Harvest Hosts owner Joel Holland, a transplant who runs his business from the Vail Valley

Joel Holland was burned out, even though, by many measures, he had it made. At 17, he’d founded a Northern Virginia tech company that later grew to 100 employees. Young and committed but without kids to tie him down, Holland basked in his entrepreneurial success. “It was really cool,” he says, “until it wasn’t. I got tired of being in the city and the traffic and sitting in a cubicle. After a while, it was just soul-sucking.”

Holland sold the company and, with his partner, a veterinarian (now his wife), bought an RV. They spent the next two years visiting every state in the Lower 48, ultimately landing in Vail in 2016. He played for a year—until that, too, lost its luster. Intrigued by the nomadic lifestyle, Holland contacted the owners of Harvest Hosts, a sort of Airbnb for the #vanlife crowd that provides members with places to park their rigs overnight. He asked if they would consider selling and allowing him to take their business to the next level. They struck a deal in 2018. “I wanted to prove that you really could build and run a business from anywhere,” he says—i.e., Vail.

Harvest Hosts’ revenue grew tenfold in the first two years, unintentionally becoming a leader in the Vail Valley’s newest demographic of movers and shakers, which has exploded since the pandemic began early in 2020: tech and finance CEOs with global influence who steer their businesses from the heart of ski country. Some were already second homeowners who relocated full time. Others realized, like Holland had, that city living actually cost more and delivered a lower quality of life. “I know everyone says Vail is the most expensive place to live, but my wife and I saved a ton of money moving to Vail from Arlington, Virginia,” says Holland, who is 36. “Our house was half the price, and we don’t have to pay $1,000 a month in Uber bills anymore.”

What’s more, after an initial dip in membership and site traffic last spring, Harvest Hosts seized on road-trippers’ pandemic wanderlust, spent $1 million on Facebook ads, and doubled its membership in five months. In January, the company raised $37 million in funding to continue its expansion. “It’s become a meaningful company, and one of the things I’m most proud of is that it’s being done in Vail, Colorado,” Holland says.

Drummond Road Capital founder and CEO Morris Wheeler says, "The biggest challenge is that people who aren’t here are stuck on the fairy tale."

Morris Wheeler can relate to the balance. The founder and CEO of Drummond Road Capital, one of the top early-stage venture capital investors in America, Wheeler ran his firm from Cleveland for 13 years. Since moving to Edwards, where he’d kept a second home since 2009, full time last year, he’s fallen in love with this place, and with his new routine (in winter, that means waking at 4:30 a.m., working until 7:45, skiing for a few hours, then coming home and working again). “This is going to sound weird,” the 60-year-old says, “but the biggest challenge is that people who aren’t here are stuck on the fairy tale. I talk to people in New York and San Francisco and even in Cleveland, and they think I’m spending my life skiing. And I’m like, yeah, I got 60 days of skiing in this year, but I’m also working 50 hours a week. They can’t grasp it. They can’t understand it.”

Wheeler was encouraged in his move by a friend, Elizabeth Kraus, who’d been running her venture-capital fund, MergeLane, from East Vail since 2019. Kraus, who is 39, cofounded her firm in Boulder five years earlier. She invests mainly in companies with women in leadership. For years, she worried that living in the mountains would leave her bored or distracted, but ironically, she says, living here has helped her business grow and provided a balance she could not find on the Front Range.

Elizabeth Kraus, MergeLane cofounder and chief investment officer, says, "The percentage of people here who have resources and talent is higher than most places in the world."

“The percentage of people here who have resources and talent is higher than most places in the world, maybe even higher than anywhere in the world,” Kraus says, citing as examples former CEOs of public companies who retired to Vail. “I think what makes it especially advantageous is they move here thinking they’re going to be content skiing and biking, but they’re wired to be Type A CEOs, so they get bored just skiing and biking. The other thing is, there’s a ton of sex appeal to running a fund here, and that has helped me connect with people all over the world who think it’s an interesting way to live one’s life.”

Holland has seen Harvest Hosts grow from three employees before the pandemic to 25 as of this writing, with perhaps 15 to be added by the end of 2021. “In the past, we had to find people who wanted to be remote employees. And today we’re simply finding good employees,” he says. “We tell people we’re always going to be remote. You can live anywhere you want.” This he knows from experience.  


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