Chip Short first came to the Keys in 1996 for a winter sailing seminar held at Plantation Yacht Harbor. With a high-stress job that regularly sent him cross country, the jet-setting computer tech had no idea he’d be back.

However, after flying around the bay in a sleek catamaran, Chip and his wife Barb stopped for a cocktail at Plantation Yacht Harbor’s legendary “Lagoon Saloon,” (sadly now demolished) and immediately realized they were hooked on our island community. “We found out that if you tipped the bartender, when he saw your boat coming in, he’d make cocktails and deliver them to you in the water!” Chip says. “It’s sort of strange how life turns around— I never thought I’d actually be working here someday!”

Now Chip runs Founders Park Watersports, a job that finds him selling ice cream to kids, renting lawn chairs to tourists, and giving beginner sailing lessons to excited students— all while working on one of the most beautiful beaches around for a company that he created with his lovely wife, Barb.

“In my previous job, by the time a customer got a hold of me, it was on the phone and they were mad and angry— they’d been on hold for a while,” Chip says. “The environment here is when people walk up they’re, on a beach and generally in a good mood to begin with. It’s done a lot to reduce my blood pressure.”

Sailor-turned-student, then back again
Originally from Ohio, Chip first tasted the sailing lifestyle as a boat-tender on Lido Beach near Sarasota. Besides renting out dinghy’s to random resort goers, the enthusiastic 17-year old would often show up to work as crewman on the area’s countless race yachts. Here, at Sarasota’s Saturday “Beer Can Races,” young Chip was at the beck and call of fun-loving captains who needed help raising sails and hauling lines. “Basically I was ‘rail-meat’ on somebody else’s boat,” Chip says with a smile. “Usually I ended up giving out cans of beer.”

Giving up his life on the water to grow up, Chip then attended college at Florida State University, where he toiled to earn his master’s degree in electrical engineering. Upon graduation, the tech savvy student used his mastery of the growing internet technology field to blissfully bankroll on the late 90’s tech bubble. Here, Chip continued his fast-paced life not as a sailor, but as a surfer of sorts. Building a large internet company in Clearwater Florida, he eventually sold his successful, nationwide business to a ravenous Japanese technology firm before the bubble went pop. Reinstated as the company’s director, Chip was then able to take the company lead on a team of tech-savvy computer nerds before calling it quits and making his way to the Keys. Pursuing his passion for sailing and his love for the outdoors, the savvy sailor returned to Plantation Yacht Harbor to set up shop on the beach and start Founders Park Watersports.

He even brought his best buddy Jim with him.

Unlikely friends
Chip first met his Mohawk-wearing, punk-rock guitar playing, friend Jim while studying computer technology in Tallahassee. According to Chip, both lived in FSU’s student slums, with Jim’s apartment literally in the backyard of Chip’s house and behind the football stadium.
The two future friends couldn’t have been less alike.

While Chip wholeheartedly studied for his grueling exams and practiced martial arts, Jim did things like drive VW Beetles onto his front porch and create fake crash scenes with stolen crash test dummies complete with pools of phony ketchup blood.

Yet after putting up with dozens of sleepless nights, bottle rockets through his window, and invasions of random chickens, Chip finally gave in and accepted his new neighbor’s madness for what it was.

“The semester I met him I had calculus, physics, and chemistry all at the same time,” Chips reports with a sigh. “They were these loud, obnoxious punk rockers with loose women, beer cans, farm animals, and who knows what else over there!”

Delivering his spin on the story Jim (who is coincidently still Chips neighbor) says “Yeah, my roommates and I were screaming young punk rockers in the early 80’s. We had a band called Paisley Death Camp. If we wanted to have band practice at 3 a.m., we’d hang out and practice at 3 a.m.”

“I also had a chicken named Fido,” he explains.

Confessing his respect for the studious young scholar, Jim continues “Chip was always next door doing his homework and studying away. Basically, he set the only good example in our neighborhood— that’s why we liked him. Plus, he was the only mechanic that would work on our junked-out cars.”

And so the friendship was formed.

Still a resident of Chip’s neighborhood, Jim now lives in Chip’s guesthouse. “I don’t know why he keeps me around,” he says with a laugh. “But I’m sure glad he does.”

Worth fighting for
Chip met his beautiful wife Barb while attending a beginner’s class at the FSU Tae Kwon Do Club. Both students took to the unique martial art with gusto, and eventually rose through the ranks to earn their black belts while slowly falling in love. However, it wasn’t so easy for Chip to win the heart of the violent vixen. “She was dating the Tae Kwon Do instructor at first, and so I had to take a couple of beatings,” Chip jokes. So after proving his might, the young warrior sealed the deal on a relationship with Barb that would stand the test of time and bring the couple’s love of competition to nearly every aspect of their careers. Now retired from their lives as Tae Kwon Do practitioners, the couple now regularly stomp the competition as small boat sailors— an activity they say is filled with just as much grace, technique and competition.

Accomplished small boat sailors, Chip and Barb Short regularly compete in area regattas and once zoomed through New York Harbor in the Statue of Liberty Race. Accomplished small boat sailors, Chip and Barb Short regularly compete in area regattas and once zoomed through New York Harbor in the Statue of Liberty Race.

Chip and his best buddy Jim. Chip and his best buddy Jim


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