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What It Takes to Be a Successful 50+ Business Owner

The 'Main Street Entrepreneur' author found a few patterns across America

By Richard Eisenberg

Some professors do their research in laboratories or libraries. But when Utah State University business school’s Michael Glauser wanted to learn what successful small business owners in small-town America had in common, he hopped on a bike.

With his son Jay and two others from his My New Enterprise team, in the summer of 2014, Glauser — executive director of the Jeffrey D. Clark Center for Entrepreneurship at Utah State — wheeled 4,000 miles, interviewing 100 entrepreneurs in 100 cities from Oregon to Virginia. That turned into his new book, Main Street Entrepreneur,  which, Kickstarter contributors willing, will also become a documentary. (The campaign needs to raise about $16,000 more in 28 days to meet its goal.)


Although Glauser met small business owners of all ages, I spoke with him specifically about the achievers who were in their 50s and 60s, in hopes of helping Next Avenue readers who want to launch businesses or make the ones they have more successful. Highlights from our conversation:

Next Avenue: Why did you want to bike across America to interview small-town entrepreneurs?

Michael Glauser: My main motivation was that I’m very concerned that technology is eliminating jobs in just about every single industry. There’s a ton of evidence that this is happening and will accelerate at a rapid pace. Anything that can be automated will be automated.

Students at my university are getting fewer interviews and job offers now, so my concern was that self-employment or entrepreneurship will be more and more critical. We thought: "Where can we go where people are creating jobs where there are no jobs?"

That led to this epic venture across America, looking for role models to teach us how to handle the employment shift.

And why did you want to go to small towns?

People are tired of big cities with pollution and crime and want to live in smaller communities. If you study corporate America, you fly on planes and drive rental cars and stay in chain hotels. Here, we wanted to immerse ourselves in the communities and really savor the flavor of the country and see what we can learn in the Era of Me, Inc.

About how many of the hundred entrepreneurs you met were 50 or older?

I’d say at least 40 percent were. The owners we wanted to talk to had to have businesses that had been around for a minimum of five years; most of them were in business for 10, 12, 15, even 20 years. And a lot of them started the businesses in their fifties; some started them in retirement.

What advantages did you find that people 50 or older have for starting a business?

The obvious one is that they’ve been in an industry for a number of years, so they really know it and related industries. For example, we met Sam Spayd, from Florence, Ore., who flew planes for United for 25 years and then started the sightseeing business Aero Legends with a World War II biplane.

These older entrepreneurs have made a lot of contacts. They have mentors. They know the suppliers and manufacturers. They know the competitors, who makes what and where the gaps are.

Some of these people have taken an idea to their employer and said "We’re missing something" and the employer has said "We don’t do that." So the entrepreneur leaves and does just that.

The second thing is they know how business works; they’re not young or naïve. And they’re pretty sure their business idea will work before they launch it. They don’t need to take big risks because they know what the problem is and they have resources — not necessarily money. The resources could be mentors or an office at home with equipment or maybe they have the team members they need already.

And what did you find were the disadvantages people 50 or older had for starting a business?

The advantages far outweigh the disadvantages. One downside is that when you start a company in your thirties, you have a lot of energy to work all day and all night. It’s kind of a young person’s game in some ways. And when you’re naïve, you do some things you probably wouldn’t do when you’re older. And sometimes they work out pretty well.

Tell me about one or two of the Main Street Entrepreneur successes who were over 50.

There’s Mary DeLima who opened DeLima stables in Harrodsburg, Ky., after being in the equestrian industry for 25 or 30 years. She’d been teaching lessons and creating events and training horses her whole career. So it was easy for her to say "I will do it on my own." We saw many people like that.

And Dave Twombly, who’s also in Florence, Ore. He was in the garbage industry for number of years and saw large companies buying up small, independent companies. People then became unhappy with the bureaucracy and the service they were getting and said: "Why don’t you start one?" He had experience and contacts and people said, "I’ll patronize you." Now, he’s been around with his business, Central Coast Disposal, for more than 15 years.

What were some of the things the Main Street Entrepreneurs over 50 had in common?

One thing we noticed was that they were really excited to do something where they’d be making a contribution and doing something they were passionate about. It was not just about money. They knew they had to make money, but they loved their town and wanted to create jobs there and do something better than anyone else.


Take Richard Chaves of Chaves Consulting in Baker City, Ore. He created a call service center to employ people in the town he loves and he’s now up to 70 people. He can’t wait until he creates the hundredth job.

What lessons do these owners offer for people over 50 who want to start businesses?

The first thing I’d say, and it’s something I preach a lot: It’s easier to create a company now than it’s ever been, for a number of reasons.

There’s a growing preference for small, local companies. If people can buy local, they love to do it. They’re even willing to pay a little bit more because of the backlash against big box stores.

Also, powerful technologies now let you do business with the same kind of tech equipment that only large corporations could afford in the past — cell phones, computers and online publishing. The technology also lets you reach markets far beyond your geographic location; you can market to the world.

And there are a lot of new financing formats, like crowdfunding, to test products before you spend a lot of money on them.

You write that one of the keys to success, is to start with a clear purpose. Tell me about that.

If you’re not driven by something bigger than yourself, it’s hard to get through the first three to five years. It takes that long for sustainability to engage your team members and your customers. Having a clear purpose is the fuel that fires the venture.

Another key, you say, is to build on what you know. That sounds like something older entrepreneurs might have over younger ones. Is it?

About a third of the people we interviewed worked in the exact industry they started a business in and another third had worked in a related industry.

You don’t want to fall in love with an idea; you want to inventory your background and ask yourself, "What problems have I seen and what skills do I have that I can use?"

Launch opportunities and not ideas is another key from the book. You want to have evidence that people are asking for what you plan to offer.

What about finding people who can help your business succeed?

You need to develop a supporting cast. Find a brain trust of mentors who know the industry and maybe they also know what you don’t know about things like marketing or manufacturing. Try to include customers in the development of your business, too. That way, they will feel like this is "our" company, and they’ll be loyal.

And you recommend pivoting to multiple revenue streams. Why is that a good idea and how do you do it?

This is so fascinating. Most of the people in the book had three or four streams of revenue, all related to the same industry. They’re not doing different things, like construction and restaurants. They started a core product and built a community of people buying it and then they said: "Now we have customers who like it. What else might they buy?"

The goal is to provide a complete solution to your customers’ problem. If you can do that, they will come to you.

Photograph of Richard Eisenberg
Richard Eisenberg is the former Senior Web Editor of the Money & Security and Work & Purpose channels of Next Avenue and former Managing Editor for the site. He is the author of "How to Avoid a Mid-Life Financial Crisis" and has been a personal finance editor at Money, Yahoo, Good Housekeeping, and CBS MoneyWatch. Read More
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