A foundation of faith — with Cheryl D. George

Cheryl D. George remembers the incident that set her on the path to an insurance career.

A young woman from her community died after a battle with cancer. Her husband and family had no money to pay for a funeral, so they were forced to raise the funds needed to pay for her final expenses.

George vowed that she would do everything she could so that no other family would have to fundraise for a funeral. That vow inspired a career change from a business consultant to a life insurance agent.

Today, she is managing director of Atlanta-based Insure With Cheryl, an independent insurance agency specializing in life and health insurance that she founded in 2012. 

George’s practice primarily serves solopreneurs, those who are self-employed and have anywhere from one to five people working for them.

“I lean toward serving female entrepreneurs who are moms, heads of household, usually singles, but I have a lot of male clients as well,” she said.

George said she focuses on self-employed clients “because those in the self-employed market don’t have a good financial road map.

“W-2 employees have structure. They have 401(k)s, and they have life insurance and health insurance through their job, and they have all these different protections in place. As solopreneurs, we’re trying to figure it out. We don’t have it. We’re just trying to stay above water. So I like to work with self-employed so I can bring structure to them. I understand their plight because I experienced it for 30-something years, and I’m still experiencing it. It’s like they’re my tribe.”

A portfolio — not just a policy

“You should have different things inside that portfolio to protect you when life starts happening,” she said. “My model and my theme is: Protection is the plan. When I talk to clients about their goals, their dreams, their aspirations, what their business is and how they got into it, their highs and their lows — I’m listening and taking notes. If I see a way I can connect them to another client who can help their business, I’ll do that. If I see an article that will help their business, I’ll share it.”

Entrepreneurs often lack someone who believes in their vision, George said. 

“Most of the time, they’re the first one in their family to step out into entrepreneurship. Their family thinks they’re crazy for leaving a good job, and they don’t see that person’s vision until they hit success. It’s a lonely road, and they don’t have someone cheering them on. So I am their cheerleader, and I listen intently because that’s what I needed and wanted when I went out on my own.”

The skills that George had in her prior career as a business consultant transferred well into the insurance business.

“I understand business structure very well. So when I’m talking to these entrepreneurs, I see the holes, the shortcomings in their plan. I can see whether their insurance is improperly structured or that they don’t have certain things in place, and I’m able to point that out to them. I can see that they don’t have proper systems in place or that they can’t get proper financing from the bank. A lot of my entrepreneur clients call me for consulting. So my background helps me, especially since my target market is self-employed folks.”

George spent the early part of her life in New York before moving to Chicago, where she spent 10 years. She has an honorary doctorate in business administration from a Christian college in Chicago. Her move to Chicago was inspired by searching for something new after her daughter married and left home.

“I wanted to do something different in my life,” she said. “I knew a pastor who was heavily into the mission field, and I wanted to do something with my life in that regard. My faith is important to me. It’s very big. I wanted to get into the mission field and learn more about that. The plan was to go to Chicago for six months to learn from her. But that six months turned into 10 years.”

Faith is the foundation

George said her faith is the foundation of her practice.

“It is how I choose my clients. It is how I care for my clients. I pray for my clients daily. I motivate my clients through prayer in conversations. I strongly believe that my agency is not my work or my career. I believe it’s my assignment from God that I help navigate these families, these entrepreneurs who are heads of families. That’s why working with single moms is so important to me. It’s transforming the lives of multiple generations, on multiple levels, and so I believe this is my calling. This is what I’m supposed to be doing.”

George has many multigenerational clients. 

“When I do the initial assessment with clients and they tell me how many children they have and their names and their sex, I ask what they are into and what are they about,” she said. “When I talk to the client, I want to talk to the spouse and children as well. I want to know what goals the children have because the children’s goals affect the household finances. If a child wants to be a doctor or wants to play soccer or whatever, those are expenses that the parents must incur.”

She also reaches out to clients on birthdays or when they are ill.

“I’ve sent people coloring books and chicken soup,” she said. “I’m not the traditional advisor. As I said, this is my tribe. I can’t do the things I do for my family without my clients. Because they trust me, I want to be a good steward for what they have entrusted me with.”

Supporting communities at home and abroad

George is a Top of the Table member of the Million Dollar Round Table and is a member of Pan American Life Insurance Group’s 2025 Chairman Club. But beyond these industry honors, George is most proud of her work in supporting communities both overseas and in her own backyard.

In August 2024, she financed the completion of an orphanage in Uganda after the construction was halted during the COVID-19 shutdown. 

“It’s the project of a good friend of mine,” she said. “In 2023, he told me that the orphanage was sitting there abandoned, half done. I said, ‘Let’s go ahead and finish this project, and it will be my 60th birthday present to myself.’ It’s a six-bedroom, six-bathroom building for the children. Now we’re going to do the landscaping and furnish it, so we need to buy a washer and dryer, a refrigerator, bunk beds and everything the children need so they can move into the building in September. Then in December, we’ll do Christmas in Uganda.”

Christmas in Uganda has been a tradition for George for the past 15 years, where she feeds an entire village three meals a day for a week. She also sends resources that children need to be fed, housed and educated.

“It costs us maybe $1,200 to feed about 200 children,” she said. “I also sponsor six children in boarding schools in Uganda because there aren’t places to house them. I pay for their school fees, their boarding fees, their meals, clothes, medical bills, whatever they need.”

In addtition to her work in Uganda, she also has done mission work in Abuja and Lagos in Nigeria and Sierra Leone.

“I saw the need of the people,” she said of her interest in mission work. “I have a friend who has been in the missionary field for 15 years, working in 41 countries. Sometimes he needs help, and he shares stories of people with needs — usually medical needs — and I send money to help.”

Back home in Atlanta, George volunteers with and supports organizations that help women who are victims of domestic violence. She also does back-to-school drives for children in need. 

She recently created the Cherish Foundation, which is aimed at funding programs to help communities at home and abroad. In June, the foundation will launch a financial literacy program in partnership with local churches. The foundation also will fund scholarships to vocational schools and for entrepreneurship.

Excited about tech

George is using her computer science degree to develop digital tools for her clients. 

“Some of the tools are free, some are paid, but they will support the work that we’re doing and automate a lot of the processes that we’re doing manually,” she said.

She also wrote her first book, Fire Your Bank, which was published in February. In 2025, she created a financial planner called “Flowing Financially,” which was designed for the self-employed. The planner includes several trackers for clients to list their saving, spending, investments and income. She is now in the process of turning that planner into an app.

“We also created an assessment that clients can do. One is free, and then there’s another one that costs $69 but it gives you a 15-page report of your financial makeup — not just insurance, but everything,” she said. “It shows you the areas where you are strong, where you can use more help and where you’re totally exposed. And then it gives you a 12-to-24-month road map on how to get yourself in order and insulate yourself from things that most people who are not in this industry don’t think about.”

George said she is excited about these new products, and she plans to expand her practice and add more advisors. But she doesn’t want to grow to the point where she loses sight of why she is in the business.

“Even though we are building a boutique agency, I don’t want it to be so large that the culture gets lost,” she said. “It’s important that I stay tapped into my clientele. I don’t want them to become numbers on a page.”

Susan Rupe is editor in chief, magazine, for InsuranceNewsNet. She formerly served as communications director for an insurance agents' association and was an award-winning newspaper reporter and editor. Contact her at [email protected].