October 13, 2024
They say you should prepare for the worst and hope for the best.
I failed at it last week.
I prepared for absolute chaos and was expecting the apocalypse.
Let me tell you why.
Hurricane Milton was looming, and it was supposed to be the biggest, nastiest storm Florida had ever seen.
With four properties in Florida’s southwest, valued at approximately $10M, I was on edge.
Two self-storage facilities in Fort Myers and Naples, one in Lehigh Acres, and a small-bay industrial property in Fort Myers.
Just dodging the aftermath of Hurricane Helen, I wasn’t feeling lucky.
Helen had only cost us $500 in minor roof damages.
The Fear Sets In
On Monday, my partner Shea called me and said, “Hey, there’s another storm developing”
My gut twisted.
Every forecast showed the storm zeroing in on Fort Myers.
My first thought: This is it.
I started running numbers in my head, looking at the insurance deductibles—5%, 10%—and figuring out that we would be out anywhere from $500K to $1M.
I was going in circles.
Also, my mom lives in Naples.
I called her that same night and told her to pack her bags and head to Miami.
By 6 a.m. Tuesday, she was on her way, safe and sound.
But me?
I was still wrestling with the disaster that was brewing in my mind.
Panic on the Rise
By Tuesday, it was official—Milton had upgraded to a Category 5, and every news outlet was screaming about the “catastrophic damage” it would bring.
The monster in my head went full throttle.
I wasn’t just thinking about roof damage anymore. I started picturing everything being wiped out.
The buildings would be gone.
Insurance companies wouldn’t pay.
Banks wouldn’t refinance loans.
Tenants would leave.
We’d be stuck with debt and investors’ capital, with no real estate to back it up.
The idea spiraled so far that I actually started rationalizing a post-disaster plan.
We’ll raise a fund, buy the wreckage at pennies on the dollar, and wait for the market to bounce back.
It’s a terrible plan, but what choice would we have?
Wednesday morning, I woke up to the mayor of Fort Myers saying, “If you don’t leave now, you will die.”
My stress levels were off the charts. I was ready to brace for the worst.
Shea and I prepped a plan: we’d bring in crews from Chicago, get my truck and trailer loaded up, and be ready to head down and clean up the carnage.
Shea was lucky to find a contractor.
He braced the garage doors on the industrial property.
We expected them to blow off like they did in Hurricane Ian.
At this point, I wasn’t fun to be around.
Honestly, I was miserable.
The Turnaround
By Wednesday afternoon, something changed.
The models shifted.
Milton was headed north. The forecasts showed lower wind speeds for Fort Myers—about 60 mph.
After Hurricane Helen, which hit us at 70 mph, I realized we might actually be okay.
The cameras at our Fort Myers properties went down around 7 p.m. on Wednesday.
I spent the night wondering if we passed the storm OK.
But Thursday morning, the first tweet I saw was from a guy in Tampa Bay who had stayed in his boat through the storm.
He was smiling, the bay was fine, and I knew—we were fine too.
By Thursday, we had inspected all the properties.
The damage?
One single branch had fallen at Lehigh Acres.
No roof damage, no floods, no catastrophe.
What I Learned from My 72 Hours of Fear
Here’s what I learned.
- We Suffer More in Imagination Than in Reality, that’s what Seneca said. My fear monster had a field day. I spent days drowning in worst-case scenarios, and yet, none of them came true.
- Managing a Distant Portfolio Is a Nightmare. This experience was a breaking point. We had already planned on selling our Florida properties, but Hurricane Milton sealed the deal. It’s too hard to manage properties from a distance, especially in hurricane-prone areas. We’ll only buy in regions where at least one partner is local.
- Define Your Fears, Don’t Let Them Define You. Tim Ferriss’ video, is spot on for these situations.
Hurricane Milton didn’t turn out to be the disaster I feared.
But for 72 hours, it sure felt like the end of the world.
Next time, I’ll be preparing for the worst—but for sure I’ll give the utmost weight to hoping for the best.
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Be Well,