Hemingways’ Car Trouble Sparked a Travel Guide Business For This Writer

Travel can spark unexpected businesses, and Taylor Bruce started his after hunting for stories in Key West. His story, as told to Ashlea Halpern:
I was a writer and an editor for about eight years, at magazines like Budget Travel and Southern Living. Eventually I got bored; the people and places that fascinated me weren’t the ones my bosses wanted to feature. In 2008, for example, I was reporting a story on Arcadia and passed a house in Montgomery, La., painted top to bottom with folk art. I pulled over, knocked on the door and spent four hours hanging out with Juanita, who had lived in this small town her whole life. I would never forget her story, but it didn’t fit into any magazine I knew of. 
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In 2010, I took a break to get my MFA at Brooklyn College; I wanted to . But a year later, while in the Florida Keys, new struck. My wife and I were trying to sleuth out the real Key West, reading on Wikipedia about how Ernest Hemingway’s car broke down here in the 1930s. He was stuck for three weeks. Little stories like that make a place go from “tourist destination” to getting into your bones. I decided to put down my novel and make the kind of travel guidebooks I wish existed instead — with stories as the driving force. I wanted to help people feel a place. I called them . 
For the first book, I picked a city I knew well: Nashville. I called two fiction-writer friends and asked for long-form writing that would never live in a travel magazine. J. Wes Yoder wrote about his fear of snakes, and Tony Earley wrote about raising his two adopted daughters in East Nashville, weaving in the history of the neighborhood — from Jesse James to minor league baseball. I asked dozens of locals for recommendations of the best, most unique things to do. The reporting took three months. Then I had the book illustrated, which is cheaper to print than full-color photographs — but also classic and timeless.
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A month before the Nashville guide went to print, I started full-time at a large New York branding agency. I’d been funding Wildsam out of personal savings, so I needed the money. I also wanted to learn how to .
When 2,000 copies of the Nashville guide arrived at my 500-square-foot New York City apartment in October 2012, distribution was my first big hurdle. I called Nashville stores I loved the most, and whose owners I knew: Imogene + Willie, Billy Reid and Parnassus. They put the books in their stores, and others followed. I also put up a basic website for online sales. We sold out in four months. Locals were buying just as much as travelers — not something I expected. I repeated the process for books in Austin and San Francisco, working nights and weekends for nine months. 
Then a cryptic email arrived from J. Crew: “We’ve seen your guides and would like to talk about a project.” A month later, I was sitting with J. Crew’s global marketing team, discussing a J. Crew x Wildsam neighborhood-guide series, pegged to the opening of their new London stores. They accepted my proposal, and I turned in my two-week notice. Wildsam was now a full-time job.
The J. Crew project gave me a year’s runway, and a new model for . Since then, I’ve done collaborative projects for Helm Boots, Shinola and Bonobos. We partnered with Lincoln Motor Company on a Detroit book, which sold out 3,000 copies in three months. 
We now have eight city guides, which sell for $17.95 each; Los Angeles will be our ninth, plus two road-trip books — New England and the Desert Southwest. We sell in 150 stores and have had short runs in Urban Outfitters and Anthropologie. We’ve grown to a team of four people. In 2017, we’re going to launch second editions of some of our books and explore running single-page illustrated ads.
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Today, my biggest challenge is wanting to do too much — products, an event series, a promotional tour. The greatest lesson I learned at that branding agency was to . Create clarity. What makes us special is our time on the ground, having another conversation and staying at the city archives just one hour longer. Sometimes you have to turn off the ideas faucet and dig into what really sets your brand apart.