For years Durham’s Matt Williamson was known as the guy in the green pants, a branding staple of his predictive marketing firm, Windsor Circle. When the company was acquired in 2018 by New Jersey-based Output Services Group, he stayed on for a while before folding up the pants and moving to his next venture, Plum CoOwnership.
No, He doesn’t yet have plum colored pants – “not yet,” he joked. But he does have a concept, a website and a $1.5 million funding haul to get started.
For Williamson, sitting still wasn’t an option, he said.
In an exclusive interview, he talks through the idea, the concept and what’s next for Plum’s startup story.
“I just love the art of creating,” he said. “I have been very fortunate to have worked with a lot of teams but at the end of the day, I think I feel most alive with that kind of early stage creating process, doing a lot of brainstorming and risk taking to see if we can shape something beautiful out of nothing, out of thin air.”
It started on vacation.
Williamson and his wife travel with groups of friends regularly and, toward the end of the trip, they go through the common lull of not wanting it to end.
“Somebody says, 'Why are we renting this place,'” he said. “Why don’t we just buy a place together? Everybody’s like, huzzah! But nobody actually knows how to get started.”
Williamson started researching the concept of shared ownership. He discovered 60 million American households want to own a vacation home, but just 8 million exist, leaving a huge population to turn to short-term rentals or time shares. Of those 8 million vacation homes, 2 million are co-owned.
“So it’s pretty common behavior, but there’s not an easy or elegant path to doing it,” he said. “I can’t afford to buy a vacation house all to myself. The idea of being able to co-own it with folks to bring the cost down … it just makes it a lot more efficient.”
Suddenly that $800,000 Outer Banks home seems more reasonable, he said.
Williamson, for example, fishes on the Outer Banks. “But I don’t really need it during the summer because the fish aren’t really biting," he said.
The idea was to find a group of people to treat a house as a fishing villa in the fall and winter months and then hand it to a property manager to take advantage of the high season, putting the proceeds back into the maintenance of the house and its reserve fund.
The concept behind Plum not only helps said groups find each other, it also helps organize the sharing process and even connects buyers to a realtor when the kinks have been worked out. Plum goes on to help schedule the use of the house and connect owners to maintenance services.
Since groups will be together a long time, Plum helps them identify two dozen or so key decisions and deal breakers to make sure everyone’s on the same page.
“Our model is to make sure that people have made all the decisions they need to make, they’ve set their budget and agreed as a group they’re going to do this, then they enter the market just as any other buyer,” Williamson said. “We think there’s strength in numbers.”
Big plans
The startup’s launch is limited to North Carolina, but Williamson sees the concept expanding countrywide – and even internationally. He envisions someday having Plum-certified realtors.
Right now it’s just Williamson, but with the cash he’s raising, he hopes to add to the team. A securities filing shows $50,000 has been closed. The pre-seed round will total $1.5 million, led by Studio VC with participation from Tweener Fund, which is led by local serial entrepreneur Scot Wingo.
Wingo said investing in Williamson this time around was a logical play for Tweener Fund. Wingo has known Williamson since Williamson’s Bronto days. Wingo served on Windsor Circle’s board and “saw him in action.”
“Matt’s been able to take his sales orientation and build out his skill set to be a great CEO, and I’m really excited to see where he takes his second company,” Wingo said.
The concept behind Plum also drove Wingo's decision. He pointed to the “fractional ownership” concept as something “born digital” generations are adopting rapidly.
“I think Plum is at a very interesting intersection of applying those concepts to vacation home ownership,” Wingo said.
In the meantime, Williamson is enjoying being in the entrepreneurship grind, foregoing a salary as he creates what he hopes will be the next big thing.