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  • Ryan Seare, 47, was the first of his neighborhood friends to invest in a Hawaii vacation home.
  • He convinced four other families to join him at a property in Kauai where shares start at $445,000.
  • The families go for three weeks a year and barbecue on the beach, run on trails, and hike together.

Ryan Seare, Josh Phillips, and Cameron Smith had been running trails together in their Salt Lake City, Utah, suburb for eight years before they decided to take their friendship to the next level. 

Their three families, plus two others, had hunkered down together during the trying early months of the pandemic, proving to each other that their connection and camaraderie could make the jump to a new state. 

So in October 2020 when Seare decided to take the plunge and buy a vacation property in Kauai, one of Hawaii’s most verdant and popular islands, the rest of the families followed his lead.

It wasn’t the meticulously planned adventure one might assume. 

“It didn’t start with ‘Hey guys, let’s all look for a place where we can travel with our families!'” the 37-year-old Smith, who is the president and a cofounder of the pancake-mix company Kodiak Cakes, said. “It just happened randomly. Ryan talked about his experiences, and then it got Josh interested, and then it got me interested.”

For his precedent-setting investment, Seare chose Timbers Kauai, an intimate community of 47 homes tucked away on Kauai’s southeast shore near a lighthouse, a marina, and a Costco.

Seare said the 400-acre resort’s scenic landscape, and what it offers to his family in the forms of on-site activities and bonding experiences, won him and his wife over. 

The property stretches from the inland, by the island’s main airport, to a bluff overlooking the sea. A 16.5-acre organic farm and orchard is open to residents to stroll through and pluck fresh produce from, and the resort also has a two-tiered infinity pool, 17 miles of walking and biking paths, and an 18-hole golf course. 

The Phillipses use the property's 17 miles of walking, hiking, and biking trails.

The Phillips family uses the property’s 17 miles of walking, hiking, and biking trails.

Josh Phillips



Seare, Smith, and Phillips each purchased a 1/12th ownership of a residence at Timbers Kauai that grants them three weeks of use per year plus unlimited last-minute trip bookings whenever the resort has openings in its schedule. The 1/12th share costs a flat fee of $445,000. Owners also pay an annual fee of $22,295 and additional cleaning fees

Fractional ownership, like what Timbers offers, is a growing trend in the vacation-home industry that lowers the cost barrier to ownership by allowing buyers to purchase a share of a home rather than the full property. Unlike time-shares, buyers can keep the gain in value when they sell their shares. 

Timbers’ model parallels the approach of popular fractional-ownership startups like Pacaso and Ember, which have bought homes in desirable locations — like Napa and Lake Tahoe — and turned them into vacation homes with multiple owners.

They picked Kauai because it’s still relatively unspoiled

What appealed most to the five Utah families was that Kauai had resisted some of the commercialization and overwhelming tourism that Oahu and Maui have experienced.

“If you’re looking for retail therapy, and you’re looking for amazing experiences dining out,” Seare, a 47-year-old interior-design showroom owner said. “Kauai is probably not the place for you.”

The trio started off going to Kauai for at least a few of the same three weeks allotted to them annually. 

Between the Seare, Phillips, and Smith families, there are 13 kids ranging in age from 2 to 17. A fourth dad who works in advertising has five kids, and a fifth in real estate has three.

Timbers sits on a craggy bluff overlooking the ocean.

Timbers sits on a craggy bluff overlooking the ocean.

Timbers Kauai



Still, there’s something for everyone to do on the property — and perhaps best for the parents of the older kids, the property’s staff act as friendly, albeit watchful, eyes. 

“We were able to hang out with each others’ families at the beach, and then I was able to run with those guys in the morning,” Smith said. “It actually made it more fun.”

When the families are together in Hawaii, they head down to the beach for days in the surf as well as barbecues with new friends they’ve made in Kauai. They also get into what Phillips, a 47-year-old general contractor, called “typical Hawaii stuff” like hiking, exploring, and venturing across the island to lounge on new beaches. 

“What brings people together is time, right?” Smith said. “Sometimes when you’re on vacation, you don’t want to see people you know, because that’s part of vacationing. But vacationing with friends can also be pretty fun.” 



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