Episodes

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.

Chobani founder Hamdi Ulukaya explains how he built the world’s largest yogurt brand by prioritizing people, product, and purpose above everything else. From a single plant in upstate New York to a billion-dollar business, he shares the operational and cultural choices that turned a small startup into a category leader loved by consumers worldwide.

In this Advice Line episode, Norma Kamali advises three small-business owners on growth, storytelling, and operational resilience. Callers include Adreana Alvarez of Love Her Shop, Ahmed Ejaz of Cambridge Spectacle Co., and Robert Wolkoff of Sunny Bowls. The conversation shows how authenticity, local identity, and customer connection can be stronger growth tools than generic marketing.

Long before travel influencers and smartphone GPS, Rick Steves built a $100 million travel empire by giving away his core travel content for free. He shares how he skipped formal corporate planning, letting his Rick Steves Europe team grow organically as needs arose, and turned his early experience backpacking Europe on bread and jam into trusted, no-frills travel advice that became best-selling guides and 30,000 annual pre-pandemic tour bookings. It’s a masterclass in authentic, audience-first entrepreneurship that defies conventional business wisdom.

Jim Koch of Boston Beer Company teams up with How I Built This alumni Kim Jones, Lance Kesner, and Amy Dana to field caller questions. A Toronto electrician, Bellevue broth maker, and Ponte Vedra rum founder each pitch their biggest challenges — from pricing small trades to launching real innovations.

After falling in love with Buenos Aires' legendary gelato shops, Josh Hochschuler returned to Dallas with a bold plan: bring authentic Argentine gelato to America. He raised $600,000, opened Talenti in 2003, and watched the product catch fire — even as the retail model collapsed. A pivot to wholesale, a $1 million investment in 2007, and a $500,000 radio gamble on Publix in 2009 turned the brand into a national powerhouse. Unilever acquired Talenti in 2014, and today it's the best-selling gelato brand in the United States.

Eric Ryan, co-founder of Method and serial entrepreneur behind brands including Welly and Tandy, joins Guy Raz on the Advice Line to help three early-stage founders navigate real business challenges. Aubrey in Franklin, Tennessee seeks mentorship to scale her growing bakery and restaurant group. Maggie from Chicago weighs whether raising outside capital is the right move for her innovative luggage brand, Props Luggage. And Matt in Scottsdale, Arizona looks for a path to get his convertible glove company, FlipMitts, onto retail shelves. Eric shares lessons drawn from decades of building and scaling consumer brands.

How do you turn a side hustle into a retail empire that popularized the untucked shirt? Chris Riccobono, co-founder of UNTUCKit, started the company while working at GE Healthcare, launching with a $150,000 investment and a lot of skepticism. From near-bankruptcy after a $750M acquisition fell through in 2020, UNTUCKit rebounded to more than 80 stores and a growing wholesale business. In this episode, Riccobono explains why an idea everyone laughed at became a category-defining brand — and what it took to survive when success almost slipped away.

Marcia Kilgore joins the Advice Line to guide three early-stage founders through growth challenges. Victor in Fort Worth weighs brick-and-mortar expansion against retail distribution for his Mexican sweets brand. Lydia in Seattle seeks to scale her small-batch botanical skincare line while overcoming fear of failure. Jack in San Francisco wants to maintain customer excitement throughout his custom bike bag brand's purchasing process. Kilgore draws on her experience building Beauty Pie, Bliss, and Soap & Glory to offer candid advice on scaling, risk, and staying true to your brand.