How I Built This with Guy Raz

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 Ramtin Arablouei. It was edited by John Isabella. Our audio engineer was Jimmy Keeley. You can follow HIBT on X & Instagram and sign up for Guy’s free newsletter at guyraz.com or on Substack. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Tony DeRosa

Co-founder

HTHearsay Brewing and Theater

Monica Soni

Founder

Tres London

Sandy Dinegar

Co-founder and COO

Brain Buffs

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 financed its first production run How one perfectly timed opportunity launched the business Why "smart money" isn't always smart How investor and founder incentives can be completely misaligned The warning signs hidden inside a term sheet Timestamps: 06:11 – Lily's years at Microsoft, and the money that helped launch a business 11:55 – Serena repaints an old table and discovers people will pay for her designs 24:21 – “No bunnies, ducks or choo choo trains.” Lily and Serena meet, and decide to sell high-end baby linen: 36:01 – $100,000 in orders... for products that didn't exist yet 37:38 – The cash-flow hack that kept the company afloat 46:14 – “They patted us on the head.” Patronizing investors, and a predatory term sheet 51:28 – The financial crisis forces a complete reinvention of the business 58:47 – The lawsuit, the boardroom battle, and the investor who nearly brought Serena & Lily down 1:03:26 – Why acquisition offers couldn't save the company—and the lesson every founder should hear This episode was produced by J.C. Howard, with music by Ramtin Arablouei. Edited by Neva Grant, with research help from Katherine Sypher. Follow How I Built This: Instagram → @howibuiltthis X → @HowIBuiltThis Facebook → How I Built This Follow Guy Raz: Instagram → @guy.raz Youtube → guy_raz X → @guyraz Substack → guyraz.substack.com Website → guyraz.com See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Serena Dugan

Co-founder

Serena & Lily

Lily Kanter

Co-founder

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. 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. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Chris Riccobono

Co-Founder

UNTUCKitGreatness Wins

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 valuable assets any business can build. What you'll learn The hiring philosophy that transformed customer service into a competitive moat and has helped Sweetwater fend off much larger competitors Why under-cutting competitor prices and offering discounts isn’t always the answer to fuel sales and growth Why the best salespeople aren’t always don’t think of themselves as salespeople - and don’t have to come from sales or marketing backgrounds Why training people—not technology—may be the biggest, best investment a company can make How saying "no" to bad products strengthened customer trust The leadership principle: empowering employees to solve problems without asking permission Timestamps 05:39 — The saxophone player who never meant to build a billion-dollar company 09:11 — How turning his VW van into a mobile recording studio was the first step in building a business 14:37 — The $20,000 keyboard synthesizer that changed his life forever 21:27 — Chuck gets into retail - almost in spite of himself 34:39 — Why Sweetwater refused to compete on price 37:51 — How Chuck and his early team started to learn the power of customer service 44:45 — Inside "Sweetwater University" and being a Sales Engineer: 13 weeks of training before an employee answers the phone 46:55 — Leadership rule for employees: Never ask permission to do the right thing 1:03:19 — Why Amazon hasn’t stopped him This episode was produced by Casey Herman with music by Ramtin Arablouei, and edited by Andrea Bruce 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 → @guyraz Substack → guyraz.substack.com Website → guyraz.com See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Chuck Surack

Founder

Sweetwater

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 produced by Carla Esteves with music by Ramtin Arablouei. It was edited by John Isabella. Our audio engineer was Robert Rodriguez. You can follow HIBT on X & Instagram and sign up for Guy's free newsletter at guyraz.com and on Substack. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Curt Richardson

Founder

OtterBox

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 mission-critical software Why Toast intentionally stayed small before scaling The leadership lesson Aman learned after almost breaking the company How Toast survived COVID after restaurants shut down What founders should look for when choosing a co-founder Timestamps: 11:25 — The frustrating restaurant experience that inspires Toast 15:41 — The first product fails—and reveals a bigger opportunity 16:43 — Building Toast: “We grossly underappreciated what it would take.” 26:05 — Why nearly every investor said “No.” 32:31 — Toast’s disastrous first launch: writing credit card numbers by hand 34:18 — Pitching hundreds of restaurant owners before finding believers 38:08 — Why customer obsession beats competitor obsession 44:17 — Bringing in a new CEO: “We need to rethink how we do things here.” 52:31 — The biggest lessons from building a $2 billion company This episode was produced by Sam Paulson with music by Ramtin Arablouei. It was edited by Neva Grant with research help from Casey Herman. Our engineer was Kwesi Lee. Follow How I Built This: Instagram → @howibuiltthis X → @HowIBuiltThis Facebook → How I Built This Follow Guy Raz: Instagram → @guy.raz YouTube → guy_raz X → @guyraz Substack → guyraz.substack.com Website → guyraz.com See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Aman Narang

Co-Founder & CEO

Toast

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 Ramtin Arablouei. It was edited by John Isabella. Our audio engineer was Jimmy Keeley. You can follow HIBT on X & Instagram and sign up for Guy's free newsletter at guyraz.com and on Substack. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Kenneth Cole

Matt

Co-Founder

Arch NetworkApollo GraphQLSemaClockwisePPPedestrian ProjectWBWandering Soul Beer

Emefa

Founder

IKISRAELLA KOBLA

Levi

Founder

SSSwing Sculpt

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 against a corporate titan. The "Elvis Principle:” How combining unexpected design elements can create an unforgettable package The "Trojan Horse" Strategy: Why forcing retailers to buy a massive display creates the illusion of a brand overnight. TIMESTAMPS 08:15 - What selling furniture taught Tom about customer psychology 10:00 - How the Slogan “Surf Michigan” got him into the T-shirt Business 25:07 - Psycho Chihuahua, Taco Bell, and the Branding Deal that Wasn’t 33:49 - Inside the grueling battle over a chihuahua mascot. “I was the guy suing Taco Bell.” 39:35 - A dramatic legal verdict, and Tom’s branding business takes off with fancy Tequila 49:47 - The sun screen opportunity: “I saw a gigantic hole that you could drive through.” 55:03 - How Tom and his partner came up with their “badass ape” logo 1:07:36 - Opening (fake) Sun Bum headquarters in Cocoa Beach, Fla 1:10:31- Early store displays and making the brand seem bigger than it was 1:14:56 - A $400M sale to SC Johnson, and Tom starts a new company This episode was researched by Katherine Sypher and Susannah Broun and produced by Casey Herman, with music by Ramtin Arablouei, and edited by Neva Grant. Follow How I Built This: Instagram → @howibuiltthis X → @HowIBuiltThis Facebook → How I Built This Follow Guy Raz: Instagram → @guy.raz Youtube → guy_raz X → @guyraz Substack → guyraz.substack.com Website → guyraz.com See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Tom Rinks

Co-founder

Sun Bum

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 story as told by Jeni on the show in 2018. This episode was produced by Katherine Sypher with music by Ramtin Arablouei. It was edited by John Isabella. Our audio engineer was Neal Rauch. You can follow HIBT on X & Instagram and sign up for Guy's free newsletter at guyraz.com and on Substack. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Jeni Britton

Founder

Jeni's Splendid Ice CreamsFLFloura

Jesse

Co-founder

VeniceJBJesse & Ben's

Casey

Founder

JPJaju Pierogi

Callie

Founder

Ubae

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: 00:06:16 - Dealing with diabetes and epilepsy as a college student 00:12:38 - What Krishna learns from his early failures in tech 00:22:43 - The first, low-sugar cocoa puffs: “Rocks that tasted like soil.” 00:27:36 - His homemade cereal gets good enough to sell 00:32:42 - Naming the brand: classy alliteration and a nod to a Will Ferrell movie 00:44:51 - Learning to make cereal like the pros at Texas A&M 00:54:43 - Krishna moves from NYC to Indiana to make sure the cereal is made right 01:01:04 - Whole Foods, Costco, and becoming a household brand This episode was researched and produced by Chris Maccini with music composed by Ramtin Arablouei. It was edited by Neva Grant. Our engineer was Kwesi Lee. Follow How I Built This: Instagram → @howibuiltthis X → @HowIBuiltThis Facebook → How I Built This Follow Guy Raz: Instagram → @guy.raz Youtube → guy_raz X → @guyraz Substack → guyraz.substack.com Website → guyraz.com See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Krishna Kaliannan

Founder

Catalina Crunch

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 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 newsletter at guyraz.com and on Substack. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Ronnen Harary

Co-founder & Co-CEO

Spin Master

Ann

Founder

YCYearly Company

Felix

Founder

ICIsland Bee Company

Matt

Co-Founder

Arch NetworkApollo GraphQLSemaClockwisePPPedestrian ProjectWBWandering Soul Beer

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 lipstick Why retailers initially rejected e.l.f. How a single magazine mention launched e.l.f.'s online business The retail insight that unlocked national expansion How a false rumor generated 18,000 orders a day The emotional toll of a $225 million acquisition that collapsed at the eleventh hour Timestamps: 00:10:28 — How to make (decent) makeup for just $1 00:18:35 — The dollar stores say no 00:24:32 — Glamour comes calling, and e.l.f has 30 days to build a website 00:38:27 — The question from a Target buyer that leaves Joey speechless 00:39:56 — The H-E-B test that proves everyone wrong 00:46:36 — “That’s news to me!” The viral rumor that sends Joey back to China 00:59:42 — Scaling to tens of millions in revenue 01:07:15 — “It was crushing.” The L’oreal sale that never happened 01:12:02 — After e.l.f: Joey stops watching House of Cards and gets back to business This episode was produced by Carla Esteves with music composed by Ramtin Arablouei. It was edited by Neva Grant with research by Olivia Rockman. Our audio engineer was Patrick Murray. Follow How I Built This: Instagram → @howibuiltthis X → @HowIBuiltThis Facebook → How I Built This Follow Guy Raz: Instagram → @guy.raz Youtube → guy_raz X → @guyraz Substack → guyraz.substack.com Website → guyraz.com See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Joey Shamah

Co-founder

e.l.f. Cosmetics

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 Ramtin Arablouei. It was edited by John Isabella. Our audio engineer was Robert Rodriguez. You can follow HIBT on X & Instagram and sign up for Guy’s free newsletter at guyraz.com or on Substack. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Susan Griffin-Black

Co-Founder & CEO

EO Products

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 took to redefining dining. What You'll Learn: The unglamorous economics of rock concerts and restaurants How rejection, romantic heartbreak, and failure can become powerful motivators Why he believes he's spent his career "throwing the party" without attending it How building the right team of designers can make a restaurant feel magical Why Stephen says today's entrepreneurs have a much harder path than his generation did The model Stephen says new restaurateurs should follow today Timestamps: 00:06:03 — A lonely childhood: Making up skits in his room 00:09:49 — Losing his mother at age 19 00:11:17 — Starting a comedy club: Deli by day. Stand up at night 00:20:49 — Going broke and reneging on a bank loan 00:28:26 — Music promotion: Feeling like a fraud while promoting U2, Madonna 00:36:52 — A New York martini bar inspires Stephen to start his own 00:42:20 — The bold design behind a line-out-the-door restaurant 01:03:31 — Opening Buddakan in New York: “I can’t do anything better. This is Sgt. Pepper” 01:09:08 — Starting a restaurant today: “I would say don’t do it … but if you do, keep it smaller” This episode was produced by Alex Cheng with music composed by Ramtin Arablouei. It was edited by Neva Grant with research by Sam Paulson. Our audio engineers were Patrick Murray and Robert Rodriguez. Follow How I Built This: Instagram → @howibuiltthis X → @HowIBuiltThis Facebook → How I Built This Follow Guy Raz: Instagram → @guy.raz Youtube → guy_raz X → @guyraz Substack → guyraz.substack.com Website → guyraz.com See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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 Isabella. Our audio engineer was Robert Rodriguez. You can follow HIBT on X & Instagram and sign up for Guy’s free newsletter at guyraz.com or on Substack. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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: 05:52 - A mom Who Worked for Eleanor Roosevelt 09:18 - The Impromptu Interview That Changed Maxine’s Career 16:00 - Becoming One of the Few Female Fortune 500 Executives 18:43 - Why She Walked Away From Payless 21:27 - The Beanie Baby Disappointment That Sparked Build-A-Bear 26:14 - Designing the First Store: “Make it Like Willy Wonka.” 37:53 - Opening Day — and a Line Out the Door 39:53 - Defending the Brand Against Copycats and Lawsuits 45:53 - Scaling to Hundreds of Stores and Going Public 58:25 - Letting Go: Stepping Down as CEO and Building a Legacy This episode was researched by Rommel Wood and produced by Kerry Thompson, with music by Ramtin Arablouei, and edited by Neva Grant. Follow How I Built This: Instagram → @howibuiltthis X → @HowIBuiltThis Facebook → How I Built This Follow Guy Raz: Instagram → @guy.raz Youtube → guy_raz X → @guyraz Substack → guyraz.substack.com Website → guyraz.com See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Maxine Clark

Founder

Build-A-Bear Workshop

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 Arablouei. It was edited by John Isabella. Our audio engineer was Jimmy Keeley. You can follow HIBT on Twitter & Instagram and sign up for Guy's free newsletter at guyraz.com and on Substack. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Christina Tosi

Founder

Milk Bar

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: 07:20 - Tobi discovers snowboarding–and meets his future wife–on vacation in Canada 11:25 - Building a new kind of snowboarding company 29:35 - Pivot point: skateboards or software? 34:25 - The night before Tobi’s wedding, Shopify switches business models 45:25 - The 2008 financial crisis hits… revealing a huge opportunity 58:55 - After a decade, Shopify goes public This episode was produced by Casey Herman with music composed by Ramtin Arablouei. It was edited by Neva Grant. This archive episode was produced by Katherine Sypher. Follow How I Built This: Instagram → @howibuiltthis X → @HowIBuiltThis Facebook → How I Built This Follow Guy Raz: Instagram → @guy.raz Youtube → guy_raz X → @guyraz Substack → guyraz.substack.com Website → guyraz.com See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Tobias Lütke

Co-founder and CEO

Shopify

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 1-800-433-1298. And be sure to listen to Tim Ferriss’s founding story as told by Tim on the show in 2020. This episode was produced by Noor Gill with music by Ramtin Arablouei. It was edited by Andrea Bruce. Our audio engineer was Cena Loffredo. You can follow HIBT on X & Instagram and sign up for Guy's free newsletter at guyraz.com and on Substack. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Tim Ferriss

Author and Investor

Tim Ferriss

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 one of the most unlikely brand-building stories in modern retail history — involving surf culture, trademark wars, miraculous timing, brutal financing mistakes, and a product the fashion world initially dismissed. Today, UGG generates more than $2.5 billion a year in sales. You’ll hear how Brian: Turned rejection into problems to solve Discovered marketing insights that changed UGG forever Survived years of cash-flow disasters Lost control of the company and regained it a couple of times. Used surf culture to build an emotional connection with customers Nearly quit… over and over again… And how he eventually sold UGG to footwear giant, Decker Timestamps: 09:51 Brian's eureka moment that led to the birth of UGG 12:41 The first sales trip results in ZERO sales 21:10 The mantra that kept Brian going while doing odd summer jobs to survive 28:32 Brian gets a critical lesson in marketing…from some 12-year-old kids 51:59 Brian’s most effective strategy for retail: the “Six-Pair Stocking Plan” 56:42 On track to regain his ownership - Brian hits a huge snag 01:01:57 A midnight phone call from Australia saves the business 01:11:28 Brian gets the last laugh in the trademark dispute - and acquires a boot factory 01:14:54 Pamela Anderson wears UGGs on the set of Baywatch 01:23:39 A chance meeting in the Atlanta airport leads to a deal to sell UGG This episode was researched and produced by Casey Herman, with music by Ramtin Arablouei, and edited by Andrea Bruce. Follow How I Built This: Instagram → @howibuiltthis X → @HowIBuiltThis Facebook → How I Built This Follow Guy Raz: Instagram → @guy.raz Youtube → guy_raz X → @guyraz Substack → guyraz.substack.com Website → guyraz.com See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Brian Smith

Founder

UGG

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 episode was produced by Sam Paulson with music by Ramtin Arablouei. It was edited by John Isabella. Our audio engineer was Jimmy Keeley. You can follow HIBT on X & Instagram and sign up for Guy’s free newsletter at guyraz.com or on Substack. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Jeffrey Hollender

Co-founder

Seventh Generation

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 flavored peanut butter in his apartment How launching in Boulder gave him a big advantage How he learned when to listen to feedback, and when to ignore it The deal he made with Whole Foods: “I’ll stock the shelves myself.” How the squeeze pack transformed the business, and why it almost didn’t work The power of naïve persistence in entrepreneurship Timestamps: 00:09:35 — The obsessive recipe experiments that became Justin’s edge 00:16:25 — Getting support from Boulder’s startup food community 00:21:28 — Raising $35,000– and shocking his family: “I wanna make peanut butter!” 00:42:51 — The farmers market feedback that changed the product line 00:46:56 — Justin talks his way into the first Whole Foods 00:51:47 — Justin’s gets into more stores, but sales start to stagnate 00:53:35 — The mountain bike ride that sparked the squeeze-pack idea 01:19:43 — The brand gets sold, Justin gets fired…and invited back This episode was produced by J.C. Howard, with music by Ramtin Arablouei. Edited by Neva Grant, with research help from Alex Cheng. Follow How I Built This: Instagram → @howibuiltthis X → @HowIBuiltThis Facebook → How I Built This Follow Guy Raz: Instagram → @guy.raz Youtube → guy_raz X → @guyraz Substack → guyraz.substack.com Website → guyraz.com See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Justin Gold

Founder

Justin's

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 Ramtin Arablouei. It was edited by John Isabella. Our audio engineer was Jimmy Keeley. You can follow HIBT on X & Instagram and sign up for Guy's free newsletter at guyraz.com and on Substack. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Sarah LaFleur

Founder and CEO

M.M.LaFleur

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 loss How Jensen defends his demanding management style Why past failures still haunt him Key Moments From the Interview: 00:07:51 — Jensen Huang’s childhood at an unusual Kentucky boarding school 00:14:50 — Why Jensen left a stable career to help start NVIDIA 00:17:14 — NVIDIA’s first failure: the NV1 disaster 00:19:51 — The desperate trip to Japan that gave the company a lifeline 00:23:11 — “The only idea we had” for prototyping: the emulator Hail Mary 00:30:53 — The book that shaped Jensen’s thinking about innovation 00:35:04 — Why NVIDIA kept investing in CUDA while Wall Street lost faith 00:41:38 — The moment AI researchers discovered the power of NVIDIA’s chips 00:53:17 — Jensen on fear of job loss from AI, and why America risks falling behind 01:01:56 — Knowing what he knows now, would he do it again? Yes — and no This episode was researched and produced by Alex Cheng with music by Ramtin Arablouei. It was edited by Neva Grant. Our engineers were Patrick Murray and Robert Rodriguez. Follow How I Built This: Instagram → @howibuiltthis X → @HowIBuiltThis Facebook → How I Built This Follow Guy Raz: Instagram → @guy.raz Youtube → guy_raz X → @guyraz Substack → guyraz.substack.com Website → guyraz.com See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Jensen Huang

Co-founder & CEO, NVIDIA

NVIDIA

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 newsletter at guyraz.com or on Substack See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

John Gabbert built a massive furniture brand. But in order to do it, he had to defy his family. John grew up working at his dad’s furniture store in the suburbs of Minneapolis. It sold classic, American-made furniture, with flowery prints and curved legs. But in 1972, John took a life-changing trip to Sweden, where he discovered an obscure store called IKEA. It was selling an entirely different type of furniture: simple, modern, and inexpensive, with a manufacturing process they controlled. To John, it looked like the future of furniture. The only problem, his dad didn’t agree. That disagreement led to a 10-year family rift—but also a new business. In 1980—zafter a deal to buy out his dad broke down—John spun out his own furniture brand, Room & Board. Today, it sells hundreds of millions of dollars of furniture in its own classic designs, mostly made by small American manufacturers. This is the story of how John did it, without outside investors, and without chasing growth for growth’s sake. What You’ll Learn Why the right thing for your business might be the hardest thing for your family How John connected with young boomers—not their parents The key to long-term success: growing slow and saying “no” Why John refused private equity money Why Room & Board transitioned to employee ownership Timestamps: 00:06:10 - Gabberts: flowery furniture in a fake living room 00:09:41 - Becoming president of the family business at age 23 00:13:33 - A fateful trip to IKEA in Sweden: “That's what the future needed to be” 00:18:36 - John tries to buy out the family business… until his dad backs out 00:35:47 - Design inspiration from modern art—and steel frames 00:46:38 - Why making furniture in America makes sense 00:55:27 - Investors come to call… and John says no 01:01:48 - The decision that transferred ownership to employees This episode was produced by Chris Maccini with music composed by Ramtin Arablouei. It was edited by Neva Grant with research help from Rommel Wood. Our engineers were Patrick Murray and Kwesi Lee. Follow How I Built This: Instagram → @howibuiltthis X → @HowIBuiltThis Facebook → How I Built This Follow Guy Raz: Instagram → @guy.raz Youtube → guy_raz X → @guyraz Substack → guyraz.substack.com Website → guyraz.com See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

John Gabbert

Founder & CEO

Room & Board

Today’s callers: Anthony from Miami considers the best method to grow his pop-up outdoor movie theater business. Then Andrew in San Francisco asks how to set his cat wrestling toy apart from competitors. Finally, Melissa in Massachusetts seeks strategies for getting busy parents excited about her healthy frozen muffins. Plus, Jonah shares what’s next for Buzzfeed as the company marks 20 years of business. Thank you to the founders of Motion Flix, CATSUMO, and Unrefined Foods 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 Buzzfeed’s founding story as told by Jonah on the show in 2017. This episode was produced by Katherine Sypher with music by Ramtin Arablouei. It was edited by Casey Herman. Our audio engineer was Kwesi Lee. You can follow HIBT on X & Instagram and sign up for Guy's free newsletter at guyraz.com and on Substack. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Jonah Peretti

Co-founder, BuzzFeed

BuzzFeed

Gregg Renfrew started a movement by making better-for-you cosmetics, then enlisted an army of women to build the business through direct sales. But after selling Beautycounter, she was pushed out of the company she created. Then she got to do something almost no founder gets to do: She bought her company back. Then lost it again. Then took the risky step of rebuilding it into a new brand, now called Counter. This is a story about ambition, humility, and second chances. Gregg learned her first lessons by launching an early online wedding registry and selling it to Martha Stewart. She briefly led a clothing company and was summarily fired—by messenger. In this candid conversation, Gregg talks about the bold innovation she brought to the beauty industry, and the lessons she learned from working with difficult people—including, at times, herself. What You’ll Learn: How to build a movement—not just a product The hidden risks of “growth at all costs” Why direct sales (done right) can outperform traditional DTC The emotional toll of being fired from your own company How to rebuild your identity after losing your business What it takes to come back—and do it differently the second time Timestamps: (00:06:15) – Selling Xerox machines and getting doors slammed in her face (00:08:09) – The early inspiration for an online wedding registry. (00:16:44) – The brutal lesson of the dot-com crash: “growth at all costs” (00:21:58) – Standing up to Martha Stewart: “I was cocky.” (00:23:51) – Getting fired as CEO… by messenger… in front of her team (00:32:47) – The moment she realized the beauty industry had a massive gap (00:35:25) – “Clean beauty didn’t exist”—and why that made it so hard (00:47:04) – Building a 60,000-person sales force, scaling to hundreds of millions in sales (00:46:40) – Selling Beautycounter for $1B… and losing control months later (01:00:13) – The emotional aftermath of being pushed out—and what came next This episode was produced by John Isabella with music composed by Ramtin Arablouei. It was edited by Neva Grant with research help from Noor Gill. Our engineers were Patrick Murray and Jimmy Keeley. Follow How I Built This: Instagram → @howibuiltthis X → @HowIBuiltThis Facebook → How I Built This Follow Guy Raz: Instagram → @guy.raz Youtube → guy_raz X → @guyraz Substack → guyraz.substack.com Website → guyraz.com See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Gregg Renfrew

Founder

BeautycounterCounter

Today’s callers: Barbara in Massachusetts wonders how her nutrition education theater company might live on past her own involvement. Then Jeff in Illinois looks to carry the momentum from his Ninja Warrior-inspired gyms to form a professional league around the sport. And Vince in Virginia weighs the risks from introducing new SKUs for his men’s organic underwear brand. Plus, David breaks down the resource management necessary to keep an airline aloft as rising fuel prices grip the industry. Thank you to the founders of FoodPlay Productions, Ultimate Ninjas, and Gotchies 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 JetBlue’s founding story as told by David in 2019. This episode was produced by Sam Paulson with music by Ramtin Arablouei. It was edited by Casey Herman. Our audio engineer was Kwesi Lee. You can follow HIBT on X & Instagram and sign up for Guy’s free newsletter at guyraz.com or on Substack. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

David Neeleman

Founder

JetBlueJetBlue AirwaysAzul Airlines

In the late 1990s, Shep and Ian Murray looked at a shrinking category–men’s ties–and saw an opportunity: a necktie isn’t just functional. It’s expressive. It can signal identity, taste, aspiration. With no fashion experience and no outside investors, the Murray brothers started making colorful ties inspired by their childhoods in Martha’s Vineyard — tiny whales, sailboats, island street signs. What began as a small, improbable tie business grew into Vineyard Vines: a half-billion-dollar lifestyle brand with more than 100 stores and major department store distribution. In this episode, Shep and Ian talk about why they quit their stable jobs to turn a sleepy product into a national brand, which began as a family business and remains so to this day. What you’ll learn: Why a great business can start in a category that everyone thinks is dying How to build distribution when you have no roadmap and few connections What bootstrapping teaches founders that outside capital often doesn’t How improvised marketing can create outsized attention Knowing the difference between a fashion brand and a “brand” brand Timestamps: 00:10:22 - The brothers both hate their desk jobs: “How was your day?” “It sucked.” 00:11:20 - Vineyard Vines starts on a family trip, with a nudge from a hotel manager 00:13:46 - Early designs: whales, fish, jeeps, street signs 00:25:39 - Finally quitting their jobs– they’re thrilled, their parents–not so much 00:30:42 - Landing their first order for $1800. “We’re never gonna have to work anymore!” 00:34:40 - The brand gets a boost from a PR stunt during the Clinton-Lewinsky scandal 00:47:00 - The “Get to $5 million” mentor advice that kept them focused 00:49:23 - The brothers open their first store - and realize they have a lot to learn 01:01:18 - The 2008 financial crisis, and the brutal inventory decisions that help save the business 01:09:06 - Why stepping back from the CEO role didn’t work — and what it taught them about brand culture This episode was produced by Kerry Thompson with music composed by Ramtin Arablouei. It was edited by Neva Grant with research help from Casey Herman. Follow How I Built This: Instagram → @howibuiltthis X → @HowIBuiltThis Facebook → How I Built This Follow Guy Raz: Instagram → @guy.raz Youtube → guy_raz X → @guyraz Substack → guyraz.substack.com Website → guyraz.com See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Shep Murray

Co-Founder

Vineyard Vines

Ian Murray

Co-Founder

Vineyard Vines