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.&nbsp;&nbsp;&nbsp;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.&nbsp;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.&nbsp;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.&nbsp;What you’ll learn:&nbsp;<ul><li>Why a great business can start in a category that everyone thinks is dying</li><li>How to build distribution when you have no roadmap and few connections&nbsp;</li><li>What bootstrapping teaches founders that outside capital often doesn’t</li><li>How improvised marketing can create outsized attention</li><li>Knowing the difference between a fashion brand and a “brand” brand</li></ul>Timestamps:&nbsp;<ul><li>00:10:22 - The brothers both hate their desk jobs: “How was your day?” “It sucked.”</li><li>&nbsp;00:11:20 - Vineyard Vines starts on a family trip, with a nudge from a hotel manager</li><li>00:13:46 - Early designs: whales, fish, jeeps, street signs&nbsp;</li><li>00:25:39 - Finally quitting their jobs– they’re thrilled, their parents–not so much</li><li>00:30:42 - Landing their first order for $1800. “We’re never gonna have to work anymore!”</li><li>00:34:40 - The brand gets a boost from a PR stunt during the Clinton-Lewinsky scandal</li><li>00:47:00 - The&nbsp;“Get to $5 million” mentor advice that kept them focused&nbsp;</li><li>00:49:23 - The brothers open their first store - and realize they have a lot to learn&nbsp;&nbsp;</li><li>01:01:18 - The 2008 financial crisis, and the brutal inventory decisions that help save the business</li><li>01:09:06 - Why stepping back from the CEO role didn’t work — and what it taught them about brand culture</li></ul>This episode was produced by Kerry Thompson with music composed by Ramtin Arablouei. It was edited by Neva Grant with research help from Casey Herman.&nbsp;Follow How I Built This:Instagram → <a href="https://www.instagram.com/howibuiltthis/" rel="noopener noreferrer" target="_blank">@howibuiltthis</a>X → <a href="https://x.com/howibuiltthis" rel="noopener noreferrer" target="_blank">@HowIBuiltThis</a>Facebook → <a href="https://www.facebook.com/howibuiltthis" rel="noopener noreferrer" target="_blank">How I Built This</a>Follow Guy Raz:Instagram → <a href="https://www.instagram.com/guy.raz/" rel="noopener noreferrer" target="_blank">@guy.raz</a>Youtube →<a href="https://www.youtube.com/channel/UCNSfrxNEmCruNtjIzxCBHjg" rel="noopener noreferrer" target="_blank"> guy_raz</a>X → <a href="https://x.com/guyraz" rel="noopener noreferrer" target="_blank">@guyraz</a>Substack →<a href="https://urldefense.com/v3/__http:/guyraz.substack.com__;!!Iwwt!RZoD751oWzUzoqqdJiqaoL6HdJfRHDUO1TKvYJ424d3Udn7-Pw9Nj6nEsauh9zcgEvLjUEc$" rel="noopener noreferrer" target="_blank"> </a><a href="http://guyraz.substack.com" rel="noopener noreferrer" target="_blank">guyraz.substack.com</a>Website →<a href="https://urldefense.com/v3/__http:/guyraz.substack.com__;!!Iwwt!RZoD751oWzUzoqqdJiqaoL6HdJfRHDUO1TKvYJ424d3Udn7-Pw9Nj6nEsauh9zcgEvLjUEc$" rel="noopener noreferrer" target="_blank"> </a><a href="http://guyraz.com" rel="noopener noreferrer" target="_blank">guyraz.com</a>See Privacy Policy at <a href="https://art19.com/privacy" rel="noopener noreferrer" target="_blank">https://art19.com/privacy</a> and California Privacy Notice at <a href="https://art19.com/privacy#do-not-sell-my-info" rel="noopener noreferrer" target="_blank">https://art19.com/privacy#do-not-sell-my-info</a>.

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Shep and Ian Murray: Vineyard Vines. A Stale Product Transforms into a Lifestyle Brand.

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