How I Built This
Guy Raz | Wondery
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. New episodes release on Mondays and Thursdays.
Recent Episodes
Serena & Lily: Serena Dugan and Lily Kanter. They Built a $20M Brand—Then One Investor Almost Destroyed It
Aug 3, 2026Lily Kanter and Serena Dugan, co-founders of luxury home goods brand Serena & Lily, discuss how they built a $20M business from a chance meeting in 2003. Starting with crib bedding designs, they achieved rapid early success when a competitor exited the market the same weekend their first catalog launched. The episode focuses on how rapid growth created cash flow crises and how poorly-structured investor deals nearly destroyed the company before a family office acquisition cleaned up their cap table and allowed them to scale.
Advice Line with Chris Riccobono of UNTUCKit
Jul 30, 2026Chris Riccobono, co-founder of UNTUCKit, returns to advise callers on the Advice Line. He discusses how his apparel business has navigated recent challenges including tariff impacts and expansion into wholesale retail, while also running a parallel athletic brand called Greatness Wins. Riccobono offers strategic guidance to three entrepreneurs: Adrian Alvarez (Aero Shorts), Preet (Snug Safety), and Derek (Hockey Ninja), addressing brand scaling, customer acquisition, and growth strategy in competitive markets.
Sweetwater: Chuck Surack. How a Customer Service Strategy Built a Billion Dollar Online Pro Audio and Music Company.
Jul 27, 2026Chuck Surack founded Sweetwater, now a $2 billion online retailer of musical instruments and professional audio equipment, by building the business around exceptional customer service and dedicated sales engineers rather than competing on price. Starting from a recording studio in his VW van in Fort Wayne, Indiana, Surack became a Kurzweil synthesizer dealer in the mid-1980s, then expanded into a comprehensive music equipment retailer by prioritizing long-term customer relationships and product expertise. In 2021, Surack sold a majority stake to Providence Equity Partners while retaining operational influence and a minority stake, allowing the company to accelerate growth while maintaining his core values around employee support and community investment.
Advice Line with Curt Richardson of OtterBox
Jul 23, 2026Curt Richardson, founder of OtterBox and chief visionary officer, returns to the Advice Line to mentor three entrepreneurs seeking growth and scaling strategies. Richardson discusses how OtterBox evolved from a startup to a $1.1 billion revenue company before consolidating focus on phone cases and mobile accessories, and shares insights on product-market fit, customer retention, and the importance of systems thinking. The episode covers guidance for a game show events business seeking to scale nationally, a fairy-tale-inspired tea brand working to regain momentum post-maternity, and a circular-economy baby gear startup navigating early-stage marketing channel selection.
Toast: Aman Narang. How a Long Wait for the Dinner Check Launched a $2 Billion Business.
Jul 20, 2026Aman Narang, co-founder and CEO of Toast, discusses how a frustrating wait for a dinner check at a Boston restaurant inspired him and his co-founders Steve Fredet and John Grimm to build a mobile payment app—which ultimately pivoted into a comprehensive cloud-based point-of-sale platform for restaurants. Starting from a failed consumer app in 2012, Toast evolved into a purpose-built system replacing legacy restaurant technology, growing to support nearly one in five U.S. restaurants and generating over $2 billion in annual revenue. Narang recounts the company's early struggles to gain traction, the decision to replace the entire restaurant operating system rather than just payment processing, surviving COVID-19 through rapid pivots to off-premises solutions, going public in 2021, and returning as CEO in 2024 to lead the next phase of growth.
Advice Line with Kenneth Cole
Jul 16, 2026Sun Bum: Tom Rinks. The Secrets of a Master Brand Builder (2023)
Jul 13, 2026Advice Line with Jeni Britton of Jeni's Splendid Ice Creams (2025)
Jul 9, 2026Catalina Crunch: Krishna Kaliannan. From Homemade Keto Cocoa Puffs to Breakfast Aisle Breakthrough
Jul 6, 2026Advice Line with Ronnen Harary of Spin Master/PAW Patrol
Jul 2, 2026
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