10 Unexpected Stories of Fame and Fortune
We often think of insurance as something we need for cars, homes, and health. But what if I told you that insurance also played a surprising role in the lives of some of the most famous people in the world? That is right. Insurance is not just for the average Joe and Jane. Some celebrities have made money through it, worked in it, or used it as a stepping stone to stardom.
Whether they started off selling policies or became the face of big-name companies, these ten celebrities have fascinating connections to the world of insurance. And believe me, their stories are worth hearing. This blog is written for everyone, including Grandma sitting with her knitting needles. We are keeping it warm, easy to follow, and filled with stories that might just make you say, “Well, I never!”
Let us dive into the world of fame, fortune, and insurance with these ten remarkable tales.
George Clooney
From Insurance Sales to Movie Sets
Date of Birth: May 6, 1961
Country: United States
Estimated Net Worth: $500 million
Before George Clooney was dazzling the world in Hollywood films, he tried his hand at insurance sales. That is right, the silver-haired heartthrob once walked door to door selling insurance policies. George admitted that this job was not exactly his dream, but it taught him valuable skills. He learned how to deal with rejection, how to connect with people, and how to keep going when things got tough.
Though his time in the insurance world was short-lived, it helped build the confidence and charisma that would later make him one of Hollywood’s most respected actors. It is a good reminder that even the most glamorous stars often start from very humble beginnings.
Meet Flo from Progressive
Date of Birth: February 8, 1970
Country: United States
Estimated Net Worth: $6 million
You might not recognize her name, but you definitely know her face. Stephanie Courtney is the actress behind Flo, the peppy spokesperson for Progressive Insurance. With her bright smile and blue headband, Flo became a household name, turning Stephanie into a star in her own right.
Before landing this iconic role, Stephanie was a struggling actress doing odd jobs to make ends meet. Once she got the part, everything changed. Not only did she become famous, but she also helped Progressive become one of the most recognized brands in America. Her work as Flo is proof that even a commercial gig can lead to fame and financial stability.
Kevin Miles
Jake from State Farm
Date of Birth: July 5, 1990
Country: United States
Estimated Net Worth: $2 million
If you have seen a State Farm commercial lately, then you have seen Kevin Miles. He plays Jake, the helpful and down-to-earth insurance agent who is always there when you need him. Kevin’s portrayal has made him one of the most familiar faces on television.
What many people do not know is that Kevin was once a struggling actor working in Chicago. He took on the role of Jake as a way to pay the bills. But thanks to his charm and relatability, the campaign took off. Now, Kevin is a celebrity in his own right, all thanks to a clever insurance campaign and a red polo shirt.
Anne Rice
Claims Processor to Queen of Vampires
Date of Birth: October 4, 1941 (passed away December 11, 2021)
Country: United States
Estimated Net Worth: $60 million (at time of death)
Before she wrote bestselling books like Interview with the Vampire, Anne Rice worked in the insurance world. Specifically, she was a claims processor. This job involved a lot of paperwork, patience, and attention to detail.
While it might not sound glamorous, this job gave Anne the time and space to think creatively. She would often daydream about characters and stories while working her day job. Eventually, she began writing, and the rest is history. Her journey is a beautiful example of how steady work can support big dreams.
Tommy Maddox
From Football Field to Insurance Office
Date of Birth: September 2, 1971
Country: United States
Estimated Net Worth: $2 million
Tommy Maddox had a unique career. He was a professional football quarterback, playing in both the NFL and the XFL. But what is truly surprising is what he did between games. During his time away from the field, Tommy worked in the insurance industry.
That is right. When football opportunities slowed down, he stepped into the world of insurance to support his family. It gave him a reliable income and a sense of purpose. Later, when he returned to football, he did so with a stronger understanding of life beyond the game. Tommy’s story shows that it is never a bad idea to have a backup plan.
Evel Knievel
Daredevil with a Sales Pitch
Date of Birth: October 17, 1938 (passed away November 30, 2007)
Country: United States
Estimated Net Worth: $3 million (at time of death)
Evel Knievel was known for his death-defying motorcycle stunts. But before he was flying over buses and breaking bones, he was selling insurance. Evel worked as a salesman, going door to door trying to convince people to buy policies.
It may seem like a strange beginning for a man who lived on the edge, but it makes sense. Selling insurance requires confidence, quick thinking, and a bold personality—all things Evel had in spades. His sales days helped shape the showman he would later become.
Chris Lane
Country Star with an Insurance Past
Date of Birth: November 9, 1984
Country: United States
Estimated Net Worth: $2 million
Country music fans know Chris Lane for his chart-topping hits and smooth voice. But before he was touring the country and singing love songs, Chris worked in the insurance industry.
It was not a glamorous job, but it paid the bills and allowed him to pursue music on the side. Eventually, his talent was discovered, and he made the leap into full-time music. Still, he credits his time in insurance with teaching him discipline and perseverance.
Harland Sanders
Colonel Sanders Sold Insurance First
Date of Birth: September 9, 1890 (passed away December 16, 1980)
Country: United States
Estimated Net Worth: $3.5 million (at time of death)
You know him as the founder of Kentucky Fried Chicken, but before he wore that white suit and black bowtie, Harland Sanders sold insurance. He worked as an insurance agent in Indiana, knocking on doors and talking to families about their financial futures.
His time in sales gave him the communication skills and grit that would later help him build a fast-food empire. It also gave him a deep understanding of customer service. The Colonel’s early days in insurance played a surprising role in his recipe for success.
Junior Bridgeman
NBA Star to Business Tycoon
Date of Birth: September 17, 1953
Country: United States
Estimated Net Worth: $600 million
Junior Bridgeman played professional basketball for the Milwaukee Bucks, but what he did after his sports career is even more impressive. During off-seasons and eventually after retirement, Junior worked in the insurance and business world.
He built a fortune by investing in restaurants, bottling plants, and insurance services. His success is a shining example of what happens when athletes think beyond the game. Junior became a role model not just for athletes, but for anyone looking to turn hard work into long-term wealth.
Brewer Twins
From Runways to Risk Management
Date of Birth: Derek and Keith Brewer, born September 15, 1973
Country: United States
Estimated Net Worth: $1 million (combined)
Identical twins Derek and Keith Brewer made a name for themselves as fashion models. They appeared in magazines, walked runways, and even acted in commercials. But in 2013, they made a surprising career move—they opened their own insurance agency in California.
Their agency focused on helping people find affordable and reliable insurance coverage. The twins used their fame to bring attention to an industry that is often overlooked. Their story proves that beauty and brains can go hand in hand.
Insurance may not be the first thing you think of when you hear the word “celebrity,” but as you can see, it has played a powerful role in many famous lives. From door-to-door sales to starring in commercials and even running agencies, these ten individuals show that insurance can be a stepping stone to greatness.
So next time you see a commercial or sit down with your local agent, remember—behind that policy might be the beginning of something truly remarkable.
And who knows? Maybe your own journey has a surprising twist just waiting to unfold.
