilding burned relationships, and selling emotion through digital channels.
- Michelle Whaler's Journey and Philosophy on Startup Advice
- Elective Study Abroad: Converting Enthusiasm into Bookings
Thrive Causemetics: Karissa Bodnar. How $150 a Day in Sales Turned into a $150 Million Beauty Business with a Mission
Sep 14, 2026Summary Preview
Carissa Bodner shares her journey of building Thrive Cosmetics from a purpose-driven side hustle into a multi-million dollar beauty brand. After losing her close friend Christy to cancer at age 24, Carissa left her job at L'Oreal to create cosmetics that would work for people going through cancer treatment while giving back to those in need. Starting with $100,000 in life savings and working from her kitchen, she spent years developing innovative products before a viral moment in 2016 transformed the business from $78,000 to $30 million in revenue within months. Today, Thrive Cosmetics generates over $150 million annually while remaining profitable, privately held, and committed to its social mission.
- Early Passion for Beauty and Self-Taught Chemistry
- Career Path Through L'Oreal and Finding Her Mentor
Advice Line with Kip Tindell of The Container Store
Sep 10, 2026Summary Preview
Kip Tindall, co-founder of The Container Store, returns to discuss retirement, the challenges of retail, and advises three entrepreneurs on their businesses: a magic cooling wand for kids, a personalized gift engraving company, and an innovative sleep product that went viral. The episode explores themes of patient growth, customer service excellence, and building lasting brands beyond viral moments.
- Kip Tindall on The Container Store's Journey and Bankruptcy
- The Changing Nature of Retail and Customer Service
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Kim Vaccarella shares her remarkable journey from high school dropout and waitress to building Bogg Bag into a $100+ million brand. Starting with an idea inspired by Crocs material in 2008, Kim faced devastating setbacks including $30,000 in defective inventory and considered quitting multiple times. After persevering through financial struggles, depression, and years of working two jobs, she grew the washable beach bag company methodically over 15 years. The story includes a dramatic trip to China where she threatened to burn down a factory, turning down a $100+ million acquisition offer, and eventually securing investment from fashion industry veterans while maintaining majority control.
- The Origin Story: From Struggle to Inspiration
- The Bog Bag Idea: Inspiration Strikes at the Beach
Advice Line with Ben Goodwin of Olipop
Sep 03, 2026Summary Preview
Ben Goodwin, co-founder of the $2 billion prebiotic soda brand Olipop, joins Guy Raz to advise three entrepreneurs navigating growth challenges in the food and beverage industry. The episode covers scaling a ghee-based snack brand, building a gluten-free bakery business, and revitalizing a struggling 50-year-old food co-op. Throughout the conversation, Ben emphasizes the importance of taste over education, maintaining mission integrity, and trusting entrepreneurial instincts.
- Introduction and Olipop's Recent Rebrand
- Geelish: Scaling a Ghee-Based Snack Brand
Late July Snacks: Nicole Bernard Dawes. Crackers and Cookies were Failing… Tortilla Chips Saved Them
Aug 31, 2026Summary Preview
Nicole Bernard-Dawes, daughter of Cape Cod Potato Chips founder Steve Bernard, shares her journey building Late July organic snacks from near-bankruptcy to a $100 million business acquired by Campbell's. Starting in 2003 with organic crackers, the company struggled for years until pivoting to tortilla chips in 2009—right after her father's death and a $3.5 million loan being called in. The business transformed into a national brand before being sold. Nicole then launched Nixie Beverage Company, creating organic sparkling waters and sodas, navigating the ultra-competitive beverage space with lessons learned from her previous ventures.
- The Cape Cod Chips Foundation
- Launching Late July and Early Struggles