INSURANCE STORIES
-
The $100,000 Clerical Error
HOW “SET IT AND FORGET IT” INSURANCE CAN KILL YOUR BUSINESS A few weeks ago, my phone rang on a mid-Friday afternoon. A mutual friend connected me with a business owner who faced a sudden, terrifying crisis. This owner runs a successful moving company. They have nearly two dozen employees and a fleet of box…
-
The Axe and the Algorithm: Why Insurance Still Needs a Soul
I spent yesterday morning staring at two monitors in my home office, dissecting the fine print of some insurance requirements for a job. My client, an IT managed services firm, was heading into a project at a property in Texas. They sent me two documents—the insurance requirements, and a vendor endorsement form from the property…
-
The High Seas of a Water Damage Claim
This is a story about the day my four-year-old son accidentally flooded our house. But more than that, it’s a story about the moments when your own competence hits a ceiling—and who you know matters just as much as what you know. The Sound of Rushing Water It was an evening in the fall. My…
-
The 550-Day Lesson
Why Your Estate Plan is Only as Good as Your Last Beneficiary Audit In November 2021, my father passed away overseas. He did everything meticulously, in preparing us for this day. He had a Family Trust. He had a detailed Will. He had spent two decades walking my sister and me through his strategy so…
-
The $50,000 “Joust”
Why Your Agent Needs the Courage to Be Disliked It was a Friday afternoon, the “quiet hours” at one of the most popular high-end Italian steakhouses in the city. We were in the bar area—leather sofas, velvet chairs, the smell of kitchen prep beginning to drift through the room. I stood at a high-top table…