The 2 Biggest Regrets of My 20-Year Entrepreneur Journey (So Far)

Let me tell you something real.

After 20 years in business… after building multiple 7-figure companies… after helping thousands of healthcare professionals create freedom and wealth…

I still carry two big regrets.

And no, it’s not the typical “I should’ve started sooner” or “I should’ve worked harder.” It’s deeper than that.

I’m sharing these with you not because I need therapy (though hey, we all do). I’m sharing them because maybe — just maybe — you’re sitting on the same opportunities right now. And I’d hate for you to wake up in 5 or 10 years feeling what I felt this week.

REGRET #1: The Billion-Dollar Idea I Never Executed

In 2007, my business partner Mike and I created a circuit-based workout concept called CIRKIT. It was functional fitness. It was short, high-intensity. It was scalable. We planned to ship people equipment — bands, weights, mats — and deliver the workouts online or in-studio.

Sound familiar?

Yeah… it was F45 before F45.

And guess what?

We never launched it.

We talked about it. Dreamed about it. Sketched it out on napkins. Hyped it up.

But we didn’t execute.

Now, every time I walk into an F45 — and I go there often because I actually love their workouts — I’m hit with this gut-punch reminder that we had it first… but they had the balls to build it.

And I can’t blame them. The truth is, ideas don’t win — execution does.

The next billion-dollar idea might be in your notes app right now. Or sitting in your head while you’re too busy trading time for money, second-guessing yourself, waiting for the perfect conditions that never come.

Let me say this as plainly as I can:

Your idea doesn’t need to be perfect. It needs to be DONE.

Go do it.

REGRET #2: Renting When I Should’ve Ownedits

Here’s the other one. This one still stings.

I had three clinics. Two of them were leased. I paid one landlord over $1.4 million in rent over nearly two decades.

Then last year — boom. He sold the building. New owner. And in 30 days, I was out. Gone. Just like that.

And it happened again with another clinic six months later.

Two locations, gone.

All because I didn’t own the building.

And the worst part? Back in 2006, he offered to sell it to me for $580,000.

I said no.

I didn’t have the confidence. I didn’t think I had the resources. I didn’t think I was “ready.”

Now? That building is worth millions. And I walked away with nothing.

Let me tell you something that hurts more than making a mistake: realizing you had the chance to win, and you passed on it.

So now, I don’t rent anymore. I own. I bought into a commercial property with a dermatologist as the tenant. I’m the landlord now.

That mistake taught me something simple:

“If you don’t own it, you don’t control it.”

Same with your clinic. Same with your time. Same with your income streams.

Here’s What Both Regrets Have in Common

Looking back, both mistakes — not launching CIRKIT and not buying that building — came from the same thing:

Fear.

Fear of failure. Fear of messing up. Fear of looking stupid. Fear of losing money.

But here’s what I’ve learned: you will either pay the price of discipline now… or the price of regret later.

There’s no escaping the bill.

The “safe” route isn’t safe. It’s just quieter regret.

The loud kind shows up in your chest when you walk into an F45 that should’ve been yours… or when you write your final rent check on a building you could’ve owned for half what you paid in lease.

So what do I do now?

I go.

If I believe in something, I move on it.

This year, I launched a brand new business that’s already doing $85,000+ in revenue — in less than 8 months. Because I didn’t wait. I didn’t overthink. I trusted myself. I trusted the process. I trusted God.

And it worked.

And if it hadn’t? I would’ve learned something valuable. Either way, I win.

If You’re Reading This, Maybe It’s Your Turn

If you’re a PT, OT, dietitian, whatever… and you’ve been sitting on that idea…

Or you’re in a clinic where you pay rent, but you feel like you don’t really own anything...

Then this is your warning — and your invitation.

Don’t wait. Don’t overthink. Don’t let fear write your story.

“Execute on the idea, even if it’s imperfect.”

“Buy equity in your life, not just hours on the calendar.”

You’ve been called to something bigger. Don’t silence that voice.

Let my regrets be your reminder.

Want Help Taking Action?

If this hit you in the gut… good. You’re supposed to feel something. That means you’ve still got something to build.

I’ve built a free community for healthcare entrepreneurs who want help turning ideas into income, and hours into ownership.

If that’s you — come join us.

👉 https://www.facebook.com/groups/thesuccesscommunity

Talk soon,
Greg Todd
Much Love

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