How to Be a Millionaire in Flip-Flops


Sue Cooper with the quintessential millionaire in flip-flops, Jimmy Buffet. (Photo: Sue Cooper)

A few years ago Sue Cooper found herself in a funk. She’d just gotten out of a 15-year relationship and felt plain awful. Nothing was helping. One morning she made a command decision: Just start saying yes. She would say yes to invitations, to activities, to parties, and most importantly to life.

"It got me out of that funk just like that," she told me, snapping her fingers. "By saying yes, I circumnavigated the world, got picked up to race paddleboards, and changed my entire life."

You can tell, after just a few minutes of meeting her, that Sue Cooper is the kind of person who isn’t afraid to change her entire life.

Today, Cooper is a professional paddleboarder, franchise business owner of Lazy Dog Adventure Outfitters, and the author of the inspirational book “Millionaire in Flip-Flops.” She wrote the manual for the Special Olympics for paddleboarding. She travels the world with friends while racing and promoting her Lazy Dog brand. She does what she loves every day.

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Lazy Dog’s home base at Hurricane Hole Marina in Key West, Florida. (Jo Piazza/Yahoo Travel)

Her experiment in yes was the second great life change for Cooper, a striking blonde with a year-round tan, who used to work in corporate America for a shoe giant based in Connecticut. At age 27 she even won an Executive of the Year award.

"I woke up the next day and I was miserable and I realized my whole life was work. Everything," Cooper said. "Right then and there, I decided to quit. I decided I would live the life I only thought I would have once I was retired."

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Hiking the Na Pali coast of Kauai, Hawaii. (Photo: Sue Cooper)

Cooper loves to work, so just bailing on the work force wasn’t going to be an option for her. The difference was that she wanted to enjoy what she was doing.

"I thought ‘I love the warm water and the island life.’ I didn’t just want to drop out," Cooper said.

She headed south, about as far south as you can go in the continental United States: Mile Marker 0 on U.S. Highway 1. Even though she’d only been kayaking once before, she found work as a kayak guide in Key West, Florida. That soon turned into a small business renting out kayaks. It wasn’t easy in the beginning. Best known for spring breakers, bar crawls down Duval Street, and around-the-clock happy hours, Key West wasn’t exactly a mecca for healthy living and athleticism.

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All of that was starting to change around the millennium and Cooper was right there for it. In 1998, Cooper’s best friend drew a design of Camillo, a globe-trotting border collie called “Lazy Dog,” who was a little famous on the island. Something clicked. Right there was the birth of Lazy Dog, the adventure outfitting company. They printed T-shirts and made kayaking and paddleboarding into a real business.

"Eventually I bought him out," Cooper said. "I knew I wanted to stay here forever. I love being here every single day."

Cooper began hiring her friends and encouraged a work culture of well-being, happiness, honesty, and respect. She urged her team members to travel, alone, and together. As long as her employees give her a month’s notice, she tells them they can go off and travel and still have a job when they get back. When she goes to Hawaii for paddleboard races, she rents a house on VRBO and takes everyone along with her.


"I love what I do," Cooper says. (Photo: Sue Cooper)

Everyone who works at Lazy Dog adores the water. They have the largest rental fleet of kayaks and stand-up paddleboards (known as SUP) on the island where they offer kayak and paddleboard ecotours and back-country snorkeling. Most of the Lazy Dog crew have been there for over eight years, and a few for 12 years. 

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"We all joke that we are each other’s longest relationships," Cooper says about her coworkers. 

Each morning Cooper wakes up at 5:30 for a Key West ritual, boot-camp training with Tommy Taylor, a former master chief in the Navy who conducts workouts for free  three times a week at the naval base in Key West.

Taylor peppers his training with motivational speaking.

"You’re done by seven and you feel like you can do anything," Cooper says.


Meet Casey, the second-generation of Lazy Dog. (Jo Piazza/Yahoo Travel)

Cooper walks her dog Casey with a cup of tea, a holdover from a childhood spent in the U.K.

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She starts her work day at Lazy Dog at 9 a.m., doing everything from leading kayak and SUP adventures through the mangroves to renting boards and boats. She sticks around until 1 or 2 and then gets some work done on the computer, often on the laptop while sitting outside in the sunshine.

So what does it mean to be a millionaire in flip flops?

"Instead of chasing the millions I wanted to live a life that most millionaires would love to be living," Cooper said. "For me, it was always about following the passion instead of the money. If you do that then the money will come."

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