InSurOp-Ed: On This Day 30 Years Ago: What I’ve Learned

On May 28, 1993, I walked into my father’s insurance agency which housed a new business concept supporting independent agencies. SAN Group (Satellite Agency Network Group) was 5 cubicles in the back of the office. I was employee #5 and we had 28 member agencies. In a few years, SAN would become the foundation of SIAA’s national model. 

I was a mediocre student, a mediocre athlete and really didn’t know what I wanted to do. I did know that I needed to work.   I arrived on my first day wearing a hand me down blue suit and tie, penny loafers affectionately adorned with the pennies, holes in the soles and a toe sticking out.

That day I made a commitment to myself that I would strive to be the best at the career I was beginning, wherever it took me. I’d work harder, smarter (where I could!) and more hours. I’d listen, learn, and strive to be the best at whatever I did. No more mediocrity. While I am not sure if I achieved that goal, I do know that I have learned some great lessons over 30 years:

Your wife, husband, partner and kids must come first.  While work and business are important, that foundation and support system is what motivates you, makes you successful and gives you something to come home to. That is your North Star. 

Listen and observe. No one ever learned anything from talking. This includes taking a few moments to have a personal conversation even with business on the mind.  

Mentors matter. You’ll look back and see that you had significant, insignificant, short-term and long-term mentors. Many times, you didn’t even know they were a mentor until you look back at the lessons that formed your career.

Not all who influence you will be positive role models. You can learn just as much from what NOT to do by watching others. We can learn from other’s mistakes, not just our own. We can learn how to treat people by seeing how others fail at that skill. 

Always be willing to learn, listen to others, don’t be afraid to ask questions and take criticism or re-direction, as hard as it can be. Surround yourself with smarter people. You don’t have to know it all, you just need a team that covers each other’s blind spots.

Humans are a difficult species, but we cannot have business or personal success without those around us. Find common ground and build success together. 

If you are in a leadership role, know this: The people around you are watching. What you do, what you say, how you treat others and how you behave does matter.  

I’d be lying if I said I get this right every time, but I’ll tell you that these are the standards I aim to meet….30 years into this journey. I bet I have more to learn.

Strive to be your best.  

This post originally appeared on Mr. Masiello’s LinkedIn page on May 28, 2023. It is reprinted here with his permission.

CEO, SIAA; Book Author at Insurance Agency 4.0; Independent Agent Advocate, Insurance Distribution Futurist

Matt Masiello has responsibility for executive management of the largest alliance of independent insurance agencies in the United States and its related companies, providing leadership to senior executives of SIAA and Master Agencies across the country.