Advice Line with Christina Tosi of Milk Bar

Advice Line with Christina Tosi of Milk Bar

Today’s callers: Whitney in Utah  wonders how to bridge the gap between pre-seed and institutional investment for her fitness/retail combo space. Then Chloe in the U.K. considers which markets to target for her at-home crafting kits. And Christy in Washington wants to convert gifters into repeat customers for her coffee flavoring brand. Plus, Christina’s take on why Milk Bar is better served with her as Chief Experimenter rather than Chief Executive.   Thank you to the founders of The Beau Collective, Cotton Clara, and Vashon Island Coffee Dust.  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 [hibt@id.wondery.com] or call 1-800-433-1298.  And be sure to listen to the story of how Christina founded Milk Bar [https://art19.com/shows/831bd173-0992-41b7-b1eb-112db904d947/episodes/e30b17f9-3ecb-493a-8880-f30efd9290b0/embed] from our episode back in 2019. This episode was produced by J.C. Howard with music by Ramtin Arablouei. It was edited by John Isabella. Our audio engineer was Jimmy Keeley. You can follow HIBT on Twitter [https://twitter.com/HowIBuiltThis] & Instagram [https://www.instagram.com/howibuiltthis] and sign up for Guy's free newsletter at guyraz.com [http://guyraz.com/] and on Substack [https://guyraz.substack.com/]. See Privacy Policy at https://art19.com/privacy [https://art19.com/privacy] and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info [https://art19.com/privacy#do-not-sell-my-info].

Shopify: Tobias Lütke. How a snowboarder built a $150 billion business (2019)

In 2004, German programmer Tobias Lütke was living in Ottawa with his girlfriend. An avid snowboarder, he wanted to launch an online snowboard shop, but found the e-commerce software available at the time to be clunky and expensive. So he decided to write his own e-commerce software. After he launched his online snowboard business, called Snowdevil, other online merchants were so impressed with what he built that they started asking to license Tobi's software to run their own stores. Tobi and his co-founder realized that software had more potential than snowboards, so they launched the e-commerce platform Shopify in 2006. Since then, it has grown into a publicly-traded company with over 7,000 employees and $11 billion in revenue. Timestamps:  * 07:20 - Tobi discovers snowboarding–and meets his future wife–on vacation in Canada * 11:25 - Building a new kind of snowboarding company * 29:35 - Pivot point: skateboards or software? * 34:25 - The night before Tobi’s wedding, Shopify switches business models * 45:25 - The 2008 financial crisis hits… revealing a huge opportunity  * 58:55 - After a decade, Shopify goes public This episode was produced by Casey Herman with music composed by Ramtin Arablouei. It was edited by Neva Grant. This archive episode was produced by Katherine Sypher. Follow How I Built This: Instagram → @howibuiltthis [https://www.instagram.com/howibuiltthis/] X → @HowIBuiltThis [https://x.com/howibuiltthis] Facebook → How I Built This [https://www.facebook.com/howibuiltthis] Follow Guy Raz: Instagram → @guy.raz [https://www.instagram.com/guy.raz/] Youtube → guy_raz [https://www.youtube.com/channel/UCNSfrxNEmCruNtjIzxCBHjg] X → @guyraz [https://x.com/guyraz] Substack → guyraz.substack.com [http://guyraz.substack.com] Website → guyraz.com [http://guyraz.com] See Privacy Policy at https://art19.com/privacy [https://art19.com/privacy] and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info [https://art19.com/privacy#do-not-sell-my-info].

Advice Line with Tim Ferriss (August 2025)

Entrepreneur, author, and podcaster Tim Ferriss joins Guy on the Advice Line to answer questions from three early-stage founders. Plus, Tim shares the inspiration behind his latest venture, Coyote—a 10-minute card game that encourages time spent with friends and family. First, Lauryn from San Francisco asks about the best way to scale her biodegradable ear plugs in two very different directions. Then Emily from Kansas City weighs whether DTC or wholesale is where to focus her accessory brand after Taylor Swift wore one of her rings and sales exploded. And finally, Kimberly in Woolwich, Maine wonders how to incentivize her customers to pre-order her high-quality, sustainable, clothing.  Thank you to the founders of GOB, EB & Co, and K. Becker Designs 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 [hibt@id.wondery.com] or call 1-800-433-1298. And be sure to listen to Tim Ferriss’s founding story [https://art19.com/shows/831bd173-0992-41b7-b1eb-112db904d947/episodes/ad5b84a9-ae91-450d-aee1-1e431d2bfa57/embed] as told by Tim on the show in 2020.  This episode was produced by Noor Gill with music by Ramtin Arablouei. It was edited by Andrea Bruce. Our audio engineer was Cena Loffredo. You can follow HIBT on X [https://x.com/HowIBuiltThis] & Instagram [https://www.instagram.com/howibuiltthis/] and sign up for Guy's free newsletter at guyraz.com [http://guyraz.com/] and on Substack [https://guyraz.substack.com/]. See Privacy Policy at https://art19.com/privacy [https://art19.com/privacy] and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info [https://art19.com/privacy#do-not-sell-my-info].

UGG: Brian Smith. How an epiphany, surfers, and $500 launched an iconic sheepskin footwear company.

In 1978, Brian Smith quit his accounting job in Australia and headed to California with a surfboard, some savings, and ambition. He figured California was where he’d find an idea or a product to bring back home to Australia to build a business. A year in, he was still looking. But then he saw an advertisement in a surfing magazine for Australian sheepskin boots. Uggs were so widespread in Australia at the time, the name was a generic term - like flip flops - not a brand. Brian was immediately stoked: these boots were virtually unknown in America. If he could get ugg boots for sale in the U.S., they would be a huge success! Almost nobody else agreed. For years, Brian lived on the edge of collapse. He sold boots from the back of his van and worked construction and golf course maintenance jobs to survive. Retailers laughed him out of stores. He lost control of his company twice. At one point, he literally crawled across the floor from stress, ready to walk away forever. And yet…he kept going. What followed was one of the most unlikely brand-building stories in modern retail history — involving surf culture, trademark wars, miraculous timing, brutal financing mistakes, and a product the fashion world initially dismissed. Today, UGG generates more than $2.5 billion a year in sales. You’ll hear how Brian: * Turned rejection into problems to solve * Discovered marketing insights that changed UGG forever * Survived years of cash-flow disasters * Lost control of the company and regained it a couple of times. * Used surf culture to build an emotional connection with customers * Nearly quit… over and over again… * And how he eventually sold UGG to footwear giant, Decker Timestamps: * 09:51 Brian's eureka moment that led to the birth of UGG * 12:41 The first sales trip results in ZERO sales * 21:10 The mantra that kept Brian going while doing odd summer jobs to survive * 28:32 Brian gets a critical lesson in marketing…from some 12-year-old kids * 51:59 Brian’s most effective strategy for retail: the “Six-Pair Stocking Plan” * 56:42 On track to regain his ownership - Brian hits a huge snag * 01:01:57 A midnight phone call from Australia saves the business * 01:11:28 Brian gets the last laugh in the trademark dispute - and acquires a boot factory * 01:14:54 Pamela Anderson wears UGGs on the set of Baywatch * 01:23:39 A chance meeting in the Atlanta airport leads to a deal to sell UGG This episode was researched and produced by Casey Herman, with music by Ramtin Arablouei, and edited by Andrea Bruce. Follow How I Built This: Instagram → @howibuiltthis [https://www.instagram.com/howibuiltthis/] X → @HowIBuiltThis [https://x.com/howibuiltthis] Facebook → How I Built This [https://www.facebook.com/howibuiltthis] Follow Guy Raz: Instagram → @guy.raz [https://www.instagram.com/guy.raz/] Youtube → guy_raz [https://www.youtube.com/channel/UCNSfrxNEmCruNtjIzxCBHjg] X → @guyraz [https://x.com/guyraz] Substack → guyraz.substack.com [http://guyraz.substack.com/] Website → http://guyraz.com/guyraz.com [http://guyraz.com] See Privacy Policy at https://art19.com/privacy [https://art19.com/privacy] and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info [https://art19.com/privacy#do-not-sell-my-info].

Advice Line with Jeffrey Hollender of Seventh Generation

Today’s callers: Kristina in Ohio looks for avenues beyond organic social media to market her furniture designed for toddlers and parents alike. Then Phil in Michigan considers the best messaging to brew interest in his farm-made cherry vinegar. And Caroline in California scouts new ways to cultivate curiosity around her plant-based dog food. Plus, Jeffrey discusses the quiet momentum of social businesses as they navigate ‘greenhushing’ and a polarized political climate. Thank you to the founders of Twenty Five and Pine, Red Truck Orchards, and Petaluma 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 [hibt@id.wondery.com] or call 1-800-433-1298. And be sure to listen to Seventh Generation’s founding story [https://wondery.com/shows/how-i-built-this/episode/10386-seventh-generation-alan-newman-and-jeffrey-hollender/] as told by Jeffrey and his co-founder Alan in 2021. This episode was produced by Sam Paulson with music by Ramtin Arablouei. It was edited by John Isabella. Our audio engineer was Jimmy Keeley. You can follow HIBT on X [https://x.com/HowIBuiltThis] & Instagram [https://www.instagram.com/howibuiltthis/] and sign up for Guy’s free newsletter at guyraz.com [http://guyraz.com/] or on Substack [https://guyraz.substack.com/]. See Privacy Policy at https://art19.com/privacy [https://art19.com/privacy] and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info [https://art19.com/privacy#do-not-sell-my-info].