Life Lessons From 11 Entrepreneurs Over 50 (2023)

Entrepreneurship is a growing trend among those aiming for financial independence or early retirement. But what about when retirement happens right on schedule? Older people, too, are turning to entrepreneurship to fill idle time, pursue a passion, or increase savings.

While 30 under 30 lists and sensationalized tech startup stories dominate the media, the truth is, more than half of those running small businesses in the US are over the age of 55. And, the likelihood of entrepreneurial success only increases with age. A 50-year-old founder is twice as likely as a 30-year-old to build a company that goes public or gets acquired.

Meet 11 older entrepreneurs and learn how their years of experience—both in life and at work—have created a great foundation for starting a business from scratch.

From roasting coffee beans to raising alpacas to developing inclusive skincare, these inspiring founders over 50 pursued entrepreneurship over retirement, building companies on nothing more than a great idea and decades of life experience.

1. Carl Churchill

Carl Churchill became an entrepreneur later in life, after serving many years in the army and working for other startups. When the 2008 recession hit and Carl lost his job, his family lived on dwindling emergency savings, selling their possessions to stay afloat. Then, they changed their plan: they’d cash out their 401(k) and sell coffee beans.

Now, Carl works alongside his wife, Lori, on their business, Alpha Coffee. The Churchills slowly grew the brand out of their basement and into two physical storefronts. They’ve recovered much of their old lifestyle, too—and Carl and Lori hustle seven days a week to keep it that way.

“We feel really good about where we are now,” says Carl. “We’re paying off our mortgage. We’re adding benefits for our employees. We’re doing good for the community. Our kids look up to us and are very proud of the business that we’ve built as a family.”

2. Trisha Trout

In 2008, Trisha turned 50 and she and her husband, Timothy, had just built a new home, where they were living with their two teenage sons. But by June Timothy was diagnosed with leukemia and passed away later that fall.

As the breadwinner, Timothy had been responsible for managing the finances of the household. Now, Trisha was on her own. The economy was crashing, forcing the family to sell everything they had—including their home.

As Trisha realized the life insurance payments would eventually run out, she turned to a favorite hobby as a way to earn income. Now she runs Prairie Sage Soap Co., a business she built by learning everything from scratch. “Having a small business requires focus,” she says. “which is just what a grieving person needs to carry on.”

Now 64 and a grandmother, Trisha is thankful for the little things. “I’m thankful for small pleasures like feeding the birds and squirrels, and for the fact that I can afford to go to Starbucks almost every day!”

3. Katonya Breaux

Katonya Breaux noticed the lack of clean and effective sunscreen options for people of color. In 2014, she was moved to create her own. After two years of experimenting, she founded Unsun Cosmetics, an editor-favorite brand of mineral-based, tinted sunscreen products sold online and through more than 5,000 CVS locations in the US.

“If you’re going to start a business, start something that really matters, start something that generates buzz, something that people want to talk about. Don’t just make another thing that’s already on the market, make it something special,” Katonya says.

4. Rob Urry

After retiring at the age of 52, Rob Urry bought a 40-foot fifth-wheel trailer to travel through his home state of Utah and beyond. While outfitting the trailer with necessary lighting—headlamps, lanterns, flashlights—he was disappointed with the options on the market. So he decided to design his own.

Rob emerged from retirement to start Kogalla, a high-performance lighting brand for adventure and travel. “After the romance of retirement wore off, I found myself needing to create and build something, so I jumped back into the business world,” he says. “I had always wanted to start my own business, but I just had a hard time breaking free.”

While his career as a music exec prepared him for many aspects of being an entrepreneur, there was still a learning curve. “My advice to other other entrepreneurs is that if you don’t want to jump headfirst into social media, SEO, email, and web design, take on a business partner who does.”

5. Nonna Nerino

For several years, Nonna Nerina was hosting intimate cooking classes from her home in a small Italian village. Then the pandemic hit. The popular tourist attraction suddenly had no clients. A friend of the family suggested moving to a virtual format, and Nonna Live was born.

Now, with the help of her grandaughter Chiara Nicolanti, 86-year-old Nonna broadcasts her cooking workshops to fans all over the world. The business has even evolved into physical products, working with a partner to bottle the unique gold olive oil that’s native to her region.

Learning the technology was the hardest part of the transition for Nonna. “She is a strong spirit,” Chiara says. “She doesn’t listen to me. She goes her own way.”

6. Rowena Montoya

Rowena and Frank Montoya lived a comfortable life that allowed them to travel, raise five children, and help less fortunate family members get back on their feet. During their heyday, Rowena often joined her husband on business trips, making her homemade caramels to give to his clients. But in 2009, the US financial crisis forced Frank to close his own business’ doors.

While Frank was rebuilding, Rowena discovered that her caramels might have a market of their own. She bootstrapped to turn her candy hobby into her own company while the couple lived on a fraction of their former income. JulieAnn Caramels are now carried in stores across the US and have even been featured on the Home Shopping Network.

“I’m not a quitter,” says Rowena. “I’ve taught this principle to my children, and so now the roles are reversed, and they cheer me on. And I can’t give up, because that’s not what I taught them to do.”

7. Sonja Detrinidad

After investing 16 years in a successful career as a mortgage professional, Sonja Detrinidad saw the industry change—and the stress was piling up.

As a distraction, Sonja challenged herself to update her home’s landscaping on a $0 budget, blogging about her misadventures. Soon, others were seeking out her plant-sourcing skills. After positioning herself as a personal plant shopper, taking requests through WhatsApp, Sonja quit her job to sell plants full time.

Sonja soon switched her business model, launching Partly Sunny Projects as an ecommerce store in March 2020. “I thought, ‘Who’s going to want to buy plants during a pandemic?’” she says. “And the answer was: everyone.”

Partly Sunny is now pulling in more orders than Sonja can manage on her own. Her husband steps in to help where he can, and she recently brought on employees. Much of her success comes from her popular TikTok account, where she is known for her candid plant content. “I’m a woman in my 50s and in menopause,” says Sonja. “I don't have the energy to put on a facade of somebody that I’m not.”

8. Jaswant Kular

Jaswant Kular wanted an easy way to teach her daughters the art of traditional Indian cooking. She found that many products on the market contained fillers, artificial ingredients, and lots of fat. At 60, she began preparing her own spice blends.

Urged on by the positive response from friends and family, Jaswant exhibited at a food festival— and completely sold out. Jaswant’s Kitchen, a company she runs with her daughters, now sells products online and in more than 100 stores.

Jaswant logged many hours in the kitchen to refine her recipes, but it was pure life experience that she credits with her success as an entrepreneur. “There is no way I could have done this business when I was younger,” says Jaswant. “I did not know what the world around me needed. I had to have the experience of all these years to get where I am today.”

To other aspiring entrepreneurs her age, Jaswant tells them to overcome fear. “You are about to have the best time of your life,” she says. “It is finally your turn to live your life the way you want. It is a lot of work, but the reward is also that much greater.”

9. Colleen and Jim Seiler

Colleen and Jim Seiler had more than 25 years’ experience selling odor control products to customers. In 2011, a friend was diagnosed with cancer and was prescribed medical cannabis to ease her symptoms. She wanted to mask the smell of the smoke, and came to Colleen and Jim for help.

In 2013, the couple (both over 50) deferred their retirement plans and started Kushley, a line of organic consumer products to eliminate smoke smell. They grew the brand by “pounding the pavement,” Colleen says, and introducing the brand at trade shows and conferences.

While technology has been the most challenging aspect of running the business, Colleen says the key is “embracing and hiring the young minds affluent in today’s technology.” To others in her shoes, she offers, “Make sure it is a passion at this age. This is a time to enjoy what you are about to embark upon.”

10. Carole Baskin

Carole Baskin has had a long career as a serial entrepreneur, long before she became a household name when she was prominently featured on the hit series Tiger King.

Carole’s primary business, Big Cat Rescue—a non-profit sanctuary aiming to help end the abuse of wild cats bred and raised in cages—was founded in 1992. At 55, Carole opened a second for-profit store to support legislative work to protect exotic cats.

The business isn’t a retirement project or even Carole’s full-time job. She’s been a real estate investor since she was 19 (and still is). Carole says that her age is an asset because she’s learned over time what’s really important. “The success of serial entrepreneurs comes from trying and failing,” she says. “Every time you succeed, you learn a little. Every time you fail, you learn a lot!”

And what does Carole have to say to other aspiring entrepreneurs over the age of 50? “Do it! The kids are out of the nest. Now is the time to really dig in and change the world.”

11. Bernie Rothrock

When Bernie Rothrock retired after 30 years of teaching, he accepted his brother-in-law Tom’s offer to manage his alpaca ranch. When Tom passed away, much of the herd was sold and the ranch was purchased by new owners who allowed Bernie to keep 11 alpacas on the property. Bernie continued to care for them as pets, with no intention to breed them for profit. “Alpacas are just really nice, neat little animals,” Bernie says. “And our grandkids love them.”

Bernie’s son Drew suggested to his Dad that he should start a small business with his newfound free time. Since alpacas need to be shorn for the hot summer months, Bernie decided to turn the output into usable products. He built Maximus & Penelope, named for two of the animals, selling alpaca wool socks through an online store.

At this stage of life, Bernie is happy breaking even and having a little extra money to travel and enjoy a peaceful retirement. Growth isn’t on his radar at the moment, but he’s still a new business owner, after all. “I really did not have that entrepreneurial bug, if you will,” he says. “It was happenstance. Things just worked out.”

Feature image by Marcus Aurelius

Entrepreneurs over 50 FAQ

Is it too late to start your own business at 50?

It’s definitely not too late to start your own business and become a successful entrepreneur. In fact, it may be the best age to do so. With more experience, fewer expenses, and possibly access to more financial capital than your younger counterparts, you can be your own boss with less risk.

What business can I start in my 50s?

An entrepreneur over 50 can start any kind of business. An older entrepreneur may be inspired to pursue a big idea, turn a hobby into a brand, or save extra money for later years. Consider starting a business for your own demographic, such as a health product or fitness businesses catering to the over-50 audience.

Who are some successful entrepreneurs over 50?

Some examples of successful entrepreneurs over 50 include Bobbi Brown, Arianna Huffington, and Edith Cooper. A number of entrepreneurs even founded their own companies after the age of 50, including Julie Wainwright, who launched the brand The RealReal, McDonald’s founder Ray Kroc, and Bernie Marcus who created The Home Depot with co-founder Arthur Blank.

Life Lessons From 11 Entrepreneurs Over 50