Williamson’s New Startup Makes Vacation Home Ownership More Accessible

Plum aims to make vacation home ownership more accessible to the average American family.

Matt Williamson is a familiar name on the Triangle tech startup scene. He was an early employee at Durham-based Bronto Software—which sold to Netsuite in 2015 for $200 million—and then the Co-Founder and CEO of predictive marketing startup Windsor Circle, which was acquired by Output Services Group in 2018. [Editor’s Note: Williamson talked about the latter deal as a guest on our Exit Stories podcast.]

Now Williamson is back as the founder of Durham-based Plum, a platform to make vacation home ownership more accessible that is raising a $1.5 million pre-seed round, some of which is already closed and in the bank. 

This round will enable the startup to hire its first team and grow from a prototype to full platform. New York-based Studio VC is leading the round, while Spiffy CEO Scot Wingo’s Triangle Tweener Fund has also added funding.

The idea for Plum started buzzing around in Williamson’s brain a few years ago as a result of his own yearly vacations.

Inevitably every year during these vacations, someone would ask the question: “Why are we renting? We should just buy a place together.”

This usually took place after a few glasses of wine and prompted everyone to take out their phones and start browsing Zillow. But then, Williamson noticed, nothing ever happened. 

“Nobody seems to take the next step,” Williamson said. “And when I started digging in on that, why doesn’t anybody take the next step? It turns out that it’s hard. Where do you get started? And how much do you need? And how do you come to an agreement on the location? It just stays as a dream, and nobody actually executes on it.”

So he formed Plum last year, now calling it the simplest way for people to buy and own a vacation home together. It capitalizes on a large market, as Williamson said 60 million American households want to own a vacation home and only 8 million vacation homes exist currently—demonstrating significant unmet demand.

For most Americans, Williamson said, vacation home ownership is out of reach financially. But gathering together a group of owners changes the financial equation and makes it far more accessible to the average American family. With Plum, a co-ownership group of five could buy an $800,000 house, for example, and get 10 weeks of vacation time a year for less than $700 a month each.

Plum’s platform enables group of buyers to co-own and manage vacation homes.

And the process is made simple on Plum. Co-owner groups can set rules, codify those rules, create an operating agreement, buy a house and then manage the house—all through the platform.

Plum is early on in its evolution, still coding the first parts of the platform. But this has been an intentional decision, Williamson said. With his past startups, he saw that it’s tempting to code right away. With Plum, Williamson wanted to make sure he listened to his potential customers first, spending around two months doing nothing but client interviews, hearing the good, bad and the ugly on how people own vacation houses together.

The importance of product-market fit was a key lesson Williamson gained during his time at Windsor Circle. With Windsor, he said they thought they had the perfect solution right out of the gate but failed to see that their early adopters didn’t reflect the market at large, leading to some hiccups along the way.

“We drank our own Kool-Aid,” Williamson said. “And then as we scaled, we didn’t quite figure out or realize that the mass majority of the market wasn’t as innovative as the early adopters. The early adopters, by definition, are willing to take risks.”

At first, Williamson saw Plum as a way to open up co-ownership for all houses, not just vacation homes. But he’s decided to start with vacation houses, already a large market by itself. If Plum can get that nailed down, he might expand into primary homes as well.

After those months of interviews, Williamson built a basic tool and started servicing his first customers. 

The profit potential of a service like Plum is wide-ranging. Initially, Plum plans to take a 1 percent commission at closing for each successful vacation home purchase. Additionally, to have access to all of the tools at Plum’s disposal, users will pay $99 a month. At some point in the future, Plum may offer pre-packaged services for co-owners to set up security systems, cable, furniture, pest control and other services.

A Platform For The Modern Worker

While the pandemic initially stopped travel altogether, Williamson said being stuck in our homes sparked a greater desire to invest in vacation homes.

“The pandemic has permanently changed the way that we were,” Williamson said. “The ability to work from home has shifted to the ability to work from anywhere. And if you can work from anywhere, why not work overlooking the waves or watching the leaves in the mountains?”

Plum Founder Matt Williamson was formerly the Co-Founder and CEO of Windsor Circle, which had a successful exit in 2018.

Operating out of Durham’s co-working space American Underground, Williamson said that Plum has just started its mission to make vacation ownership more accessible. The next steps are to close its funding round, get the early team in place and build the first product to success.

“We really want to demonstrate that there’s demand for group ownership and that we’ve got a process and a mechanism to bring them all the way through that experience,” Williamson said.

Startups like Pacaso and Ember have already demonstrated the vacation home market has great potential, albeit in different market segments than Plum, Williamson said. Unicorns Pacaso and Ember both focus on the luxury market and multi-million-dollar homes. Now Plum is going to make vacation home ownership more attainable for the middle and upper-middle classes.

“They’re proving rather hands-down that this model works,” Williamson said of Plum’s competitors. “They’ve demonstrated that they can pull it off, so I feel very confident that we can take a different take on that same interest, and we can open it up to 10 times as many people.”

For those who want to find out more about Plum, the startup is hosting an open house with Monarch Realty at the Transfer Co. Food Hall in Raleigh on Thursday, March 24 from 4-7 p.m. The details for the event are here.

About Suzanne Blake 362 Articles
Suzanne profiles startups and innovation for GrepBeat. Before working at GrepBeat, Suzanne attended UNC Chapel Hill, obtaining a degree in journalism and political science. Previously, she wrote for CNBC, QSR Magazine, FSR Magazine and The Daily Tar Heel.