The Boomers Issue

Daring to start a business when you’re over 50

At an age when they’re supposed to be considering retirement, baby boomers are gambling on new ventures.

Friends Jim Donvan and Sue Thompson at Firefly Moon, the Arlington gift shop they operate.
Keith Bedford/Globe Staff
Friends Jim Donvan and Sue Thompson at Firefly Moon, the Arlington gift shop they operate.

ALMOST AS SOON AS the Canadian-born psychoanalyst Elliott Jaques coined the term “midlife crisis” in 1965, it became the source of menopause jokes and cartoons about balding men buying convertibles. But, in fact, the kind of reckoning that takes place for many people around 50 — the age the youngest baby boomers turned just last year — today more often spurs them into trying to build rewarding second acts.

“There’s not a lot of evidence for a midlife crisis,” says Margie Lachman, a psychology professor at Brandeis University and the director of the Lifespan Initiative on Healthy Aging. “The midpoint is just a natural time for reflection, for looking back and looking ahead, asking is this all there is and seeing that there’s still time to realize your dreams.”

These days, those dreams often find form in launching a new business. A recent Gallup survey found that boomers are among the fastest-growing groups of entrepreneurs in the United States and are more than twice as likely as millennials to be planning to start a new venture within the next 12 months. Today nearly a quarter of new entrepreneurs are 55 to 63, up from 14 percent two decades ago. And more than 8 out of 10 of boomers surveyed by Gallup described their entrepreneurship as a lifestyle choice they hoped would allow them to work more independently, pursue their passions, or increase their incomes.


All three happened for Jim Donvan after he opened Firefly Moon, his Arlington Heights gift shop and gallery, with Sue Thompson, his best friend since college. Today, the two help customers pick out funky scarves, handmade jewelry, and whimsical home goods, and they have a habit of finishing each other’s sentences.

Get Today's Headlines in your inbox:
The day's top stories delivered every morning.
Thank you for signing up! Sign up for more newsletters here

For years, Donvan had traveled the world while working on and off at Harvard, where Thompson was in human resources; he later started a two-man carpentry business with her husband, Jeff Thompson. But in 2008, as carpentry work was drying up thanks to the recession, everything seemed to go south at once. Donvan, who was then 51, tore his rotator cuff and shortly after fell and broke his hip. Then his mother-in-law got sick and within weeks passed away. “I thought if I got hurt again, that could be it,” Donvan says. “Then my mother-in-law’s death woke me up to how short life is and how vulnerable everybody is.”

Fate, though, had wins for Donvan as well as losses. He and Thompson, both Arlington residents, had long toyed with the idea of starting a business together, having considered a counseling service, a restaurant, or a gift shop. Now they began to discuss it more seriously. By coincidence, the same year Donvan’s life turned upside down, health issues left Thompson feeling that she “couldn’t quite keep up with the Harvard thing.”

“Then,” says Donvan, “I saw that this commercial spot had opened up here in the Heights and I thought If I wait much longer I’m going to run out of time.” He signed the lease and went to work with Jeff renovating the space while he and Sue worked out issues like stock, payment systems, and marketing, all on a shoestring budget of less than $30,000. Now, four years in — despite a few wrong turns with the inventory and a couple years of taking no salaries — he and Thompson are making it work and are happier than ever. “When I was at Harvard I put in 35 hours a week and it felt like 80,” Donvan says. “Now I do 60 and feel like I don’t work.”

Donvan and Thompson certainly aren’t alone. As the largest generation in American history marches toward retirement age, it’s confounding traditional expectations once again. At an age that saw their parents leaning back to play morning mah-jongg and afternoon golf, boomers are leaning in, and, as with everything else they touch, they’re doing it on their own terms.

From left: Jonathan Fryer, Vinny O’Brien, Joe Sullivan, and Andrew McCabe at their Medfield distillery.
Keith Bedford/Globe Staff
From left: Jonathan Fryer, Vinny O’Brien, Joe Sullivan, and Andrew McCabe at their Medfield distillery.

FORMER CONTRACTOR JOE SULLIVAN and his business partner, lawyer Jonathan Fryer, both of Dover, are also lifelong friends — the 60-year-olds met in kindergarten — and were also affected by the recession. “In the downturn, our building business just kind of came to a halt,” says Sullivan, “and we decided to close it down around 2011.” About six months later, Fryer, who had helped found Watch City Brewery in Waltham in the mid-1990s, suggested starting a distillery along with two other buddies, real estate developer Andrew McCabe, 47, and Fryer’s law partner, Vinny O’Brien, 58.

“It’s fun to do something entrepreneurial again and fun to do something completely different,” Sullivan says. “My motivation was having a new challenge.”

He’s had plenty of challenges since AstraLuna Brands officially launched in 2013. Among them: finding an old office building to rent in Medfield, followed by the yearlong process of getting federal, state, and town permits for the new business. With a consultant, the four partners have also worked out the recipes for their first few rum and vodka products and learned how to make them, from sourcing ingredients to bottling. They’ve assembled their 16-foot-high distilling apparatus and other manufacturing equipment themselves, with only pictures for guidance. And lately, they’ve been knocking on the doors of bars and liquor stores all over the state asking them to try a few bottles.

One thing that wasn’t too much of a worry for the partners was financing. Because they’d all been in business before and had a large percentage of equity to put down, they were able to secure loans pretty easily. Still, taking out a big loan and using retirement savings is something Sullivan doesn’t like to think about too much. “It’s scary,” he says, “but since I had another business, I kind of knew the risks. And I don’t really look at it that I’m close to retirement. I always figured my retirement plan would be, the day they put you in the ground, you’re retired.”

Experts do warn against betting your nest egg on a dream. Although boomers are collectively considered this country’s richest generation — despite the recession, the 65-plus segment’s median net worth is up 38 percent since 1995 — its wealth isn’t distributed equally. Nearly a third of 55-and-over households in the United States have no money at all put aside for retirement. Critics of the boomer entrepreneurship boom, such as William Galston of the Brookings Institution, have said that encouraging older people to put their limited resources toward startups is irresponsible, especially since there would be so few years to recover should financial disaster strike.


And starting a business can be expensive. Mark Allio, regional director of the Massachusetts Small Business Development Center (SBDC) Network at the University of Massachusetts Boston, reminds his would-be entrepreneur clients that it’s important to have not only startup capital but also working capital to feed the business until it grows toward profitability. “It’s a longer haul than people expect,” Allio says, “and it’s an issue for many midlife entrepreneurs who may be on a pension or using retirement savings.”

That explains why most people approach their new business with an abundance of caution. According to the 2012 Global Entrepreneurship Monitor report, sponsored by Babson and Baruch colleges, 69 percent of entrepreneurs started their companies in their homes, aided by consultants if the need arose. A paradigm shift has left the “freelance economy” continuing to grow even as the recession that brought it to the fore fades into history, and clever businesspeople can use that to their advantage. “You can start affordably by getting help for your business from independent contractors,” says Jeff Williams, CEO of, a startup coaching firm specializing in entrepreneurs older than 50. “You only pay them when you use them.”

Williams uses himself as an example. His public relations consultant used to work for a large ad agency but had a baby and wanted more flexible hours. When Williams needs something done, he hires her for $75 an hour rather than having to pay someone an annual salary (and likely benefits as well). “There are businesses where you need full-time employees,” Williams concedes. “But grow to the $50,000 or $100,000 mark using contractors and vendors as much as possible, and then you can start to afford an employee.”

Gayle Piraino got her business off the ground in just that way a decade ago. For 18 months after launching her marketing firm GAP Promo, Piraino says, “it was just me and my dog Montey working in the basement of my house.” Piraino, who is 59, continued working out of her home for another year and a half, first taking on a part-time employee, then a full-time one, then a couple of interns. By the time she rented office space in Gloucester, she had six people working for her; she now employs 15.

Piraino not only added employees judiciously, but she also found a back door into the hypercompetitive world of beverage promotions. Since she’d already been in the field for 12 years before striking out on her own, she was able to snag licensing deals with three big brands she had worked with before by going after neglected corners of their businesses. “It was about building relationships,” she says. “It didn’t have to be their biggest initiative ever. We were new in the game, and people aren’t going to give you their biggest projects right off the bat. I had to prove myself, so we would be available for whatever project came our way. And we treated it like a million-dollar project even though it was only a $10,000 project.” Today her clients include Diageo (which owns Guinness and Smirnoff), MillerCoors, and Mohegan Sun.

One thing Piraino says she wishes she’d known when she started was that even if you’re a solo entrepreneur, you needn’t go it alone; local SBDCs, SCORE (Service Corps of Retired Executives) chapters, and other groups offer free or low cost financial advice and education. At Salem State University’s Enterprise Center, Piraino found professional advice and a friend, Annmarie Linnane, who was going through some of the same challenges she was.

“I came out of an environment where I’d always had a team to brainstorm with,” says Linnane, owner and president of Women on the Move, a moving service based in Marblehead. “Being an entrepreneur can be isolating, and it’s nice to meet people who just get it.”

Unlike Piraino, Linnane found a wholly new career literally knocking on her door in 2009. Linnane had been in pharmaceuticals from 1984 to 2008, moving 14 times all over the world. During her most recent relocation, from Philadelphia to the North Shore, a woman from the neighborhood came and asked Linnane for her empty moving boxes when she was finished with them, and they got to talking about the moving process. When they reconnected a few weeks later, Linnane recalls, “she said, ‘I own this company that I work on out of my home, called Women on the Move, and would you like to buy it?’ ”

Coincidentally, Linnane was on a sabbatical from her marketing job and being headhunted by two Boston firms. She told both she’d come on as a consultant; in the meantime, she checked out and eventually bought the woman’s company. “Basically, I was moved so much myself,” she says, “I realized there was a huge gap in the industry.” Communication often broke down during the moving process, and she knew she could do things differently. “I am a risk taker by nature, and I said, ‘There’s got to be a better way to do this.’ ”

Linnane built on the original owner’s concept over time. “They were ad hoc before,” she recalls. “There was no payroll, no tracking, no bona fide billing.” So the first step was the unsexy but necessary work of building systems and procedures before she could start to build the business. Today Linnane employs 12 professional packers and an office manager, and has overseen 600 moves and counting.

Donna Latson Gittens started her Watertown advertising firm with $3,000.
Keith Bedford/Globe Staff
Donna Latson Gittens started her Watertown advertising firm with $3,000.

Donna Latson Gittens, too, started with almost nothing but her own perseverance. She’d been in the television business for more than 20 years, starting as a sales assistant and working her way up to producer, when her bosses said she needed an MBA if she ever wanted to become a general manager. She got one at Northeastern but was then told she’d have to move to a smaller market to fulfill her dream. “As I was thinking about what to do next,” she says, “my father passed away, and that was my aha moment.” Her father, Timothy Latson, was a postal worker and the union steward in Boston. “He always pushed us to try new things,” she says. “What rang in my head was You just went back to school and got the MBA. Now try something new. See if that piece of paper really works.”

Gittens took $3,000 in savings, a Rolodex, and a computer she’d received as a gift, rented a space in Watertown, and started her advertising firm. Eighteen years later, she and her partner, Judi Haber, run MORE Advertising, which has 10 employees and a client roster that includes the Red Sox and UMass Boston. And while her MBA didn’t get her precisely where she thought she wanted to be, she doesn’t regret going back to school. “I connected with a whole group of people I never would have met in a million years,” she says. “It’s another thing to add to your menu when you’re an entrepreneur: You have to constantly be learning.”

THAT KIND OF NEVER-ENDING CHALLENGE seems to be what drives older entrepreneurs to take on something new at a time when many people their age are thinking of winding down.

It’s not uncommon to start a business with the idea of building it for a few years and then moving on, though it rarely seems to work that way. “My vision was of myself and a couple of other people working remotely,” says Piraino. “I would be in Florida January through March, doing X amount of volume, and that was going to be it. I’d live happily ever after. I had a 10-year plan, but it just never evolved that way. Instead, it took off.”

Linnane, too, thought she’d spend a few years growing Women on the Move and then hire a manager so she could launch a company focused on pharmaceutical marketing. She still might — if she can find the time. “At the initial stage it is absolutely 24/7,” she says. “If you don’t go 24/7, you will never make it a success. I don’t believe entrepreneurs are workaholics, but we love what we do.”

Gittens agrees. “In this world of everyone saying they’re an entrepreneur,” she says, “you have to ask yourself, ‘Do you like vacations? Do you like going out to have dinner every other night? Do you like to go home at 5 o’clock?’ If you say yes to any of those, you’re not an entrepreneur.”

For Jim Donvan, the satisfaction of being his own boss brings him more happiness than “security” ever could. Firefly Moon’s sales are growing every month, and he and Thompson — his professional other half — are considering a second location. “For anybody thinking about starting their own business,” Donvan says, “I would say don’t wait and just dream about it. Get off your butt and take the plunge. Don’t . . .”

“ . . . let your fears stop you,” says Thompson, as usual, completing his thought.


Hing Soo Hoo in the kitchen at Jook Sing Cafe, his latest venture.
Keith Bedford/Globe Staff
Hing Soo Hoo in the kitchen at Jook Sing Cafe, his latest venture.

ONE OFTEN HEARS ABOUT the risk of failure in entrepreneurship, or of growing ahead of your earnings, or of mistakenly hiring employees you can’t really rely on. But there’s another risk you don’t hear too much about for second-act ventures: that you may become so addicted to yours that you never want to leave. Take it from Hing Soo Hoo, who at 76 recently opened the Jook Sing Cafe in Chinatown.

After working in Chinese restaurants around Boston for more than 30 years, and even briefly running his own place, Soo Hoo went into business for himself for good, starting Chinatown Cafe in 1989, when he was in his 50s, then Harrison Cafe in 2001. But when his wife, Mary, died in 2005, running two places became too much — they had been partners in life and in work, and the emotional toll of being in the restaurant without her was draining. Soo Hoo sold Chinatown Cafe, let his children take over the other restaurant, and stepped into retirement.

But that didn’t last long. “I was bored,” Soo Hoo says.

“About 2011, he started talking about maybe we should fix the place up, open longer hours,” says his daughter Jadine. “It was a three-year conversation. We didn’t push him either way, but eventually he decided we’d close and redo everything and come back with longer hours, a bigger menu, a bigger kitchen.”

Now Soo Hoo is in Jook Sing Cafe every day, opening its doors at 6:45 in the morning and not heading home until around 10 at night. “That’s how much I love working in the restaurant,” he says.

But how long does he think he’ll continue? “Maybe till 80 or 90 years old,” he exclaims. “If the right opportunity came, I would open another restaurant. I’m still looking for that good opportunity.”

Elizabeth Gehrman is a frequent contributor to the Globe Magazine. Send comments to [email protected].