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Life Lessons From 11 Entrepreneurs Over 50

by chien nguyen · 5 min read

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.

11 inspiring entrepreneurs over 50

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

Portrait of Alpha Coffee founder Carl Churchill and his wifeCarl 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

Portrait of Trisha Trout drinking coffee on a porchIn 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

Portrait of Katonya BreauxKatonya 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

Portrait of Rob Urry hikingAfter 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

Portrait of Nonna Nerino and her grandaughter ChiaraFor 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.”

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