How I Built This with Guy Raz

On a trip to Las Vegas, Chris Riccobono found himself wearing the same J.Crew shirt over and over; it was the only dress shirt he had that looked good untucked. All of his other button-downs were too long and looked sloppy. His buddies all said they had the same problem, so Chris decided to seize the opportunity and launch UNTUCKit with a friend. Keeping his day job as a GE salesman, he embarked on a crash course in how not to make a shirt. Thousands of defective button-downs later, UNTUCKit hit its stride, and the big fashion brands began to copy the untucked look. In 2020, UNTUCKit came within inches of a lucrative acquisition, then nearly went bankrupt, but today has grown into a thriving brand. This episode was produced by J.C. Howard, with music by Ramtin Arablouei. Edited by Neva Grant, with research help from Kerry Thompson. You can follow HIBT on Twitter & Instagram, and email us at hibt@id.wondery.com. 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.

Serial entrepreneur Marcia Kilgore — founder of brands like Beauty Pie and Soap & Glory — joins Guy on the Advice Line, where they answer questions from three early-stage founders managing uncertainty and risk. Today, we meet Victor in Fort Worth, the co-founder of a Mexican-style sweets and treats venture who wonders if he should focus on expanding brick-and-mortar operations, retail presence, or both. Then Lydia in Seattle, a former disease researcher who is ready to grow her small batch botanical skincare line, but needs help overcoming her fear of failure to get to the next step. And Jack in San Francisco, the founder of a custom bike bag and accessories brand who’s trying to figure out how to maintain customer excitement throughout the entire purchasing process so as not to lose momentum. Thank you to the founders of Sol Dias, Clērstory, and Wompy Bikes for being 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 Marcia Kilgore’s original How I Built This episode as told by Marcia on the show in 2018. This episode was produced by Carla Esteves 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. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

The dashboard in your car – the interface on your Zoom screen … many of the products we interact with every day were created with the collaborative software Figma. Figma is a kind of Google Docs for design, created by Dylan Field and Evan Wallace after they won a Thiel fellowship in 2012. Dylan was just 20 when he became CEO. The only other job he’d had before that….? was college intern. He eventually figured out how to manage his team, and grew the company enough to attract a 20 billion dollar acquisition bid from Adobe. The deal fell through, but Figma continued to grow, and recently filed for an IPO. This episode was researched and produced by Kerry Thompson with music composed by Ramtin Arablouei. It was edited by Neva Grant. Our engineers were Patrick Murray and Jimmy Keeley. You can follow HIBT on X & Instagram, and email us at hibt@id.wondery.com. 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.

Kickstarter co-founder Perry Chen joins Guy on the Advice Line, where they answer questions from three early-stage founders about what they really want from investment deals and acquisitions. Today we meet Jesse in Dallas, who's debating whether or not he should sell part or all of his cold plunge tub business. Then Catharine in Oregon, who's trying to figure out how to move on from the daily grind of her hot sauce brand. And Joe in Chicago, who has an ambitious vision for his chicken sandwich chain. Thank you to the founders of Modtub, HYCH, and Fry the Coop 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 Kickstarter’s founding story as told by Perry on the show in 2017. This episode was produced by Alex Cheng with music by Ramtin Arablouei. It was edited by Andrea Bruce. Our audio engineer was Neal Rauch. 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.

Bill and Leigh Keith had an extraordinary childhood, travelling the country in a school bus with their parents and ten siblings. Along the way, their dad fed them a homemade concoction of peanut butter, honey and supplements rolled into bite-sized snacks. When the family fell on hard times, the older siblings decided to sell their home and bet everything on turning their family recipe into a refrigerated energy bar. The family hand-rolled millions of bars and gave out samples at festivals and grocery stores in Northern California. They eventually got Perfect Bars into Whole Foods, Costco, and major retailers throughout the country, and in 2019, the company was acquired by Mondelēz International. This episode was researched and produced by Chris Maccini with music by Ramtin Arablouei. Edited by Neva Grant. Our engineers were Kwesi Lee and Ko Takasugi-Czernowin. You can follow HIBT on X & Instagram, and email us at hibt@id.wondery.com. Sign up for Guy’s free newsletter at guyraz.com. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Sir Kensington’s co-founder and former CEO Mark Ramadan joins Guy on the Advice Line, where they work through business challenges with three early-stage founders. Today we meet Pat, a physician assistant working to bring his solution for clogged sinks to major retailers. Then Lucas, a chef whose local quick service taco joint is fending off national competition. And Beth, a working mom whose baby products brand is caught in the "messy middle" between launch and mass scale. 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 to hear the story of how Sir Kensington’s was founded, check out Mark's first appearance on the show in 2023. This episode was produced by Sam Paulson 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.

In 2008, Vicky Tsai walked away from a startup job and set out to rediscover herself on a trip to Japan. In Kyoto, she had an unforgettable meeting with a geisha, and learned about the face creams and blotting papers that the traditional Japanese hostesses had used for centuries. But as she contemplated selling those products in the U.S., experts on both sides of the Pacific told her it would never work. Strapped for money and juggling multiple jobs, Vicky worked out of her parents' garage, pitching her new brand—Tatcha—on QVC and steadily growing it. In 2019, Unilever acquired Tatcha for a reported $500 million. This episode was produced by Jed Anderson with music composed by Ramtin Arablouei. It was edited by Neva Grant. You can follow HIBT on X & Instagram, and email us at hibt@id.wondery.com. 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.

Springfree Trampoline founder Steve Holmes joins Guy on the Advice Line, where they answer questions from three early-stage entrepreneurs. Plus, Steve’s tariff navigation guidance for businesses manufacturing products outside of the U.S. First we meet Ikechukwu in Maryland, who’s trying to lean into a core demographic without alienating customers from his activewear brand. Then Cody in Nevada, who’s building a year-round advertising strategy for a largely seasonal product: DEET-free bug repellant. And Kenesha in Ontario, who’s looking to maintain the momentum of a viral moment for her Caribbean-inspired chocolate. Thank you to the founders of Veii Apparel, Grand Tongo, and One More Cocoa 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 Springfree Trampoline’s founding story as told by Steve and the trampoline’s inventor Keith on the show in 2019. This episode was produced by Sam Paulson with music by Ramtin Arablouei. It was edited by John Isabella. Our audio engineer was Gilly Moon. 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.

As a young entrepreneur in the Wild West days of the internet, Alex Tew was drawn to meditation for its simple calming power. Together with fellow tech founder Michael Acton Smith–known for hits like Moshi Monsters–the two brainstormed ways to bring the ancient practice of meditation into the 21st century. In 2011, they bought the domain calm.com, built an app, and started producing meditations and Sleep Stories, narrated by celebrities like Matthew McConaughey and Idris Elba. Despite initial pushback from investors who insisted no one would want to meditate on their phone–let alone pay for it– the Calm app grew to a valuation of nearly $2 billion, with 180 million total downloads. This episode was researched and produced by Katherine Sypher with music composed by Ramtin Arablouei. It was edited by Neva Grant. Our engineers were Patrick Murray and Robert Rodriguez. You can follow HIBT on X & Instagram, and email us at hibt@id.wondery.com. 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.

This week, Guy is joined by Travis Boersma of Dutch Bros. Coffee, Michael Preysman of Everlane and Chris Ruder of Spikeball in a special “mashup” episode of Advice Line. First, Andy from Nashville is wondering if a brick and mortar burger joint will supercharge growth for his food truck business. Then, Tiffany from Cape Cod is looking to break into large retailers with her inspirational jewelry brand. And finally, Peter from South Dakota is evaluating whether to expand his ice skating apparel to overseas markets. Thank you to the founders of Bad Luck Burger Club, T. Jazelle and Rink Rabbit. 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. This episode was produced by Kerry Thompson 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 or on Substack. To hear our guests previous episodes: Dutch Bros. Coffee: Travis Boersma | Advice Line with Travis Boersma Everlane: Michael Preysman | Advice Line with Michael Preysman Spikeball: Chris Ruder | Advice Line with Chris Ruder See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Western wear is having a moment – and so is the upstart Western brand Tecovas. Founder Paul Hedrick is a Texan who realized that cowboy boots were either too expensive or too cheap, so he decided to create a premium brand with an attainable price. He traveled repeatedly to the cowboy boot capital of the world – León, Mexico – to obsess over every detail, and later he expanded his DTC business to make a surprising bet on brick-and-mortar stores. Today, beyond boots, Tecovas sells jeans, shirts, dresses, hats, and bags, and this year, the company expects to do more than $300 million in sales. This episode was produced by Alex Cheng with music composed by Ramtin Arablouei. It was edited by Neva Grant with research help from Iman Maani. Our engineers were Patrick Murray and Robert Rodriguez. You can follow HIBT on X & Instagram, and email us at hibt@id.wondery.com. 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.

Rivian founder and CEO RJ Scaringe joins Guy on the Advice Line to answer questions from three early-stage founders. He also gets into how trade policies and shifting tariffs are impacting the automotive supply chain. First, we meet Ashley from Southern California, who’s deciding whether to take outside capital to take her altruistic ice cream brand worldwide. Next, Kwadwo in North Carolina is debating leaving his full-time job to go all in on his handcrafted furniture brand. Then Robert in British Columbia is looking to grow his backcountry skiing invention beyond the early adopters. Thank you to the founders of Vedder’s Organic Ice Cream, Crafted Glory and Zoa Engineering for being part of the 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 Rivian's founding story as told by RJ on How I Built This in 2022. This episode was produced by Iman Maani. 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.

Substack was founded to create an escape vehicle for writers: Chris Best and Hamish McKenzie imagined a world where writers didn’t have to rely on legacy publications or corporate advertisers, but could instead create a more direct and meaningful relationship with their audience. Despite early skepticism, Chris and Hamish were confident that many people would pay a few dollars a month to subscribe to their favorite newsletters, on subjects ranging from politics to sports to tech. Today, Substack has over 35 million active users, and while many of its offerings are free, a number of its content-creators make upwards of $500,000 a year. This episode was produced by J.C. Howard, with music by Ramtin Arablouei. Edited by Neva Grant, with research help from Iman Maani. You can follow HIBT on Twitter & Instagram, and email us at hibt@id.wondery.com. 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.

Virgin Group founder Richard Branson joins Guy on the Advice Line, where they answer questions from three early-stage founders. Plus, Richard’s recent adventures in bungee jumping, ziplining, space exploration and more—all in the name of promoting some of his brand’s latest offerings. First we meet Lola from New York City, who’s looking to maintain a personal touch as she scales her travel accessory brand. Then Ross from Phoenix, who’s wondering how to make a splash with his above-ground pool rental business. And Andrew from Cumberland Gap, Tennessee, who wants to start selling his small-batch granola in locations beyond his juice bar. Thank you to the founders of Silver & Riley, Now Pools, and The Juice Spot/Lone Wolf Granola 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 Virgin's founding story as told by Richard Branson on How I Built This in 2017. This episode was produced by Chris Maccini 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. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Brad Baxter sidelined a promising career in the car industry to build a better cat litter box – an undertaking that embarrassed his kids and eventually prompted his wife to ask "what’s the endgame here?” That endgame turned out to be Litter-Robot, an automated self-cleaning litter-remover that helped propel Brad’s company, Whisker, to roughly $300 million in sales this year. This episode was produced by Sam Paulson with music composed by Ramtin Arablouei. It was edited by Neva Grant with research by Carla Esteves. Our engineers were Patrick Murray and 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.

Duolingo co-founder Luis von Ahn joins Guy on the Advice Line to answer questions from three early-stage founders. Plus, Luis shares insights on how data can help entrepreneurs understand what their customers really want. First, Steph in Chicago wonders how to manage expansion opportunities for her art-filled vending machines. Then Blair from Atlanta discusses his challenge of selecting which products to focus on with his tech accessories brand. And finally, Stephanie in Indiana considers the best way to fund more employees for her growing business designing living plant walls. Thank you to the founders Good Things Vending, Bair, and Naturspire 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 Duolingo’s founding story as told by Luis on the show in 2020. This episode was produced by Katherine Sypher with music by Ramtin Arablouei. It was edited by Casey Herman. 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.

Cookware is a $73 billion global industry - awash in all kinds of pots and pans. Like, if you’ve ever cooked scrambled eggs, you've probably used a non-stick frying pan. They’re inexpensive and everywhere. But they’ve been dogged by complaints: many can’t handle high heat, like broiling or searing, and they scratch easily. So, when Danny Winer came across a new non-stick technology at a trade show overseas, he jumped on it, co-founding Hexclad with a buddy. Danny was convinced it could be adapted to the U.S. market - and be a hit. He was right! In just under ten years, Hexclad grew into a $500 million company. This episode was produced by Kerry Thompson, with music by Ramtin Arablouei. It was edited by Andrea Bruce, with research help from Katherine Sypher. Our engineers were Jimmy Keeley and Gilly Moon. You can follow HIBT on Twitter & Instagram, and email us at hibt@id.wondery.com. 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.

Sweetgreen’s co-founder Jonathan Neman joins Guy on the Advice Line to answer questions from three early-stage founders. Plus, Sweetgreen’s plans to automate salad assembly in the coming years. First, we meet Dini from Maryland, who's learning how to maintain her brand’s character and product quality as her pie company scales. Next we hear from Matt in Massachusetts, who’s leaning into success growing premium mushrooms for local chefs without getting too big, too fast. Then Joey in Chicago, owner of a restaurant specializing in fried chicken wings and fresh-cut fries, who’s deciding whether to introduce new products or double down on what’s already working. Thank you to the founders of Dini’s Divine Pies, Underground Mushroom Co. and Dak Dak Korean Wings for being part of the 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 to hear the founding story of Sweetgreen, check out Jonathan’s first appearance on the show in 2020. This episode was produced by Iman Maani. It was edited by Casey Herman. 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.

What started as a design project for Stanford student Evan Spiegel quickly flourished into one of the most-used social media platforms in the world: Snapchat. It only took two years for Mark Zuckerberg to make a multi-billion offer for the company. But Evan turned it down — convinced of Snap’s potential to disrupt human communication in an even bigger way. And while Evan’s path has been anything but smooth, today Snap is valued at more than $13 billion, with ambitions beyond its hero mobile app. This episode was produced by Alex Cheng with music composed by Ramtin Arablouei. It was edited by John Isabella with research help from Katherine Sypher. Our engineers were Patrick Murray and Gilly Moon. You can follow HIBT on X & Instagram, and email us at hibt@id.wondery.com. 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.

Bonobos co-founder Andy Dunn joins Guy on the Advice Line to answer questions from three early-stage founders. Plus, Andy shares the motivation for his latest venture, Pie—a new social app that fosters in-person friendships and experiences. First, Michele in Connecticut asks about the best way to position her tennis-inspired athletic brand. Then Alek from Chicago, who’s wondering how to reach more health-conscious drinkers with his naturally-flavored vodka. And finally, Sabrina in Philadelphia weighs whether a DTC or wholesale strategy is best for her handmade biscotti. Thank you to the founders Top Banana, Broda Beverage Company and Haus of Biscotti 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 Bonobos’ founding story as told by Andy on the show in 2019. 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.