What It Really Takes To Build a Food Business: Part 2

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.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: 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 [email protected] 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.

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.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: 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 [email protected] 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.

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.