BY JACK SHORT – To put it simply, Scott O’Connor is living the good life. He and his wife, Kristin, aren’t cruising the seas in luxury yachts or gambling in Monte Carlo, but he lives in a tropical paradise (let’s face it, that’s Boca Grande in a nutshell) golfing, swimming and raising rescue dogs, cats and horses on five acres just off island, while spending a quarter of the year in Montana skiing and hiking.
Hard to argue with that plan.
Scott grew up in New Jersey on Long Beach Island with his mom and two siblings. He learned to love swimming and the water early, and would revisit swimming and the sea throughout his life.
He began what might have become a career in the dining industry in high school; he started washing dishes when he was 14 and had become a restaurant manager when he graduated from Stockton University with his environmental science degree.
He had been part of a famous scandal in college when, as an intern charged with collecting water samples on local Jersey beaches, he discovered something disturbing on the shore – hypodermic needles. They would become the symbol of shortsighted waste disposal that New Jersey had a tough time shaking throughout the 80s and 90s, at least.
Undeterred, he took a job as a health inspector a year after graduating college, though the scope of his duty was wider than looking for health code violators at restaurants.
He and Kristin, who had married a year before, were making the best of New Jersey life, though she commuted an hour through Philadelphia and he drove to Atlantic City every day. Kristin had been working in the family business selling truck equipment and parts, when she came home crying one day, Scott said, and told him she wished they could just move to Florida.
“I said, ‘Let’s go.’”
That was approximately 19 years ago. Kristin’s parents had just moved to South Gulf Cove. Scott and Kristin had both worked as bartenders in college and knew they could get by, so they packed up and left.
Each one got a job at the Fishery in Placida and spent about six months slinging drinks, before they were able to move into their respective fields. Scott said Kristin answered an ad placed by the Boca Grande Club, where she began as director of operations and, after two years, started to sell realty there. She still does, though Sotheby’s has since taken over their real estate business.
Scott also works for Sotheby’s now, but didn’t come to that immediately. He went to work for an environmental engineering firm before starting his own firm, O’Connor Environmental Permitting, handling permits for marine structures and working with the DEP and the Army Corps.
Of course, permits for structures like docks, rip raps and seawalls are tied closely to real estate in a place like Boca Grande, and as the market faded, so did the need for permits.
He took over a home watch company, First Watch, before the market rebounded and he accepted a position at Sotheby’s. He had acquired his license to help Kristin, when things were much busier.
About ten years ago, they were thinking of buying a home in the keys, when they happened to take a trip to Banff and fell in love with skiing. Not too long after, Kristin went with her mother to Big Sky, Montana, to see a condominium, with predictable results.
“She called and said, ‘I hope you like it here, because I just bought the place,’” he recalled.
They spend three months out of the year skiing, hiking and horseback riding there.
Five years ago, Scott broke his ankle skiing and was turned to cycling as a means of rehabilitation, which he still does with aplomb. He teaches a spin class at Banyan Tree, if you’d like to see it in action.
“If you can follow the instructor,” he said, “and put some tension on that wheel, you can’t get more cardio bang for your buck.”
That previous introduction to cycling, combined with a love of the water, was enough to have Scott dabbling in triathlons as well.
Scott and Kristin are both animal lovers, housing two horses, three rescue dogs and a host of cats on their property, which Kristin has fixed and happily keeps as barn cats.
Scott is adamant about their rescues, McKenzie, Gallagher, and Roxy.
“There’s nothing more rewarding,” he said. “We love adopting them and giving them a home, and you can tell they appreciate it.”
They took all three dogs last year with them in a camper on a two-week road trip to Montana, and if Scott didn’t say so, it would have been obvious by listening to him, how important and therapeutic the experience of hiking in Big Sky with his dogs was.
He and Kristin are planning another trip there this year, which will be a first for their latest rescue, McKenzie. He’s not sure if McKenzie will be more like Roxy, who loves trails, or Gallagher, who loves to swim, but he’s sure she’ll find something out there on the trails to love.