Shep and Ian Murray: Vineyard Vines. A Stale Product Transforms into a Lifestyle Brand.
How I Built This with Guy Raz
Guy Raz | Wondery
4.7 • 31.4K Ratings
🗓️ 27 April 2026
⏱️ 69 minutes
🧾️ Download transcript
Summary
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.
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Transcript
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| 1:19.9 | The reality is, you know, you're standing in a parking lot on the side of the road, |
| 1:23.5 | putting on your tie, putting on, you know, we were like salesmen, you know, going into a place in the pouring rain, you know, in the fall, each day it got colder |
| 1:28.3 | and wetter and rainier. And each day, there were more nose. And like, what we found was we |
| 1:34.3 | didn't know the business and we needed to learn the business. And it was tough. |
| 1:55.8 | Welcome to How I Built This, a show about innovators, entrepreneurs, idealists, and the stories behind the movements they built. |
| 2:03.7 | I'm Guy Raz, and on the show today, how two brothers ditched their day jobs to sell neckties and built an entire brand around beach culture and The Good Life, Vineyard Vines. |
| 2:13.1 | In the late 1990s, neckties weren't exactly a growth industry. |
| 2:18.8 | Offices were getting more casual. |
... |
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