Over 50? Now Is a Smart Time to Start a Business | Small Business Retirement Plans

You know that old saw about not being able to teach an old dog new tricks? Yeah, that’s a lie. Turns out, the old dog has a few tricks of his own—or her own, as the case may be.

Consider Steve Wilson, who at 50 years old and after a career in technology, joined his wife Rebecca in starting a business selling luggage tags and scuba tags online from their home in Bentonville, Arkansas. Or consider Kay Neseem, who at 57 left her job as an occupational therapist in Virginia to launch a company selling an innovative arm brace she designed for shoulder surgery patients. Or consider Rand Smith, who, in his 50s and after a career in the optical industry in New York, opened an eyeglass shop in Kansas City, Missouri, with his wife Janeel.

They are the face of the modern entrepreneur: older, wiser after decades in the workforce, and much more likely than younger generations to succeed in their entrepreneurial efforts.

These days, older Americans are the fastest growing set of entrepreneurs. A quarter century ago—in the mid-1990s— those aged 55 to 64 represented a bit less than 15% of new entrepreneurs, according to the Ewing Marion Kauffman Foundation, which focuses on advancing entrepreneurship and education. Today, more than one in every four new entrepreneurs is in that older cohort. Indeed, the typical entrepreneur nowadays isn’t the baby-faced college student with a techie background or the adventurous thirtysomething millennial springing out on their own. It’s an empty nester between the ages of 55 and 65.

And here’s the better news: Research out of the Massachusetts Institute of Technology, Northwestern University’s Kellogg School of Business, and the U.S. Census Bureau—among numerous others—shows that older entrepreneurs are as much as three times more likely to succeed than their younger peers. Or, as the Harvard Business Review put it in 2018, “If you were faced with two entrepreneurs and knew nothing about them besides their age, you would do better, on average, betting on the older one.”

We Gen Xers and baby boomers have been in the workforce now for 30 years to half a century. You learn a thing or two in that time. No surprise, then, that Harvard research found that “work experience plays a critical role” in explaining why older entrepreneurs, statistically, have greater success and less difficulty starting a new venture than their younger peers. We have less difficulty dealing with government bureaucracy in obtaining necessary licenses. We have less difficulty applying for loans and seeking funding from investors. We tend to have broader skill sets in management and marketing, and because of our years in the workforce, we have richer industry knowledge.

Perhaps most important to our success as entrepreneurs is that we generally have fatter financial resources to help fund a new business and a deeper well of social and industry contacts we can tap into for business knowledge and access to early customers that can help a new business survive early on.

“Every step you’ve taken is a step toward your success as an entrepreneur,” says Kay Neseem, the businessperson behind Kay Kare arm braces. “You don’t all of a sudden become an entrepreneur. It has always been inside of you. It’s the path you’ve always cherished but you never thought you were capable of doing.”

Think about it this way: McDonald’s, Coca-Cola, Mary Kay Cosmetics, and Kentucky Fried Chicken…each was founded by a dreamer who was more than 50 at the time and was working in another job.

In short, age predicts success. The older you are, the greater the likelihood that you will find income and happiness chasing your passion and running your own business. Which leads us to the topic for this month’s cover story:

What does it take to be an older entrepreneur?

Building Your Business

We’ve reached a stage where the U.S. economy is perfectly primed for the rise of older entrepreneurs—and in some aspects, that’s not necessarily good.

On one hand, there’s ageism. Though age is no longer supposed to factor into hiring and firing in the U.S., thinking that it doesn’t exist is a fool’s belief. It’s an insidious practice that has shoved millions of older Americans out of well-paying jobs, often during the prime of their careers.

Then there’s the pandemic. Workers over 50 lost jobs in droves, leading to the highest unemployment rate for that cohort in at least half a century.

At the peak, the unemployment rates for workers 55 to 64, and 65+ were well into the double digits and exceeded the unemployment rate for younger workers by a margin not seen since 1948. Now, recent research is showing that finding a new job is twice as difficult for them as for younger workers.

Those two factors are helping drive older entrepreneurship out of financial necessity.

Then again, entrepreneurship “is really attractive beyond the income because [older workers] can pursue a passion,” Mindy Feldbaum told me. She’s vice president at AARP Foundation’s Workforce Programs aimed at helping older adults find economic opportunities. “They’re looking for flexibility, the ability to work remotely on their own time, and the desire to be their own boss.”

Or, as Danielle Duplin told me, they’ve reached a stage in life where “they’re now thinking ‘it’s my turn!’” Danielle is cofounder and global executive director at AGENGY, a Cambridge, Massachusetts-based collective focused on aging, which runs the Founders Over 55 Club that fosters older entrepreneurship. “You’ve had your career. You’ve been responsible to a business and family. And now these older workers are saying I want to focus on an industry [I enjoy] or a problem I want to solve or be around people that bring me passion and happiness.”

Which pretty well sums up Ross Ozer, the 61-year-old owner of Boston-based rjostudio|HANDCRAFTED, which makes bamboo bowties, tealights, and other items. Ross spent years in marketing, most recently as chief marketing officer for a division of investment giant Fidelity. But “I had stopped learning in my old job,” Ross recently shared with me. “I was bored. There were no new challenges. I stopped developing my own skill set.” So, in the summer of 2017, he left.

He’d always been a self-described “serial crafter” and had started “fiddling around with etching glass at home,” in particular Italian swing-top bottles. He was toying with the idea of selling them on Etsy as an exercise in personal branding. A former colleague saw them and ordered 100 with his company’s logo to give away as client gifts, which fueled Ross’s interest in learning about how to scale a glass-etching operation. Ultimately, that lead him to a makerspace—a collaborative workspace—in Peterborough, New Hampshire, 90 minutes from Boston.

“I was getting up at 4 a.m. to make that drive,” says Ross, “and one morning I had to laugh because I was thinking, ‘When was the last time I had this much spring in my step at 4 in the morning?’ I was energized. I was doing something I love. I had no idea what I had started, but it was fun. I was learning every day. I was learning technology. I was applying marketing. I was getting to use decades of design skills. It was all coming together.”

Today, museums and art galleries sell Ross’s products in their gift shops, and his line of wooden bowties for young boys have been picked up by a children’s retailer in Atlanta.

But as we all know, overnight success never happens overnight. It takes real effort. And it requires access to resources and an understanding of the tips, strategies, and hacks that can help improve your chances of success.

Follow Your Passion

This is the primary rule for entrepreneurs, particularly when you’re older. Yes, self-employment, on some level, is all about the money since we all need dollars to survive. But that which is done for money alone is never as satisfying as that which generates an income from doing what you love.

Passion is a necessity for a crucial reason: In the early days of starting your own business, you will invariably face challenges that make you want to throw your hands up and call it quits. Those pursuing an entrepreneurial effort just to make a buck are more likely to succumb to those frustrations. Those following a passion, however, “will work 24/7, 10 days a week to make the dream in their head a reality,” says Tom Raymond, a certified mentor with SCORE, a national volunteer organization that partners with the Small Business Administration to help entrepreneurs of all ages. “If what you’re thinking about doing isn’t your passion, set it aside and spend some time really figuring out what your passion is.

Kay Neseem found her passion early in her career as an occupational therapist. In particular, she watched shoulder injury patients—even medical staff—struggling with arm braces that were too complicated and often so painful on the neck that patients would regularly not use the brace, thereby jeopardizing their own recovery.

“I came into this thinking ‘this is not good enough—I need to make it better,’” says Kay. So, she drew a rough sketch of a better product, hired a patent attorney, and obtained a patent based on her drawing alone. Then she began using her savings to fund a prototype and get her new design in front of clinicians, the FDA, and Medicare/ Medicaid review panels.

Her design has won numerous awards, including designation as a “technology breakthrough” in medical devices. Now, she’s selling 20 to 50 Kay Kare braces a month at prices ranging between $92 and $122. Her volume looks to ramp up soon. Premier Inc., a group purchasing organization, recently brought Kay Kare into its fold, meaning Kay will have direct access to 4,100 hospitals and 200,000 other healthcare providers who use Premier to purchase medical products in bulk.

For Rand Smith, chasing his entrepreneurial passion was “about needing a better life.”

He’d been in New York for years, working in the wholesale side of the optical industry. He was commuting into the city, two hours each way every day, with his wife, Janeel, and their eight children at home. A move to Kansas City for a slower-paced life introduced him to the retail side of the industry, where he quickly realized that “I loved dealing with the public, but I didn’t like dealing with the corporate part of the job.”

So, he struck out on his own. He and Janeel, together, opened eyeSmith Sport & Fashion Optical. He was 56 years old at the time. They tapped their savings, found a 2,400-squarefoot building next to a local bank, and renovated the building to meet their needs. Today, they’re happier than they’ve ever been. Their business has grown seven-fold, and though Rand is earning less than he did working for someone else, “I have zero stress now,” he says. “We go to work together and I look forward to it because our customers are our friends.

“We love our business so much that it looks like we’re having a ball instead of working,” adds Rand. “But we work hard, and we worked hard to get here— six days a week for the first three years. The key is to know your industry and love what you’re doing. Because then you will do everything it takes to be successful at it.”

Leverage Your Experience

This dovetails with passion. Use what you know to build a business you’re passionate about.

Mindy Feldbaum at AARP Foundation notes they routinely find that older entrepreneurs succeed precisely because they’re calling on decades of experience that allows them to recognize and capitalize on problems and opportunities that younger peers don’t always see. “A lifetime of experiences” is a valuable tool for an older entrepreneur, she says.

Steve Wilson, for instance, is a certified open water scuba instructor. Only natural, then, that he saw the opportunity to create a line of tags for scuba divers to label their equipment, as well as for dive shops to label their rental gear.

Kay Neseem leveraged her knowledge of patient, doctor, and nurse frustration with existing arm braces, as well as her own experiences helping patients try to navigate the complexities of those braces.

Ross Ozer fell back on his decades of craft skills and computer-assisted design skills with Adobe Illustrator to create the patterns for his bamboo tealights as well a new line of T-shirts he’s now selling.

And, obviously, Rand Smith relied on years in the retail and wholesale side of the optical business when launching his own boutique.

This is deep, ingrained knowledge that sets you apart from others. It gives you a unique perspective. It gives you a backstory to sell to customers, clients, suppliers, vendors, investors, and bankers. And it can “give you the confidence you need to take that first step,” says Tom Raymond, the SCORE volunteer. “Your experience defines you. Use that.”

Don’t Overextend Yourself Early On

I mean that in multiple ways—in terms of money, breadth of products, and your expectations.

In the early days of their business, YourBagTag.com, Rebecca and Steve Wilson only produced what they could manage on an old sewing machine Rebecca owned and an embroidery machine they bought for about $600. At the time, Steve was working in technology for companies such as Microsoft and Oracle (where he and Rebecca met). One day a friend of Rebecca’s asked her to sew an industrial-strength luggage tag. Steve looked at the result and told Rebecca “we can market this on the internet.”

From day one, Steve says, “the goal was to never overextend ourselves. We grew very intentionally. Never taking on debt, only producing what we could with the machines we had,” even if that meant missing out on orders. As the business grew and provided cash, “only then would we add a new machine or a new process. And we never wanted to compete with the promotional products industry” that generally sells cheap merchandise. “We carved a niche, and we’ve stayed in our lane, because we know that is our strength.”

That was 14 years ago, when Steve was 50 and Rebecca was 45. Today, YourBagTag.com generates more than $150,000 annually selling luggage tags and scuba diving tags made from plastic or metal. It’s selling to the FBI, seven NBA basketball teams, and a host of dive shops, along with individual consumers.”

You might very well grow to be the next McDonald’s or Mary Kay Cosmetics. But don’t start off planning on grand visions. Know that “you are going to have bad days as you try to get this off the ground,” Kay Neseem told me. She noted that on too many occasions to count, she met with doctors who loved her product…but then told her they couldn’t stock it in their clinics because Kay Kare wasn’t part of the group purchasing organization that supplied their medical gear.

But then one day, at a vendor show in a VA hospital in Virginia, doctors and nurses saw Kay’s brace and immediately recognized its value for patients. They called the head of the purchasing department to come check it out, which lead to the chief of emergency medicine declaring “I want this.” The hospital added her new, simplified brace to its purchasing system. “Those are the moments that give you hope,” says Kay.

So, don’t let yourself think too big too quickly because you risk losing focus on the more important task of first launching the business. “But,” Kay said, “also don’t lose hope. Every day of your journey is a success, even if it’s small, because you got through the day with your passion still intact.”

Take Stock of Who You Know

One of the great strengths of age is our mental Rolodex—maybe even a physical one. We’ve all spent decades in the workforce, and that has given us a vast collection of contacts who can play a variety of roles when it comes to our entrepreneurial success. They can, for instance, serve as:

  • Sources of knowledge to help you work through a problem or challenge in an area of business that might not be your strong suit;

  • Go-betweens that can connect you to potential clients or suppliers;

  • Sounding boards offering free, honest feedback on the product or service you’re considering;#

  • Potential investors that can help you fund your entrepreneurial idea in the early stages;

  • Or even early customers, which can help you get cash flowing into the business sooner.

Whatever role they might play, your network of contacts is crucial to success. Mentally scrub your memory and jot down all the names of colleagues, bosses, customers, suppliers—whoever—that you remember dealing with favorably across your career.

“Reach out to them,” urges Danielle Duplin at AGENCY. “Find out where they are and what they’re doing, and how that might fit into your needs. These people can be allies on your journey.”

Ross Ozer, the designer of those bamboo bowties in Boston, reached out early on to colleagues at Fidelity, who ended up buying his etched glass bottles for clients. He reached out, as well, to a former colleague now living in Atlanta, which is how his bowties ended up for sale at a kid’s clothing boutique.

Kay cultivated her contacts, but not necessarily to find buyers. “I wanted validation that I was on the right track with this product,” she says. “Your contacts can be great advocates for you because when what you’re trying to do just makes sense, they end up steering you the right way.”

Rand and Janeel reached out to their local church, which was offering classes on how to start your own business. The contacts they made there “gave me confidence that this idea was really going to work,” says Janeel.

Danielle notes that your “network” should include a supportive spouse, if you’re married. Adult children sometimes interject their thoughts “and wonder why you’re putting all this money into this project,” says Danielle. That’s code for kids worried that you’re wasting their inheritance. Shunt those comments to the side and lean on a spouse who has your back because that helps set you up for success.

“We’ve been married 42 years,” says Janeel, “and I knew from a long time ago that an owning an optical boutique was Rand’s goal. I can honestly say that on the last day of his employment, he came home and I was crying. I told him, ‘I have such confidence in you, but it’s scary.’ But I also know the effort he put in during his career. I knew he knew this industry. And I knew he was going to succeed, and I assured him of that.”

Funding Is Available Everywhere

I know what you’re probably thinking: What about the money?

Certainly, starting a business takes capital. How much depends on the scale of the business you seek to start. Steve and Rebecca Wilson began YourBagTag.com with about $1,200 for that embroidery machine, a business license, a website, and some raw materials. Then again, Rand and Janeel Smith spent about $300,000 fitting out an optical boutique.

Whatever the cost, there are ways to afford it. As with the Wilsons, you can dig into your personal savings. Kay Neseem used savings and her credit card, at one point finding her $5 American Express charge rejected at an office supply store.

The Smiths tapped into Rand’s 401(k) retirement plan through a special program called Rollover for Business Startups, or ROBS. That allowed Rand to fund his business with the money he’d accumulated over decades in his retirement account, in effect replacing his traditional investments with an investment in his boutique. (There are pros and cons to this approach, so it’s best to talk to an expert who can offer an unbiased assessment.)

Beyond that, there are low-interest loans from the Small Business Administration and organizations all over the country that offer startup grants or can link entrepreneurs to investors.

And just as there are ways to obtain money for a new business, there are also creative ways to reduce your startup costs. Kay was quoted a price of $80,000 to help her obtain for her brace a so-called L-code issued by Medicare/ Medicaid.

“Every doctor and hospital I talked to,” Kay told me, “the first question was, ‘Do you have an L-code?’” Medical providers need that code to claim reimbursement for medical devices.

Kay didn’t have $80,000. Instead, she approached Medicare/Medicaid directly and explained her situation. The representative told her that the agency’s review committee only meets every few months and only selects a handful of products to consider… but could she be in North Dakota the following week to present her brace? So, Kay flew to North Dakota from Virginia, gave her presentation, and literally passed out on the return flight from stress and exhaustion.

A couple weeks later, she had her L-code…and her business was on the cusp of taking off.

The Wrap Up

As governments work to rebuild a small-business landscape devastated by the pandemic, they will rely on new entrepreneurs. Yes, there’s risk in that, for sure. But there’s also an opportunity for those who’ve always wanted to be their own boss. Equally important: There’s the potential for vast rewards that go well beyond a paycheck.

There’s the flexibility to structure your job around your lifestyle. Maybe you do want to devote all your time to building the next McDonald’s. Or maybe you want to be more circumspect and build a small business that provides you a stable, supplemental income based on a limited number of hours worked.

Maybe you don’t care about the income all that much and, instead, you’re eager to engage your passions later in life to keep your brain and body active as friends and acquaintances desiccate into a ball of wrinkles watching The Price Is Right.

Whatever rationale compels you, know this: You can succeed at this.

So many opportunities and resources and mentors and financing arrangements exists these days for the 50+ entrepreneur that society is almost begging you to get up off the Barcalounger and take a crack at starting a new business.

And if the research is right…well, there’s a good chance you’ll actually do very well at whatever entrepreneurial passion you pursue.

7 Steps to Jumpstart Your Business


Do you have what it takes to be an entrepreneur? These steps can help you transform an entrepreneurial idea into a viable venture.

  • Consider your experience: What is your work history and what hobbies and interests do you have? If money wasn’t important, what would you love to do?

  • Research your niche: Does something already exist similar to what you have in mind? Can you create a better version of it? And does this product category or service deliver meaningful sales?

  • Test your idea: Not all ideas will resonate with potential buyers. So, test your idea among people you trust to give you honest, critical feedback.

  • Investigate resources: Look for mentorship programs locally and nationally that can help you design a business plan and find funding.

  • Build a prototype: This won’t apply to every idea, but if your idea is a physical product, build an example of it to show potential buyers, investors, and lenders, and so you can obtain a patent.

  • Network: Find the people who can help you build your business, who will invest, or who will be a customer. Do this through your contacts or trade shows.

  • Rely on your support network and your passion: There will be dark moments when you feel like the business won’t survive. A supportive spouse or a mentor can steer you through those moments. And so can your passion. It will drive you forward if you’re intent on making your product or service a reality.

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