We recently connected with Matt Layson and have shared our conversation below.
Matt, appreciate you joining us today. Early in your career, how did you think through the decision of whether to start your own firm or join an established firm?
My family has been doing insurance for 4 generations, so of course I went my own way out of college and got into audio visual production. I was doing well, had great employees, the best boss I’d ever had. But I didn’t want to be doing physical work into my 60s so I decided to look at different careers. After a lot of soul searching my dad presented me an opportunity to learn the insurance business to eventually take it over one day.
One of the ways I make decisions is by asking myself, “Would I wonder what if and regret not trying this in the future?” The answer was a firm yes for me, so I changed careers and that was about 5 years ago.
It really was scary taking a massive pay cut, going from being an expert in my field to knowing nothing, that was really humbling. Even though I had multiple family members in that industry, I’d never done the work myself. My wife had to take a full time job to bridge the gap in our finances but we knew what owning a business could mean in the long term.
I had to take active steps to make sure people knew I was no longer the “music guy” I needed to become in their mind “the insurance guy.” There were a lot of moments where failure wasn’t an option, like I have to pass the licensing test because if I don’t I can’t work at the agency. Then it became, I have to make enough sales to justify being here. And now after a lot of consistent effort, most of those big road blocks are behind.

Matt, before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?
I’m a commercial insurance agent, at a family owned independent agency CalRose Insurance in Everett Washington. What I do is I work with dozens of insurance companies, to find the best combination of coverage and cost for my clients. But by far the most important part of that job is explaining how this stuff works.
Most people only know about insurance from what the advertising tells them every day, insurance should be cheaper. Is this the only question you ask when you’re buying a house, a car, or phone? Of course not, you ask about what it does for you and how it does it. My job is to talk people through the different complex coverages and explain how they work, so they can decide if that’s important to them or not.
Some people think insurance is a scam, I get that comment constantly on tiktok where I do a lot of educational content about Insurance. But who have that opinion I’ve found the root cause is a lack of understanding, which is why we spend a significant amount of time educating clients and prospects, far more than most agents.
We sell policies as simple as personal auto insurance and home insurance. I personally spend most of my time in commercial insurance, areas that are more interesting and complex. I really like working on data breach risks as that’s something few insurance agents truly understand and the coverage itself is more complicated than most policies.

What do you think helped you build your reputation within your market?
Doing educational video content has been a big differentiator for me. It forces me to continually work on my communication, I explain things now so much more simply and quickly than I did when I first started. The habit has also shown a lot of people in my local business community that I’m different and I know what I’m talking about.
One thing I wasn’t aware of, was that I’m doing something different. I’ve learned that people across the country in my industry know who I am, because I’m trying to bring the complex and weird insurance industry down to a simple level everyone can understand. Historically insurance agents never wanted to give any advice away for free. Most insurance agents can’t explain their product, market, or anything without using a lot of internal terms that only they understand. Because I flipped both of those things upside down with my approach, I’m starting to build a reputation in my industry.
Do you have any insights you can share related to maintaining high team morale?
One thing we’ve done well that maintains a high morale in our team is we let the team self manage. We give them the principles, the why behind the process. This way when they are doing their work, they are viewing everything with the right lens, so even if they make a mistake they’re heading in the right direction. This is why we repeat the phrase, “Bring your brain to work.” We want and expect our people to think.
A lot of managers will approach training like, “I’m busy and want to rush through this so don’t ask any questions just do what I say.” Then they get surprised and angry when a horrendous error happens. Management won’t realize their lack of explaining the why, strongly encourages employees to not say anything when they see a problem and encourages them to not think about what they are doing. They didn’t know the bigger picture, so when they got in a situation where they had to make a judgment call on their own, they missed the point.
The only other advice I’d give is learn the balancing act of caring for and know your people well, but do not forget it is an employee employer relationship. It’s really sexy in some circles to be “friends with your employees” but that is a really easy way to cause a lot of drama in your work that can even get you sued. You absolutely must be empathetic, you must know your people personally so you know how to best communicate with them and motivate them. But if you cross the line to friend, when they need to leave regardless of circumstances, that can really cloud your judgement and may leave you open to being taken advantage of. The balancing act should always be in your mind and you should always feel the tension, cause when you don’t feel the tension, you either care to little about your people or to much.
Contact Info:
- Website: https://calroseins.com/
- Instagram: https://www.instagram.com/mattlayson/
- Facebook: https://www.facebook.com/calroseinsurance
- Linkedin: https://www.linkedin.com/in/matt-layson-0b3a967b/
- Other: https://www.tiktok.com/@matthewlayson?lang=en
Image Credits
Watkins Photography did my headshot.

