HBCU Innovators: Getaway Society

Two Hampton University alumni have made vacation home rentals their business with a $5 million portfolio.


Reading Time: 8 minutes

Carrington Carter and Calvin Butts Jr. followed the usual path of most college graduates—they both got good corporate jobs in pharmaceutical marketing, but after meeting up through the Hampton University alumni network they started to realize that they were like-minded when it came to their future goals. Eventually, Carter went on a trip to the Poconos that inspired him to reach out to Calvin Butts Jr. with a proposition for business that changed the trajectory of both their lives.

“A group of myself and other Hamptonians would go on a ski trip during Presidents Weekend every year, probably for about three or four years straight. And when it came time for me to plan the trip, find the house, talk to the owner, collect everyone’s money, I would realize how much the owner of the house was making from what we paid,” Carter tells AURN. “I realized the potential opportunity in the vacation rental home space. I saw the long term growth potential in the industry. I saw the changing behavior in preferring vacation rentals over hotels, especially for large groups and large families and that’s why we decided to jump into the space.”

Neither Carrington Carter nor Calvin Butts Jr. had formal training or an extensive background in real estate, but Carter wrote a solid business plan, presented it to Butts, and from there they figured out how to leverage their networks, and money they had already made working 9-5’s to launch the Getaway Society⁠—a vacation home rental service that consists of a $5 million real estate portfolio. Together, the dynamic entrepreneurship duo owns vacation properties in popular destinations such as Martha’s Vineyard, the Poconos, and Hilton Head, and they are working on expanding to Florida, and eventually internationally. The pair also co-own McKinley Carter Enterprises, a real estate investment and property management company, as well as East Chop Capital, a private equity firm that helps people create and grow businesses, as well as obtain financial education on how to raise money and find investors. 

South Carolina – Hilton Head Palmetto Manor. Photo Credit: Jack Manning III, JAXONPHOTOGROUP/ Getaway Society

Both men are passionate about building wealth and teaching other people how to do the same, and it all started with Carter’s fateful trip to the Poconos. AURN caught up with the duo to discuss some key points about how they became entrepreneurs in the investment property space and how anyone can leverage their network for entrepreneurial success. 

AURN: What you’re doing can seem like it’s unattainable to the average person so talk about how you raised the necessary capital once you decided that this is what you wanted to do.  

Calvin Butts Jr: I didn’t think that owning a large luxury vacation home was possible. Carrington is also a wealth strategist and he helped me realize that I can utilize—like many of us, you have to save money—but there are different ways to utilize IRAs, 401Ks, and investing in funds and different stuff like that, and being able to cash them out and taking the risk on buying land and buying property. Just utilizing our resources as a way to obtain this wealth opportunity to buy different types of real estate.  

Don’t be afraid and look into it. Approach it like you would anything else. Create a plan, do your research, go visit. There’s a lot of folks that are in this space that could be mentors, and we have folks reaching out to us now and asking us questions about why this location and what would you do here and there so there’s a lot of folks that are willing to help and share their experiences. But I would say be a guest first. Go experience it like how Carrington did in the Poconos. I think that was such a good way of getting first hand experience about what is happening, how can it be different, how you can improve it, and I think we often go back to his encounter from check in to check out and the paperwork, and we look at that for how to enhance the experience for our guests. We often go back to his trip to the Poconos and revisit that and learn from it. 

South Carolina – Hilton Head Palmetto Manor. Photo Credit: Jack Manning III, JAXONPHOTOGROUP/ Getaway Society

Carrington Carter:  First and foremost, I’m very big on setting goals. The key to most things in life is setting goals and getting definite about what you want and when. So, buying real estate or vacation rental homes—if that’s what you really want to do— get really crystal clear on what you want and how you plan to get there, and maximizing all your resources at your disposal from your 9-5, like your 401k. Clear communication with your spouse or close friends or close family for how you can pool your resources because you can do more together than you can individually. Think about how to start an LLC with them or a partnership so that you can invest together. 

I’m also big on not living within your means but below your means, especially when you’re younger. It’s important to live below your means and make smart and savvy investments because you have the power of compound interest and those wise financial decisions will pay off over time. And budgeting. I know most people don’t like the b-word but it’s important. I don’t necessarily believe in analyzing every single dime that goes in and out, but it’s important to be absolutely aware of exactly what’s coming in and out, and set an anchor for what you want to spend in different categories, and conceptualize what your budget is and what’s left over, hopefully, at the end of every month. Then, you can start to put that money toward your goals. If one of which is a vacation rental home or a real estate property then you can start putting action behind what goes into the account. 

Left: Carrington Carter Right: Calvin Butts Jr.

AURN: How do you do the research that goes into this? 

CBJ: One, we travel a lot as Carrington mentioned. Through our network and social media we see a lot of the trends on where people are going. We do a lot of research of top ten beaches, top ten travel destinations, we’re looking ahead at where the airlines are looking for new routes. We really do a lot of strategic thinking and forward thinking to try to figure out what is hot now, what is trending in the right direction and where things are going. That has led us to some of the great locations like Hilton Head, Martha’s Vineyard, Destin, Sarasota, and Orlando, Florida, where the numbers show potential for opportunity and success there are strong. 

AURN: What are some of the tools you use to keep you productive and that help you to manage business and properties? 

CBJ: One would be Slack. We’re in Slack constantly one on one, we have Slack channels for every property, we have Slack channels for new areas of focus, Slack channels for investors, Slack channels for conversations around venture capital and some other things and so we use that probably minute by minute. We tend to communicate on that probably multiple times and then for managing the properties there’s a list, I will let Carrington go through those but as far as running the business and managing our properties and us as partners, obviously relying on our financial tools of being able to transfer money and keeping our account running smoothly. Slack as far as our ability to communicate back and forth, Dropbox and other cloud based tools as far as keeping different agreements related to our properties organized, but it’s really neat to hear how much technology we use to manage our day to day.

Marthas Vinyard – Oak Bluff Pirates Cove. Photo Credit: Jack Manning III, JAXONPHOTOGROUP/ Getaway Society

CC: We recently had an investor retreat earlier this month in Hilton Head and I was presenting, and in one slide I brought up that what we’re doing and how we’re able to manage these properties as a very lean operation literally was not available three years ago. It’s technology that has allowed us to do that. Calvin mentioned some of the apps we’re able to use. Airbnb has a phenomenal app, Vrbo has a phenomenal app, being able to allow us to manage our booking calendar being able to send out communication, collect payment, all in the platform that are literally managed on our [phones]. But all the technology we use Samsung SmartThings app, which allows us to open and close the house remotely, give codes unique to guests when they check in and check out, carbon monoxide detectors; houses are equipped with Amazon Alexa products where guests can play music and turn off and turn on locks; NoiseAware is technology that allows us to manage guest noise levels in the house. It does not record any conversations but it measures decibel levels in the house to protect our guests. Just in case there’s a noise complaint, we’re able to ensure that it’s not our house because we measured the decibel levels.

We have a lot of diff bank accounts in different locations so with Paypal, with Venmo, with Cashapp, we’re able to send thousands of dollars of payments across different bank accounts. We’re able to pay our vendors and our partners and maintain those good relationships. And just with marketing, a whole host of tools  that we use to market our business—obviously Facebook, Instagram, Mailchimp, Canva for graphic design—so just three years ago a lean operation like this would not have been able to exist but we appreciate the advent of technology. 

Marthas Vinyard – Oak Bluff Pirates Cove. Photo Credit: Jack Manning III, JAXONPHOTOGROUP/ Getaway Society

AURN: Have you ever faced any kind of discrimination? 

CBJ:  I don’t know if we’ve been treated differently getting feedback or anything, so from a vacation rental standpoint, no. But with other real estate investments that we have in other places, I feel like  we have experienced discrimination in lending, when we’re trying to get loans to renovate and do real estate development in certain locations. Unfortunately, it still happens today but Frederick Douglass said, “Without struggle there is no progress,” so ironically, that struggle in obtaining financing from banks and other lending institutions led us to starting a private equity company called East Chop Capital, and that’s all about pooling our private resources to do more than we can individually. When I say pool our resources, I mean private equity, obtaining private money. Because we’ve had a proven track record in the vacation home rental space, we now have the backing of quite a few investors, which would make it easier for us to accomplish our goals without having to depend on bank loans. 

Marthas Vinyard – Oak Bluff Pirates Reef. Photo Credit: Jack Manning III, JAXONPHOTOGROUP/ Getaway Society

AURN: You two also mentioned how your wives play big roles in the business. Talk about that familial support. 

CBJ:  April, who is my wife, is tremendously involved in all the finances and bookkeeping. She designed one of our homes from start to finish and she will travel to the homes and do house checks if needed. She has helped recruit guests to our homes via organizations she’s involved in. So, I would say it’s a true partnership and I know Kia, Carrington’s wife, has been significantly involved in houses and different layouts. When we’re scouting and traveling to locations they often travel with us, and have an opinion on this house vs. that. There’s nothing like a woman’s touch, so it has been great. 

Marthas Vinyard – Oak Bluff Pirates Reef. Photo Credit: Jack Manning III, JAXONPHOTOGROUP/ Getaway Society

CC: Our wives have been very helpful from a design standpoint. A woman’s touch is very important in a hospitality and design type business. My wife is a writer by trade. She’s a medical writer. So, marketing perspective, website, email marketing and social media stuff as well. So she’s a great add in that aspect and then also having two income earning households in the real estate business and being able to leverage that income earning potential really allows you to scale your portfolio much more aggressively, so it’s been a great ride with both of our wives helping us to build these businesses. 

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