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Gary Kompothecras may be larger than life, but he’s also down to earth

Siesta Key resident and entrepreneur Gary Kompothecras has been called many things. “Creator” is his favorite.

Gary Kompothecras and his family live in one of the largest houses on Siesta Key — a three-story, 13,560-square-foot estate on Point of Rocks Road.
Gary Kompothecras and his family live in one of the largest houses on Siesta Key — a three-story, 13,560-square-foot estate on Point of Rocks Road.
Photo by Lori Sax
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By simple biography, he’s a husband to his wife, Beth, and father of six kids, ages 12 to 28. He’s a chiropractor-turned-businessman, who owns everything from a pioneering and wildly successful accident attorney referral service to a Siesta Key bar to a bottled water business. A resident of Siesta Key, he’s a landowner and real estate developer, seeking to bring a first-of-its-kind hotel to the Key in the face of vocal opposition. Any quick glance at Gary Kompothecras’ bio would also have to include philanthropist and political donor, given he supports and backs a range of causes, from mostly Republican candidates to charities that work with and help children with autism and their families. (Two of his adult children have autism.)

And, at some level, even at 62 years old, Kompothecras remains something else: a lifeguard who grew up poor in Queens, N.Y., and has lived most of his adult life with an Olympic pool-sized chip on his shoulder. 

“He’s a guy’s guy,” says Sarasota entrepreneur Jesse Biter, who has known Kompothecras for more than a decade. “He’s like the Jay Leno of Siesta Key, wearing a white shirt and blue jeans.”

One last easily applied label? Kompothecras is rich. 

That can be seen in what’s one of the largest houses on Siesta Key — his three-story, 13,560-square-foot estate on Point of Rocks Road. The mansion, which Kompothecras built over seven years, is on a 31,702-square-foot lot and was valued at $18.38 million in 2023. The house and land cost around $10 million to build, and originally included a bowling alley, which has since been taken out. 

That house is known not only locally but also to a global audience as a go-to spot on the hit MTV reality show “Siesta Key.” The show debuted in 2017 and starred Kompothecras’ son Alex for 42 episodes in the first three seasons. (The show is now called “Siesta Key: Miami Moves,” and mostly takes place in South Florida.) 

Kompothecras championed and bankrolled the show in its early days. Adding another label, that of producer, Kompothecras has since dabbled in other movies, including the forthcoming flick, “The Man in the White Van,” based on the true story of a stalker in a small town in Florida in the 1970s. The movie stars Madison Wolfe, Ali Larter and Sean Astin, among other Hollywood names.

“People call me a serial entrepreneur,” says Kompothecras, who goes by Dr. Gary with a last name pronounced kom-PAHTH-uh-kras. “I don’t have hobbies. I don’t like golf. I just like creating stuff and creating businesses. I don’t want to run things, but I like to create businesses and let other people run them.”

Success breeds success 

Attaching a label to Kompothecras that goes deeper than wealthy serial entrepreneur, controversial developer or owner of a huge house requires an ability to dance in and around the varying circles of his life. 

One big circle? Success. That’s come in waves, mixed with a few setbacks.

Asked how he came up with the idea to concentrate the referral business around a 1-800 number, Kompothecras says, “I just wanted to have something that people could remember easily.”
Photo by Lori Sax

A notable business success is the ubiquitous 1-800-ASK-GARY line, an accident attorney and medical referral service. Kompothecras founded that company in 1996. According to him, it now has 28 offices in three states, making some $100 million a year in revenue with a payroll of several hundred employees. The business has spawned multiple competitors. It’s also attracted multiple detractors, such as the Florida Bar, which once investigated the practices of 1-800-ASK-GARY and similar attorney referral firms.

Kompothecras came up with the idea for 1-800-ASK-GARY after spending several years running a multidisciplinary medical clinic in Florida that treated people after auto accidents. He saw a gap in what patients knew about the auto insurance process and what medical work should be covered. 1-800-ASK-GARY has since filled that gap for hundreds of thousands of people, and Kompothecras earns a fee with every lawyer referral.

Asked how he came up with the idea to concentrate the referral business around a 1-800 number, Kompothecras says, “some of that is trade secrets, but it was really easy to get that 1-800 number. I just wanted to have something that people could remember easily.” 

Right place at right time

While success hasn’t always come easily to Kompothecras, he does have a knack of putting himself in the right place at the right time, by ideas, guts, vision or some combination of all three. 

There was the time, soon after he graduated from USF in the 1980s, when Kompothecras says a lot of people were becoming stockbrokers, so he thought he would, too. He found a bank he wanted to work for in Sarasota, cold-called a manager there and said, “There’s a really great guy you have to hire; he’s really hungry for this job.” The manager asked Kompothecras who this person was. “I said, ‘it’s me,’ and I got the job.” 

Kompothecras did well as a stockbroker, earning enough to buy a BMW. For someone who grew up with nothing, sleeping on an old couch at his grandmother’s house, that was a big deal. He later started a shipping business — but that went bankrupt when he was 30. Up next? Chiropractic college. That led him to start his medical clinics, and later, 1-800-ASK GARY. 

More recently, Kompothecras bought a bar: In 2019, he acquired the Crescent Club, a 70-year-old institution on Midnight Pass Road on Siesta Key. That purchase has led Kompothecras to push forward on other real estate ideas, including his big dream of building a hotel attached to a global flag. That project, approved by Sarasota County commissioners in 2021, would be a seven-story, 120-room hotel on a 1.17-acre site on Old Stickney Point Road, near the south bridge to the Key. He would also build a five-story parking lot on an adjacent site. 

The hotel project, which remains in legal limbo, has brought Kompothecras another label: greedy developer. That’s the gist of dozens of Facebook and other social media posts when a local media publication writes a story about the project. Other opposition is more organized, and in some cases, the legal side is led by Lourdes Ramirez, a Siesta Key resident and former Sarasota County Commission candidate. 

Ramirez sued Sarasota County, alleging commissioners violated the county’s comprehensive plan when it approved the Kompothecras proposal and another hotel project on the Key. Ramirez cites density and infrastructure issues in her opposition. “There are a lot of reasons why we shouldn’t have mega hotels,” she told the Siesta Key Observer in August. “We can have hotels out here, but keep it reasonable.”

Kompothecras bristles at accusations he’s not looking out for the Key or is a carpetbagger, or any of the other accusations. He notes, for one, that he’s lived on Siesta Key since 1983 — longer than most and more devoted to its future.

“I want to build a world-class hotel on Siesta Key,” he says. “I’m determined to get this done. I’m not going to let them derail me from building this hotel.”

One more Kompothecras jab, against some opposition from Siesta Key condo owners who complained about his hotel’s proposed height. “They’re not entitled to that view for the rest of their lives.” 

Friendships matter

Kompothecras has even more labels. Another is generous. His longtime friend, Manatee County Supervisor of Elections Mike Bennett, a former state senator from Bradenton, has known Kompothecras for decades. Bennett says during the crux of the 2008-09 real estate recession some deals he was a partner on went sour. He needed a loan of about $1.3 million or faced foreclosure of a property. Banks were no longer an option. Bennett mentioned it to Kompothecras — not for a handout, but more as a vent. “Gary said, ‘Consider it done. I’ll lend you the money. When do you need it?’” Bennett recalls. “I asked what he needed as collateral. He said, ‘I trust you.’”

“People only know him because of his hotel development,” adds Bennett. “It’s a shame because he’s really an amazing guy.”

Gary Kompothecras is a man of many labels: entrepreneur, physician, hotel developer, TV and film producer, family man and visionary.
Photo by Lori Sax

Another example? Kompothecras has often hosted pool parties for 100-plus kids who played in a flag football league sponsored by Evie’s Tavern & Grill in Sarasota. Evie’s owner Mike Evanoff has been to many of those events, witnessing the dropped jaws of the young attendees. “These kids would never get a chance to be at a house like that,” Evanoff says. “They would never get an invite like that.”

The flipside to Kompothecras’ generosity and loyalty: Don’t cross him. “You don’t burn him in a business deal,” Bennett says, “because if you do, he will light you like a short match.”

Always all in

His generosity, meanwhile, is seemingly only matched by his gregarious nature. 

There was the fundraiser Kompothecras hosted for Gov. Ron DeSantis before the last gubernatorial election at his Siesta Key home. Not content with the usual party favors, Kompothecras brought a live elephant — the symbol of the Republican Party — to the event. 

David Ramba, a Tallahassee lobbyist and longtime friend of Kompothecras, recalls another scene. It happened several years ago when Ramba joined Kompothecras on a trip to the Bahamas. Kompothecras spent all day in the pool with his kids. Then the pair played blackjack from 10 p.m. to sunrise. The wins and losses mostly evened out, never going deep either way, but the hours were raucous. “Every card was a cheer or a jeer,” Ramba says. “Gary is always all in.”

The all-in label applies to Kompothecras when he works on political causes, too. That’s especially true for his efforts on childhood vaccinations in the late aughts, which stems from his belief that his children’s autism came from an ingredient in vaccines they received when they were infants. (Multiple science publications have published articles debunking the vaccination-autism theory.)

“When you’re in Tallahassee with Gary, you are not doing anything else and not doing any work,” says Ramba. “You are with him all day long. He wants to get answers. He’s like a bulldog. He’s not going to back down from anyone, and he’s not scared to pitch anything to anyone.”

All in has occasionally brought Kompothecras some unwanted attention. He was charged with driving under the influence, for instance, in an early morning police stop in February 2018. Authorities alleged he was driving a silver Porsche 100 mph on Interstate 75 in Manatee County around 2 a.m. Those charges were dropped six months later in a case where Kompothecras’ attorney says his client was innocent — not merely a dropped case for lack of evidence on a technicality.

Kompothecras, taking all the ups and downs of his life, above all labels himself a positive person who advises others to fail forward and always look for what’s next. “When something bad happens, you have to keep working,” he says. “Keep going.”


Mark Gordon

Mark Gordon is the managing editor of the Business Observer. He has worked for the Business Observer since 2005. He previously worked for newspapers and magazines in upstate New York, suburban Philadelphia and Jacksonville.