The Life and Success of Dr. Gary Kompothecras: A Multifaceted Entrepreneur and Creator

Dr. Gary Kompothecras is known for many things, but his favorite title is “Creator.” He is a husband and father of six kids, ranging in age from 12 to 28. Kompothecras has built a successful career as a chiropractor-turned-businessman, owning various businesses including an accident attorney referral service, a bar, and a bottled water company. He is also a landowner and real estate developer, currently working on bringing a unique hotel to Siesta Key. In addition to his business ventures, Kompothecras is a philanthropist and political donor, supporting causes such as autism awareness and Republican candidates.

“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.”

“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.”

The Success of 1-800-ASK-GARY

One of Dr. Gary Kompothecras’ notable business successes is the creation of the 1-800-ASK-GARY line, an accident attorney and medical referral service. He founded the company in 1996, and it has since grown to have 28 offices in three states, generating around $100 million in annual revenue. The idea for 1-800-ASK-GARY came to Kompothecras while running a medical clinic that treated people after auto accidents. He noticed a gap in knowledge about the auto insurance process and decided to create a service that would help people navigate it. The 1-800-ASK-GARY line has filled that gap for hundreds of thousands of people and has become a successful business for Kompothecras.

Right Place at the Right Time

Kompothecras has a knack for being in the right place at the right time. After graduating from USF, he wanted to become a stockbroker. He cold-called a bank manager in Sarasota and convinced them to hire him. This opportunity allowed him to earn enough money to buy a BMW, a significant achievement for someone who grew up with very little. Although he faced setbacks, such as bankruptcy and a failed shipping business, Kompothecras persevered and eventually found success in the chiropractic and business world.

“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.”

Building a Hotel and Facing Opposition

In 2019, Kompothecras purchased the Crescent Club, a well-known bar on Siesta Key. This acquisition sparked his interest in real estate development, leading him to pursue his dream of building a hotel. Despite facing opposition from some Siesta Key residents, Kompothecras received approval from Sarasota County commissioners in 2021 to construct a seven-story, 120-room hotel. He remains dedicated to the future of Siesta Key and believes that his hotel will be a positive addition to the community.

“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.”

A Generous and Gregarious Personality

In addition to his business ventures, Kompothecras is known for his generosity and outgoing nature. He has supported friends in times of need, offering financial assistance when they faced foreclosure. Dr. Gary Kompothecras is also known for hosting unique events, such as a fundraiser for Governor Ron DeSantis, where he brought a live elephant to symbolize the Republican Party. His friends describe him as someone who is always “all in” and willing to take risks.

“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.”

Despite the ups and downs he has faced, Kompothecras maintains a positive attitude and encourages others to do the same. He believes in failing forward and always looking for the next opportunity. Kompothecras advises others to keep working and never give up, even when faced with challenges.