Episodes

Ben Chestnut built a $12 billion company by accident and never took a dime of outside investment. What started as a lowly email tool at a struggling web design agency became the platform millions of small business owners now depend on every day. His story is proof that serving an overlooked market, staying profitable from day one, and refusing to chase investor demands can beat every conventional playbook in Silicon Valley.

Franchesca Thompson hosts an advice-line episode where three entrepreneurs bring real business challenges to Jamie Siminoff for candid, no-BS feedback. Iyin Akinlabi-Oladimeji of Luji's Chocolate shares his scaling struggles, Jamie Siminoff discusses Ring's hardware adoption journey, and Victor Hugo Hernandez of ErgoFlex Desk walks through furniture logistics. Each caller gets direct, actionable advice on branding, product-market fit, and operational discipline that applies far beyond their specific industry.

Amy Errett launched Madison Reed at 56 after a career in banking, consulting, and venture capital—a late entry into the beauty industry most founders would never attempt. The idea came from her wife's frustration finding a decent at-home hair color, and Amy ran with it. She built a prestige formula from an Italian manufacturer, raised $4M in Series A before the 2014 launch, and moved fast through a subscription model and a bold Groupon strategy.

Guy Raz sits down with Daniel Humm, chef and owner of Eleven Madison Park, for an exclusive update on his landmark 2021 decision to make the world-famous restaurant 100% plant-based. Four years after that announcement upended fine dining, earning EMP its three Michelin stars as the first purely plant-based restaurant to achieve that distinction, Humm reveals why he is now reintroducing fish, shellfish, and his iconic honey-glazed duck. He explains the creative, cultural, and economic forces behind the shift, and why the restaurant remains fundamentally plant-based at heart.

Jason McGowan and Sawyer Hemsley built Crumbl from a single Logan, Utah storefront into a 1,000-location cookie empire using A/B testing, a tech-driven delivery app, and an early bet on TikTok. The cousins share how they optimized the recipe through blind taste tests, turned pink boxes into a brand signature, and grew faster than most franchise models in history.

Guy Raz brings Mei Xu back to the Advice Line, this time to take calls rather than pitch. The Chesapeake Bay Candle founder and former diplomat answers questions from three founders who have already built real businesses but hit walls at the next level. Sasha Millstein needs an operator for her frozen pot pie company, Tara Parkinson is weighing D2C against wholesale for her towel-dress brand, and Lindsay Gallas wants to crack school district sales with her math curriculum platform.

Simon Cowell turned a mailroom job and a series of near-failures into a blueprint for modern music and television empires. After dropping out of school and surviving a bankrupt label, he built Syco Entertainment by trusting his instinct for what mass audiences actually want—not what critics say they should want. His leap into reality TV wasn't planned, but it allowed him to scale that instinct across American Idol, The X Factor, and a global talent roster that includes Kelly Clarkson and One Direction.

Isaac Larian of MGA Entertainment hosts a special Advice Line episode, taking calls from three founders navigating growth challenges. Libby Mochan of Fulton discusses scaling sustainable arch-support insoles amid macro uncertainty. Megan Foster of T is for Taught shares how a play-based learning subscription can break through with grandparent marketing. Robin Hall of Town Hall Outdoor Co asks how to take calculated risks and whether a name change could help his kids' outdoor apparel brand stand out.

Mike Rypka went from a troubled teenager immersed in drug use to building Torchy's Tacos, a fast-casual empire with more than 130 locations and over $300 million in annual sales. Starting with nothing but a beat-up barbecue trailer turned food truck in Austin in 2006, Rypka created a cult brand built on bold tacos, a rebellious devil mascot, and an insistence on "Damn Good" food. Decades of sobriety and relentless hustle turned one man's second chance into one of America's fastest-growing restaurant chains.

Music manager Troy Carter joins Guy Raz on the Advice Line to help three early-stage founders work through real business problems. Madelyn in Arizona is growing a postpartum meal delivery service without losing her local community focus. Tyler in Oregon wants stronger influencer partnerships for his water purification brand. Gina in Minnesota is figuring out how to market a clothing line that matches dogs with their owners. Troy, who built Atom Factory and guided the careers of Lady Gaga and John Legend, shares hard-won lessons on audience building, authentic partnerships, and standing out in a crowded market.

Will Ahmed turned a Harvard squash player's frustration into WHOOP, the wearable that transformed how athletes and everyday users understand recovery, sleep, and physical strain. He launched the company in 2012, fought through investor doubt and near-bankruptcy, and built a device that now serves elite sports teams and fitness enthusiasts around the world.

In this episode, Justin McLeod shares the personal and professional journey behind building Hinge - the dating app designed to be deleted. From a breakup in college to a Harvard Business School class project, McLeod reveals how his own frustrating experience with online dating inspired him to create a platform built for meaningful connections. He opens up about the challenges of building a dating app in a crowded market, the philosophy behind Hinge's 'designed to be deleted' mantra, and the pivotal moments that turned a small startup into a global phenomenon generating over $400 million in annual revenue. McLeod also discusses the surprising decision to step down as CEO in December 2025 to launch Overtone, an AI-powered dating startup backed by Match Group, and what he believes the future of dating technology holds.