How Five Retirees Turned Their Passion into a Business

Call it boredom, call it opportunity, or even call it inevitable. Not only are U.S. retirees heading back to work in retirement — they're also running the show.

Take Jim O’Connell, a New Orleans-based newly minted charter boat captain for GetMyBoat.com, an Airbnb-like boat rental company that allows entrepreneurial boat owners to rent out or charter their vessels to customers.

"I’d been sailing for many years by the time I retired, and I had wanted to have a way I could supplement the maintenance costs of the boat," he says. "So I decided I would go get my captain's license and do sunset charters on Lake Pontchartrain."

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O’Connell, who duly earned his U.S. Coast Guard Captain's license and began hosting sailing charters on his boat, says now he gets to meet people, earn money and enjoy being on the water.

"It’s a great option for many retirees who may own a boat but don't have a reason to go out on the water as much as they'd like," he notes. "By hosting charters, you have the opportunity to use your boat, meet new people and earn money in your retirement."

He's not alone.

According to Teamshares, an employee-owned business services company, 40% of small business owners are Baby Boomers. A separate study found that between 1996 and 2007, U.S. citizens aged between 55 and 64 had a higher rate of entrepreneurial activity than those aged 20 to 34.

So what's giving older entrepreneurs the edge?

Benefits of age and experience

Having a successful career to lean on and learn from gives older business owners a big advantage.

“Our recent report on 'solopreneurship' shows that Americans aged 65-plus make up about 15% of all solopreneurs,” says Andrew Chamberlain, principal economist at Gusto, an online payroll, benefits and HR software platform for small and medium-sized businesses.

Chamberlain says Baby Boomer and Gen X solopreneurs — business owners with no employees — often launch businesses with higher starting salaries than younger founders.

"While solopreneurs in general see revenues grow from about $290,000 in year one to over $500,000 by year five, older founders tend to pay themselves more in the early years compared to Millennials and Gen Z (who often reinvest in growth)," he says.

"These experienced entrepreneurs may launch with stronger networks, existing client relationships, or initial credibility, advantages that often come with age and career history," Chamberlain says.

But the numbers don’t tell the whole story. Those who’ve launched businesses in retirement have real tales to tell, often covering the emotional side of the journey they took — and how they're thriving because of it.

Here are five retirees who started their own businesses and are loving the experience, regardless of their age.

Dawn LaFontaine, owner of Cat In the Box LLC, Ashland, Mass.

Dawn LaFontaine started her pet products business, Cat In the Box, when she was 59 years old.

"My husband had just lost a job he'd held for 15 years, and I'd applied for several jobs I was overqualified for and didn't even get asked back for a second interview," LaFontaine says. "I decided that I was going to have to take control over my own working future, even though I hadn’t been working, if I was going to have one."

LaFontaine says she’s never looked back.

"My products have been featured in the Boston Globe, Parade Magazine and Fox News, among many others, and are in boutique pet stores around the country and in Europe," she notes. "Last year's sales were up 84% and are on track to double this year."

Her advice for retirees thinking about starting a business in retirement is twofold:

"Just start," she says. "Don't wait for the perfect idea to come to you. It's more about execution than product, and you'll probably need to pivot at some point anyway."

She also advises older Americans to stop analyzing and start doing, but with a plan. "Start very small so you don't jeopardize your life savings," she adds. "It's possible to start a business on almost nothing."

Janice Costa, owner of Canine Camp Getaway, East Durham, N.Y.

Janice Costa turned a side gig into something much more profound when the global pandemic forced her into an early retirement.

"I’d been dabbling with the idea and I decided to grow it into a real business rather than either just retiring, or going back into the workforce," she recalls. "Essentially, I went from a hobby to an S-Corp running Canine Camp Getaway, a business that plans vacations for dogs and the people who love them."

After working nearly 27 years in a corporate job for a company that required long hours and changed hands every three to five years, Costa says she was, well, dog-tired.

"When the pandemic pretty much forced me into retirement, I had mixed feelings," she says. "I'd started doing an annual dog vacation years ago, largely because I traveled a lot with my job, and felt it was unfair to leave my dogs behind for vacation when I was gone so much already."

Costa turned that idea into Canine Camp Getaway, feeling people might share her desire to go on vacation without leaving their dogs behind. She was right on the money.

The idea was to create a vacation where people could meet like-minded dog lovers while enjoying dog sports, activities, classes, vet seminars, dog-friendly evening entertainment and dog-focused charitable initiatives.

"I revamped the structure to become an S-Corp, started using QuickBooks, and began advertising in earnest,” she says. “I began doing more with selling [branded] merchandise at my events, and I added a second location, with multiple vacations a year in both New York and Pennsylvania."

Today, Canine Camp Getaway brings together as many as 130 guests per event and, depending on the size of the gathering, it offers anywhere from six to 11 classes every hour of the day during vacations, with courses on agility, nose work, hiking, swimming, dock diving and barn hunting, among others.

"I not only get to work with dogs, which I love, but I get to feed my creative spirit, coming up with new classes, craft ideas and event themes," Costa says.

Michael McCaman, cofounder and chief strategy officer of Orion Therapeutics, Union Bridge, Md.

Michael McCaman worked in the biotech industry for 35 years, always as a team member and team leader, but never a project owner.

"I was doing consulting at the time and met a young man with an idea and a patent application that I felt I knew how to develop and apply to the new gene editing field," he says. "We talked and agreed to make a startup out of it."

The company, Orion Therapeutics, was founded to develop nanoparticles for delivering RNA, like Moderna or Pfizer's COVID vaccines. "The special lipids (fat molecules) used to make those vaccines are painfully expensive to access, so we thought we could be a disruptive force in the growing mRNA delivery field and offer a safer, cheaper lipid option," McCaman says.

McCaman felt his knowledge and network with the industry were sufficient to make a go of it. "I had the luxury of saying I do not need any salary (yet) since I had and still have consulting income," he says. "That made it a pure play of passion and curiosity for me, which is really nice and allows me to stay calm all the time."

Age played a part in the decision, too.

"To attempt something like this as a younger man with a family to raise would have taken a lot more confidence than I had at that time," he explains.

Karen Hastie, founder of the Chamber Perks App, Sudbury, Ontario

Karen Hastie launched her technology startup business at 60, an age when most retirees or people approaching retirement have a different mindset; primarily, they want to slow down. "I realized I didn't feel that way," Hastie says. "I didn't feel 'done' yet, despite being a small business owner for 30 years. I felt I had more to give, both to myself and my community."

As Hastie phrases it, she realized that her age was her strength.

"I wouldn't have to start this business to put food on the table, so I could bring more purpose and passion to it," she says. "Moreover, my wins and failures as an entrepreneur have taught me enough to do this with confidence. I didn't think I was crazy to be levelling up at 60. If anything, I felt ready for an exciting chapter of life."

Hastie’s business, Chamber Perks App, a Canada-based Chambers of Commerce services provider, is thriving. "We’re doing well, both in numbers and in the value it is creating for small businesses, local Chambers of Commerce and communities," she says.

Hastie advises entrepreneurial retirees to steer their own path and ignore the naysayers.

"Don't live your life meeting society's expectations, and this applies especially during retirement," she advises. "While you might feel intimidated by all the new skills out there, remember that your wealth of experience and knowledge is a unique strength that will take you farther than you can imagine."

Drew Parker, creator of The Complete Retirement Planner (TCRP), Seattle, Wash.

Before deciding to retire, Drew Parker knew that he needed a detailed financial plan to ensure the timing was right and that he was financially prepared.

"I couldn't find a planning tool that didn’t rely on misguided assumptions and generic benchmarks, and that didn't require a math degree or 75-page user’s manual," Parker says.

"I also learned that 75% to 80% of households had no written financial plan and had no idea how to create one."

Parker saw that knowledge gap as an opportunity to not only help himself, but others, too.

"Having experience building financial planning tools for a $5 billion company, I created a planning tool for individuals based on the same financial planning principles used by professional advisers."

He created The Complete Retirement Planner (TCRP) for less than $600, as well as starting a corporation, designing an e-commerce website and making TCRP available for everyone online.

Parker describes TCRP as "easy for anyone to use, with plenty of notes and explanations, so calculations can be followed/understood, and all the detail needed for a comprehensive financial plan."

"Sales were slow at first, but word spread and within a year we had customers in every state," he says. "TCRP has grown every year since, with new features being added."

Parker says that retirees shouldn’t hesitate to use their skills and experience to make a difference for others. "It’s a good idea to challenge yourself, and to have some fun," he says. "You can always 'build a better mousetrap' or provide a better service, as long as you are passionate about it."

Will there be roadblocks? Sure, Parker says. "But you can overcome them, as you have in the past."

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