My Tesla FSD Experience as an Insurance Agency Owner & Claims Exec

My Honest (and Slightly Life‑Changing) Tesla Experience: An Insurance Guy’s Take

If you’ve spent more than 10 minutes around me lately, you’ve probably heard me talk about my Tesla. And listen, I get it. Nobody likes that guy who won’t shut up about his electric car, his CrossFit gym, or his air fryer. But here we are. And because I’m not just a Tesla owner, but also an insurance agency owner and a senior executive at an insurance claims company, my obsession comes with a slightly different twist.

So I promise this is different.

This is the story of how a guy who absolutely hates driving ended up falling head‑over‑heels for a car that basically drives itself and what that means for the future of insurance, auto claims, and maybe even humanity. (Okay, humanity might be a stretch. But still.)

The Tesla Origin Story (AKA: How the Waymo Robotaxis Turned Me Into a Believer)

To fully understand why I bought a Tesla, you need the real story; the Arizona Waymo Week of 2025.

My family and I were vacationing in Arizona, and I noticed these fully autonomous Waymo robotaxis cruising around like they owned the streets. No drivers. No stress. Just AI confidently flexing on humanity.

Naturally, I wanted to try one.
And that’s when the magic happened.

My Famous $15 Parking Moment

One night we drove to a restaurant in Scottsdale, and the parking lot was full. The only option? Paying $15 to park in a spot that should’ve cost $0.02 based on the size of my rental car.

As I pulled in, I noticed Waymo after Waymo picking people up.

So after dinner I checked the app just to see the cost.

My jaw dropped.
The roundtrip Waymo would’ve been cheaper than the $15 parking fee and that included tip.

At that moment, I said out loud:
“I am officially done driving.”

From that point forward, I took around 20 Waymo rides in one week. Grocery store? Waymo. Dinner? Waymo. Quick coffee run? Waymo. Random urge to test AI’s risk tolerance at left turn signals? Waymo.

By the end of the trip, I realized two things:

1. I never wanted to manually drive again, and
2. If Waymo could do this, Tesla had to be close.

Fast forward to September 2025… enter my 2026 Tesla Model S.

The Best Car Buying Experience of My Life

Tesla’s buying process is basically the Chick‑fil‑A of car sales — shockingly smooth, friendly, and slightly too easy.

No sleazy sales tactics.
No finance manager ambush.
No “today only!” fear mongering.

Just:

• A test drive
• A quick FSD demo
• A calm “buy now or buy later”

Two days later, I purchased it online from my couch on a Sunday and picked it up Monday. At the delivery center, I signed one piece of paper (thank you Illinois plate registration) and that was it.

Easiest vehicle purchase I’ve ever made.

Driving Experience: When Software Becomes the Driver

My Tesla arrived with FSD v13.7 — already impressive. I used it 65–75% of the time.

Then November came.

Then FSD v14.2 dropped.

Then they added Mad Max Mode, and that’s when I started telling people, “This car might be smarter than I am.”

Since that update, Tesla now tracks my FSD usage and I'm at 84%.
That's not a typo.
I drive… about 16% of the time.

The Legendary 6.5‑Hour Missouri Drive

I tested its limits on a trip with my daughter to the University of Missouri.

What should have been a slightly exhausting six‑hour highway trek turned into:

• Me relaxing
• Podcasts playing
• Snacks being eaten
• Zero stress
• FSD doing 95% of the work

Superchargers were easy; park, plug in, pee, snacks, done.
It took maybe an hour longer than a gas car, but it felt like I was chauffeured the whole way.

I’d take that trade any day.

Insurance Claims Executive Perspective: A Collision‑Reducing Reality

With 4,000+ miles under my belt, let me be clear:

Tesla FSD could legitimately reduce at‑fault accidents at scale.

The car reacts faster than humans.
It doesn’t get distracted.
It doesn’t get emotional.
It won’t speed up just because someone cut it off at the merge point.

I’ve yet to experience a single scenario where I felt FSD would cause an accident.

If I were running an insurance carrier (again: I’m not, but play along), I’d seriously consider:

Discounted auto physical damage rates for drivers who can prove 80%+ FSD usage.

Liability still matters because humans will always be humans.
Comprehensive coverage still matters because weather doesn't care about your feelings.

But collision?
FSD changes the game.

Insurance Agency Owner Perspective: The Coming Shift

As the owner of Pro Insurance Group, I can see a future — distant, but real — where:

• Collision claims drop significantly
• Auto physical damage policies shrink
• FSD reduces overall accident volume
• Coverage starts shifting toward liability + comprehensive

This could reshape traditional personal auto insurance.

And yes, that could reduce the size of the auto insurance book.

But we are a long way from this becoming normal:

• Not enough Teslas
• Not enough FSD adoption
• Other automakers are behind
• Most people still like holding the wheel (for reasons I personally cannot understand)

Still: the writing is on the wall.
And it's fascinating.

Final Thoughts (Unfiltered)

In less than six months, my Tesla has transformed how I think about vehicles, safety, insurance, and road travel in general.

Unless someone catches up to Tesla’s FSD — and nobody’s close — I don’t see myself driving anything else.

As for the Cybertruck?

If you love yours, I’m happy for you…
But I can’t personally justify driving something that looks like a stainless‑steel toaster dressed as a tank for Halloween.

If Tesla ever releases an FSD update that also handles grocery shopping, teenage debates, and morning chaos, I’ll happily sign a lifetime beta‑tester contract.