Hendrickson Insurance
Hendrickson Insurance
Dennis Hendrickson runs Hendrickson Insurance, an independent Florida agency in Sarasota writing both commercial and personal lines for the Gulf Coast: Bradenton, Tampa, St. Petersburg, and the communities in between. Before insurance he managed shopping centers. Before that he was a Division I tennis player at UNC Charlotte, and before that he was a New Jersey high school kid whose record forced the state to rewrite its rules. That last part explains how he works a file.
In New Jersey high school tennis, only the top first- and second-singles players in the state could qualify for the season-ending state singles championship. Third singles could not, no matter how good they were. Dennis played third singles for East Brunswick High School. He went 43-1 over two seasons and was ranked 107th in the country in the 16-and-under division. He did not lose a regular-season match in two years.
In March 1991 the New Jersey State Interscholastic Athletic Association changed the rule specifically because of him, opening the state singles tournament to nationally ranked, unbeaten third-singles players. The Star-Ledger reported that in high school tennis circles it was already known as the Dennis Hendrickson rule. The state tournament director said it plainly: after seeing what Hendrickson and his teammates had done, they had to take a good look at the rule.
"If a player has good enough credentials, no matter what position they play, they should have a chance to play in the state singles tournament." Dennis Hendrickson, age 17, The Star-Ledger, March 14, 1991.
The next season East Brunswick won its first state Tournament of Champions and finished the year ranked number one in New Jersey at 27-2. In the final against Newark Academy, with the match tied, Dennis clinched the state title at third singles, 6-1, 7-5. He finished the season 25-3 and was the 1992 Middlesex Conference champion.
And the rule he had inspired a year earlier did exactly what it was meant to do. East Brunswick became the first school in state history to send all three of its singles players into the semifinals of the state singles tournament. He changed the rule, then he used it, then his team made history with it. That is the whole pattern of how he operates.
Coming out of East Brunswick with that record, Dennis was recruited by Columbia University in the Ivy League, by Rutgers, and by the United States Naval Academy. He chose UNC Charlotte, a Division I program in Conference USA where he could play from the first day. That was his call, and he made it the way he still makes them: he looked past the name on the letterhead at where he would actually get to compete, and he went there.
Dennis played four years of NCAA Division I tennis at UNC Charlotte in Conference USA, earning four varsity letters and a degree in Business Administration. The numbers on his letterman plaque are the school's, not his: 42 career singles wins and 18 in doubles. He won a career-high 14 singles matches as a freshman, which led the team, and 13 as a sophomore, tied for second on the squad. Over four years he played singles flights two through six and every doubles flight. His 42 career singles victories were the most of any letterwinner on the 1996 team, seven wins shy of the school's all-time top ten, on a senior-year squad that went 13-9 against one of the toughest schedules in program history.
That freshman season earned him a congratulatory letter from his state senator and two assembly members back in Trenton. He is on the cover of the 1996 UNC Charlotte men's tennis media guide, and the school's official record book lists him on the all-time roster, 1992 to 1996.
After Charlotte, Dennis studied journalism at Harvard University, and he is a member of the Harvard Club of Sarasota today. He spent years managing shopping centers before he ever wrote a policy, which is why plaza and strip-center owners talk to him as a peer who has read the leases and chased the certificates, not as a salesman. Then he built Hendrickson Insurance as an independent agency in Sarasota writing both commercial and personal lines, so the people who own the buildings and the businesses get one accountable person for the homes, cars, and boats too.
Long before he sold a policy here, Dennis was a kid training at Nick Bollettieri's academy in Bradenton, the same stretch of coast he now serves. The academy in those years was the hardest tennis room in the world. He trained alongside players who went on to win Grand Slams, among them Iva Majoli, the 1997 French Open champion, whom he beat in practice, and he hit with Jimmy Arias, Bollettieri's first star and a top-five player in the world. He grew up a ranked junior in the Eastern section, competed nationally through his teens, and came back to the game as an adult, coaching competitive juniors and adults in Sarasota. The Gulf Coast is not a market he moved to. It is where the whole thing began.
Dennis was diagnosed with cancer and went through a full course of radiation to beat it. The machine in the photo is the one that did the work, a Varian TrueBeam, and he lay under it session after session while it did. He took the picture because he wanted to remember what he was up against.
He will tell you that tennis got him through it. Not the strokes. The part of the game that teaches you to show up for a match you might lose, play it one point at a time, and never quit in the middle of it. That is how he handled radiation, and it is how he handles a bad renewal or a claim a carrier is fighting. He has been on the wrong end of the odds. He knows what it is to need someone in your corner who does not flinch.
Dennis lives and works in Sarasota, in the same storms his clients ride out. On October 10, 2024, the day after Hurricane Milton came ashore at Siesta Key, he was at his neighborhood gas station when Governor Ron DeSantis walked in with the state emergency management team on a tour of the damage. They talked for a minute, the governor gave him a fist bump, and both went back to work. Dennis took the photo.
The point is not politics. The point is that when a named storm hits this coast, the agent handling your claim is here, with the same wind and the same water, not reading about it from a call center in another state. He knows which roads flooded because he drove them.
Every renewal is a contest. The carrier wants a higher premium and a narrower policy. You want the opposite. The agent in the middle either fights that out on your behalf or forwards the email. Most forward the email.
Dennis was recruited by Columbia, Rutgers, and the Naval Academy, played four years of Division I tennis, and got a state rule rewritten at 17 because he would not accept a no. Nobody gets recruited at that level, or plays at that level, on talent alone. It takes a person who works a problem until it gives, shows up when it is not convenient, and treats a rule as something to be examined rather than obeyed. That is the person on your renewal, on the claim a carrier is slow-walking, and on the commercial building three other agents said could not be placed.
Dennis spent years managing shopping centers before he was ever an agent, so when a strip center or plaza owner calls, he is talking to someone who has read the leases, collected the certificates, and dealt with the tenants. He writes both commercial and personal lines because the people who own the buildings also own homes, cars, and boats, and it is easier on you when one person sees the whole picture and is accountable for all of it.
He does not have a call center. When you call Hendrickson Insurance you get Dennis, and he does not let go of a file until it is won. He has been that way since he was 17.
One more thing about him. He once stopped on a three-lane highway and crossed all three lanes of moving traffic on foot to pull a kitten out of the road before she was run over. He put his own life on the line for a kitten. She lived. That is the same person who picks up when a carrier is trying to walk away from your claim.
Commercial property, strip centers, business liability, and the homes, autos, boats, and umbrella policies of the people who own them. Sarasota, Bradenton, Tampa, St. Petersburg, and the Gulf Coast.
Dennis Hendrickson changed a New Jersey state tennis rule at 17 and played four years of Division I tennis at UNC Charlotte. Today he writes both the commercial and the personal insurance for Gulf Coast owners himself, and he works a renewal or a claim the way he played: nothing conceded, no point given away.
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