Who doesn’t have a tale of woe, frustration or sometimes triumph when it comes to the insurance industry
Published in the San Diego Union-Tribune, March 30, 2026
by Neil Senturia
Sometimes you just have to sit back and give entrepreneurship a break. Here are two true stories. Make of them what you will.
I own a sailboat. A new sail was stolen off the boat. I know that sounds nuts, but just stay with me. OK, we have insurance. I call the insurance company, the woman takes my report and tells me that an adjuster will call soon to explain the next steps. I remind her that I have been a customer for more than 20 years.
The adjuster calls. “Your policy has two features, one is a deductible of $1,904 (I did not ask how they arrived at that number), and your policy also has a depreciation of 80% on any sails.”
I said that the jib was new and cost $8,000.
“Yes, I see that, we have a copy of your invoice. But we can only give you 20% of $8,000, which is $1,600.”
I said, yeah, but my deductible is $1,904, so effectively you are going to give me nothing.
He answers: “I believe your math is correct.”
I suggested to him in a calm, soft, polite voice that I was considering burning his building down, taking out a full-page ad in The New York Times about the company and of course canceling my insurance. But, as a first step, may I speak to a supervisor?
A day later, a supervisor calls and says they have reviewed all the various fine print and she would be delighted to waive the 80% depreciation and is there anything else I can do for you? Ask yourself, how can you not love America?
Now I am telling this story, not because it is unique but because it is ubiquitous, and I am asking all my readers to send in their favorite insurance story. Go ahead, make my day.
But as the famous pitchman, Ron Popeil, says, “but wait, there’s more.”
I have a comptroller (fancy name for an accountant). He tells me this story. He has parked his car in the same place for 15 years, in front of his office, right up to the red curb, but never into the red. Never. A week ago, he parks as usual and goes about his usual business, goes to the bank and then at noon comes back to his car, only to find flashing lights and two police cars. He is about to get a ticket. For what? For parking in a red zone. Huh?
The police officer says that the fire department had alerted them about this fire hazard, and sure enough my accountant looks down, and his car is half in the red zone. How can that be? He calls the city, finds the division called “painting red curbs,” and asks if they had recently painted that particular street.
Yup, they painted it that morning — while he was in the bank. You cannot make this stuff up. The ticket was $65, and my friend decides that he will not fight it, and even more to the point, he is framing the ticket to hang on his wall.
Once again, faithful readers, let me have it. Go big. In this world, at this time, a little insanity can go a long way.
Now, finally back to our regular programming.
A thought about raising money. While my personal nature in that area is more of the high-level, 10,000-foot circus barker, big picture, don’t sweat the nickels, let the sunshine in — that model will not cut it today. If you need to cross the infamous “valley of death,” then rigor and substance are the requirements.
Our little AI company has just completed a proctology exam in anticipation of receiving some significant funding. It was indeed a cleansing experience, and while much has been written about the value of regular colonoscopies for your personal health, I must confess that it is also good for your company.
A rigorous, highly buttoned-up deck and data room are going to be more successful in this funding environment than the casual, arm-waving set of statements and claims that have little or no concrete data to support them.
“Looking good, Billy Ray. Feeling good, Louis.”
The days of the back of a napkin are over. You can use it to wipe your chin or ….
Rule No. 823: Life is better when you’re laughing.