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 with the owner, a man who considered me part of his inner circle.
He’s a quintessential “Alpha”—blunt, assertive, a lover of luxury goods and straight talk. We were looking over a one-page insurance proposal.
I pointed to a specific line item: Spoilage Coverage.
He pushed back immediately. He didn’t see the point. He saw an extra premium; I saw $50,000 of prime-cut Kobe beef sitting in a display fridge that could turn into a total loss during a single winter power outage.
The “Inner Circle” Paradox
When you’re an advisor to high-performance people, there is a temptation to “keep the peace.” You’ve shared drinks, attended events together, and talked shop for years. You don’t want to be the “insurance guy” nag.
But in that moment, standing face-to-face, I felt a surge of excitement.
I knew his personality—an Enneagram 8 who respects competence over compliance. I “interrupted his interruption” and told him directly: “You need this!!!”
The Hidden Cost of “No”
To a business owner, a $50k loss is a hit to the balance sheet. But the real cost of a spoilage event is the “Curse of Knowledge” that most owners ignore until it’s too late:
- The Reputation Hit: If you can’t serve your signature steaks on a Saturday night, word spreads.
- The Operational Chaos: Reservations drop by double digits, instantly. Staff lose shifts. The “experience” you’ve built your brand on evaporates while you’re cleaning up the mess.
- The Blame Game: If that freezer fails and there’s no coverage, the owner won’t blame his own frugality. He’ll blame his agent for not standing his ground.
Skin in the Game
I didn’t push for that coverage just to check a box. I did it because I have Skin in the Game.
As an independent, commission-only agent, my only real currency is my reputation and the trust of my clients. If I see a gap in your coverage and I don’t force you to see it, I’m not doing my job. I’d rather have a “joust” with a client today than a funeral for a business relationship tomorrow.
Clients are right to be suspicious of coverages they don’t understand. But an agent who thinks holistically about your risks has the right to push back.
If I see a gap, I’m going to tell you—and I’m going to make sure you understand why it matters.
If you think you might have a gap or two… it might be worth a chat. You can book here.