Yacht entrepreneur meets demand for high-end water access

All Brian Crotty wanted to do was buy a boat. 

Going on three years later, the self-dubbed accidental entrepreneur now helps oversee a multimillion-dollar luxury boating brand based in Sarasota — with potential for more growth. 

A former tech CEO, Crotty and his wife, Peggy, purchased a 38-foot yacht named Top Shelf in December 2023. Turns out the couple the Crottys bought the boat from, in Osprey, south Sarasota County, also operated a charter business, Kokomo Charters for eight years. It also turns out that couple was moving away. 

“I didn't buy (the boat) for a business,” says Crotty. “I bought it because I wanted a boat, but then I figured, well, let's also use it as a tax write-off…To do that, you have to make it a business asset, which means you have to make it a charter boat.”

So he bought Kokomo Charters from the couple. At the time, he was the CEO of Atlanta-based Fusion Connect, a multinational technology company, so when the phone started ringing from people looking to go boating through Kokomo Charters, he passed along the project to Peggy. 

Photo by Lori Sax

Crotty retired from his corporate career in 2024, moved from Palm Beach with his wife to Lakewood Ranch and now has four boating-related businesses in his portfolio: Kokomo Charters, Kokomo Yacht Club, SRQ Yacht Management and Offshore Sailing School. Peggy is a co-owner in all of them.

While he declines to disclose exact revenue, Crotty says Kokomo Charters and Kokomo Yacht Club combined are a multimillion-dollar brand, and each of his companies is a “standalone profitable entity.”

Currently, Kokomo Charters and Kokomo Yacht Club have a fleet of 22 boats. Crotty owns several vessels, and about 17 other vessels have contracted with the company through a revenue-sharing program he says helps offset the costs of ownership; the vessel owners allow him to use their boats for charters and/or members, and he gives them a portion of the revenue. He estimates he has $24 million to $25 million in yachts under management.

Crotty, who had a 30-year career as a corporate executive, says he discovered there is “this real demand for boating in Sarasota that we didn’t know existed” when first moving to the area.

“If you're in Sarasota and you're not on the water,” Crotty says, “you're missing half of the greatness of Sarasota.”

Luxury focus

It was through owning his first couple of boats and offering to charter them that Crotty discovered the Sarasota market for luxury boating.

After buying his second yacht — Memory Maker — in 2024 so he, his wife and their dog could travel up and down the Gulf Coast, they made it a charter; and, he says, right away, it was chartered for 30 days.

“There's only so much access to the waterway compared to the massive level of growth happening on land” in Sarasota, Crotty says — calling out an issue Sarasota County elected officials have been grappling with for years. There are also not enough slips so if people even wanted to own a boat, he says, they may not have anywhere to put it.

“If you don't own a boat and you want boating as an event once or twice a year, that's where we've got Kokomo Charters,” Crotty says.

Through Kokomo Charters, people can charter a yacht or other vessel for a few hours to days. The typical charter is four hours, with rates ranging from $350 to $1,800 an hour, Crotty says. Clients range from those who want to visit restaurants and sandbars to others conducting burials at sea. Sunset charters generate significant interest, as do special occasions, he adds. 

“I can't tell you how many surprise engagements, weddings, family reunions [and] college graduations” the Kokomo fleet has hosted, Crotty says. “We can do anything to make that spectacular.”

Crotty’s approach to hospitality as a luxury brand is simple, he says: “The answer is — there is no no. You just find a way to make it happen. ”

He notes he's had the entire executive teams of the St. Regis Longboat Key Resort and The Ritz-Carlton, Sarasota on his vessels, and both recommend Kokomo Charters to their guests through their concierge services.

“I’m luxury-focused,” Crotty says, which aligns with those brands. “Everything I do is high-end.”

To provide an elite experience for clients, Kokomo vessels do all their pickups and dropoffs at The Quay in Sarasota from a private dock where there is also private parking for the boaters at Ocean Prime restaurant. Ocean Prime and Morton’s Market also provide a significant amount of catering for his clients while they are on outings, Crotty adds.

Handling the day-to-day operations— and making sure the promise of an elite experience comes to fruition — for Kokomo is Peggy Crotty, who provides concierge service, doing everything from answering the phones to keeping boats stocked with supplies.

"If someone's asking me for something, I'll figure out how to do it," says Peggy Crotty, whose requests have ranged from hiring private chefs to tracking down hard-to-find alcohol to coordinating a mermaid-themed birthday party. "We've also done lots of engagements where we have the photographer on the boat — he pretends that he's a mate in training, and he hides the camera."

‘Boating as a lifestyle’

Seeing there was a different category of boaters in the market — who wanted more than a charter — Crotty started Kokomo Yacht Club in 2024.

“If you want boating as a lifestyle, and you really want to have it where you have access as if you had your own boat,” Crotty says, that’s when people join Kokomo Yacht Club. 

Kokomo Yacht Club is designed for those who want to go boating at least five to seven times a year, Crotty says. It starts at $19,900 to join, with tiered levels going up to $74,900 a year, based on how much people plan to use their membership. 

Many members are former yacht owners who don’t want to deal with the maintenance anymore, those who considered ownership but economics didn’t make sense or smaller boat owners looking for something more. Membership provides access to boats in multiple categories, from power catamarans to center consoles to yachts.

“We just give you the pure joy of boating with none of the hassle of ownership,” Crotty says. Kokomo Yacht Club, which is a virtual club, not a physical marina, includes boats from Sarasota to St. Petersburg, where he has slips at the Vinoy Marina.

There are perks for members, like fireworks shows, watching the St. Pete Grand Prix from a super-yacht and access to the exclusive Useppa Island in Lee County.

“The surprising component of the yacht club was it wasn't just members wanting to be out on a boat,” Crotty says. “They're looking for an excellent social experience. They want to spend more time with other members.”

Photo by Lori Sax

Membership has been climbing in the past year, according to Crotty, ranging from young executives with families to seniors who don’t want to deal with yacht maintenance.

“The club continues to grow beyond our wildest expectations,” Crotty says in an August interview aboard I’m Lovin’ It, a 48-foot multihull yacht docked at Marina Jack in Sarasota. “We have several dozen members. We don't disclose exactly how many, but it's continuing to grow at a nice pace.”

Kokomo Yacht Club, he notes, provides recurring revenue, unlike the charter business. To allow for access and growth, he says, he has slips around the region, which can cost upwards of $2,400 a month.

More businesses

Once he owned his first few boats and was tasked with maintaining them, Crotty started SRQ Yacht Management to service vessels like his because he figured other owners were facing the same challenge. 

“We didn't get into this to be in the boat business,” Crotty says of all his ventures. “We are reacting to the needs of the market and not overshooting the moon.”

His latest business acquisition came as the result of his being attuned to some changes in the market. Crotty acquired Offshore Sailing School, which was started in the 1960s by a Naples couple, Steve and Doris Colgate, who are in the National Sailing Hall of Fame and one of whom, Steve, was an Olympian. Crotty acquired the school at the end of 2025, after the business declared Chapter 11 bankruptcy.

Offshore Sailing School is based in St. Petersburg, though he plans to run it out of Sarasota and St. Pete. It provides education for those looking to be captains or boaters. In addition to sailing, it teaches people how to operate powerboats.

“If you want to learn to boat, we can teach you to boat,” Crotty says. “You can end up renting boats anywhere in the world with our certification.”

Next wave

In five years, Crotty estimates the sailing and powerboat school could be his largest asset, as he plans to employ workers to staff the program and expand geographically.

“With everything that we've got, it's quite an ecosystem," Crotty says, from the charters to the club to maintenance to the school.

“What's next is to continue to be opportunistic,” he adds, while also being in the moment. “I think we've got a good thing going,...I'm in no rush to get there.”