The Rountree Agency

06/15/2026

🎙️ I Worked For The Insurance Company Before I Opened My Agency...

One of the questions Chuck Claypool asked me on the Brokers Hot Seat Podcast was what makes The Rountree Agency different from other agencies.

The answer is simple.

I've spent 17 years sitting in almost every seat in the insurance industry.

I started in personal lines.
I sold life insurance.
I worked on the corporate side.
I worked for an insurance carrier.
Then I opened my own brokerage.

Working for a carrier gave me a unique opportunity to see how underwriting decisions are really made, what carriers look for, and where business owners often get blindsided when a claim occurs.

That's why we built The Rountree Agency differently.

We don't try to be everything to everyone.

Instead, we've focused on industries we know extremely well:

🚛 Contractors & Fleets
🍽️ Restaurants
🏋️ Fitness Facilities
⚒️ Service Businesses

Because insurance isn't about finding the cheapest premium.

It's about understanding your risk before a claim forces you to.

Check out this clip from my conversation on Brokers Hot Seat Podcast and let me know your thoughts.

https://youtu.be/F9FJHR2kRAI?t=38&si=x2ydjTEVZFeqt85T

06/15/2026

NEW PODCAST EPISODE

I recently had the opportunity to join Chuck Claypool on the Brokers Hot Seat Podcast to talk about something every business owner needs to hear...

👉 Insurance is NOT about finding the cheapest premium.

The biggest risks in your insurance program are usually hidden in the exclusions, limitations, and gaps you don't discover until a claim happens.

In this episode we discuss:

✅ Why I left the carrier side of the industry to build my own brokerage
✅ How niche insurance programs create better outcomes for clients
✅ Why "cheap insurance" can become the most expensive decision you make
✅ Captive insurance programs and how they work
✅ Building businesses, teams, and systems using AI and technology
✅ The lessons learned from starting over and building The Rountree Agency

We also dive into my passion for helping business owners understand risk before it becomes a problem.

If you're a contractor, restaurant owner, gym owner, fleet operator, or business owner who depends on insurance to protect everything you've built, this episode is for you.

🎙 Watch the full episode:
https://youtu.be/F9FJHR2kRAI?si=kBS65QsqGmt0qKeE

A big thank you to Chuck Claypool and the Brokers Hot Seat Podcast for the invitation.

Remember...

You can pay for risk management now...
or pay for mistakes later.

www.ACA22.com
www.CoachTreeChalkTalk.com

06/14/2026

We are here to help put your hardearned back in your wallet.

Go buy cool stuff for your business, pay your staff or your self a bonus...JUST DO NOT GIVE IT TO THE INSURANCE CARRIERS!!!

Not even for 1 more day! We dont care when you renewed, we can get you out od the stinky policy and smelling like roses by the end of the day!

WWW.ACA22.COM

BUILT FOR THE BUSINESSES THAT BUILD AMERICA!

Watch this video on HeyGen

06/13/2026

Thats rad!

06/13/2026

Can't wait!

🚨 MONDAY MORNING 🚨

I got put in the hot seat...

This Monday at 9:00 AM, my episode of the Brokers Hot Seat Podcast goes live, and we tackle one of the biggest mistakes business owners make when buying insurance.

Here's a hint...

The most expensive insurance policy isn't always the one with the highest premium.

In fact, some of the cheapest policies can cost a business hundreds of thousands of dollars when a claim exposes a coverage gap.

We also dive into:

🔥 Why I left the carrier side of the insurance industry
🔥 How niche insurance programs create better outcomes
🔥 The truth about captives and alternative risk programs
🔥 Building a business from scratch
🔥 Using AI and technology to scale operations
🔥 Why business owners need a risk advisor, not just an insurance agent

If you're a contractor, restaurant owner, gym owner, fleet operator, or business owner, you're going to want to catch this one.

Set your reminder for Monday at 9:00 AM.

Trust me... we didn't hold anything back.

06/13/2026

🚨 MONDAY MORNING 🚨

I got put in the hot seat...

This Monday at 9:00 AM, my episode of the Brokers Hot Seat Podcast goes live, and we tackle one of the biggest mistakes business owners make when buying insurance.

Here's a hint...

The most expensive insurance policy isn't always the one with the highest premium.

In fact, some of the cheapest policies can cost a business hundreds of thousands of dollars when a claim exposes a coverage gap.

We also dive into:

🔥 Why I left the carrier side of the insurance industry
🔥 How niche insurance programs create better outcomes
🔥 The truth about captives and alternative risk programs
🔥 Building a business from scratch
🔥 Using AI and technology to scale operations
🔥 Why business owners need a risk advisor, not just an insurance agent

If you're a contractor, restaurant owner, gym owner, fleet operator, or business owner, you're going to want to catch this one.

Set your reminder for Monday at 9:00 AM.

Trust me... we didn't hold anything back.

06/05/2026

Crowd favorite...coming baxk at you!

Workplace safety is no joke!

One wrong move and someone's life and your business can change in an instant.

We dont just write WC policies! We help you build a wall of protection for you and your employees.

Preventing the injury from even happening is where our focus is.

Give us a call at 904-539-4637 for a complimentary onsite risk review.

Let our experts see if there may be any possible ticking time bombs hidden in your safety manuals, light duty or return to work programs.

05/28/2026

BIG ANNOUNCEMENT

This morning, Coach Tree will be LIVE on WSOS 103.9 at 10:00am for a 30-minute interview talking all things:

🔥 American Commercial Auto Insurance
🔥 Coach Tree’s Chalk Talk (CTCT)
🔥 Small business owners
🔥 Contractors & truck people
🔥 The broken insurance industry
🔥 Building a brand built for the people who build America

We’re talking trucks, business, blue-collar culture, and why we’re shaking up one of the most boring industries out there.

If you’re a contractor, service business owner, fleet owner, or somebody grinding every day to build something for your family… this one’s for you.

Tune in to WSOS 103.9 FM Radio - St Augustine and come hang out with Coach Tree.

05/25/2026

Today we remember.

Memorial Day is not just about cookouts, long weekends, and the start of summer.

It’s about the men and women who gave everything for this country 🇺🇸

A reminder from American Commercial Auto Insurance:

Under the U.S. Flag Code, the American flag should fly at half-staff from sunrise until noon on Memorial Day… then be raised to full staff for the remainder of the day.

That transition matters.

The flag at half-staff honors those we lost.

The raising of the flag at noon is a reminder that we carry on because of their sacrifice.

Today we honor the fallen, their families, and the freedoms their sacrifice protects.

From all of us at American Commercial Auto Insurance…

Thank you to those who gave everything for America. 🇺🇸

05/22/2026

Best in the biz!

Thank you to one of our May sponsors. CritterPro The Wildlife Removal Professionals. The #1 Rated Wildlife Removal Company Serving North and Central Florida

https://www.critterpro.com/