Resy and Eater: Ben Leventhal

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idea—a mobile payment app—flopped.But that failure revealed a much bigger opportunity.Restaurants were struggling with outdated software that many owners hated.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.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: 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 [email protected] 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.

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 LEARNChihuahuas 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.TIMESTAMPS08:15 - 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 companyThis 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 → @howibuiltthisX → @HowIBuiltThisFacebook → How I Built ThisFollow Guy Raz:Instagram → @guy.razYoutube → guy_razX → @guyrazSubstack → guyraz.substack.comWebsite → guyraz.com See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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 [email protected] 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.

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 LearnHow to turn a health challenge into a business opportunity The art and science of baking with esoteric ingredientsWhen to trust partners and when it’s best to take charge yourselfWhy the DTC model is great for some industries and disastrous for othersTimestamps:00:06:16 - Dealing with diabetes and epilepsy as a college student00:12:38 - What Krishna learns from his early failures in tech00:22:43 - The first, low-sugar cocoa puffs: “Rocks that tasted like soil.”   00:27:36 - His homemade cereal gets good enough to sell00:32:42 - 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&M00:54:43 - Krishna moves from NYC to Indiana to make sure the cereal is made right01:01:04 - Whole Foods, Costco, and becoming a household brandThis 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 → @howibuiltthisX → @HowIBuiltThisFacebook → How I Built ThisFollow Guy Raz:Instagram → @guy.razYoutube → guy_razX → @guyrazSubstack → guyraz.substack.comWebsite → guyraz.com See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.