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How a Durham entrepreneur scored investment from former Netflix CEO


Matt Williamson
Matt Williamson
TBJ File Photo

Plum, the latest startup out of Durham entrepreneur Matt Williamson, has snagged $175,000 in Entrepreneur magazine’s Elevator Pitch contest. And the investment – which is on top of more than $1 million he had already raised – is coming from Netflix’s first CEO, Marc Randolph.

Entrepreneur Elevator Pitch is a show where entrepreneurs step into an elevator and have just 60 seconds to pitch their business on camera to a board of investors. If investors like what they hear, the elevator doors will open, revealing a boardroom – and an opportunity for funding and mentorship.

And for Williamson, they liked what they heard.

“We’re launching the Airbnb of co-ownership,” he told the investors in the elevator.

Williamson was asking for $175,000, with a $9.5 million post valuation cap at a 20 percent discount. And Randolph said he could help – both with the capital and scaling expertise.

“This is about the skills of building a business and scaling a business,” Randolph said. “This is about the challenges you don’t even know exist yet and I can assure you that I have spent four decades mastering some of those skills.”

And with a handshake, it was a done deal.

How he did it

Williamson is no stranger to winning competitions.

In 2014, he won Google for Entrepreneurs’ inaugural Demo Day in front of AOL cofounder Steve Case with his last company, Durham’s Windsor Circle.

That pitch was five minutes. But the pitch he delivered in Entrepreneur magazine’s Elevator Pitch contest for Plum, his vacation home co-ownership startup, had to be just 60 seconds.

Williamson said in an interview after the win that his secret sauce is always preparation. 


“There were seven seasons worth of these episodes … so I just turned them on,” he said. “Literally I had a couple of days where, while I was working, I had episodes just running on a monitor.”

He had a notebook handy, and when something worked, he wrote it down. When something an entrepreneur said didn’t work? He wrote that down too. And he just crafted a pitch.

Then it came down to practice – and timing. His first pitch practice was three minutes long.

“How do you tell the story of everything you’re sacrificing, months on end of no salary, putting your whole family through the experience – you’re pitching it’s the next billion-dollar idea – how do you do that in 60 seconds?” he said.

He practiced, practiced, practiced. He mumbled his 60-second pitch under his breath throughout the whole flight to Miami, on the way to the hotel, from the hotel to the production facility.

“I probably said that same 60 seconds over 100 times,” he said.

But practice – at least in this case – seemed to make perfect, as not only did he win the investment, but he landed the exact investor he had been targeting.

Randolph, outside of his experience with Netflix, had experience in two-sided market places – which is what Plum is delivering. On one hand are buyers – coming together in groups to buy vacation houses. On the other side are the real estate agents bringing in the supply.

Williamson said Randolph gets it. Already they’ve exchanged several emails – and Williamson is confident that the partnership will help the five-person company deliver.

Williamson said the company has some advantages as interest rates go up. 
“Rising interest rates, that’s okay, divide it by five people,” he said.

And the co-ownership model may allow high net-worth individuals to bypass mortgages completely. Instead of putting 20 percent down and financing, what if five people come together with 20 percent each and outright buy the vacation property?


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