Think insurance is boring? This Fort Wayne entrepreneur says it offers accessible career advancement

Insurance isn’t a “sexy” career. That’s no secret to Matt Booker. A 40-year-old resident of Fort Wayne, he started his own agency under American Family Insurance Company about a month before the COVID-19 pandemic began.

In many ways, the uncertainty unleashed by the pandemic underlines the value of Booker’s work, preparing clients for the unexpected. 

“The only thing more expensive than having insurance is not having it,” Booker says.

Through his business, he makes it a point to demystify the value of many types of insurance for his clients, ranging from auto to home, life, and business insurance. He also shares the benefits of a career in the insurance industry, where agency owners can enjoy the freedoms of entrepreneurship without the burdens of college debt.

While Booker earned a degree from Indiana University in 2006, he notes that insurance is an industry where you don't need a degree to succeed.

“You just need the opportunity to be exposed to it and to learn,” Booker says. 

By doing just that, he’s built his own agency, Matt Booker American Family Insurance Agency at 6070 E. State Blvd., where he’s hired two employees and encourages others to join the field as a route to accessible career advancement.

As a whole, Fort Wayne is among the top specialty insurance markets in the U.S., making it ripe with opportunities to get plugged into the field.

Input Fort Wayne sat down with Booker to learn more about his experience becoming an insurance agency owner during the pandemic and his advice to others looking to launch ventures of their own. 

Portrait of Matthew Booker, owner of Matt Booker Insurance Agency.

IFW: How did you get into the insurance industry and get the idea to start your own agency?

MB: Nobody grows up thinking, "Oh, I want to be an insurance man."
I was born and raised here in Fort Wayne. I had the privilege of going to Weisser Park Elementary School, Arlington Elementary School, Memorial Park Middle School, and South Side High School.

Then I graduated from Indiana University, Bloomington, where I majored in sociology, telecommunications, and African-American studies. My goal in college was to better understand the world around me, better understand how to connect with people, and better understand my position in the world.

Once I graduated, I decided I would get involved with insurance because I had a friend tell me there's a job where you can travel the country, move to Florida, and make decent money. At first, insurance sounds boring. But once I tried it, I saw I was good at it, and I said to myself, “Well, Matt, to be successful in something, you have to take those experiences you've already had.” 

I was working for American Family Insurance, and I enjoyed the company. So I decided that I would start my business as an agency owner because it allowed me to spend more time at home with my kids. I started this business because I wanted to contribute something to my community, be near and take care of my family, make a living, and be able to enjoy myself recreationally.

Matthew Booker and Evelyn Booker chat at their office at 6070 E. State St.

IFW: Did you always know you would be an entrepreneur someday?

MB: As I look back, I think I have always been an entrepreneur. School influenced me heavily with the way I see the world. 

When I was in school, I had candy from the neighborhood store, and people out at Arlington Park couldn't get that candy. One young lady asked me, “Hey, I'll give you money to get that candy.” I thought to myself: I paid 2 cents for this. I'll charge her 5 cents, and I'll pay for my own candy with the profits, so that's what I did.

So I had the candy all bagged up, and I had people's names on it. Then the librarian grabbed me, took me to the principal's office, and took the girl's bag from her. Once I got to the office, I realized she thought I was selling drugs. 

Here I was, a fifth-grader, slanging candy, and she really thought I was selling drugs. Sometimes, we are subjected to stereotypes, even as young kids, but at the same time, what's inside of us will yearn to come out.

IFW: What was the pandemic like for you as a new business owner?

MB: I launched my agency in February of 2020, and I will never forget that I was all ready for it; I was doing training, and then the pandemic hit, and it changed a lot of things.

I realized I had left a job with a steady income to start my own business. You want to talk about second-guessing yourself? I thought: “What did I just do?”
As an agent, my business was based upon going out, meeting people, and interacting with them, and we were at a time when the world said we can't do that. So I was thinking: “How am I going to make a living?”

Then the schools shut down, too. My home office became my only office. I worked from home with two kids in the living room on iPads, sometimes watching TV. I would literally have (my children) William and Mya running into my office, screaming at each other, and I've got Ms. Smith on the phone, trying to sell her automobile policy. 

In some ways, it created a challenge of how to meet people, but in other ways, it forced people to see who they were working with and what was going on. I just appreciate my clients who chose to do business with me and understand those circumstances and operate from a position of grace.

The exterior of Matt Booker Insurance Agency on State Street.

IFW: As the pandemic subsides, tell us about your office, employees, and methods of doing business these days.

MB: My office is located near State and Maplecrest behind Haley Elementary. I have two full-time staff members who work with me. Even though we have a physical space, we often do business via text and telephone. If you want to connect with us on Zoom or Microsoft Teams, we offer that, too. 

One thing the pandemic taught us is that you can connect with people in different ways. You just have to keep connecting with people.

IFW: After you started your business, you enrolled in SEED Fort Wayne’s Build Institute program, a nine-week startup education program for early-stage entrepreneurs. What inspired you to enroll?

MB: I actually think I saw an ad on Facebook, and as a young business owner who was socially isolated in the time of COVID, how else do you meet other people doing what you're doing? 

At that point, it's not about doing insurance. It's about taking this idea and making it a reality. It's about functioning in an environment where you don't have all the skills you need to be successful and understanding that those skills are only going to be acquired through relationships and connecting with other people. So when I saw the Build Institute, what they did and how they did it, I was interested. 

I had already written a business plan, but building a sustainable business was a work in progress, and I decided, “Hey, I can benefit from this.” I'm going from, I have this idea of how I want to do business in an industry that has been around for a while. But how do I tailor my business plan and the steps I take to execute my plans in a way that I can be successful? 

I was a little nervous at first, too, because I wasn’t sure my business, as an agency owner for American Family Insurance, would fit SEED’s definition of an “entrepreneur.” In this type of business, people often think that since I work with a national brand, I already have all the “secrets.” But even working with a larger company like mine, you still spend a lot of time working on your own business behind the scenes, marketing, and making decisions about payroll, policies, procedures, and systems. 

I technically knew that going in, but I didn’t really know it until I started to experience it firsthand. And the Build Institute helped me formalize my processes for making decisions.

Matthew Booker and Evelyn Booker work together on an insurance account.

IFW: What did you find to be the most valuable aspect of participating in the Build Program? 

MB: The most valuable aspect of participating in the Build Program was realizing that there are other people out there who don't have it all figured out, but they're willing to take a chance. There are resources out here to get those things done, and as an entrepreneur, it's par for the course to not have it all figured out.

IFW: What does success in your business look like for you? 

MB: My business has grown tremendously in two years, I'm excited about the next two years.

Success for me is helping people understand what they're buying when they buy it, giving them the best possible value, and when they need it, it's there. Yes, profits do matter, but what matters even more than that is creating a sustainable business where I'm able to introduce other people to the field of insurance before they go to college and collect all that college debt. 

On that note, success for my business is also about creating sustainable employment for people and offering jobs to individuals who might not have considered going into this industry. Going into insurance is a great way to build a successful career for yourself without the burden of college debt.

Portrait of Evelyn Booker, a sales specialist at Matt Booker Insurance Agency.

IFW: How are differentiating yourself and your business in the insurance industry from those who came before you?

MB: I think I make insurance more accessible. Every slice of your identity gives you the opportunity to connect with someone. So me, being a Black man, maybe I connect with other Black men, or because I am a father or a Christian. That all builds trust and the ability to connect with people. 

I think when people see me in insurance, it begs the question of how I got involved with that, and I can share my story, and then remind them that they don't need to go to college to do this. It’s something that requires a professional degree and you can make a living with it as long as you acquire the skills and have the opportunity to do it. Every chance I get to talk to young folks about insurance, even if it’s about buying insurance, I talk to them about considering it as a career. 

IFW: What advice do you have for other people, especially People of Color, starting businesses in Fort Wayne?

MB: I think you have to be courageous. You have to take a chance. You have to look for mentors who look like you and also those who don't look like you. You have to be willing to fail, and I think you have to have some degree of faith that you are moving as you are directed to. You want to continue to learn and grow. The quote I have over my desk is, “Get better every day.” You just have to find one way to improve every single day. 

IFW: When you say, look for mentors who look like you and who don’t, what do you mean by that? 

MB: I think when you see people who look like you, you see a possibility. But those aren't the only people you have to learn from. Some of my mentors are of the opposite sex or a different race. The principal or the key defining features of a mentor is someone who believes in you and someone who's going to pour into you and that's not limited to what they look like. At the same time, when you become a mentor, you're not a good mentor if everybody you mentor looks like you, period. If it's just you, but younger, you're offering far less than what you could be.

My charge to entrepreneurs would be: Take advantage of this entrepreneurial ecosystem that Fort Wayne and Allen County is trying to create, but then be courageous and reach out and try to build relationships with other people. Because at the end of the day, that's why I got involved with Build. I saw the opportunity to connect with the entrepreneurial ecosystem that Fort Wayne is trying to build here.

This story is part of an Entrepreneurship series made possible by underwriting from SEED Fort Wayne. To learn more about SEED, visit its website at

Read more articles by Desaray Bradley.

Desaray is expecting to graduate from Purdue University Fort Wayne in the spring of 2021 with a bachelor's degree in Communication: Media and Culture and a minor in Public Relations. She enjoys traveling, photography, and short story writing in her free time.