Don’t Be an Entrepreneur If You Can’t Handle This…

Good morning.

I’m standing in Indian Rocks Beach. Sun’s out. My son’s in line grabbing breakfast.

And I’m staring at a house.

Not just any house.

A house that was completely destroyed less than a year ago.

Flooded.
Gutted.
Ruined.

Let me tell you why that matters.

The House That Got Wiped Out

In 2023, one of my clients rented that exact house for her first live event.

Nothing crazy. About 18 people.

She paid around $7,000–$8,000 for six days. At the time, that house was renting for roughly $800 a night.

Prime location.
Great vibe.
Beautiful setup.

That event became the launchpad for what is now a wildly successful program in her business.

But then…

September 27th, 2024.

The storm came.

That house? Destroyed.

Water damage everywhere. Completely gutted. It sat vacant for nearly a year.

And here’s what most people don’t see:

Someone bought it.
Someone rebuilt it.
Someone poured hundreds of thousands of dollars into it.
Someone dealt with permits, red tape, contractors, delays.

Someone took a massive financial risk.

And today?

It’s back on the rental market.

That’s entrepreneurship.

The Part Nobody Talks About

Everyone loves the “own a business” part.

Everyone loves the “freedom” part.
The “be your own boss” part.
The “work from anywhere” part.

But let’s define entrepreneur correctly:

An entrepreneur is someone who owns and operates a business and is willing to do so at high financial risk.

You don’t get to pick two out of three.

You don’t get:

• Ownership

• Operation

• But no risk

That’s not how this works.

And I think this is where a lot of people fool themselves.

They want control.

They want upside.

But they don’t want volatility.

Let Me Make This Personal

Last year, my family and I moved out of our house and decided to turn it into a short-term rental.

Sounds cool, right?

“Asset.”
“Passive income.”
“Smart move.”

Yeah… okay.

Let me tell you what actually happened.

To convert that house into a legitimate short-term rental in this area, I had to put about $50,000 into it.

Furniture.
Upgrades.
Safety compliance.
Permits.
Locks.
Liability considerations.
All of it.

The house was ready by mid-to-late July.

And then…

July? No renters.
August? No renters.
September? No renters.

You know what I did get every single month?

Bills.

$3,000.
$4,000.
$5,000.

Something breaks.
Something needs upgrading.
Something is a “liability.”
Something needs replacing.

Money bleeding out.

Month after month.

No applause.
No Instagram highlight.
No “look at this passive income.”

Just pressure.

And frustration.

But here’s the key:

I wasn’t behaving like someone who “owns a property.”

I was behaving like an entrepreneur.

High risk.
Uncertain timeline.
Delayed gratification.

Fast forward to today.

From January 1st through the end of May?

86% occupancy.

Now it’s working.

Now it’s profitable.

Now it looks smart.

But most people would have bailed in month three.

Can You Stomach It?

Here’s the real question:

Could you handle losing money for five straight months?

Could you handle pouring $50K into something that gives you nothing back for a season?

Could you sleep at night knowing it might not work?

If the answer is no — that’s not a character flaw.

It just means you might not be wired for entrepreneurship.

And that’s okay.

There’s another option.

Entrepreneur vs. Intrapreneur

An intrapreneur:

• Takes ownership.

• Operates at a high level.

• But doesn’t carry high financial risk.

They thrive inside an organization.
They build.
They lead.
They create value.

But they don’t bet the house.

An entrepreneur?

We bet.

Not recklessly.
Not stupidly.
But willingly.

Because we understand something most people don’t:

Volatility is the price of upside.

You don’t get the reward without the swings.

Self-Awareness Is Power

I believe every one of you can own something.

I believe every one of you can operate something.

But not everyone can handle the emotional and financial swings that come with high risk.

And that’s not weakness.

It’s self-awareness.

The danger is pretending you’re built for something you’re not.

The danger is saying “I want the freedom” but panicking when the first five months don’t pay you.

Entrepreneurship is a game.

I like playing it.

I’ve built myself into someone who can handle the volatility.

But that took years.

So before you say you want to “start a business” or “build passive income” or “escape the grind”…

Ask yourself:

Am I willing to handle the part nobody posts about?

Because if you’re not…

Don’t be an entrepreneur.

But if you are?

Then welcome to the game.

—

If this hit you in the gut a little, good.

That means you’re thinking.

And thinking is the first step before you ever place a bet.

Much Love,
Greg

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