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IYG’s newest hire, Robbie LaGuardia, is a Naval Academy grad who is applying the lessons he learned in the service to selling yachts.
Robbie LaGuardia was practically born with saltwater pumping through his veins. He grew up on Martha’s Vineyard—that hallowed New England playground—and spent his early years literally surrounded by the sea. “I’ve always taken it as a point of pride that I was a proper Islander,” he says.
“Everywhere I went when I was a kid, there was water. So you really learn to love it, because it’s a part of your everyday life.
Early Years
LaGuardia’s career in boating got off to a precocious start. At an early age he began piloting the launch boat for the Vineyard Haven Yacht Club and also became scuba certified to clean hulls in the marina. “I was doing stuff that, looking back, I’m kind of surprised my parents were OK with me doing as a kid,” he says with a laugh. “But my parents had a Hinckley Sou’wester 30, and we were on it all the time, so boats and boating just came naturally to me.”
The Service Comes Calling
It was a passion that LaGuardia would take with him when the family moved to New Bern, North Carolina, yet another boating hotspot. In New Bern LaGuardia kept sailing, but he also began playing other sports, and it was there that a new kind of job began to whisper in his ear. “I had a lot of great mentors, particularly some coaches, who encouraged me to go into the military,” he says. “New Bern is close to Camp Lejeune and Carolina in general has a lot of strong military ties, so it was something that was just always around and seemed natural.”
But again, military service was also something in his blood. His father, uncles, and grandfather had all served in the Navy, and when LaGuardia visited a friend at the U.S. Naval Academy in Annapolis he was immediately taken by the active curriculum. “By the end of high school I knew that I was tired of just sitting at a desk,” he says. “Don’t get me wrong, I was a pretty good student, but that life just wasn’t for me. When I went to the Naval Academy and saw the guys doing not just schoolwork, but also boxing, wrestling, and obstacle courses, I was like ‘OK, this could be something that works well for me.’”
Finding Bermuda
LaGuardia applied and was accepted. (This fact alone belies his claim that he was a “pretty good” student. With an acceptance rate in the high single digits, the Naval Academy has no need for students who are “pretty good.”) At Navy, LaGuardia walked on to the sailing team and worked his way up to skipper. The team did all sorts of serious races—Annapolis to Newport, Marblehead to Halifax, and a journey to Bermuda, among them.
You put eight college kids in a boat in the ocean with nothing but a sextant and tell them to find Bermuda, that will help build confidence for sure,” he says.
In 2018 LaGuardia graduated and was commissioned as a Surface Warfare Officer. He served onboard cruisers and destroyers, and deployed twice: once to the Middle East and once to the South China Sea.
Being in the service taught me a lot about honesty, integrity, and the value of hard work,” he says.
After six years, LaGuardia called it quits in the Navy and began thinking about the future. But his active nature soured him on the usual management consulting gigs that naval officers often find themselves shoveled into.
A Fortuitous Connection
As luck would have it, IYG’s Patrick Hopkins’ mother taught high school in New Bern, and knew LaGuardia’s parents. She mentioned to them that their son might like the yacht brokerage business, and that’s how LaGuardia found himself on a plane bound for the 2024 Miami boat show. There he shadowed Hopkins and got his first taste of the business. It was a flavor that agreed with him. He got his first yacht sales job at a brokerage up in Long Island. After 18 months in the Northeast, he got the call from IYG to come down to Florida.
The Big Leagues
LaGuardia was assigned to work alongside George Jousma in the Palm Beach office. In Jousma he will no doubt find yet another strong mentor, as George is one of the most experienced yacht salesmen on Earth.
So how is LaGuardia finding the transition from protecting global trade routes to selling multi-million dollar yachts? It turns out, pretty smooth actually.
You know, you can walk down Worth Avenue and Palm Beach can feel a little overwhelming, for sure,” he says. “But once you step aboard a yacht with these guys, and everyone is in flipflops and sunglasses and you’re just looking around a boat—and you both have this passion for the same thing, you’re really just two people with common interests following their passion,” he says.
“I think the class ring from Navy helps a lot,” he continues. “People down here are very patriotic and they respect the service and I get a lot of thanks yous from people, and honestly I think it opens a lot of doors,” says LaGuardia, who already has a Sunseeker 52 and a Sabre 45 under contract.
One thing he has found funny in his new career is sea trials. Some people—thinking he is a newbie—have asked if he’ll be OK behind the wheel of a 90-footer. “I just have to laugh,” he says. “I’m used to driving a 509-foot destroyer in the South China Sea. As long as I don’t look over my shoulder and see the Chinese navy shadowing me outside the Port Everglades Inlet, I think I’m going to be just fine.”
