Episodes

Jim McKelvey, co-founder of Square, lost a $2,000 sale when a customer wanted to pay with American Express but his studio only took Visa and MasterCard. That moment, holding his iPhone and realizing it couldn't read a credit card, sparked a question. Years later, that question became a $10 billion company. McKelvey shares how Square navigated regulatory mazes, built simple hardware, and turned a lost sale into a payments empire by inventing an entire stack, not just a product.

Guy Raz hosts an Advice Line special with Chomps co-founders Pete Maldonado and Rashid Ali, who offer real-time guidance to three founders facing growth dilemmas. Yadi Derisse contemplates expansion beyond her successful campus empanada shop. Zachary Bonder wrestles with e-commerce logistics for his frozen pies. Josh Shrenko seeks direction for his niche Smallmouth Bass apparel brand. The Chomps founders draw on their 13-year journey to advise on scaling thoughtfully, avoiding premature complexity, and staying close to core customers.

John Osher turned a $20,000 garage prototype into Spinbrush, the $5 electric toothbrush that became America's best-seller and generated a $475 million exit. Guy Raz sits down with Osher to explore how in-store demos, relentless iteration, and a landmark deal with Procter & Gamble built a consumer empire—and why the success came with deep personal regret about what was lost along the way.

Julia Hartz, co-founder of Eventbrite, returns to The Advice Line to help three founders navigate critical business challenges. From balancing dual revenue streams to building print magazine audiences in a digital world, Hartz shares her hard-won wisdom on creating sustainable flywheels and community-driven growth. Her insights bridge the gap between startup idealism and operational reality.

Reed Hastings co-founded Netflix in 1997 and led it from a DVD-by-mail service into the world's leading streaming platform, pioneering original content with House of Cards and expanding to over 190 countries. His counterintuitive management philosophy replaced the corporate family metaphor with a championship sports team mindset, favoring radical candor, high talent density, and generous severance for adequate performers. Hastings stepped down as CEO in 2023, passing the reins to Ted Sarandos and Greg Peters, and now chairs the board while pursuing a new challenge: running a Utah ski resort.

Guy Raz hosts an advice line featuring Betterment founder Jon Stein, who helps three entrepreneurs navigate scaling challenges. Dan Criss of Heretic Yerba seeks focus among multiple growth paths, Mike Smith of MTS Woodworking debates taking on debt to expand his basement workshop, and Maggie MacDonald of Floofball weighs channel priorities for her soccer-themed dog toy line. Stein draws on his fintech experience to offer practical guidance on sequencing growth, pricing power, and strategic channel selection.

Two French sports executives left comfortable corporate jobs to create a running shoe that looked like a "clown shoe"—with an absurdly thick midsole. Runners mocked it until they tried it. The Hoka's plush cushioning reduced fatigue and made downhill running feel effortless. Despite 98% of retailers rejecting the design, word spread through ultrarunners. A partnership with Deckers Brands accelerated growth, transforming a $3 million startup into a $2 billion giant by making "maximalist" running mainstream.

Mark Cuban cuts through startup noise with unfiltered advice for five founders facing real growth barriers. Dan Janssen's Imperium Shaving needs to scale beyond niche without raising capital. Kristin Ruud's Northern Classics struggles to stand out in a crowded heritage market. Lucy Dana's One Trick Pony hit a content ceiling. Macy Schmitt's Girlyish Skincare faces fierce competition. Cuban delivers tactical, no-BS guidance on positioning, distribution, and brand storytelling. This episode delivers a masterclass in honest feedback—exactly what early-stage founders need to hear.

Kurt Listug and Bob Taylor built Taylor Guitars from a $3,700 shop into a global brand. Their success came from innovative guitar design, controlling the entire production process, and focusing on sound quality. They pushed the industry forward by adopting CNC technology early and leading the way in sustainable tonewood sourcing. The result: instruments that changed expectations for acoustic guitars.

Guy Raz hosts Monica Nassif on the Advice Line to tackle real founder challenges. Allison Ombres needs help scaling her wig brand Encelia Hair beyond organic growth. Nick Harmon wants to focus Randomals after viral success stretched the team thin. Ben Rothenhafer asks whether he's ready to expand his chandelier cleaning business. Monica shares hard-won lessons about discipline, supply chains, and building brands that last.

Gymboree founder Joan Barnes reveals how building a children's retail empire came at a devastating personal cost. She shares the moment she recognized that her success was destroying her marriage and mental health, and the courageous decision to leave the company she built. This episode uncovers entrepreneurship's hidden toll and confronts the question: when does building something become the very thing that breaks you?

Warby Parker co-founder Neil Blumenthal joins host Brian DeMint for a no-holds-barred advice session. Three founders, Kimber Crandall of Pearl Pop, Neil Blumenthal himself, and Tanner McCraney of Cowboy Country Club, bring their toughest business challenges. From scaling production to brand positioning, Blumenthal cuts through the noise with hard-won lessons from building a billion-dollar brand. This is founder-to-founder advice at its most real.