Issue #151 An Unexpected Lesson From the Day I Was Fired From the Company I Co-Founded

There are certain moments in life that divide our story into a before and an after and we often do not recognize them while they’re happening. It’s only when looking back through the rearview mirror, that we realize we crossed an invisible line and never fully returned to the person we were before.

One of those moments for me began over breakfast.

For years, my chairman and I had a standing monthly morning meeting and it had become part of our leadership rhythm. Every few weeks we’d meet to stay aligned, work through challenges and think about the future of the business together. It became a ritual and, since as I respected his time, I always came prepared. 

That morning was no different.

I arrived with my iPad full of notes. After we ordered breakfast, I opened it and began walking through the agenda I had prepared. There were strategic decisions to discuss, opportunities we were evaluating, leaders we were developing and a handful of issues I wanted his perspective on. 

I gave him my high-level agenda and then I looked up and asked a question I had asked dozens of times before.

“Is there anything you’d like to add?”

He paused for a moment before replying.

“There’s only one thing on my agenda today.”

“Today will be your last day working for the company.”

For a few moments I wasn’t sure I had heard him correctly.

Shock has a strange way of slowing time. I can still picture the iPad sitting open in front of me, its screen filled with notes prepared for a future I assumed I would help build. Then, with only a few words, everything changed. 

The future we’d planned for was still there; I simply wasn’t part of it anymore.

My first reaction wasn’t really about the shock of losing the company.

It was more about the grief of losing someone I trusted.

A Different Kind of Loss

The person sitting across the table wasn’t just the chairman of the company, he had been my business partner for more than ten years. Together we had lived through experiences that shape people for life. 

We’d stared bankruptcy in the face more than once. We’d experienced the uncertainty that comes from wondering whether you’d survive another month, followed by the satisfaction of building something meaningful despite what seemed like impossible odds. 

Together we had guided a fragile business, that was often on the verge, to become a thriving enterprise that we eventually merged into a larger entity that gave us market clout.

He was more than just my business partner, he became a mentor, a trusted advisor and, eventually, someone I considered a genuine friend. 

My overwhelming emotion that morning wasn't anger so much as the feeling of being gut punched. However time has a way of softening certainty. Looking back now, I can appreciate that leadership sometimes requires decisions that leave everyone carrying some measure of pain, and I’m sure that breakfast wasn’t easy for him either. 

Today my own lived experience has given me the ability to extend grace in ways I couldn’t that morning, but grace and honesty aren’t opposites. The truth is that I felt deeply wounded by someone I trusted.

Perhaps even more difficult to admit was the embarrassment that I felt. How was I going to explain this to my family?  How do you tell the team you have mentored, colleagues in the industry and the overall market, that you’ve been fired from the company that you were a founder of? 

Even more important, how do you explain the true meaning of what happened to yourself?

Bent Rim

When breakfast ended, I drove home.

I pulled into the driveway but never went inside. Instead, I walked straight to the garage, loaded my mountain bike into the back of my truck and headed toward my favorite trail network.  On route, my mind was racing as I replayed the breakfast conversation over and over, trying to make sense of what had just happened. 

When I arrived, I chose a trail called Bent Rim. As the name suggests, Bent Rim is a very technical trail, where many bikes (and bodies) are broken. It’s a double black diamond carved into the Niagara Escarpment, filled with rock gardens, awkward ledges and narrow lines where every decision matters. The first time I visited this trail, I genuinely didn’t believe it was possible to ride it. It looked less like a trail and more like a collection of obstacles that no reasonable person would voluntarily attempt.

Then I started riding with people who were better than me.

One of the great gifts of spending time with people who are further ahead is that they quietly redefine what’s possible. Watching someone clean a section I was convinced couldn’t be ridden slowly changed the story I was telling myself. Eventually, the question was no longer, “Is that even possible?” It became, “how can I develop the skills to be able to ride it?”

None of that mattered that afternoon.

I wasn’t trying to become a better rider. I wasn’t chasing personal records or hoping to clean a section that had frustrated me before. I simply needed somewhere that matched what was happening inside me.

Bent Rim isn’t peaceful; it’s punishing in the best possible way. The rocks push back. Every section requires effort. Every line demands commitment. It doesn’t care whether you’re frustrated, embarrassed or trying to make sense of your life. It simply demands your full attention. You don’t have the luxury of replaying a painful breakfast conversation while deciding whether to brake, commit or change your line. When you finish the ride you will be physically exhausted, often scraped and covered in dirt, but somehow lighter than when you began.

As I was writing this newsletter, I decided to pull up the Strava file from that ride and noticed a couple things. I had completely forgotten that I’d posted a picture of Jerry Maguire as part of the ride record. At the time, it seemed like the closest comparison I could find. But what truly surprised me, was discovering that I’d set a personal record on all the timed sections of the trail.

I smiled when I saw it.

At the time, I thought I’d gone there because I was frustrated and didn’t know what else to do. It would take me years to realize that something much deeper had drawn me there.

Looking back now, I don’t think I was grieving the loss of a role nearly as much as I was trying to reconcile how a relationship I valued so deeply had arrived at this moment. Somehow, without consciously thinking about it, I found myself heading to the one place where my mind wouldn’t be allowed to wander.

Perhaps that’s the irony.

On one of the hardest days of my professional life, I was more present and focused than I had been in some time. I couldn’t have explained that to you then but now I understand that Bent Rim wasn’t simply giving me somewhere to ride. It was giving me somewhere to be while the life I thought I knew was quietly coming apart.

The Question I Wasn’t Asking

Many people have asked me over the years how a founder gets fired from his own company.

The answer is both simple and complicated.

Months earlier, I had merged our company, where I was the majority shareholder, with another to become a much larger organization. From a business perspective, it was the right decision. Together we built an enterprise generating well into nine figures in revenue, with offices around the world and, with greater scale and influence.

Economically, the merger created enormous value.

Culturally, it was another story.

Over time, differences in leadership philosophy became impossible to reconcile, and eventually the board decided the company needed to make changes.

Initially I thought that was the story.

Now I don’t.

That the fateful breakfast simply exposed something that had been developing inside me for a very long time. In the busyness of life, I had simply chosen not to see it.

For nearly three decades, my life had been defined by calendars, meetings, flights, acquisitions, customers, leadership teams and decisions that needed my attention. Every day was full, and people always needed something from me. I was on the treadmill of more, and it seemed to move a little faster every year. I never really questioned it because it had simply become the rhythm of my life.

What I didn’t recognize at the time was how easily a full calendar can begin answering questions it was never meant to answer.

Questions like…

Who am I really?

Where do I find my sense of worth?

What gives my life significance?

Without realizing it, I had slowly allowed what I did to shape who I believed I was. That wasn’t obvious while the calendar was full; it only became obvious when it suddenly became quiet.

I don’t think that breakfast marked the end of one chapter nearly as much as it forced me to consider another.

At the time, I believed I was grieving the loss of a company.

It would take me years to understand what I had really lost.

And that’s where I’d like to begin next week.

One Question

Most of us will never be fired from a company we founded, but all of us build our lives around things that can change. Our careers, titles, businesses, achievements and even the feeling of being needed get reinforced over time and soon become a defining part of who we think we are.

I certainly didn’t recognize how much these factors shaped me until they were suddenly taken away.

It took an unexpected breakfast, an empty calendar and years of reflection for me to begin separating what I did from the deeper questions of who I was and, ultimately, what made my life matter.

So, there is one question I’d invite you to sit with this week:

Where do you derive your sense of worth?

If your answer is based on anything that can quickly change—health, wealth, power or fame—I would suggest you may want to reconsider it.

You can learn from my experience, as you don’t need to wait for something unexpectedly to be taken away before you begin asking that question.

‍