Canceled by my Underwriter

My Entrepreneurial Journey - Part II

My Journey Derailed

After my family fired me, I launched into entrepreneurship. Fast forward 15 years, I had a successful business, held board seats in industry groups and felt I was at the top of my game.? Life was going well until one day, with one phone call, it all fell apart.???

My business was a niche market insurance agency, and I was an agent. Many of you know what business I’m talking about, but for those who do not, I wrote title insurance for aircraft. The name of my agency was Aircraft Title Insurance Agency. Creative, I know.?

Our structure was like other insurance agencies. Think of State Farm, for example. State Farm acts as the underwriter who carries the risk and pays out on the policies (hopefully). Still, they have insurance agents around the country who issue policies to clients on the underwriter’s behalf. Our business was comparable, except we were writing title insurance instead of liability insurance. It was like real estate title insurance.??

Unfortunately, the fateful day came when my underwriter called and said they were getting out of the business. They no longer wanted to write title insurance policies for aircraft.???

And just like that, the company I’d worked so hard building became a shell of itself with nothing left to offer. It felt like my world was falling apart. I remember lying on my bedroom floor crying, wondering what was happening and what I was going to do next. Unlike the time my family fired me, I couldn’t just reopen my doors with a new name and offer the same great service. Without an underwriter, I couldn’t issue title insurance at all. However, instead of accepting defeat, I set out on a quest to save the business and product I loved.??

First, I tried to find a new underwriter to pick up the product. On that road, I learned a lot about the world of underwriting and discovered that, by law, only title insurance companies can issue title insurance policies. That ruled out a large segment of the insurance underwriter market leaving only a few viable options to pursue. I spent some time with a local underwriter, explored international underwriting options and did everything I could to find someone to pick up the product. But in the end, nothing seemed to work.???

Not to be deterred, I took the next logical step and set out to create my own underwriting insurance company. Harkening back to my MBA days, I freshened up my skills and wrote a full business plan for a title insurance company. But the stakes were a lot higher this time around. Writing a business plan in grad school for a grade is one thing; when?your entire future is on the line, it's an entirely another. This business plan became the basis for finding investors to launch my company. Just like Shark Tank, it was a harrowing experience, full of highs and lows, hope and rejection. But I learned, grew and kept plugging along, refusing to give up without a fight.?

One day, I was sitting on my back patio reflecting on all that was happening, and I had a vision of what life would be like if I found the investors I was seeking. I realized I would no longer be working for myself, but for people whose main focus would be on making a return on their investment. That’s not necessarily a bad thing, but it made me realize that the future I was trying to create would likely not look like the past I was trying to recreate. Still, I kept on fighting.???

Investment opportunities tend to run on momentum. I had a lot of support from the industry when the news first broke, but as the year wore on, excitement began to wane. I remember vividly in December 2014, I felt the momentum shift. And die. It was the Christmas season, and I was sitting at my parents’ house in their wingback chair enjoying the fire and reflecting on all that had happened over the last year. I thought about the last group of potential investors we were talking to, and I just knew they had decided not to invest. At that point, after stubbornly refusing to accept defeat for more than a year, I finally decided it was time to give up and move on.??

I don’t blame my underwriters or anyone else for what happened here. This was a business decision based purely on financial analysis. At the end of the day, title insurance for aircraft was too much of a niche market to be financially attractive to investors or underwriters.???

Because I could no longer issue title insurance for aircraft, I would have to branch out into a different line of work and rebrand myself entirely. This process came with its own challenges and experiences that I will discuss in my next post.???

What about you? When, where and how has your entrepreneurial journey been derailed? I know COVID-19 interrupted many small businesses’ plans. If you are one of those, my heart goes out to you.???

No matter what your story is please share it below. I’d love to hear it.???