Guy Raz dives into the stories behind some of the world's best known companies. How I Built This weaves a narrative journey about innovators, entrepreneurs and idealists—and the movements they built. Order the How I Built This book at https://www.guyraz.com/
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Bogg Bag: Kim Vaccarella. The $100 Million Business She Almost Abandoned
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 and raising two kids.How COVID turned Bogg Bag from a beach product into a “beach and beyond” product.How Kim got a massive acquisition offer–and why she turned it down. Why Kim thinks Bogg Bag can eventually become a billion-dollar brand.Chapters:06:36 - Growing up without financial security08:17 - From high-school dropout to a six-figure career17:19 - Reading “Mommy Millionaire” and dreaming of inventing something 19:41 - The Crocs-on-the-beach moment 24:56 - Kim hits a wall with Crocs, so she decides to make Bogg Bag herself33:33 - The early prototypes and a nervous visit to a boutique: “I don’t know what this is, but I think I need it.” 41:16 - The first big shipment, a $30,000 defect, and a decision to pull the plug 47:13 - A massive natural disaster presents an opportunity 52:15 - “Now I gotta make this damn bag”54:45 - A factory showdown in China59:52 - Starting over with $120,00001:01:51 - The trade-show “timeshare” in a tiny booth 01:07:12 - Finally quitting her day job01:10:42 - COVID boosts the business01:13:28 - The acquisition offer that could have changed everything01:23:40 - Learning to lead a much bigger company01:26:13 - The dream of a family legacy This episode was produced by J.C. Howard, with music by Ramtin Arablouei.Edited by Neva Grant, with research help from Sam Paulson.Follow How I Built This:Instagram → @howibuiltthisX → @HowIBuiltThisFacebook → How I Built ThisFollow Guy Raz:Instagram → @guy.razYoutube → guy_razX → @guyrazSubstack → guyraz.substack.comWebsite → guyraz.comSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Advice Line with Ben Goodwin of Olipop
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 Kerry Thompson with music by Ramtin Arablouei. It was edited by John Isabella. Our audio engineers were Cena Loffredo and 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.
Late July Snacks: Nicole Bernard Dawes. Crackers and Cookies were Failing… Tortilla Chips Saved Them
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 ownThe pros and cons of financial vs. strategic investorsWhen to cut a product that isn’t workingWhy the fine print in a contract is so importantHow the hardest decision might be the best one for your family and the businessTimestamps:07:22 - The car crash that launched a potato chip company21:00 - Pregnant and craving crackers: The birth of Late July Snacks36:54 - The organic cookies that tasted great but nearly sunk the business40:49 - Tragedy and crisis: a father’s death and a $3 million loan in default50:31 - A tortilla chip Hail Mary57:29 - Nicole’s first big sales call… and her last chance to save the company1:08:49 - “The big fish eats the small fish.” A food giant acquisition1:13:36 - Nicole launches a new brand, moving from a hard category–to an even harder one This episode was researched and produced by Chris Maccini with music composed by Ramtin Arablouei. It was edited by Neva Grant. Our engineer was Robert Rodriguez. Follow How I Built This:Instagram → @howibuiltthisX → @HowIBuiltThisFacebook → How I Built ThisFollow Guy Raz:Instagram → @guy.razYoutube → guy_razX → @guyrazSubstack → guyraz.substack.comWebsite → guyraz.comSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Advice Line with Daymond John of FUBU
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 music by Ramtin Arablouei. It was edited by John Isabella. 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.
YETI: Ron and Ryan Seiders. How Two Brothers Turned a $400 Cooler Into a $2 Billion Brand
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 LEARNWhy 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 for years without venture capitalWhy a simple $30 stainless-steel cup—not the famous $400 cooler— transformed YETI into a mass-market brand.TIMESTAMPS 6:10 — A free-range childhood of hunting and exploring10:02 — Early businesses: fishing rods and boats 15:30 — Roy’s early frustrations with coolers. “The hinges would break, the latches would snap.” 31:20 — The last-minute flight to the Philippines that led to YETI40:53 — People didn’t love the name–but they remembered it 47:49 — Why people were willing to spend $400 on a cooler 1:01:18 — The phone call that nearly pulled the plug on the business1:06:30 — How Roy and Ryan turned a catastrophe into a stronger company1:22:27 — From coolers to cups: A $30 product changed the trajectory of the brand 1:25:44 — Why the founders eventually moved on from YETI This episode was researched and produced by Carla Esteves, with music by Ramtin Arablouei. It was edited by Neva Grant. Our audio engineers were Maggie Luthar and Jimmy Keeley.Follow How I Built This:Instagram → @howibuiltthisX → @HowIBuiltThisFacebook → How I Built ThisFollow Guy Raz:Instagram → @guy.razYoutube → guy_razX → @guyrazSubstack → guyraz.substack.comWebsite → guyraz.comSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Advice Line with Carlton Calvin of Razor
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 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.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Bobbie: Laura Modi. How a Baby Formula Startup Took Market Share From Two Industry Giants
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 AmericaHow she spent nearly $200,000 of her own savings before raising outside capitalHow 64 investor pitches helped her tell a better storyHow a public apology changed the trajectory of the companyWhy Bobbie turned away thousands of customers during its fastest period of growthWhy Laura moved to Washington, D.C., and how she thinks about federal oversightTimestamps:13:17 – The emotional experience that revealed a massive business opportunity23:09 – Laura learns about the two companies that had a lock on U.S. formula25:52 – Quitting Airbnb, starting Bobbie while pregnant, risking her savings38:52 – Pitching 64 investors—and the brutal feedback that fueled her to keep going50:04 – The FDA shuts the company down after two weeks1:01:14 – Building a community while waiting nearly two years for approval1:09:11 – Launch day, and selling out faster than expected1:13:59 – Why Laura shut off new customer orders during the infant formula shortage1:17:12 – Buying her own manufacturing plant to control Bobbie's future1:20:19 – Navigating Washington, regulation, and building a mission-driven brandThis episode was researched and produced by Alex Cheng with music by Ramtin Arablouei. It was edited by Neva Grant. Our audio engineer was Robert Rodriguez. Follow How I Built This:Instagram → @howibuiltthisX → @HowIBuiltThisFacebook → How I Built ThisFollow Guy Raz:Instagram → @guy.razYoutube → guy_razX → @guyrazSubstack → guyraz.substack.comWebsite → guyraz.comSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Advice Line with Bobbi Brown of Jones Road Beauty (September 2025)
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 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 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.
MadeGood: Salma and Nima Fotovat Lost Their First Business.They Grew Their Next One Into a Snack Giant.
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 edgeHow 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 setbackTimestamps:6:05 - Growing up in Iran during wartime, and emigrating to Canada 11:55 - Their dad’s new business: “Why are North Americans not eating nougat?” 19:25 - Building the family’s first snack bar brand—and losing it overnight34:20 - The next business: going all in on healthier school snacks42:30 - Fixing a 200,000-bar production error with alcohol wipes 48:30 - Landing MadeGood’s first retail store51:10 - The 100-mile radius marketing strategy 56:50 - The lure of new products: from human treats to dog treats See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Advice Line: "Strategy Sessions"
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.
Serena & Lily: Serena Dugan and Lily Kanter. They Built a $20M Brand—Then One Investor Almost Destroyed It
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 runHow one perfectly timed opportunity launched the businessWhy "smart money" isn't always smartHow investor and founder incentives can be completely misalignedThe warning signs hidden inside a term sheetTimestamps:06:11 – Lily's years at Microsoft, and the money that helped launch a business11:55 – 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 yet37:38 – 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 business58:47 – The lawsuit, the boardroom battle, and the investor who nearly brought Serena & Lily down1:03:26 – Why acquisition offers couldn't save the company—and the lesson every founder should hearThis 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 → @howibuiltthisX → @HowIBuiltThisFacebook → How I Built ThisFollow Guy Raz:Instagram → @guy.razYoutube → guy_razX → @guyrazSubstack → guyraz.substack.comWebsite → guyraz.comSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Advice Line with Chris Riccobono of UNTUCKit
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.
Sweetwater: Chuck Surack. How a Customer Service Strategy Built a Billion Dollar Online Pro Audio and Music Company.
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 learnThe hiring philosophy that transformed customer service into a competitive moat and has helped Sweetwater fend off much larger competitorsWhy 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 backgroundsWhy training people—not technology—may be the biggest, best investment a company can makeHow saying "no" to bad products strengthened customer trustThe leadership principle: empowering employees to solve problems without asking permissionTimestamps05:39 — The saxophone player who never meant to build a billion-dollar company09:11 — How turning his VW van into a mobile recording studio was the first step in building a business14:37 — The $20,000 keyboard synthesizer that changed his life forever21:27 — Chuck gets into retail - almost in spite of himself34:39 — Why Sweetwater refused to compete on price37:51 — How Chuck and his early team started to learn the power of customer service44:45 — Inside "Sweetwater University" and being a Sales Engineer: 13 weeks of training before an employee answers the phone46:55 — Leadership rule for employees: Never ask permission to do the right thing1:03:19 — Why Amazon hasn’t stopped himThis 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 → @howibuiltthisX → @HowIBuiltThisFacebook → How I Built ThisFollow Guy Raz:Instagram → @guy.razYoutube → guy_razX → @guyrazSubstack → guyraz.substack.comWebsite → guyraz.comSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Advice Line with Curt Richardson of OtterBox
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.
Toast: Aman Narang. How a Long Wait for the Dinner Check Launched a $2 Billion Business.
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 pivotWhy investors rejected Toast again and againHow to convince customers to replace mission-critical softwareWhy Toast intentionally stayed small before scalingThe leadership lesson Aman learned after almost breaking the companyHow Toast survived COVID after restaurants shut downWhat founders should look for when choosing a co-founderTimestamps:11:25 — The frustrating restaurant experience that inspires Toast15:41 — The first product fails—and reveals a bigger opportunity16:43 — 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 hand34:18 — Pitching hundreds of restaurant owners before finding believers38:08 — Why customer obsession beats competitor obsession44:17 — Bringing in a new CEO: “We need to rethink how we do things here.” 52:31 — The biggest lessons from building a $2 billion companyThis 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 → @howibuiltthisX → @HowIBuiltThisFacebook → How I Built ThisFollow Guy Raz:Instagram → @guy.razYouTube → guy_razX → @guyrazSubstack → guyraz.substack.comWebsite → guyraz.comSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.