Elliott Caldwell

Airbnb investing done for you 🏡

Top 25 largest Airbnb property management company in the country 📈

Tampa/St Pete🏝️

DM 'Turnkey' to find a cash flowing BnB

[Elliott Caldwell @ECaldwell30]

I stopped waiting for freedom and built it instead.

[Elliott Caldwell @ECaldwell30]

Leadership is a privilege.
People trust you with their effort, their time, their belief. Your job is to turn that trust into something bigger.

[Elliott Caldwell @ECaldwell30]

Most people want the lifestyle before they’ve earned the discipline. Flip that, and the lifestyle builds itself.

[Elliott Caldwell @ECaldwell30]

Great leaders don’t build followers. They build more leaders.

[Elliott Caldwell @ECaldwell30]

The hustle means nothing if you forget who you are hustling for.

Make time. Be present. That’s wealth.

[Elliott Caldwell @ECaldwell30]

The hard part isn’t starting. It’s staying consistent when no one claps.

[Elliott Caldwell @ECaldwell30]

New property going live soon 😍

Going to break records!

[Elliott Caldwell @ECaldwell30]

Forget the fancy car. True success is never missing a moment that matters.

[Elliott Caldwell @ECaldwell30]

The real flex? Booking a vacation without asking your boss. That’s financial freedom.

[Elliott Caldwell @ECaldwell30]

We've cracked the code.

April results for our property management business

48 new contracts
4.57 - average bedroom count
$117,242 - average Airdna Rentalizer

3 owners churned (All homes sold)

Looking forward to scale our sales team and before we know it be at 500 contracts in a month.

While continuing to drive the best operations and owner success in the business to keep owner churn at industry lows.

To the moon!

[Elliott Caldwell @ECaldwell30]

Average is overcrowded. The top is quiet—most people quit before they get there.

[Elliott Caldwell @ECaldwell30]

Today, team member #100 starts.

Two and a half years ago, we were just a property management company.
Now? We're a low 9-figure collective of 9 companies (and a rebrand is coming soon).

It’s underestimated how important EVERY single team member is.
When one fails, we all fail. When one slacks, we all slack.

I know it's cliché, but I’ll say it anyway:
We have the best team on the planet.
A-players across the board.
If you’re not an A-player, you simply won't make it here.

Here are 3 ways we've built a 100-person A-team:

1. Final Interview = Final Filter

I personally do a final interview with every new hire.
I ask one simple question: "What drives you?"
It’s not just about the answer — it’s about the emotion behind it.
I’ve had candidates tear up.
What we do isn't rocket science — it can be taught in 30 days.
But drive? That’s built deep inside you.
As Nick Saban says:
"Mediocre people don’t like high achievers, and high achievers don’t like mediocre people."
If you are mediocre, you simply won't make it here.

2. Relationships Come First

Especially with our leaders.
We know life outside of work is messy — family struggles, loss, trauma.
We spend more waking hours with our team than anyone else.
So we lead with friendship and empathy.
That creates loyalty, consistency, and a place people want to be.

3. We Focus Relentlessly on Low Turnover

Turnover is such a silent killer of companies.
So far in 2025, we haven’t lost a single team member.
How?
-We pay way above industry standard.
-We build a mission bigger than ourselves.
-We create infinite growth paths:
With 9 companies growing, C-suite opportunities open up constantly.
No ceilings. Only momentum.

We will be a 10-figure brand in less than 3 years.
And the only way to get there?
A+ hires at every single position.
Here's to the first 100. Here's to the next 1,000.

Go. Fight. Win. And Kick Ass.

[Elliott Caldwell @ECaldwell30]

The truth about success? It’s not thrilling. It’s boring work, relentless discipline, and silent sacrifices.

[Elliott Caldwell @ECaldwell30]

Everyone wants results. Few are willing to endure the repetition.

[Elliott Caldwell @ECaldwell30]

Show up so consistently that your results become undeniable.

[Elliott Caldwell @ECaldwell30]

People don’t burn out because they’re doing too much—they burn out doing things that don’t matter.

[Elliott Caldwell @ECaldwell30]

Most people aren’t lazy. They’re just addicted to comfort.

[Elliott Caldwell @ECaldwell30]

If you knew how close you were, you’d stop hesitating.

[Elliott Caldwell @ECaldwell30]

One year of insane focus can change your entire life.

[Elliott Caldwell @ECaldwell30]

Success doesn’t respond to hope. It responds to habits.