In the late 1990s, Shep and Ian Murray looked at a shrinking category–men’s ties–and saw an opportunity: a necktie isn’t just functional. It’s expressive. It can signal identity, taste, aspiration. With no fashion experience and no outside investors, the Murray brothers started making colorful ties inspired by their childhoods in Martha’s Vineyard — tiny whales, sailboats, island street signs. What began as a small, improbable tie business grew into Vineyard Vines: a half-billion-dollar lifestyle brand with more than 100 stores and major department store distribution. In this episode, Shep and Ian talk about why they quit their stable jobs to turn a sleepy product into a national brand, which began as a family business and remains so to this day. What you’ll learn: Why a great business can start in a category that everyone thinks is dying How to build distribution when you have no roadmap and few connections What bootstrapping teaches founders that outside capital often doesn’t How improvised marketing can create outsized attention Knowing the difference between a fashion brand and a “brand” brand Timestamps: 00:10:22 - The brothers both hate their desk jobs: “How was your day?” “It sucked.” 00:11:20 - Vineyard Vines starts on a family trip, with a nudge from a hotel manager 00:13:46 - Early designs: whales, fish, jeeps, street signs 00:25:39 - Finally quitting their jobs– they’re thrilled, their parents–not so much 00:30:42 - Landing their first order for $1800. “We’re never gonna have to work anymore!” 00:34:40 - The brand gets a boost from a PR stunt during the Clinton-Lewinsky scandal 00:47:00 - The “Get to $5 million” mentor advice that kept them focused 00:49:23 - The brothers open their first store - and realize they have a lot to learn 01:01:18 - The 2008 financial crisis, and the brutal inventory decisions that help save the business 01:09:06 - Why stepping back from the CEO role didn’t work — and what it taught them about brand culture This episode was produced by Kerry Thompson with music composed by Ramtin Arablouei. It was edited by Neva Grant with research help from Casey Herman. 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.