From his homemade mobile car wash business to owning one of the most successful insurance companies in the state, James Mason is the personification of the entrepreneurial spirit.

“Truth is, I’ve never had a job in my life,” Mason said. “I’ve never had a salary one day in my life. I’ve just gone from one deal to the next.”

After he graduated from college, Mason said his mother inquired as to what he planned to do with his life. Looking at the morning newspaper and reading the savings and loan crisis headline, he answered that he was going into real estate.

“I didn’t have any money, but I was willing to work hard,” Mason said. “I went around to all the banks and just started negotiating to take their distressed realty off their balance sheet.”

Mason continued, “I didn’t have a dollar, but some of them believed in me and I started buying real estate.”

After acquiring several properties and securing an impressive portfolio, Mason connected with a good friend and entered the world of insurance.

In 2006, Mason purchased Bluegrass Insurance Company in Elizabethtown.

“At the time, it was a little agency with two people,” Mason said. “I grew it into one of the largest insurance companies in Central Kentucky.”

Mason claims the success of any business relies on customer service and putting the needs of the client first.

“The first thing you do, is you’ve always got to put your customers first,” Mason said. “You can’t be successful in any business if you don’t do that. If you are always focused on serving your customers, the rest sort of works itself out.”

While most insurance agents have thousands of customers, Mason said he has fewer than a hundred.

“People hire me because they have very complicated insurance problems,” Mason said. “I focus on getting to know my customers really well and being intimate in their business. I enjoy the serving part of it.”

Denise Joy is the office manager at Bluegrass Insurance and has worked with Mason for 20 years.

“We have been friends for over 22 years and worked closely together the last 20,” Joy said. “What I tell most people that come to work for us is that ‘James is going to be one of the smartest people they will ever meet.’ And he truly is, but that is not what I would say draws people to him. What people admire about him and what draws people to him is his ability to relate to everyone on many levels and his great desire to help people advance their life.”

“In our office specifically, we always interview persons not necessarily because we have a job opening but because he is willing to hire people based on their abilities,” Joy continued. “Many times, we hire someone and then work a job around the person.”

While the insurance business requires much of his time, Mason said about 50% of his schedule is spent with the banking industry.

“I consult with lots of banks, I used to at least. I help banks be successful,” Mason said. “I used to work with three banks, and now I work with just one, Magnolia Bank.”

“Gathering deposits and making loans is an extremely risky business, and that’s all most banks know about making money,” Mason said. “It’s humbling that people trust us with their money, and we have to make sure we are good stewards with it.”

One of the people Mason has helped along the way is Tom Masterson, founder and CEO of T.E.M. Group.

“When I first started my business in 1999, TEM Electric (now TEM Group) grew fast,” Masterson said. “And like all small businesses, with the fast growth came cash-flow problems. I had gone to my bank, and they would not loan me the large amount of money I was asking for. James was a successful businessman at the time. I decided to approach James to see if he could point me in the right direction.”

Masterson said Mason asked to see his business plan and after reviewing it said he personally would loan him the money.

“With that money, I was able to take on more and bigger jobs, make payrolls on time, pay my vendors on time and invest in more equipment and tools,” Masterson said. “It was an aha moment and catapulted TEM into the successful company we are today.”

Mason said he likes to think of himself as the guy who finds less risky, more risk-adjusted types of returns.

“Its’ really fun to try to help (bankers) be more efficient and get everyone on the same page to see the future differently,” Mason said. “I enjoy the strategic component in all of that. There’s a certain harmony in it that I really enjoy. I find the math interesting, and it’s a good use of my natural talents.”

Mason said he would not be the man he is today if not for his life’s two most important role models, his mother and his wife.

His mother, Rebecca Shaver Mason Irvine, was an English teacher in Elizabethtown. After she married Mason’s father, Eddie Mason, a member of the Kentucky Basketball Hall of Fame, the couple moved to Chicago where Mason was born.

Eddie Mason was from West Point, and soon the family moved to Louisville where Mason grew up and eventually met his wife.

“A family connection reached out to my mother and said their daughter was going to med school, and asked if she knew of a good place where she could live,” Mason said. “My mother offered her carriage house. And Leigh Anne Pearman, who is now my wife, moved into my mother’s carriage house.”

Mason said he met Pearman and fell in love.

“I asked her out a thousand times, and she said no nine hundred and ninety-nine times,” Mason said with a smile. “She finally said she would go out with me, and so I said, ‘Then I’m never going to let this date end.’ ”

Having helped countless people and businesses along the way, Mason said it’s important how people view success.

“Be very careful how you measure success,” Mason said. “It’s never about the money. It’s always going to be about the relationships. Be careful how you measure your own success.”

“James lives life to its fullest and engages with everyone that he meets; he is an incredible listener,” Joy said. “He feels deeply for everyone around him and strives to take care of each person.”

Amy Smith can be reached at 270/505-1416 or