The CEO Endgame

In 2022 one of my companies grew byseven figures– without me.

June 07, 2023

Believe me, it’s been fun to watch this business flourish, but few people understand the depth and breadth of the painful lessons I have learned along the way.

Strap in, because I’ll share my story in a moment. First, let’s talk about you.

Entrepreneurs are born, not made

Entrepreneurship is not like becoming a pilot, where you can train and become one. You can no more train someone to become an entrepreneur than you can keep an entrepreneur from starting something new. You are so obsessed about building your own thing, you’re virtually unemployable.

Charting your own course, and turning ideas into substance is your default.

As an entrepreneur, you naturally seek freedom, not boundaries.

The problem is that most entrepreneurs build monsters, not machines. If you stop working, your business will fail. You are the business.

This is why most entrepreneurs feel trapped in their own dream they’ve built.

You can't stop working. There are no other options. You think the only solution is to work harder, grow more and one day things will get better.

If you’re like me, you pour every part of your being into growing your business — without ever considering the consequences on your family, health, enjoyment of this life, and business.

Growth as an Outcome is a Fool’s Errand

I know this to be true because I nearly lost everything dear to me.

The business was wrecking my life.

It demanded everything from me, yet I wasn't making money.

We were $90,000 in debt. At least, that’s what I thought. The debt was upwards of $150,000. I tried to declare bankruptcy and realized, “Oh shoot. I cannot escape from this kind of debt.”

That’s when I knew the only way out was through the mess.

I knew the way I’d been running the business for the previous eight years wasn’t working, and I was out of time waiting for it to pan out.

So, almost overnight, I changed everything about my business, including:

Service offerings

Sales processes

Building a niche

They say the best creativity is born from desperation. I wish I didn’t know how true that was.

(If you’re wondering how I changed those parts of my business and how I knew what to do, I promise to come back to that.)

False Hope

A year later, I had paid off all of my debt, the business was growing, and I even had some money in the bank.

I thought I was killing it!

I thought my marriage was great. My wife is my best friend. We never had crazy, contentious fights. We had three kids (now four). Life was good.

When my wife came to me and gave me her ring, I was stunned. She was direct, “Hey, I love you. But you can gain the whole world and still lose me.”

That was my first wake-up call.

Being laser-focused on my business blinded me to the needs of the people I loved most, and I never knew how much I was hurting them.

The second wake-up call happened simultaneously as the stress of the business triggered shingles.

Our conversation and my health led me on a journey to create balance in my life.

I realized that if something didn’t change, I’d lose my marriage, business, and sanity.

At the time I only saw two options: sell the business or shut it down.

And I didn’t love either option.

So I created my own.

The Third Option

Instead of selling the business or shutting it down, I built it to where I had the option to sell or let it run without controlling my life while funding my lifestyle.

I created Optionality.

This helped save my marriage, support my family, empower my business to grow without me, and gave me the opportunity to build and spend time on the things I want.

And what I’ve come to realize is that’s what entrepreneurs really want.

We don’t just want more money or growth, those are a means to an end.

We want to spend as much or as little time in our business as we want, while still funding our dreams. We want to sell on our terms or not at all. What you want is Optionality, and my mission is to help you achieve it.

Next week, I’ll share more about optionality and how it can lead to success, confidence, and the ability to make decisions based on what brings you energy.

Talk soon,


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