When I started my agency back in 2006, I went all in. I took the 10% hit on my 401K and cashed it out. 

My family went from a comfortable 6-figure salary to a very low 5-figure income overnight. I had a big mortgage, four young children, an ageing car, and no savings. Thankfully, I had an amazing wife who never wavered in her support for me (though she had every reason to), so we forged ahead.

My plan (if you want to call it a plan) was simple: Work my tail off to learn as much as I could as quickly as I could while getting as much business as possible in the shortest amount of time possible. 

If I succeeded, we wouldn’t go broke. If I didn’t, well … you know.

But I was full of enthusiasm and believed this path could work as my exit strategy from the corporate life in which I had grown very comfortable. It’s not that this life was bad; it’s just that I couldn’t move. Not again. Not One. More. Time. And that was looking more likely by the day.

So, with this in mind imagine my reaction when an MGA told me directly, “You’re going to want to quit three times before you make it.” He didn’t smile when he said it and he didn’t follow up with any encouragement. To say that he had thrown ice water on my dream was putting it mildly. I filed it away as a bit of a joke, but I quickly realized what he was saying.

The first time I almost quit was during the horrific New England winter of 2011-2012. Snow piled up high and packed hard onto roofs 4 feet deep. Buildings started coming down everywhere in Hartford County CT, and my clients were no exception. My loss ratio soared at a time when my income was still dangerously low, and I spent that winter helping to move numerous complex claims forward towards a good resolution.

It was at this time, however, that I learned my first good lesson: These are the times when we as agents really make a difference. We visited every claim and worked hard to assure our clients they would be made whole. And the policies we had written performed exactly as we hoped they would, earning lifelong friendships and trust. As agents, we exist for times such as these.

The next time I wanted to quit was when I reached a revenue ceiling I just couldn’t climb over. I didn’t have enough revenue to support hiring a person, but I couldn’t continue to grow the agency unless I did. It seemed like checkmate. We were so close, but we couldn’t grow anymore.

It was at this point that I realized the second big lesson of my career as agency owner: an agency needs structure to grow, and unless the owner spends time creating that structure, there is a finite limit to how far it can go. Armed with this we started creating systems, workflows, SOP’s and tools that enabled me to confidently shift much of that work to staff while freeing me up to sell. It was a game changer.

The last time I wanted to quit was when everything shifted underneath me. We were experiencing success, but we had entered a hard market, and our carriers had become decidedly uncompetitive in several key industries we served. The phones were ringing off the hook about price increases, but our options were few. 

It was then that I learned the third key lesson in my career: Know who you are and who you serve. 

You see, as an agency, we never emphasized price. Ever. In fact, it was a key component of our client “filter” to screen out pure price buyers. So, armed with a clientele that valued and trusted us as an agency, we got to work. Coverages, deductibles, re-shopping where possible; everything was on the table, and we worked hard for every client, no matter how small. Our thought was that if our clients were going to be paying someone less money, we preferred them to pay us rather than another agency.

The result was astounding. Throughout that entire hard market, we rarely lost a client, and I estimate that our retention rate was still high 90’s. And not surprisingly, we started getting new referrals from those clients we had helped as they sent their friends to us.

It’s been many years since those days, but I look back fondly on them as some of the best times of my life. And although I wanted to quit 3 times, I’m so glad I didn’t. It ended up being the best life I could have imagined, and I wish I had done it 20 years earlier. In the end, when I decided to sell my agency, I left behind 1000 close friends, many of whom were with me back during that fateful winter and were still going strong thanks to the trust they placed in us.

Disclosure: No AI was used in the writing of this article.