Photography by Alex Stafford By Molly McCartney March 1, 2011

Baby boomers have determined social and economic trends for the last 65 years, and now they’re reshaping retirement. A 2009 study by the Ewing Marion Kauffman Foundation reports on “The Coming Entrepreneurship Boom,” and notes that, contrary to popular assumptions, the highest rate of entrepreneurial activity belongs to the 55-64 age group. “The 20-34 age bracket, which is usually identified with swashbuckling and risk-taking youth (think Facebook and Google), has the lowest,” the report says.

Factors that are shaping this flurry of entrepreneurship are longer, healthier lives; a recession that’s taken its toll on boomers’ 401(k)s; the continued decline of lifetime employment, especially among men over age 50 (no more gold watches for 30 years of service); and the know-how that comes from decades of experience. Plus, many boomers like to work. It’s a big part of their identity, and they’re carrying that need for purpose and meaning into their next phase of life. Here are six boomerpreneurs right here at home.


Name: Sue Ellen Addicott

Age: 64

Former profession:Conference director in Washington, D.C.

Retired at age: 54

New company: Senior Moves, manages downsizing for seniors

Biggest challenge: Learning a new field

Biggest strength: Experience

Senior Moves

In 1998, Sue Ellen Addicott retired from her Washington, D.C., job as a conference director and moved to Sarasota with her jazz musician husband. She learned to play bridge. She did volunteer work. But she felt something missing. In 2007, she got the idea that many older people in the Sarasota region, especially those without children here, needed help downsizing into independent living facilities,. Families also need help closing homes when older relatives die, she thought. So why not start a business that helps seniors move? And call it Senior Moves?

“I saw firsthand with my own parents the emotions that people experience with this process,” she says. “And I thought this is a job that requires organization, which I can do. And people skills, which I have.”

With a $10,000 personal investment, she launched Senior Moves in January 2007. “At first I thought I had invented the concept. But in fact, I found an association of senior move managers, which was good because I didn’t have to invent everything. Art Mahoney with the Small Business Development Center at State College of Florida mentored me on marketing. Another person mentored me on how to draw up a business plan and a financial plan,” she says.

By October 2007 Addicott had her first customer. “We do everything with the move except transporting the goods,” she says. “I come in and offer a complimentary consultation to get the lay of the land. I can do a floor plan of the new residence for the clients by measuring their new place and their furniture. And that helps with a lot of the decisions about what can go and what can’t.”

Today Addicott, 64, has eight part-time employees who do the packing and unpacking, and then work to get the empty house into condition for sale. She has a website, a blog and even a radio show from noon to 1 p.m. on Saturdays on Sarasota’s WRMY-AM.

Since launching her company, Addicott says she has helped about 150 families move. “We made a profit in 2010 for the first time,” she says. She plans to keep the business going as long as she enjoys it and has good health. “At some point I need an exit strategy,” she says. But not yet.


Name: Brian Weiner

Age: 56

Former profession: Founded Noalart Graphics in Boston

Retired at age: 46

New company: The One to One Group, employs eight and creates direct mail campaigns for nonprofits and websites for donors.

Biggest challenge: Starting anew and unknown

Biggest strength: Experience

The One to One Group

In the 1990s, Brian Weiner established and built a pioneering digital printing business in the Boston region called Noalart Graphics. He sold that company in June 2000 “at the peak of the dotcom boom” and retired at the age of 46. Or so he thought. “One beautiful winter day in Boston I am sitting and reading the newspaper and eating a sandwich,” he remembers, “when my wife sits down and says, ‘I married you for better or worse but not for lunch. You cannot sit around my kitchen. Go do something with your life.’”

Weiner, now 56, says that dictum led him to start a new business that uses a data-driven approach to help nonprofits raise money through mailers. The One to One Group, as he and his partner, Dana Place, call their company, has raised about $64 million for charity since its founding in October 2003.

Why Sarasota? “The short version is that I had a noncompetitive agreement with the buyer [of Noalart Graphics] that I had to be 100 miles away,” he says. “And if you are going to be 100 miles from Boston, you might as well go where the weather is warm. After a year of looking for warm weather markets with a high net worth, and where there is significant competition for nonprofit dollars, it boiled down to Sarasota and Charleston, S.C. We liked Sarasota more because it had a broader depth of resources, especially in the arts. We knew we would always be Yankees in Charleston. So we came to Sarasota.”

Age and experience made it easier for Weiner to start a new business: “You have the advantage of having walked the road before. You know where the potholes are.”

The One to One Group employs eight people at its Lakewood Ranch headquarters and works with 50 to 100 not-for-profits at any given time. The first year the company brought in about $2 million for its clients, but now is “bringing in about $12 million a year for them,” Weiner says.


Name: Deb Knowles

Age: 58

Former profession: Founder, Corporate Healthcare Strategies and The Raleigh Group

New company: Gray Swan Solutions, a web strategy consulting firm

Number of employees:10

Biggest challenge: Learning new technology

Biggest strength: Business know-how

Gray Swan Solutions

In 2007, Sarasota’s Deb Knowles, then 55, got a call from her nephew, Ben Hodous, 25, in Portland, Ore. He wanted her help starting a new business. “He said it involves websites and new technology and emerging ways of communicating,” Knowles remembers. “I had sold my last company before there was e-mail. But I was so fascinated I said, ‘Yep, let’s do it.’”

Knowles, who had founded and sold two companies by the time she was 42, says her nephew’s call for help came just in time. “I had tried retiring for a few years and found that my brain cells were dying. I told my husband I could hear them going pop, pop, pop.”

Gray Swan Solutions, the company founded by Knowles and Hodous, helps clients realize the marketing potential of the web. The company today has 10 employees but no physical location. “Each person works from home with his or her computer, and it creates a virtual company,” says Knowles. “Our clients are all over the country; most we have never seen in person.” Their Sarasota clients include Sarasota Brides, Gifford-Heiden Insurance and the Southwest Florida Spine Institute.

Knowles says Hodous “force fed and dragged me into the new technology. We would use GoToMeeting, where I could see his computer screen on my screen and he would walk me through demonstrations of the new technology, how to use it and how important it was. He tutored me over the Internet from Portland.”

Knowles brought her business know-how to the venture. “Ben wanted me for my experience in running a company and managing clients,” she says.

Knowles loves what she is doing. “I learn something new every hour,” she says. “It requires me to keep my brain fully engaged to keep up with what the employees—the 20-year-olds—are doing as the technology advances. I don’t ever see me stopping.”


Names: Lenora and Larry Woodham

Ages: Lenora, 60, and Larry, 63

Former profession: Category manager, Winn-Dixie, and commercial real estate agent, Wagner Realty

New company: Bunker Hill Vineyard

Number of employees: None

Biggest challenge: Learning a new field

Biggest strength: Willingness to learn and work hard

Bunker Hill Vineyard

As a category manager in charge of the Sarasota warehouse for Winn-Dixie, Larry Woodham bought many different categories of food and drink—including wine. “I became very familiar with the wine industry and how it operates,” he says. So familiar that when he retired 12 years ago, he bought 23 acres of land near the town of Duette in Manatee County and planted a vineyard.

Since then, he and his wife, Lenora, have toured other Florida vineyards to learn more about winemaking while allowing their own vines to mature. “You have to train the vines,” says Woodham, 63. “If you let them go, they will lie on the ground or go up a tree. This is a long process, and if you don’t have a passion for it, don’t grow grapes.”

But all that work has been worth the effort. “It is so rewarding to be able to take a raw agricultural product like grapes and turn it into a value-added product,” Woodham says. Then there is the making of the wine, which he describes as a science and an art. The Woodhams have been making test wines for several years and have now begun to produce and sell 10 different wines at their Bunker Hill Vineyard. “We produce the gold standard of Florida wines,” says Lenora, 60. “We sell on-site, we do tours and tastings.”

Larry Woodham, who traces his family roots back to Bradenton founder Iredell Turner, is amazed that Florida has never developed a significant wine industry. He estimates that U.S. retail wine sales amount to about $30 billion annually and that probably $25 billion of that is spent on California wine.

“We have everything other places have—climate, soils, environment, everything is here,” he says. “If we can grow this industry in Florida, we can employ a lot of people.”

The Woodhams intend to work “forever” at their grape growing and wine making. “You only get one shot at life,” he says. “You have to recognize what you want to do in your heart and go do it.”


Name: Dan Miller

Age: 50

Former profession: Software entrepreneur

Reason for new company:Intellectual stimulation

New company: BizTank, Pongo Software and INgage

Biggest challenge:Making community connections, determining which projects to pursue.

Biggest strength: Experience and contacts

BizTank, Pongo Software, INgage

Dan Miller moved from Boston to Sarasota in 2001 after selling his second software company and immediately dived into the entrepreneurial scene. “I was too young to take up golf or tennis and I wanted to get back into business,” he says. “I had done a lot of advising and mentoring in Boston, so I was looking to continue that. And I wanted a flexible lifestyle with intellectually stimulating work.” In the 10 years since, Miller, now 50, has been involved in seven different companies.

Miller and his wife were thinking of moving to Naples until his mother-in-law recommended that they check Sarasota. “We came for a weekend and just completely fell in love with the city,” he says. “And once we started to research schools for our son, we found Pine View [School for the Gifted], and we were sold.”

Miller spends most of his time today with three companies. He’s managing director of BizTank, a consulting and investing company that he owns and manages with no employees. He’s chairman of Pongo Software, an e-commerce provider of resume and career management software solutions, which he started in 2004. Pongo has about 40 employees in Boston; annual revenues have grown about 30 percent a year since its founding. He’s on the board of directors of INgage Networks (formerly Neighborhood America), a social software and services company with offices in Sarasota and headquarters in Naples. INgage has about 100 employees and “pretty good growth.”

Older entrepreneurs have an edge when it comes to starting new ventures, Miller says. “I have a library of experiences I can fall back on, and a library of network contacts,” he says. “And there is only one way to get that and that is to live your work. At age 20, you don’t have that.”

Miller, who has a second-degree black belt and plays competitive club tennis, expects to continue with his current work until his son finishes high school in a few years. After that, he says an ideal position for him would be “to not have to be anywhere at any time.” That’s possible with today’s technology. “I could have a base here in Sarasota but also experience other parts of the country, like being in New York City for a month or two, or being in Boulder, Colo. That is very appealing to me,” he says.

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