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How I Built This with Guy Raz

Guy Raz interviews the world’s best-known entrepreneurs to learn how they built their iconic brands. In each episode, founders reveal deep, intimate moments of doubt and failure, and share insights on their eventual success. How I Built This is a master-class on innovation, creativity, leadership and how to navigate challenges of all kinds. New episodes release on Mondays and Thursdays. Listen to How I Built This on the Wondery App or wherever you listen to your podcasts. You can listen early and ad-free on Wondery+. Join Wondery+ in the Wondery App, Apple Podcasts or Spotify. Start your free trial by visiting wondery.com/links/how-i-built-this now. Get your How I Built This merch at WonderyShop.com/HowIBuiltThis.

  1. NOV 10 • WONDERY+ EARLY ACCESS

    Backroads: Tom Hale. How a desk worker became a trailblazer in active travel

    In his 20’s, working an office job he hated, Tom woke up in the middle of the night with a wild idea: why not take people on bike trips? No playbook. No investors. Just a sense that he could make a living doing what he loved. His first trip? Four guests riding through Death Valley, pitching their own tents. From there, Backroads scaled to hotels, while weathering a bike burglary, a van rollover in the desert, 9/11, the Great Recession, and a pandemic that brought tourism to a halt. Today, Backroads runs 5,000+ trips a year in 60+ countries. This is a masterclass in savvy cash flow, scrupulous quality control, and dogged iteration. If you care about travel, brand, or building a services business at scale—listen to this. What you’ll learn: How a 5,000 mile solo bike trip laid the groundwork for Backroads The first guided trip in Death Valley: four people, high winds, 50 miles/day How to get your stolen bikes back: confront the thief yourself The “collect early, pay late” flywheel that powered growth without investors How Backroads survived 9/11, 2008, and COVID—and what changed after each shock Avoiding the Instagram trap and delivering peak, uncrowded experiences Timestamps: 7:24 – Tom’s epiphany and the eight pages of notes that started Backroads 10:15 – From cubicle to road bike: the solo trip that shaped the company’s DNA 12:46 – Trip #1: Making mistakes in Death Valley—and learning fast 24:47 – Tom’s DIY recovery operation after a warehouse burglary 29:21 – Cash without capital: spend your deposits, pay hotels later 30:55 – The Nevada rollover: walking out of the ER…and running the next trips 40:06 – Recovering after 9/11 and the financial crisis—and rebuilding the company’s value prop 45:46 – Post-COVID surge, and avoiding the tyranny of the travel selfie This episode was produced by Casey Herman with music by Ramtin Arablouei. It was edited by Neva Grant. Our audio 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

    51 min
  2. 12H AGO

    Babylist: Natalie Gordon. How a new mom used nap time to build a $500M business.

    In 2010, software engineer Natalie Gordon was pregnant– and fed up with the overwhelming baby aisles in big box stores.  So she quit her computer job to code the registry she wished existed. No pink-and-blue giraffes. No allegiance to a single store. Just a universal list that let friends give the real help that new parents need—from strollers to diaper services to dog-walking. Natalie coded the first lines of Babylist during her son’s nap time. She managed customer support, pitched bloggers from coffee shops, and learned growth the hard way—first through affiliates, then with a pivotal Pinterest bet, and finally by taking on her own inventory (and all the headaches that come with it). Along the way she wrestled with hiring, firing, fundraising, and the identity shift from founder to CEO. Today, Babylist is one of the most trusted parenting platforms in the U.S., with a retail arm, editorial content, and a program for providing breast pumps.  This is a masterclass in living a problem–and building a solution.  You’ll learn: How to spot a customer pain point and design an MVP around itThe power of slow viralityHow to use a small seed round without losing controlThe painful path from affiliate revenue to first-party e-commerceStumbles with hiring – and firing– as a first-time CEOHow paid growth works on visual platforms like PinterestHow “controlling your destiny” justifies a hard shift in business modelHow coaching and feedback helps you evolve from founder to leader Timestamps: 05:32 - Learning to solve hard problems at Amazon -08:28 - Sabbatical in Latin America: Natalie’s first (failed) business and what it taught her17:50 - A meltdown in a superstore → the Babylist “aha” moment19:40 - Designing a universal registry, dog-walking included24:42 - Blitzing the mommy blogs, a  “pregnant hacker” post on Hacker News30:01 - Why $140/month revenue felt like a victory39:18 - Going solo at an Accelerator, and the agony of early hiring and firing49:29 - From “slowly viral” to real scale, and how Pinterest helped58:09 - Affiliate links to in-house inventory → piles of bassinets in the office 1:01:57 - COVID’s unexpected windfall,  the health wedge (breast pumps & beyond) This episode was produced by Kerry Thompson with music by Ramtin Arablouei. It was edited by Neva Grant. Our audio 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.

    1h 8m
  3. 4D AGO

    Advice Line with Niraj Shah of Wayfair

    Wayfair co-founder Niraj Shah joins Guy on the Advice Line to answer questions from three early-stage entrepreneurs about how to bet on themselves – and define themselves to consumers. Plus, Niraj explains why Wayfair is expanding into large-format brick-and-mortar stores. First up, Valerie in Washington, D.C., is looking for a better way to educate consumers about her dehydrated chicken stock. Then, Bree in Utah wants to know when to seek investment in her improved mineral sunscreen brand. And finally, Tess in San Antonio is wondering if she should quit her day job and go all-in on her networking and accommodation app for solo women travelers. Thank you to the founders of Cookstix, Daily Shade, and HerHouse 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 go back and listen to Niraj’s original episode from 2018, where he shares how he and his college roommate Steve Conine turned 250 single-product websites into one giant billion-dollar brand. This episode was produced by Alex Cheng with music by Ramtin Arablouei. It was edited by Andrea Bruce. Our audio engineer was Cena Loffredo. 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.

    44 min
  4. OCT 27

    Nuts.com: Jeff Braverman. From Corner Store to Snacktime Powerhouse

    A century ago, Jeff Braverman’s grandfather opened a peanut shop in Newark, New Jersey. By the early 2000s, the family business was doing $1M in sales and struggling to stay afloat. Jeff had a high-paying job in finance, but walked away from it to reinvent the business. His strategy? The internet. Something his dad and uncle knew nothing about. What happened next is wild: an AdWords experiment that blew the doors off the budding online business; a slip on national TV where Rachael Ray accidentally renamed the company; 40,000 pounds of protest peanuts that crashed servers and landed them in the New York Times; a hilariously polarizing rap jingle; and a COVID surge that tested leadership—and humanity—every single day. This is the blueprint for transforming a dusty, low-margin business into a profitable, $100M+ direct-to-consumer brand—while keeping it family-owned. It’s also a masterclass in earning trust, making risky bets, and scaling without losing your soul. You’ll learn: The mechanics of a paid-search playbook that 10x’d orders overnightHow to win over skeptical family members (and when to demand the keys to the store)The exploding-deal etiquette of buying a premium domainHow an improvised rap-jingle can be stickier than a professional ad  How Nuts.com built a robust B2B business alongside DTCCrisis leadership lessons from the COVID floor When and how a leader should hire their replacement Timestamps: 00:07:08 — Cash registers, code words, and a Newark childhood inside the peanut shop00:13:42 — The “build a website” pitch at a Jersey diner 00:29:40 — December 4, 2003: from 3 orders/day to 30 00:31:19 — Dad panics –”shut it off!”– Jeff doubles down on demand and ops00:35:26 — Losing the storefront to a hockey arena—and going all-in online00:42:29 — Jericho fans send 40,000 lbs of peanuts to CBS: press, links, and leverage00:48:38 — Rachael Ray calls them “Nuts.com” by accident… and the $700k domain deal that followed01:00:51 — The notorious Nuts.com rap jingle: how an earworm took hold01:03:11 — Offices, microbreweries, and building a sticky B2B engine01:05:08 — COVID hits: 70% call-outs, factory safety, and leading from the floor01:10:18 — Handing the reins to a new CEO: leaning into strengths, not ego This episode was produced by Sam Paulson with music composed by Ramtin Arablouei. It was edited by Neva Grant with research help from Olivia Rockman. 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.

    1h 12m
  5. OCT 20

    Magnolia: Chip & Joanna Gaines. From House Flipping to Household Name

    What happens when a charismatic home renovator marries a budding design whiz? You get the billion-dollar powerhouse that is Chip and Joanna Gaines. The Gaines’ TV show Fixer Upper became a cultural obsession, turning shiplap and farmhouse sinks into a lifestyle movement that swept America. When they walked away from that show at peak popularity, everyone thought they were crazy. Instead, they turned their business Magnolia into a thriving lifestyle brand, which includes a network, retail, restaurants, books, and a magazine. The Silos, their Waco headquarters, became an unlikely tourist destination, drawing millions. Chip and Joanna proved that faith, small-town values and authentic storytelling could compete with coastal glitz. And they did it all while raising five kids.   You’ll learn: What Chip and Joanna saw in each other—as business and life partners.How a miserable semester in New York sparked the idea for Joanna’s first store.How the Gaines’ almost went bankrupt after the 2008 housing crash—and refused to quit. Why walking away from their TV show turned out to be a brilliant move.Why faith is as important as luck.Why betting on your hometown can be a superpower. Time Stamps: 3:30 Chip’s failed dream of becoming a pro baseball player—and the unexpected path that followed. 8:20 How running a laundry in college taught Chip the economics of entrepreneurship. 14:35 Joanna’s Korean-American childhood, identity struggles, and how a toxic newsroom internship changed the course of her life. 24:10 The day Chip walked into her dad’s tire shop—and never left. 35:10 How Joanna’s first $25 “sale” encouraged her to open the first Magnolia store. 45:15 The housing crash that nearly ended their renovation business—and how they scraped their way back. 55:15 The moment HGTV called—and why Chip thought it was a scam. 1:09:10 How saying “no” to Fixer Upper opened the door to owning their own network—and their future. 1:13:09 The cultural backlash and the lessons that came with becoming America’s most famous fixer-uppers. This episode was produced by Katherine Sypher with music composed by Ramtin Arablouei. It was edited by Neva Grant with research help from Chris Maccini. 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.

    1h 34m
  6. OCT 16

    Advice Line with Stacy Madison of Stacy’s Pita Chips

    Stacy’s Pita Chips co-founder Stacy Madison joins Guy on the Advice Line to answer questions from three early-stage entrepreneurs. Plus, Stacy talks about her hard-won experience of knowing when to stick with an idea… and when to walk away. First up, Sam wants to figure out how to leverage his popular pizza instagram account into the go-to place for men to learn how to bake. Then, Alex wants to know how to make his Peruvian pisco brand stand out in a relatively unknown liquor category. And finally, Stephanie is eager to learn how she can rejuvenate what had been her family’s 88-year-old candy business.  Thank you to the founders of Dough Guy, SUYO, and Stuckey’s 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 go back and listen to Stacy’s episode from 2019 where she shares how a decision to make chips with the leftover pita from her sandwich cart led to a multi-million dollar snack category that didn’t exist before her.  This episode was produced by Rommel Wood with music by Ramtin Arablouei. It was edited by Andrea Bruce. Our audio engineer was Robert Rodriguez.  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.  See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

    55 min

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About

Guy Raz interviews the world’s best-known entrepreneurs to learn how they built their iconic brands. In each episode, founders reveal deep, intimate moments of doubt and failure, and share insights on their eventual success. How I Built This is a master-class on innovation, creativity, leadership and how to navigate challenges of all kinds. New episodes release on Mondays and Thursdays. Listen to How I Built This on the Wondery App or wherever you listen to your podcasts. You can listen early and ad-free on Wondery+. Join Wondery+ in the Wondery App, Apple Podcasts or Spotify. Start your free trial by visiting wondery.com/links/how-i-built-this now. Get your How I Built This merch at WonderyShop.com/HowIBuiltThis.

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