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Meet the HBCU Grads Who Built a $5 Million Real Estate Portfolio for Vacation Rentals

Meet the HBCU Grads Who Built a $5 Million Real Estate Portfolio for Vacation Rentals

By 2020, millennials are collectively expected to spend $1.4 trillion on traveling each year, according to data from the Vacation Rental Management Association

Contributing to this growth is the $170 billion global vacation rental industry, which consists of property owners renting out their space to short-term travelers throughout the year. 

Working to leave their own mark in this growing real estate space is Hampton University alum Carrington Carter and Calvin Butts, Jr. In 2012, the college friends joined forces to turn their love for traveling into a profitable business called Getaway Society, where they offer luxury rentals in some of the country’s most popular vacation spots. 

“Getaway Society initially started as a luxury group travel company, but we decided to pivot out of that industry for a variety of reasons,” Carter tells Because of Them We Can. “Fast forward to a couple of years when it was my turn to lead an annual ski trip to the Pocono Mountains and it was my responsibility to find a house, collect the money and work with the homeowners to secure the house. It was during this time when I started to run the numbers in my head and thought to myself, ‘Wait a minute, I think I can do this.’”


Following this ‘aha’ moment, Carter says he put together a business plan and presented the idea of buying and renting out their own vacation homes to Butts and their other college friend Jeremiah Myers. At the time, vacation rental platforms like Airbnb, HomeAway and Vrbo weren’t as popular. But, that didn’t stop the men from putting their idea into action. 

In September 2014, they put their financial resources and knowledge together, to break ground on their first Getaway Society property in the Pocono Mountains.

Today, Carter and Butts say they’ve grown their business to include a $5 million real estate portfolio that includes five properties in locations like the Pocono Mountains, Martha’s Vineyard and Hilton Head Island in South Carolina. 

Carter, who quit his corporate America job in 2017, explains that with each property he and Butts devote a lot of attention to ensuring that the home is a smart investment for their business. 

“One of the main things we look at is location,” he says. “We want something that has a history of having a consistent demand of travelers. We also want something that is close to the amenities people look for when they go on vacation like restaurants, a ski resort, shopping, beaches or close to town.”

Carter adds that they also look at the health of the real estate market to see just how well houses appreciate in that neighborhood. “This is a for-profit business and we are in the business to make money,” he says. “So we want to make sure we are generating a financial return.”

Since starting Getaway Society, Butts says one of the biggest lessons he’s learned is the value of pacing yourself when scaling a company. “You get excited about these assets because they’re bringing in money,” he says. “But you have to be patient and look at how you’re going to book six, or maybe even 12 months out, and you really have to manage your cash flow.”

Both he and Carter agree that within the next two to three years they hope to expand Getaway Society’s portfolio to include 12-15 properties that provide a luxury vacation experience to its guest. 

“From a branding perspective, I would like Getaway Society to be known as the premium luxury rental site,” says Butts. “I want us to have a very unique niche of handpicked, custom designed homes that people can go to and expect the same experience throughout our portfolio.”

Looking back, the co-founders say they’re proud of how they’ve turned their passion for traveling into a growing business, and they encourage anyone with an idea to become a “doer” in making their vision a reality. 

“One of my favorite words or phrases is to be a doer,” says Butts. “If you have an idea, just take a first step to do something, whether that’s getting your LLC or going to talk to someone about it. But, just be actionable and make moves. I think as you create ripples, ripples turn to waves, and then waves turn to currents and then all of a sudden you’re flowing and you’ve got a stream and that’s how it works.”