How I Built This with Guy Raz

This episode is available on Youtube: https://youtu.be/ZYf-DfxJg1c Brian Chesky was 26 when he and his co-founders launched Airbnb, turning a few air mattresses in a San Francisco apartment into one of the most successful startups of all time. But as Airbnb grew into a company worth more than $100 billion, Brian struggled to keep up. He hired experienced executives, trusted them to make decisions, and watched the company become increasingly chaotic. Looking back, he says Airbnb succeeded in spite of his leadership, not because of it. Then COVID hit, and Airbnb lost 80% of its business in a matter of weeks. Facing the possibility of losing everything he'd built, Brian completely reinvented the way he ran the company—and soon after, much of his life outside work, too. In this episode, Brian explains why some of the most common leadership advice can be disastrous for startups, what he learned from Steve Jobs and Barack Obama, and why the day after Airbnb’s IPO was one of the loneliest of his life. Plus, how…

Today’s callers: Dominic in London faces challenges with profitability and scaling for his foldable bike helmet. Then, Ivana in Vancouver wonders how to maintain the momentum of her pet gear brand as she prepares for the arrival of her first child. Danny in South Carolina wants to expand her nail salon concept without making major trade-offs in her family life. And Justin in Boston grapples with prioritizing the many channels in which he sells his customized footwear. Plus, Tope discusses Calendly’s new AI-powered scheduling assistant and how advances in technology are making it easier than ever to get new software applications off the ground. Thank you to the founders of Newlane, Playfield, the Nail Room, and ISlide for being a part of our show. Be sure to listen to Calendly's founding story as told by Tope on the show in 2020. Some news: This is the final episode of the Advice Line. Thanks to all of the callers and returning guests who were a part of its run, and to all of you who tuned in — you make How I…

Heather Hasson and Trina Spear saw an opportunity nobody else seemed to notice: millions of healthcare workers were spending long days in uncomfortable, ill-fitting scrubs. So they set out to reinvent them. Heather was a designer with almost no money. To join her, Trina left a prestigious job at Blackstone and cashed out her retirement. They sold scrubs out of a car, got rejected by hundreds of investors, and eventually built FIGS into a multibillion-dollar public company. Along the way, they paid $40 million to fight a lawsuit, navigated a pandemic, and watched their company’s valuation swing by billions. This week, Heather and Trina share how they built the “Lululemon of Scrubs”—and why your net worth is not the same thing as self worth. What you’ll learn How a trip to Kenya changed Heather’s view of uniforms–and led her to start her own scarf and tie business How Heather spotted an opportunity in a stale category: healthcare workers want comfortable clothes, too How free coffee became a tool for customer…

Today’s callers: Kahindo from New York is looking to reboot her African-rooted fashion brand after losing a few key retailers. Then Tara from San Diego considers avenues to educate consumers about the benefits of her wool sauna hats. And Carol from Houston wonders whether to market her collegiate purses and accessories l to students or their gift-giving family members. Plus, Seth lays out his ambitions to quadruple Insomnia’s locations and become a global chain — without turning to franchising. Thank you to the founders of Kahindo, Sauna Societé, and Desden for being a part of our show. Be sure to listen to Insomnia Cookies’ founding story as told by Seth on the show in 2024. This episode was produced by Casey Herman with music by Ramtin Arablouei. It was edited by John Isabella. Our audio engineer was Annlie Huang. You can follow HIBT on X & Instagram and sign up for Guy's free newsletter at guyraz.com and on Substack. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Loren Castle started baking cookies after surviving cancer in her early twenties. Five years later, Sweet Loren’s refrigerated cookie dough was generating just $350,000 a year. But instead of giving up, she listened to customers, and reinvented the dough without gluten, dairy, eggs or nuts. That transformation turned a small regional business into a national brand sold in more than 30,000 stores. WHAT YOU'LL LEARN How surviving cancer at 22 inspired Loren to rethink her career and develop a passion for healthier food. What working at New York’s Levain Bakery taught her about the enormous appeal—and profitability—of cookies. Why Loren decided to sell ready-made cookie dough instead of cookies Why she was totally unprepared for her first Whole Foods meeting—but went anyway Why raising her first $1 million from friends and family was much harder than she expected. Why hundreds of customer requests revealed an unmet need for allergen-free cookie dough. Why growing slowly may have saved the company. Why Loren…

Today’s callers: Lindzi from Chicago wants to expand her gourmet marshmallow brand into retail without cannibalizing her high-margin DTC sales. Then, Vivi from Hawaii considers how to best tell her sustainable swimwear brand’s story to a digital audience. And Aly from Los Angeles wonders whether a subscription model is best for her whimsical curated experiences. Plus, Tara talks about her latest entrepreneurial venture, Snackish, and how starting a new company feels different the second time around... Thank you to the founders of XO Marshmallows, Vivi’s Vacation, and Romanticize Collective for being a part of our show. Be sure to listen to SmartSweets’ founding story as told by Tara on the show in 2024. This episode was produced by Chris Maccini with music by Ramtin Arablouei. It was edited by John Isabella. Our audio engineer was Annlie Huang. You can follow HIBT on X & Instagram and sign up for Guy's free newsletter at guyraz.com and on Substack. Learn more about your ad choices. Visit…

In the early 1990’s, Tim League spent $50,000 in savings to lease an abandoned movie theater on the wrong side of the tracks—a shaky experiment that eventually grew into a thriving national chain. As Tim and his wife Karrie built theaters in Austin and beyond, they made a name for themselves by offering dinner with the movie, creative pairings (like sake with Godzilla), and roadshows where movie-goers could watch Deliverance in canoes, or Rocky on the famous steps in Philly. Alamo Drafthouse Cinema now has dozens of locations across the country, but there have been plenty of bruises along the way: a failed first theater, a fractious lawsuit with business partners, and a swan dive into the red during the pandemic. This episode was produced by Carla Esteves, with music by Ramtin Arablouei. Edited by Neva Grant, with research help from Carla Esteves. Follow How I Built This: Instagram → @howibuiltthis X → @HowIBuiltThis Facebook → How I Built This Follow Guy Raz: Instagram → @guy.raz Youtube → guy_raz X →…

Today’s callers: Mercedes in Utah tries to find harmony between quality and speed as she scales her concert attire brand for musicians. Then Danny in Colorado grapples with the tradeoffs of growing his sustainable and functional coffee brand. And Riya in Illinois wonders how to build awareness for her app that aids people affected by speech loss. Plus, Nick’s insights on how AI is changing the way we fill our grocery carts — and how grocers respond to food and nutrition trends. Thank you to the founders of Blackstrad Concert Attire, Peak State Coffee, and Voice Back for being a part of our show. And be sure to listen to Thrive Market’s founding story as told by Nick in 2024. This episode was produced by Sam Paulson with music by Ramtin Arablouei. It was edited by John Isabella. Our audio engineer was Annlie Huang. You can follow HIBT on X & Instagram and sign up for Guy’s free newsletter at guyraz.com or on Substack. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Stories about starting a business are almost always full of drama. They’re about ambition, loss, triumph, catastrophe, resilience. And they’re also full of life lessons – which is why Guy Raz launched How I Built This 10 years ago: He wanted to host a free master class in entrepreneurship, one conversation at a time. Ten years on, he’s conducted over 600 interviews with some of the world’s most successful founders, and on today’s show, he replays some of the most memorable moments and lessons. Joining him is Jamie Siminoff, the founder of RING and a former guest on the show. Why Jamie? He’s a friend, a fan, and – as you may remember from his first interview - he doesn’t hide his emotions. Timestamps: 5:10 A lightbulb switches on at an NYC bodega: “Oh my God, look at all those cherries!” 9:33 The moment Stitch Fix founder Katrina Lake realized she should start her own business. 12:04 The difference between scary and dangerous, and why it matters for founders 19:35 Eileen Fisher’s first, terrifying trade show:…

CEO and co-founder of Boll & Branch, Scott Tannen joins Ring founder Jamie Siminoff and Guy on the Advice Line to answer questions from three early-stage entrepreneurs. Plus, Jamie and Guy talk about how creating repeat customers often comes from creating social good. First, we hear from Melita in Toronto who's wondering whether to continue bootstrapping her organic clothing business. Then Eric in the Sunshine State asks which direction to take to grow his sunscreen apparel lines. And Chris in Alpine Meadows, California, is trying to figure out how to get his sleek binoculars into the hands of more people. Thank you to the founders of Q for Quinn, L Cubed Lifestyle, and Nocs Provisions. If you’d like to be featured on a future Advice Line episode, leave us a one-minute message that tells us about your business and a specific question you’d like answered. Send a voice memo to hibt@id.wondery.com or call 1-800-433-1298. And be sure to listen to the story of how Jamie founded Ring from our episode back in 2020,…

With its eco-friendly paper towels, diapers, and cleansers, Seventh Generation was one of the first—and most successful—green household brands to hit the market. But in the early 1990s, its two founders had a bitter falling out. Alan Newman and Jeffrey Hollender have barely spoken since that time, but they both agreed to come on the show to talk about the business they were both passionate about, and the delicate nature of partnership. What you'll learn: Why Alan says his great strength—and his greatness weakness—is his tendency to say “yes.” How Jeffrey and Alan lost their friendship and business partnership after only three years. How Jeffrey grew Seventh Generation into a household name—and then got fired. How two formerly estranged partners feel about partnership now. Timestamps: 5:30 - Jeffrey makes it big in Canada selling adult-learning courses… before he’s forced to leave the country 11:50 - Alan moves to Vermont on a whim, and winds up in a mail-order catalog business 24:31 - Alan and Jeffrey meet…

Today’s callers: Janell from Kentucky wonders how to build a sense of hospitality into her canned bourbon cocktail brand. Jade from South Carolina considers the upsides and risks of shipping her smoked salmon directly to customers. And Bar from Colorado considers strategies for bringing his protein-packed cous cous to quick service restaurants. Plus Danny talks about the elements of a strong company culture as described in his new book, What Could Possibly Go Right? Thank you to the founders of Ponyboy Slings, Angel Oak Smokehouse, and Boostcous for being a part of our show. If you’d like to be featured on a future Advice Line episode—where Guy and former show guests take questions from early-stage founders—leave us a one-minute message that tells us about your business and a specific question you’d like answered. Send a voice memo to hibt@id.wondery.com or call 1-800-433-1298. And be sure to listen to Shake Shack’s founding story as told by Danny on the show in 2020. This episode was produced by Chris…

Brian Rudolph started making chickpea pasta in his Detroit apartment because wheat made him feel sick. A decade later, Banza was in more than 25,000 stores, and today, it’s one of the most popular pasta brands in the country. Success was not automatic: The business barely got off the ground because the cooked pasta was turning to mush—and as Banza became known for its health benefits, a food-safety scare sent sales plunging by 30%. In this episode, Brian explains why he was inspired to create a whole new category, how he turned chickpea skeptics into fans, and how the company rebuilt trust after a public relations disaster. What you’ll learn How Brian and his brother Scott launched Banza with only $100,000. How they learned to stop chasing perfection and to ship something that was “good enough.” How crowdfunding and reality TV helped Banza land its first retail accounts. How packaging can become an important growth engine for a new brand. How transparency can rebuild trust after a PR debacle–but can’t…

Today's callers: Carrie from Paris wants to turn interest into bookings for her boutique study-abroad programs for adults. Then, Grace from Nashville considers how to re-build relationships with interior designers she may have let down early on in her furniture upholstery business. And Angel from Indiana explores how to translate the emotional appeal of her self-care soap kits into stronger online sales. Plus, Michelle explains why founders don't always need to raise outside capital, and why they shouldn’t go into business with an exit plan. Thank you to the founders of Elective Study Abroad, Grace Ann Upholstery, and Sacred Pause Soap Company for being part of our show. If you’d like to be featured on a future Advice Line episode—where Guy and former show guests take questions from early-stage founders—leave us a one-minute message that tells us about your business and a specific question you’d like answered. Send a voice memo to hibt@id.wondery.com or call 1-800-433-1298. And be sure to listen to Beyond…

Karissa Bodnar had a dream job at L'Oréal when a close friend died from cancer at age 24. It shook her up and made her reassess what she really wanted to do with her life. The answer? Build her own beauty business with a mission of “giving back.” The problem? Nobody seemed to want to carry her products. She pitched Sephora, Nordstrom, Ulta, and others—and kept hearing no. She stuck it out, pouring tens of thousands of dollars of her own savings into it, and worked a full-time job to fund the formulation of new cosmetics. Two years in, another life-changing event. Karissa posted a video of herself teaching make-up application to domestic violence survivors, and it went viral. In this episode Karissa explains why mission alone will never save a bad product, how scarcity helped her build a better company, why she resisted raising too much money, and how she turned a deeply personal loss into one of the most distinctive brands in beauty. What You’ll Learn: How Karissa's childhood experimenting with fruits and…

Today’s callers: Juliette in France wonders how to raise awareness of her “magical” cooling device—without a costly ad campaign. Then David in North Carolina looks to grow the wholesale channel of his engraved gifts business in light of thinning retail margins. And Kaitlin in California wants to leverage the virality of her supportive, bordered sheets and create an enduring sleep brand. Plus, Kip reflects on The Container Store’s bankruptcy and acquisition, and plugs patience and persistence as the keys to sustainable growth. Thank you to the folks at CoolaWand, Hazel Grove Customs, and Kaomi Sleep for being a part of our show. If you’d like to be featured on a future Advice Line episode—where Guy and former show guests take questions from early-stage founders—leave us a one-minute message that tells us about your business and a specific question you’d like answered. Send a voice memo to hibt@id.wondery.com or call 1-800-433-1298. And be sure to listen to The Container Store’s founding story as told by Kip…

Kim’s inspiration to launch a business came from an unlikely source: Her son’s Crocs. She thought the durable, washable material would make a great beach bag. So she designed one. But after investing her savings—inlcuding some of her kids’ college fund—Kim was crushed when her first major shipment of Bogg bags was defective. It knocked her so off balance, that she put the entire business on hold. Then something unexpected happened.The few thousand customers who already had a bag….clamored for more. So Kim decided to start over. She borrowed $120,000, found another factory, shared trade show booths with four other founders, and slowly built Bogg Bag into a $100 million phenomenon. What you'll learn: How getting nowhere with Crocs gave Kim the motivation to make Bogg Bag herself. Why her first $30,000 production run nearly killed the company. Why a founder isn’t always the best judge of her product How Superstorm Sandy gave new life to Bogg Bag How Kim built Bogg Bag for years while keeping her full-time job…

Today’s callers: Darin from North Carolina seeks guidance on consumer education as his ghee-based snack brand grows into major retailers. Then Sarah from Massachusetts explores scaling pathways for her ‘never-frozen’ gluten-free baked goods. And John from Ohio considers whether online sales can turn around his local food co-op. Plus, Ben comments on the drivers of Olipop’s nearly $2 billion valuation, and critiques a common piece of business advice that often holds founders back. Thank you to the founders of Gheelish, Sarah’s Gluten Free Goods, and Bexley’s Natural Foods for being a part of our show. If you’d like to be featured on a future Advice Line episode—where Guy and former show guests take questions from early-stage founders—leave us a one-minute message that tells us about your business and a specific question you’d like answered. Send a voice memo to hibt@id.wondery.com or call 1-800-433-1298. And be sure to listen to Olipop’s founding story as told by Ben in 2024. This episode was produced by…

Nicole Bernard Dawes spent much of her childhood hanging out in her dad’s potato chip factory on Cape Cod. She liked his kettle-cooked chips a lot more than the flavorless snacks in her mom’s health food store. But when she started her own business, she wanted the best of both worlds: a snack made with natural, organic ingredients…that still tasted good. Nicole launched Late July Snacks in 2003, when most consumers barely knew what “organic” meant. For years, sales limped along. Then, in a moment of crisis, she made a company-saving pivot by launching a brand new product – organic tortilla chips. Within just a few years, Late July grew to over $100M in sales, and Nicole decided to launch a new brand in an even more challenging category: soda. You Will Learn: How growing up in a family business can help–and hurt–when you launch your own The pros and cons of financial vs. strategic investors When to cut a product that isn’t working Why the fine print in a contract is so important How the hardest decision might…

Today’s callers: Cristopher from Chicago wants to expand his family’s salsa brand from farmers markets into retail. Next, Darcy in Australia considers adapting his protein bar brand’s messaging to reach beyond his core enthusiasts. Finally, Seema in Canada seeks strategies to increase B2B sales for her ethical kitchen linen company. Plus, Daymond and Guy talk about what makes a great Shark Tank pitch, and why Guy decided to start How I Built This 10 years ago. Thank you to the founders of Sabor a Mexico, Raised Nutrition and Cooks Who Feed for joining us on the show. If you’d like to be featured on a future Advice Line episode—where Guy and former show guests take questions from early-stage founders—leave us a one-minute message that tells us about your business and a specific question you’d like answered. Send a voice memo to hibt@id.wondery.com or call 1-800-433-1298. And be sure to listen to FUBU’s founding story as told by Daymond on the show in 2018. This episode was produced by Katherine Sypher with…

Roy and Ryan were avid outdoorsmen who wanted a cooler that wouldn’t break. So they built one themselves. The result was YETI: a high-end cooler that early retailers thought nobody would buy. But serious outdoorsmen did—and eventually YETI escaped its niche, becoming a status symbol at tailgates, beaches, and soccer fields. In this episode, Roy and Ryan explain how they bootstrapped YETI, survived the sudden loss of their only manufacturing partner, and later stumbled onto the $30 product that supercharged the business. WHAT YOU'LL LEARN Why solving a problem you personally experience can be more powerful than chasing a huge market. How YETI convinced people accustomed to $40 coolers to spend $300–$400. Why the brothers deliberately started with small independent retailers instead of chasing major chains. Why Roy and Ryan chose not to aggressively fight copycats How the sudden loss of their only manufacturer nearly destroyed YETI—but ultimately made the company stronger. How the brothers bootstrapped YETI…

Today’s callers: Shawn from Saskatchewan weighs whether brand-building or licensing is best for his card-based party game. Then Shirin in Texas wants to differentiate her graphic stationery in a crowded Etsy marketplace. And Mark from New Jersey works through refocusing his line of craft spirits. Plus, Carlton’s recent efforts to pass on his trendspottting talent to the next generation. Thank you to the founders of Youlogy, Honey Bespoke Stationery & Paper Goods, and Little Water Distillery for being a part of our show. If you’d like to be featured on a future Advice Line episode—where Guy and former show guests take questions from early-stage founders—leave us a one-minute message that tells us about your business and a specific question you’d like answered. Send a voice memo to hibt@id.wondery.com or call 1-800-433-1298. And be sure to listen to the Razor founding story as told by Carlton Calvin in 2025. This episode was produced by Casey Herman with music by Ramtin Arablouei. It was edited by John…

Laura Modi set out to build a better infant formula. What followed was years of setbacks: a crippling dispute with the FDA, a frustrating search for a manufacturer, and the constant fear that the company would run out of money before it reached customers. But today, Bobbie generates over $100 million a year and has captured nearly 4% of the U.S. infant formula market by challenging one of the most protected industries in America. In this conversation, Laura explains how she made it through—and why many of the moments that looked like disasters ultimately built a better company, and made her a better entrepreneur. You'll learn: Why Laura left a great job to launch one of the most heavily regulated products in America How she spent nearly $200,000 of her own savings before raising outside capital How 64 investor pitches helped her tell a better story How a public apology changed the trajectory of the company Why Bobbie turned away thousands of customers during its fastest period of growth Why Laura moved to…

Today's callers: Bob in Chicago looks to promote his cabbage-based muscle and joint rub beyond the walls of his orthopedic practice. Then Abby in Dallas wonders whether her popular social media livestreams are a sustainable way to market her trendy phone cases. And Henry in Charlotte wants to turn his mouth rinse for coffee drinkers into a mainstream oral care brand. Plus, Bobbi shares what drove her to found her new company—Jones Road—at the age of 62. Thank you to the founders of Cabbage Labs, AbbyRose, and Tannin Oral Care for being a part of our show. If you’d like to be featured on a future Advice Line episode—where Guy and former show guests take questions from early-stage founders—leave us a one-minute message that tells us about your business and a specific question you’d like answered. Send a voice memo to hibt@id.wondery.com or call 1-800-433-1298. And be sure to listen to Bobbi Brown Cosmetics’ founding story as told by Bobbi on the show in 2018. This episode was produced by Sam Paulson with music…

What do you do when the family business you've spent decades building... gets bought out from under you? That’s what happened to Nima and Salma Fotovat. Devastated, the family rebuilt a new company from the ground up. This time they set out with a new idea: build an allergen-free, organic snack brand not just for kids, but their parents. Their new brand: MadeGood. Today, the Canadian brand’s parent company does hundreds of millions of dollars in sales. But getting there meant rebuilding from scratch, fixing 200,000 mislabeled snack bars by hand, and turning a family of co-packers into branding experts. What you'll learn: How owning manufacturing can be a competitive edge How they grew a national brand with almost no marketing. Why it can be a winning strategy to say "yes" before you know how Introducing new products: the tension between research and emotion The mindset that can help you rebuild after a devastating setback Timestamps: 3:40 - Growing up in Iran during wartime, and emigrating to Canada 09:30 -…

Today’s callers: Tony in Michigan is considering bringing on partners to run different parts of his brew pub and theater business. Then Monica in London is exploring the best way to reach style-conscious parents with her line of children’s clothes. And Sandy in Colorado is seeking the ideal pricing strategy to bring his adaptive test prep platform to schools nationwide. Thank you to the founders of Hearsay Brewing and Theater, Tres London and Brain Buffs for being a part of our show. If you’d like to be featured on a future Advice Line episode—where Guy and former show guests take questions from early-stage founders—leave us a one-minute message that tells us about your business and a specific question you’d like answered. Send a voice memo to hibt@id.wondery.com or call 1-800-433-1298. And be sure to listen to our Advice Line episodes with Jeffrey Hollender of Seventh Generation, Sarah LaFleur of M.M LaFleur and Shazi Visram of Happy Family Organics. This episode was produced by Kerry Thompson with music by…

Many founders think the hardest thing about business is finding customers. It's not. It's surviving success. When Lily Kanter and Serena Dugan launched a luxury baby linen business, they had no manufacturing experience, no inventory, and barely any capital. But after their first catalog landed just as a major competitor left the market, orders flooded in almost overnight. The problem? They hadn’t made the products yet. Today, Serena and Lily has grown into one of the best known luxury home goods brands in the country. But getting there was a grind. This is one of the most revealing conversations we've ever had about unplanned opportunities, and the hidden cost of taking outside investment. From financing their first inventory with customer deposits... to walking away from a disastrous investment deal... to nearly losing control of the company they built, this episode is a masterclass in what happens when rapid growth collides with the realities of cash flow. You Will Learn: The clever way Serena & Lily…

Today’s callers: Adrian from California wants to grow his apparel company to complete with big-name athletic brands. Then, Preet from the Rockies looks for strategies to reach seniors and their children with his daily check-in app. And Derek from Virginia considers social media and professional partnerships to advertise his hockey equipment brand. Plus, Chris talks about launching a new athletic apparel brand while continuing to grow UNTUCKit. Thank you to the founders of Eras Shorts, Snug Safety, and Hockey Ninja for being a part of our show. If you’d like to be featured on a future Advice Line episode—where Guy and former show guests take questions from early-stage founders—leave us a one-minute message that tells us about your business and a specific question you’d like answered. Send a voice memo to hibt@id.wondery.com or call 1-800-433-1298. And be sure to listen to UNTUCKit’s founding story as told by Steve on the show in 2017. This episode was produced by Chris Maccini with music by Ramtin Arablouei.…

Chuck Surack never planned to build one of America's largest online retailers. He just wanted to be a musician. So right after high school, he took his sax and drove off in his old VW van to play gigs around the country. It didn’t work out. But with the audio and mixing skills Chuck learned gigging, he decided to convert his van into a mobile recording studio - and started making money fast by making recordings of local bands, businesses, and schools. The game-changer came as a one-two-three punch: first, he created a new product - digitized sound libraries - to sell nationally; second, he started selling high end pro audio gear; third, he instituted a sales culture hyper-focused on customers and relationship-building that resulted in Sweetwater’s enormous and super loyal online customer base. In this episode, Chuck shares how he built a retail giant from his garage, why customer service became his greatest competitive advantage, and why, even in the age of AI, human relationships remain one of the most…

Today’s callers: Andy from Sarasota weighs whether the path to scalability for his live game show business is through personality or product. Then, Marissa from Tampa wants to recapture sales for her fairy tale-inspired teas after taking a hiatus to focus on her family. And Vince from New Jersey wonders how to allocate marketing dollars for his sustainable baby gear company.. Plus, Curt reflects on the importance of focus in sustaining OtterBox as a leading tech accessories brand over 30 years. Thank you to the founders of Mr GameShow, Gilded Coach Teas, and Evrloop for being a part of our show. If you’d like to be featured on a future Advice Line episode—where Guy and former show guests take questions from early-stage founders—leave us a one-minute message that tells us about your business and a specific question you’d like answered. Send a voice memo to hibt@id.wondery.com or call 1-800-433-1298. And be sure to listen to OtterBox's founding story as told by Curt on the show in 2019. This episode was…

After waiting too long to pay his restaurant bill, Aman Narang thought there had to be a better way. His first idea—a mobile payment app—flopped. But that failure revealed a much bigger opportunity. Restaurants were struggling with outdated software that many owners hated. Payment systems were expensive, unreliable, and trapped on servers hidden in back offices. Replacing them cost time and money. But that’s exactly what Aman and his co-founders set out to do: create an entirely new POS system for restaurants—from scratch. They worked from an unfinished basement, answered customer calls on their own phones, crashed their first restaurant on day one, survived years of rejection from investors—and eventually grew Toast into a business that generates more than $2 billion in annual revenue. In this episode, Aman shares how a failed product became a billion-dollar company. What you'll learn: How to know when it's time to pivot Why investors rejected Toast again and again How to convince customers to replace…

Today’s callers: Matt from New York City unpacks the stigma working against his line of foot wellness products. Then Emefa in Toronto seeks a direct relationship with customers of her fashion brand in the wake of a key retailer going out of business. Finally, Levi in Rhode Island explores new audiences and product lines for his commemorative golf sculpture business. Plus, Kenneth and Guy discuss how to make social impact a real part of your business model. Thank you to the founders of Pedestrian Project, ISRAELLA KOBLA, and Swing Sculpt for joining us on the show. If you’d like to be featured on a future Advice Line episode—where Guy and former show guests take questions from early-stage founders—leave us a one-minute message that tells us about your business and a specific question you’d like answered. Send a voice memo to hibt@id.wondery.com or call 1-800-433-1298. And be sure to listen to Kenneth Cole’s founding story as told on the show in 2020. This episode was produced by Alex Cheng with music by…

Tom Rinks got his start in the commission-only "shark tank" of midwestern furniture sales. That’s where he learned what makes customers buy. Decades later, those instincts helped him grow a joke of a side hustle into a $400 million success. In 2009, he created the iconic branding for an obscure sun tan lotion, drawing on a mish-mash of surf culture, Scandinavian furniture, and Japanese streetwear. Sun Bum became a huge success, but even before that, Tom helped boost a wildly diverse range of brands: a line of tequila, a series of Christian videos, and the ubiquitous “Yo quiero Taco Bell” campaign. All were successful, though it took a prolonged legal battle for Tom to get paid for the Taco Bell chihuahua. In this episode, Tom reveals how he learned to manipulate consumer psychology, survive the brutal warfare of a stolen idea, and engineer a brand explosion on his own terms. WHAT YOU'LL LEARN Chihuahuas and Apes: How the Right Mascot can Transform a Brand What it takes to survive a five-year legal battle…

Jeni’s Splendid Ice Creams founder Jeni Britton joins Guy on the Advice Line to answer questions from three early-stage entrepreneurs. Plus, how Jeni’s newest venture Floura is tackling one of America’s largest dietary needs—fiber. First, we meet Jesse in Washington, D.C., who’s wondering how to best focus marketing efforts for his frozen french fry company. Then Casey from Boston, who's questioning the pressure she's feeling to pursue outside capital for her frozen pierogi brand. And finally, Callie from Los Angeles asks about the pros and cons of contracting a PR firm to promote her purple sweet potato pet treats. Thank you to the founders of Jesse & Ben’s, Jaju Pierogi and Ubae.co for being a part of our show. If you’d like to be featured on a future Advice Line episode, leave us a one-minute message that tells us about your business and a specific question you’d like answered. Send a voice memo to hibt@id.wondery.com or call 1-800-433-1298. And be sure to listen to Jeni’s Splendid Ice Creams’ founding…

Krishna Kaliannan wanted to start a tech company but failed at every attempt. On the side, he was teaching himself how to cook with high-protein, low-sugar ingredients. Not just out of interest, but out of necessity. As a teenager, Krishna had been diagnosed with diabetes and epilepsy, meaning he adopted a keto diet long before it was trendy. Krishna’s home experiments with pea powder and monk fruit eventually became Catalina Crunch, one of the country’s most popular high-protein, low-carb breakfast cereals and snacks. In this episode, Krishna shares how a life-changing health condition sparked an obsession with healthy baking— and a brand that reimagined snacking. What You’ll Learn How to turn a health challenge into a business opportunity The art and science of baking with esoteric ingredients When to trust partners and when it’s best to take charge yourself Why the DTC model is great for some industries and disastrous for others Timestamps: 00:03:51 - Dealing with diabetes and epilepsy as a college…

Today’s callers: Ann from Nashville asks how to adapt her jewelry business in the face of rising gold prices. Then Felix in Martha’s Vineyard considers strategies for growing his family’s legacy honey and skincare company. Finally, Matt in Massachusetts seeks strategies for maintaining a healthy work-life balance at his grief-inspired brewing project. Plus, Ronnen and Guy discuss why your 20s are the best time to start a business. Thank you to the founders of Yearly Company, Island Bee Company and Wandering Soul Beer for joining us on the show. If you’d like to be featured on a future Advice Line episode—where Guy and former show guests take questions from early-stage founders—leave us a one-minute message that tells us about your business and a specific question you’d like answered. Send a voice memo to hibt@id.wondery.com or call 1-800-433-1298. And be sure to listen to Spin Master and PAW Patrol’s founding story as told by Ronnen on the show in 2021. This episode was produced by Katherine Sypher with…

In 2004, Joey Shamah and his partner launched a cosmetics company built on an idea that made almost no sense: Sell high-quality makeup for just $1. At the time, high quality beauty products were supposed to be expensive. The biggest brands spent fortunes on celebrity endorsements, glossy ads, and premium shelf space. And every major retailer told Joey the same thing: Your idea will never work. But Joey believed he'd found a wormhole in the beauty business: spend money on the product, not fancy packaging, marketing, or celebrity endorsements. Then, pass those savings on to your customers. The brand grew slowly, but Joey knew he was onto something when a bizarre rumor spread that Bloomingdale's was buying e.l.f. and raising prices. Within days, the tiny company went from a few hundred orders a week to 18,000 orders a day. What followed was a journey from a scrappy warehouse operation in New Jersey to one of the most disruptive brands in the beauty business. You'll learn: The surprising economics behind $1…

Today’s callers: Ruchi from Chicago looks for advice on which channels to focus distribution for her probiotic skincare line. Then Peter in San Francisco considers strategies to champion his line of organic South African wines. And Dominic from Barbados asks about expanding his specialty coffee brand into international markets like the United States. Plus, Susan discusses how people and relationships can make or break your business. Thank you to the founders of Yobee, Culture Wine, and Wyndhams Bajan Coffee Roasters for being a part of our show. If you’d like to be featured on a future Advice Line episode—where Guy and former show guests take questions from early-stage founders—leave us a one-minute message that tells us about your business and a specific question you’d like answered. Send a voice memo to hibt@id.wondery.com or call 1-800-433-1298. And be sure to listen to EO Products founding story as told by Susan Griffin-Black and Brad Black in 2019. This episode was produced by Casey Herman with music by…

Stephen Starr didn’t plan to get into the restaurant business. He set out to be a radio DJ. Then a nightclub owner. Then a music promoter. Along the way, he booked a young Jerry Seinfeld for $75, promoted shows for U2 and Madonna, and spent years pretending to be more successful than he really was. Then, in his late 30s, Stephen walked into a glitzy martini bar in New York. He was so taken with it, he decided to start his own version in Philadelphia. Today, Starr Restaurant Group generates nearly half a billion dollars in annual revenue and includes some of the most successful independent restaurants in America: Pastis, Buddakan, Le Diplomate, Parc, Makoto, and dozens more. The surprising part? Stephen did not start out as a foodie. Instead, he became obsessed with the theatre of dining: design, upholstery, lighting, music. A “wow!” feeling when you walk in the door. In this conversation with Guy, Stephen talks about the hard lessons he learned in the comedy and music business, and the unexpected path he…

Today’s callers: Daisy in the United Kingdom looks to grow her barefoot shoe brand across the pond in the United States. Then Rachel in Pennsylvania considers private labeling for her protein-packed sprinkles. And Andrew in California wonders whether he should seek investment for his pleasantly-scented soil additive. Plus, Shazi discusses why entrepreneurship is one of the most creative outlets a person can have. Thank you to the founders of Freet Barefoot, SprinkleBites, and PlantAmika for being a part of our show. If you’d like to be featured on a future Advice Line episode—where Guy and former show guests take questions from early-stage founders—leave us a one-minute message that tells us about your business and a specific question you’d like answered. Send a voice memo to hibt@id.wondery.com or call 1-800-433-1298. And be sure to listen to Happy Family Organics’ founding story as told by Shazi in 2020. This episode was produced by Sam Paulson with music by Ramtin Arablouei. It was edited by John…

When Maxine Clark left a top job in retail to start a make-your-own stuffed animal store, people thought she’d lost her mind. Investors doubted it. Friends questioned it. Retail experts couldn't understand how it would scale. But drawing on more than 20 years as a retail executive, Maxine built a massively successful shopping “experience,” where kids could stuff, dress and personalize their own stuffed animals. Today, Build-A-Bear has generated billions in sales, survived the decline of malls, weathered the financial crisis, and become a global brand. WHAT YOU'LL LEARN How a failed errand—and an offhand comment by a kid–inspired a business plan How Maxine leveraged two decades of retail experience to launch Build-a-Bear How Willy Wonka and Walt Disney were early inspirations How she built a wedge against competitors How she got through the financial crisis How she knew when to step down as CEO– and how to collaborate with her successor TIMESTAMPS: 03:27 - A mom Who Worked for Eleanor Roosevelt 06:53 - The…

Today’s callers: Whitney in Utah wonders how to bridge the gap between pre-seed and institutional investment for her fitness/retail combo space. Then Chloe in the U.K. considers which markets to target for her at-home crafting kits. And Christy in Washington wants to convert gifters into repeat customers for her coffee flavoring brand. Plus, Christina’s take on why Milk Bar is better served with her as Chief Experimenter rather than Chief Executive. Thank you to the founders of The Beau Collective, Cotton Clara, and Vashon Island Coffee Dust. If you’d like to be featured on a future Advice Line episode—where Guy and former show guests take questions from early-stage founders—leave us a one-minute message that tells us about your business and a specific question you’d like answered. Send a voice memo to hibt@id.wondery.com or call 1-800-433-1298. And be sure to listen to the story of how Christina founded Milk Bar from our episode back in 2019. This episode was produced by J.C. Howard with music by Ramtin…

In 2004, German programmer Tobias Lütke was living in Ottawa with his girlfriend. An avid snowboarder, he wanted to launch an online snowboard shop, but found the e-commerce software available at the time to be clunky and expensive. So he decided to write his own e-commerce software. After he launched his online snowboard business, called Snowdevil, other online merchants were so impressed with what he built that they started asking to license Tobi's software to run their own stores. Tobi and his co-founder realized that software had more potential than snowboards, so they launched the e-commerce platform Shopify in 2006. Since then, it has grown into a publicly-traded company with over 7,000 employees and $11 billion in revenue. Timestamps: 04:55 - Tobi discovers snowboarding–and meets his future wife–on vacation in Canada 09:00 - Building a new kind of snowboarding company 24:55 - Pivot point: skateboards or software? 29:45 - The night before Tobi’s wedding, Shopify switches business models 39:15 - The…

Entrepreneur, author, and podcaster Tim Ferriss joins Guy on the Advice Line to answer questions from three early-stage founders. Plus, Tim shares the inspiration behind his latest venture, Coyote—a 10-minute card game that encourages time spent with friends and family. First, Lauryn from San Francisco asks about the best way to scale her biodegradable ear plugs in two very different directions. Then Emily from Kansas City weighs whether DTC or wholesale is where to focus her accessory brand after Taylor Swift wore one of her rings and sales exploded. And finally, Kimberly in Woolwich, Maine wonders how to incentivize her customers to pre-order her high-quality, sustainable, clothing. Thank you to the founders of GOB, EB & Co, and K. Becker Designs for being a part of our show. If you’d like to be featured on a future Advice Line episode, leave us a one-minute message that tells us about your business and a specific question you’d like answered. Send a voice memo to hibt@id.wondery.com or call…

In 1978, Brian Smith quit his accounting job in Australia and headed to California with a surfboard, some savings, and ambition. He figured California was where he’d find an idea or a product to bring back home to Australia to build a business. A year in, he was still looking.. But then he saw an advertisement in a surfing magazine for Australian sheepskin boots. Uggs were so widespread in Australia at the time, the name was a generic term - like flip flops - not a brand. Brian was immediately stoked: these boots were virtually unknown in America. If he could get ugg boots for sale in the U.S., they would be a huge success! Almost nobody else agreed. For years, Brian lived on the edge of collapse. He sold boots from the back of his van and worked construction and golf course maintenance jobs to survive. Retailers laughed him out of stores. He lost control of his company twice. At one point, he literally crawled across the floor from stress, ready to walk away forever. And yet…he kept going. What followed was…

Today’s callers: Kristina in Ohio looks for avenues beyond organic social media to market her furniture designed for toddlers and parents alike. Then Phil in Michigan considers the best messaging to brew interest in his farm-made cherry vinegar. And Caroline in California scouts new ways to cultivate curiosity around her plant-based dog food. Plus, Jeffrey discusses the quiet momentum of social businesses as they navigate ‘greenhushing’ and a polarized political climate. Thank you to the founders of Twenty Five and Pine, Red Truck Orchards, and Petaluma for being a part of our show. If you’d like to be featured on a future Advice Line episode—where Guy and former show guests take questions from early-stage founders—leave us a one-minute message that tells us about your business and a specific question you’d like answered. Send a voice memo to hibt@id.wondery.com or call 1-800-433-1298. And be sure to listen to Seventh Generation’s founding story as told by Jeffrey and his co-founder Alan in 2021. This…

At 25, Justin Gold was making experimental peanut butter in his home kitchen with a food processor and a stack of recipe journals. His singular obsession: bring new life to a tired lunchtime staple. What started as late-night experiments with honey, cinnamon and banana eventually became Justin's — one of the most influential natural food brands of the last two decades. At first, Justin got rejected by most grocery stores he approached. He worked overnight in a shared industrial kitchen, hand-filling jars one at a time. He couldn’t get a distributor, so he stocked the shelves at the Boulder Whole Foods himself. And when growth stalled… he had an idea during a mountain bike ride that would transform the company: What if peanut butter came in a squeeze pack? In this episode, Justin explains how relentless experimentation and stubbornness helped him build a category-defining brand — and how, with each entrepreneurial milestone, an even more challenging one emerged. YOU’LL LEARN: How Justin reverse-engineered…

Today’s callers: David from New Jersey struggles with self-doubt as he works to grow his muscle-scraping soap brand. Then, Marnie from Australia wants to convince customers that her colorful tick-repellent socks are worth the premium price. And David from New York wants his company to end the practice of throwing away burned out candles. Plus, Sarah recounts rebuilding her brand in the wake of the pandemic and the changing fashion preferences of professional women. Thank you to the founders of Sorsoap, Tick Socks, and Siblings for being a part of our show. If you’d like to be featured on a future Advice Line episode—where Guy and former show guests take questions from early-stage founders—leave us a one-minute message that tells us about your business and a specific question you’d like answered. Send a voice memo to hibt@id.wondery.com or call 1-800-433-1298. And be sure to listen to M.M. LaFleur’s founding story as told by Sarah on the show in 2020. This episode was produced by Carla Esteves with music by…

NVIDIA is one of the most valuable companies in human history. Its chips run the AI systems transforming everything from entertainment to warfare. But for years, almost nobody believed in co-founder Jensen Huang’s vision. Jensen spent nearly a decade pouring billions into a technology called CUDA, long before AI made it profitable. In this deeply personal conversation, Jensen tells Guy why NVIDIA’s very first chip was a catastrophic failure … and how at one point, the company was 30 days away from going out of business. Jensen also explains why he thinks fears about AI are overblown, and why he believes the next generation will have more opportunity — not less — because of AI. What You’ll Learn: Why NVIDIA nearly collapsed before becoming an AI giant How researchers sparked the AI boom using NVIDIA gaming chips How to lead through uncertainty when a huge bet hasn’t yet paid off How Jensen approaches hard decisions like an engineer We’re “doing ourselves a disservice” by being afraid: Jensen on AI and job…

Today’s callers: Kristina in Florida wants to take her local pottery workshops nationwide. Then Jim from Colorado wonders if retail is right for his quick release camera straps. And Will in Ohio hopes his business will change what consumers expect from tool rental services. Thank you to the founders of Seagrass Pottery, Lemur Strap and Tool Club for being a part of our show. If you’d like to be featured on a future Advice Line episode—where Guy and former show guests take questions from early-stage founders—leave us a one-minute message that tells us about your business and a specific question you’d like answered. Send a voice memo to hibt@id.wondery.com or call 1-800-433-1298. And be sure to listen to our episodes with Chieh Huang of Boxed, Hernan Lopez of Wondery and David Neeleman of Jet Blue. This episode was produced by Kerry Thompson with music by Ramtin Arablouei. It was edited by John Isabella. Our audio engineer was Cena Loffredo. You can follow HIBT on X & Instagram and sign up for Guy’s free…