Nathan Bullock

Founder, CEO & Co-Owner

Deserving Vacations is Nathan's first baby.

Originally from Okemos, Michigan, Nathan is a proud Michigan State University graduate who made his way south to Charleston in 2004. A year later, he began what would become a lifelong career in hospitality at Wild Dunes Resort.

Nathan started as a Reservations Associate in 2005, learning the guest side of the vacation rental business from the ground up. He moved into property management in 2007 and then into housekeeping management in 2008. By the time he founded Deserving Vacations in 2009, he had already experienced nearly every side of vacation rental management firsthand.

More than 17 years later, that broad understanding of the business is still one of Nathan's greatest strengths.

He knows what it takes to market a vacation property, what guests are looking for, what owners expect, and what happens behind the scenes to keep a property performing at its best. He's spent years building relationships with owners, learning the Isle of Palms and Wild Dunes rental markets, and developing an instinct for seeing potential in a property — sometimes before anyone else does.

And eventually, Nathan saw another opportunity.

Over the years, guests staying with Deserving Vacations would fall in love with the area and begin asking about real estate. Some were casually wondering what it might look like to own a place here. Others were serious about finding a second home or investment property.

For years, those conversations meant connecting people with another real estate company.

Nathan started to wonder: Why not us?

We already understood the vacation rental market. We knew the properties, the neighborhoods, and what guests were looking for. We could speak to the potential of a home not only as real estate, but through the lens of years of vacation rental management experience.

That idea became Deserving Real Estate.

Nathan earned his broker's license and today serves as Broker-in-Charge of Deserving Real Estate, creating a natural connection between the two sides of the Deserving family. Whether someone already owns a vacation rental, is considering buying one, or simply falls in love with Charleston during a stay, our team can now be part of that journey from a completely different angle.

For Nathan, it was never about adding another company just for the sake of growing.

It was about recognizing another way we could serve the people who already trusted us.

Today, Nathan remains deeply involved in both Deserving Vacations and Deserving Real Estate. He's our problem solver, our sounding board, our steady hand, and the person who keeps us focused on why Deserving exists in the first place.

He's the backbone of all things Deserving — and we wouldn't have it any other way.

Holly Bullock

CFO & Co-Owner

Holly's path to Deserving Vacations wasn't quite as direct — but looking back, it makes a lot of sense.

Born in Cincinnati, Ohio, Holly graduated from Tiffin University in 2007 and moved to Charleston a year later.

Her first stop? Wild Dunes Resort.

Holly began as a Resort Ambassador, where she got her first taste of the hospitality industry — and happened to meet Nathan along the way.

Her career eventually took her into Human Resources, technology, operations, and customer service, including seven invaluable years with Cincinnati Children's Hospital Medical Center and later a technology and innovation role with CommonSpirit Health.

Then, in 2021, Deserving Vacations came calling.

The company was growing quickly, and Nathan needed someone who understood people, technology, operations, customer service — and the business itself.

Fortunately, he knew someone.

Holly joined DV full-time in August 2021. She'll be the first to tell you she isn't particularly interested in titles, but since every company apparently requires them, CFO seemed to fit best.

In reality, her role covers a little bit of everything: company financials, owner relations, new-owner onboarding, payroll, technology, the website, marketing and social media — along with whatever else happens to land on her desk that day.

Her background may look unconventional for vacation rental management, but that's exactly what makes it valuable. Holly helps DV continue to grow without losing the personal approach that made it successful in the first place.

Alec Bleggi

Director of Operations & Guest Experience

If there's a question about a Deserving Vacations property, there's a pretty good chance Alec knows the answer.

A proud University of Cincinnati graduate, Alec moved to Charleston with his family in the fall of 2019. By the spring of 2021, travel was returning, Charleston's vacation rental market was taking off, and Deserving Vacations was growing quickly.

Nathan needed a right-hand man.

Alec was it.

Today, Alec touches nearly every part of the guest experience and keeps countless pieces moving behind the scenes.

Have a question about a property? Alec probably knows it. Wondering what the housekeeping schedule looks like this week? Alec built it — and made sure everyone who needs it has it. When something inevitably doesn't go according to plan? Alec is usually already working on the solution.

He communicates with nearly every guest we host, coordinates closely with housekeeping and operations, helps oversee our properties, and is one of the people we count on most when something needs to get done.

Alec also holds his South Carolina real estate license and brings a background in law, real estate, property management, and guest relations to his role.

And yes, Alec happens to be Nathan's brother-in-law.

We're a family business, after all.

When he's not keeping DV moving, Alec loves staying active and spending time with his wife, Ashley, their son, Emmett, and their dog, Millie. His Ohio roots still run deep — especially when it comes to his Cleveland sports teams.

Ben Barnes

Property Care & Operations Lead

Born and raised in Cincinnati, Ohio, Ben spent many years working for the City of St. Bernard before moving his family to Charleston in the spring of 2022.

It was the kind of work where no two days looked quite the same — and knowing how to solve a problem, work with your hands, and figure things out was simply part of the job.

As it turns out, that's pretty great training for vacation rental management.

Today, Ben is on Isle of Palms nearly every day, inspecting homes, taking care of maintenance needs, keeping an eye on the details, and helping make sure each property is ready for the next arrival.

And when something isn't?

Ben is one of our first calls.

He's the kind of person who can fix just about anything — and if he doesn't already know how, he'll figure it out.

And because apparently one brother-in-law wasn't enough, Ben also happens to be Nathan's brother-in-law.

More family business.

Outside of DV, Ben is an avid Cincinnati Bengals and Reds fan, loves Xavier basketball, and enjoys cooking. He lives in Mount Pleasant with his wife, their sons Sully and Baker, and their dog, Rudy.

Steve Messina

Property Care & Operations Specialist

When something needs to be fixed, a guest needs a hand, or an owner needs a little help while they're in town, Steve is the kind of person you want nearby.

Originally from New York, Steve is a retired FDNY firefighter with experience in property and home management. He's spent much of his career doing what he still does so well today — showing up, solving problems, and taking care of people.

Steve joined Deserving Vacations in October 2023 and quickly became an important part of our boots-on-the-ground team.

Guest locked out? Steve's there.

Something needs fixing? He's on it.

An owner is in town and needs help with a few projects? There's a good chance Steve is already figuring out how to get them done.

He's handy, a talented woodworker, and brings a can-do attitude to just about everything that comes his way. More importantly, Steve genuinely enjoys helping people — and it shows.

When Steve isn't checking on properties or tackling his latest project, you may find him surfing, cheering on the New York Islanders, or spending time with his wife Karen, their son Vaughn, daughter Reese, and their two pups.

Karen Messina

Real Estate Agent & Owner Relations

For Karen, whether it's property management, real estate, or hospitality, it has always come back to one thing:

People come first.

Her love for property management began more than 20 years ago in New York, where she managed more than two million square feet of Class A commercial office space. She led tenant services, supervised maintenance teams, and became the trusted point person for the tenants and properties in her care.

After relocating to Charleston in 2019, Karen brought that experience — and a whole lot of heart — to Deserving Vacations.

Today, she proudly has a foot in both worlds. Karen is an important part of the DV team and serves as a lead agent with Deserving Real Estate, bringing decades of property experience, an eye for detail, and a relationship-first approach to everything she does.

Karen holds a Bachelor of Fine Arts in Public Relations/Image Management from Long Island University, C.W. Post — and she'll be the first to tell you she's still a student at heart.

Outside of work, Karen is a proud wife and mom, and she brings the same energy to her personal life that she does to her work: show up, care deeply, and give it your all.

Megan Gladden

Real Estate Agent & Hospitality Specialist

Megan understands vacation rentals from a perspective that's especially valuable at Deserving Vacations — she's been an owner herself.

Originally from Greenville, South Carolina, Megan attended Winthrop University before going on to own and operate her own retail business, where she developed a strong foundation in customer service and a love for working with people.

After making Charleston home 20 years ago, Megan's path eventually led her into the vacation rental world. She owned and helped manage eight vacation rental properties throughout historic downtown Charleston and Isle of Palms, gaining firsthand experience with what it takes to own and operate a successful rental property.

Today, Megan brings more than 11 years of experience across hospitality, property management, and real estate to the Deserving team.

She's part of the hospitality team at Deserving Vacations and a real estate agent with Deserving Real Estate, where her experience as an owner gives her a unique understanding of what clients are looking for.

For Megan, a property has never been just a property. Home is personal. It's where life happens, memories are made, and new chapters begin.

When she's not working, Megan is happiest spending time with her three children, Thomas, Ava, and Gracie — whether they're at the beach, traveling, exploring Charleston, or simply enjoying time together.