How 5 families bought a vacation home together in Hawaii to live their dream – Business Insider | Dauktion

  • Ryan Seare, 47, was the first of his neighborhood friends to invest in a vacation home in Hawaii.
  • He convinced four other families to join him on a property in Kauai where shares start at $445,000.
  • The families get together three weeks a year and have barbecues on the beach, trail runs and hikes together.

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

Their three families and two others had huddled together during the difficult early months of the pandemic, proving to each other that their connection and camaraderie could leapfrog into a new state.

When Seare decided in October 2020 to take the plunge and buy a vacation home on Kauai, one of Hawaii’s greenest and most popular islands, the rest of the families followed suit.

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

“It didn’t start with, ‘Hey guys, let’s all look for a place to travel with our families!'” Smith, 37, who is president and co-founder of pancake mix company Kodiak Cakes, said. “It just happened by accident. Ryan talked about his experiences and then Josh got interested and then I got interested.”

For its groundbreaking investment, Seare Timbers chose Kauai, an intimate 47-home community tucked away on Kauai’s southeast shore near a lighthouse, marina and Costco.

Seare said he and his wife were drawn to the 400-acre resort’s scenic landscape and what it offers his family in the form of on-site activities and bonding experiences.

The property stretches from inland at 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 and pick fresh produce, and the resort also features a two-tier infinity pool, 17 miles of hiking and biking trails, and an 18-hole golf course.

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

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

Josh Phillips



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

Fractional ownership, such as that offered by Timbers, is a growing trend in the vacation rental industry that lowers the cost barrier to ownership by allowing buyers to purchase part of a home rather than the entire property. Unlike time shares, buyers can keep the appreciation if they sell their shares.

Timbers’ model echoes the approach of popular fractional startups like Pacaso and Ember, which have bought homes in desirable locations — like Napa and Lake Tahoe — and converted them into multi-owner vacation homes.

They chose Kauai because it’s relatively untouched

What resonated most with the five Utah families was that Kauai had resisted the commercialization and overwhelming tourism that Oahu and Maui have experienced.

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

The trio initially traveled to Kauai for at least some of the three weeks they were allotted annually.

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

Timbers sits on a rugged bluff overlooking the ocean.

Timbers sits on a rugged bluff overlooking the ocean.

Woods Kauai



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

“We got to hang out with each other’s families on the beach, and then I got to run with these guys in the mornings,” Smith said. “It was actually more fun.”

When families are in Hawaii together, they spend days hitting the surf and barbecuing on the beach with new friends they made on Kauai. They’re also dabbling in what Phillips, a 47-year-old general contractor, calls “quintessential Hawaiian stuff,” like hiking, exploring, and traveling across the island to lounge on new beaches.

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

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