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5 Secrets of Success From Midlife Entrepreneurs

What the 'Never Too Old to Get Rich' author learned from 20 founders

By Kerry Hannon

Boomers and Gen Xers are on the rise as entrepreneurs and the variety of businesses people are starting in mid-life is amazingly diverse. How do I know? I interviewed 20 of them for my new book, Never Too Old to Get Rich: The Entrepreneur’s Guide to Starting a Business Mid-Life. (Full disclosure: Next Avenue is the co-publisher, with Wiley, because I'm a regular blogger on entrepreneurship for the site.)

Bergen Giordani (at right) and Morgen Giordani Reamer (at left) of One Hot Cookie
Bergen Giordani (R) & Morgen Giordani Reamer (L), One Hot Cookie  |  Credit: ICON of Youngstown

Something else I learned about these startup founders: their five secrets of success.

Some of these risk takers started their businesses from a passion or hobby. Others paired up with someone younger. A few started ventures as social entrepreneurs. They range from a gin distiller to a movie maker to an interior designer and packaging manufacturer. If you’re thinking about starting a business after 50 or already have, you’ll want to hear what some of these entrepreneurs did and what they recommend for succeeding.

"If I'm at the store too much, I'm not doing my job — making sure we have the product and dealing with food costs and payroll."

One more thing about the women and men I talked with for Never Too Old to Get Rich, their paths to riches — financial and internal — were lined with challenges. But these go-getters didn’t let naysayers get in their way. Now, onto their five secrets of success:

1. Sales Skills Are Non-Negotiable

When I asked the entrepreneurs about their biggest challenges in starting a venture, their blunt response was frequently the same: sales.

“I’m not a natural salesperson,” says Paul Tasner, 73, who five years ago founded Pulpworks, a San Francisco-based firm that designs and manufactures sustainable packaging for the consumer products industry. “Being successful at sales is very difficult. I have a whole new admiration for good salespeople. It’s an art — and a science.”

Linda LaMagna, 341 Interior Design
Linda LaMagna of 341 Interior Design  |  Credit: Courtesy of Faye Sevel Photography

Sales skills were often either overlooked or considered a lower priority as the entrepreneurs hatched their plans. Yet, nearly everyone I talked to quickly realized that the ability to sell their product, service or just their idea was crucial. Selling, they said, can help you raise capital and convince those close to you that you’re not headed off a cliff with a pure leap of faith.

Sometimes, the entrepreneurs had a sales background, which proved a huge help. Take Linda LaMagna, 54, of Fort Mill, S.C, the owner of 341 Interior Design.

For more than 25 years, LaMagna’s career had been a whirlwind trajectory, including living  in Germany and the Netherlands and working in marketing and strategic planning for Spiracur, a medical device startup, and for the medical device company, ConvaTec, Says LaMagna: “It really was my passion to be in the corporate world working on the sales and marketing side.”

So what does a background in sales and marketing in the medical device industry have to do with a starting an interior design business? “I was a marketer and had to understand what the customer was thinking and what their needs were,” says LaMagna.

2. Insider Industry Knowledge Provides an Edge

It’s tempting to view the launch of a new business as a time to take your career in an entirely new direction. But that's often not the wisest strategy. The best way to leverage decades of experience and many business contacts, entrepreneurs I interviewed said, is to continue to do work related to what you’ve been doing.

Mike Kravinsky: Nextnik Films, LLC
Mike Kravinsky of Nextnik Films

Tasner said the network he’d developed in a career handling supply chains at corporations like Clorox and California Closets was a big benefit. “We don’t always have the perfect person to sit down with,” he says, “but we always have someone I know who can at least open the door to us and point us in the right direction.”

I heard a similar story from Michele Meloy Burchfield. Before she started her beverage company Blume Honey Water in her 50s, she was a director of national accounts for the Boston Beer Company and ran the MBM Group consulting firm, catering to clients such as Fiji Water and Sierra Nevada Brewing Company.

Another example: Mike Kravinsky, now 65. When he went to work as a video editor at ABC News in 1981, he figured he’d spend a year there and then head to Los Angeles to become a filmmaker. It didn’t quite work out that way. Over 29 years, Kravinsky worked as an editor and technical director for news broadcasts like World News Tonight and Good Morning America, and news magazine shows like 20/20 and Primetime Live. After retiring in 2010, Kravinsky followed his dream to be a filmmaker, but in his hometown of Arlington, Va. And he credits his previous work as critical to his success.

Kravinsky has now completed three feature films with his independent film company, Nextnik Films, and is writing his fourth. “Working in TV prepared me to be very exacting in my preparation of a production,” Kravinsky says. “Much of what I learned creatively, technically and running on deadlines on shows was movable to narrative films.”

3. You Must Love the Nitty-Gritty of Operating a Business

Ginny Corbett, Salúd Juicery
Ginny Corbett of Salúd Juicery  |  Credit: Courtesy of Michael Morgan

Although Ginny Corbett, 56, founder of Salúd Juicery, in Sewickley, Pa, loves her juices and quaffs them regularly, the art of preparing a perfect juice or smoothie isn’t what drives her. “I enjoy talking to the customers, but the truth is I’m in my business office every day,” she says. “If I’m at the store too much, I’m not doing my job — making sure we have the product and dealing with food costs and payroll. It’s not just the product you need to love. You have to love running a business to have a business.”

For Corbett, the business has also had a family affair flair, with all three of her children (ages 29, 25 and 19) habitually sampling juices, working the sales counter or helping design marketing materials, including coaching her on how to build an Instagram following to communicate with customers and post free beverage offers. She now has over 9,300 followers.

4. A Career Coach Can Smooth the Move to Entrepreneurship

“I was fortunate to have a career coach to work with as I was making the transition,” LaMagna says. “Much of the work we did was understanding: ‘What am I carrying with me through my experiences that is beneficial and supportive of this new set of skills that I want to do? How do I actually make that transition to change corporate speak to design speak? How do I introduce myself differently now that I’m not in the corporate world?’

And, LaMagna adds, “Often someone’s identity is tied to what they have done for so long, so to start something new has all those challenges with the new career, new role, new skill set — but it is also shifting your identity. How do you position yourself the first time you walk through the door into a cocktail party and someone asks, ‘What do you do?’”

5. Consider Starting Your Venture as a Side Gig

In 2013, Bergen Giordani and her daughter, Morgen Giordani Reamer, launched their dessert shop, One Hot Cookie, in their hometown of Youngstown, Ohio. The two eased into the business by initially sharing cookies they made with friends and family to get feedback. Giordani also took an executive-MBA-type program offered by the Small Business Administration – the SBA Emerging Leaders Initiative.

“The idea for the business came from our desire to do something together,” says Giordani, president of the company and a single mom. “We both love hot, gooey desserts and sweets, and since Morgen [now vice president of the operation] was a child, we would go out and get a dessert somewhere and have that special time together.”

Moreover, it was an opportunity for Bergen to find work she loved and a chance to combine that with baking cookies alongside her then-teenage daughter, an activity they’d relished doing together since Morgen was tiny.

While waiting to see if the side gig would gain traction and become profitable, Bergen worked as development director at the Rich Center for Autism, on the campus of Youngstown State University. And initially she worked part time as a bartender, too.

“I wanted to make sure Morgen — who was sixteen when we started — and I were provided for. And I attribute a lot of our ability to grow to that work ethic of working really hard on our business while I was still working outside of the business,” Giordani says.

One final reflection from me: The freedom to determine their own future was the seductive siren song for most of these small business owners, and not a dangerous one. “I now have the freedom to take on projects and execute them in my own vision,” Kravinsky says. “Each film that I do is like starting a new business. It is a new crew, new actors, new locations. That’s liberating.”

Amy Bass, owner of Nota Bene, a fine paper boutique in Pittsburgh, agreed. For her, “It meant the ability to own and create something of my own and then being directly rewarded for my hard work.”

Photogtaph of Kerry Hannon
Kerry Hannon is the author of Great Pajama Jobs: Your Complete Guide to Working From Home. She has covered personal finance, retirement and careers for The New York Times, Forbes, Money, U.S. News & World Report and USA Today, among others. She is the author of more than a dozen books including Never Too Old to Get Rich: The Entrepreneur's Guide to Starting a Business Mid-Life, Money Confidence: Really Smart Financial Moves for Newly Single Women and What's Next? Finding Your Passion and Your Dream Job in Your Forties, Fifties and Beyond. Her website is Follow her on Twitter @kerryhannon. Read More
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