Tom Cherichello did not set out to become a lawyer. He was working insurance claims part time through college, deployed to catastrophes like Hurricane Andrew in 1992 and Katrina in 2005, when a stranger on a flight to Tarpon Springs handed him a business card and told him to come work in Sarasota. That stranger was Dr. Gary of 1-800 Ask Gary, and it was Gary who later pushed Cherichello, then over 40, to go to law school. He passed the Florida bar on his first try and has since added Louisiana and was studying for New York at the time of the interview.
The backstory that separates Cherichello from most personal injury attorneys is that he worked the other side first, as an insurance adjuster and claims manager, before switching to representing homeowners and accident victims against the companies that once employed him. That experience shapes his pitch to Sarasota clients: he knows how adjusters decide what to pay and what to deny, and he says he has never lost a property damage claim, hurricane or otherwise. His closest call was a Riverview homeowner with no documentation on a denied roof claim, which settled for half in mediation.
The case that stuck with him most involves a 13-year-old girl struck by a driver in her 90s in a Sarasota mall parking lot, still limping a year later, whose insurance company offered a $13,000 settlement. Cherichello uses stories like that to warn Sarasota homeowners away from public adjusters, who take a cut and then hand unresolved claims to a lawyer anyway, taking another cut in the process. His advice is to skip the middleman and call an attorney directly when a claim gets denied or lowballed.
On the roundabout question, Cherichello does not hold back, calling them idiotic and singling out the one in front of the Van Wezel as the worst in town, joking that its construction alone sent him out to Longboat Key three times. He rounds out the conversation with a tour of his favorite Sarasota spots, from the Crescent Club on Tamiami Trail to breakfast at Salty Dog's, and recommends the show track down the founders of Brewster's on Main Street next.
What you'll take away
- Cherichello built his practice on having worked as an insurance adjuster before becoming a personal injury and property damage attorney
- He says he has never lost a property damage or hurricane claim case, with one settlement split 50/50 in mediation as his closest call
- He advises homeowners to go straight to an attorney rather than a public adjuster, who takes a percentage before handing unresolved claims to a lawyer anyway
- A Sarasota mall parking lot case involving a 13-year-old pedestrian and a lowball insurance offer illustrates the gap between what insurers offer and what victims are owed
- He calls the roundabout in front of the Van Wezel the worst in Sarasota
“I know how to get insurance claims paid, I know why they pay, I know why they deny.”
“Don't let the insurance company push you around.”
Places mentioned: Van Wezel, Longboat Key, Crescent Club, Beach Club, Salty Dog's, Brewster's