The Prison Every Entrepreneur Builds (And How to Escape It)

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Most men start a business to buy their freedom.

But what they don’t realize is that they’re usually building their own prison. This week on the podcast, I spoke with Richard Walsh—former U.S. Marine, champion boxer, author, and entrepreneur.

A man who did everything right… until everything went wrong.

In 2008, he lost it all.

Home. Income. A business he’d spent years building. And to make it even worse—he had six small kids under the age of four. No backup plan. No savings. No clue what came next. But instead of collapsing, Richard did something most men never do:

He took responsibility.

He analyzed his failure. He identified the traps. And then he rebuilt smarter. Not just for himself—but for others who were silently suffering the same fate.

He calls it “The Owner Prison.”

It’s that invisible cage entrepreneurs build for themselves while chasing the very freedom they think they’re creating.

And brother, I’ve been there too.

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Here’s what Richard taught me (and what I wish someone had told me 10 years ago):

1. Your Business Is Not Your Identity

The last point is the big one.

It sounds noble—“my“ company is an extension of me”. But it’s not noble. It’s dangerous. Because when your identity is fused with your business, you can’t let go. You don’t delegate. You micromanage. You obsess.

And the minute something goes wrong?

It’s not just a business failure—it feels like personal death. This was my story with my first startup. I thought I was the company. And when it collapsed, so did I.

Richard said it best: “Your business isn’t an extension of you. It’s a mistress. It will seduce you, pull you away from your family, and demand more from you—always more.”

Let that one sink in.

Watch the full podcast:

2. You’re Not Special—Let Go of Control

Richard told me something I would rather not hear:

But most of us never do. We convince ourselves we’re the only ones who can do it right. So we stay stuck in the daily grind. Never growing. Never scaling. Never truly free. That was me for 13 years in my first company.

And when I finally let go?

The person I trusted most scammed me. Lesson learned:

Don’t just delegate—build systems that make delegation bulletproof.

3. Systems = Freedom

If your business can’t run without you, it’s not a business—it’s a job. And the worst part. It’s a job you can’t quit.

Richard explained that every owner should be working on the 5% only they can do:

• Vision

• Growth

• High-level partnerships

Everything else should be documented, delegated, and systemized. And this is precisely what I’m building now with my ghostwriting & consulting agency.

Light, scalable, system-first.

No employees. Lean processes. Bulletproof delegation. And no more ego-driven chaos.

So what’s the real takeaway? Rock bottom is a gift—if you survive it. Both Richard and I hit it. Both of us got back up.

And both of us know now: “Freedom isn’t what you build—it’s what you protect.”

You don’t need a million-dollar exit. You need a business that runs without you. You need people in your corner. You need systems that keep the wheels turning while you sleep. You need space to live, love, and be present with the people who matter.

That’s wealth. That’s freedom.

No matter where you are right now—heading into a crisis, stuck in one, or just clawing your way out—you’re not alone.

You’re not broken. And you’re not done. Keep showing up.

Keep moving forward.

And never, ever let your business become your identity.

Until next week,

Roman

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