The Accidental CEO: How a Baseball Injury Led Me to Leading a Marketing Agency

For most of my early life, the plan was simple.

Play baseball.

I grew up in a small town in Vermont, and, like many kids who love sports, I spent most of my time thinking about the next game, the next season, the next opportunity to compete. Pitching was my thing. I loved the discipline of it. The preparation. The strategy. The feeling that every pitch was a small decision with real consequences.

For a long time, I assumed that would be my path.

Then I needed Tommy John surgery in high school.

Anyone who has been through a major injury knows the strange moment that follows. The thing that formerly felt inevitable suddenly disappears. Recovery took about a year and a half, and by the time I was healthy again, the trajectory had changed.

The version of the future I once had imagined wasn’t there anymore.

So I did what a lot of people do when their first plan falls apart. I made a new one.

I went to college and studied sport management, thinking I might still find a career somewhere in athletics. Coaching, operations, and front office work. Something connected to the world I loved.

But that plan didn’t hold either.

Toward the end of school, I thought I had a job lined up with the University of Vermont. It was the kind of opportunity that felt like a bridge between the life I’d imagined and the one I was about to start.

Then budget cuts eliminated the role before it even began.

At that point, the way forward was unclear. I was finishing school without a clear direction and without the career I thought I had been preparing for.

Looking back, that uncertainty turned out to be one of the most important moments of my life.

Because it forced me to try something completely different.

A friend referred me to an SEO role at Dealer.com. I didn’t know much about the company at the time. I definitely didn’t know much about SEO or digital marketing.

But I took the job.

And once I was there, I started learning.

One of the things sports teaches you is how to approach improvement. You show up. You practice. You analyze what went wrong. You try again. That mindset translates well to business.

SEO turned out to be a lot like pitching.

You’re constantly adjusting strategy based on feedback. You’re studying the environment. You’re learning how small changes can create very different outcomes. And you’re competing, even if the competition looks different than it does on a field.

After a few years at Dealer.com, I moved to Digital Position as an SEO account lead.

I had no idea at the time that this company would eventually become such a huge part of my life.

Within about a year, I started learning PPC so I could manage both channels. That decision changed how I saw the business. When you work across multiple parts of marketing, you begin to see how everything connects.

SEO influences advertising. Advertising influences content. Content influences how customers understand a brand.

Marketing stops looking like a collection of tactics and starts looking like a system.

That broader perspective eventually pulled me into operations.

Instead of just working on client campaigns, I started focusing on how the company itself functioned. How employees were onboarded. How internal workflows were structured. How tasks moved through the organization. How clients experienced the work we were doing.

At the time, I wasn’t thinking about leadership. I was thinking about how to make things run better.

But operations teaches you something important.

If you understand the systems behind a business, you understand the business itself.

A few years later, the CEO asked if I would take over the role.

It wasn’t something I had planned for. I didn’t grow up dreaming about running a marketing company.

But when the opportunity came, I realized something.

The strange path that brought me there had actually prepared me well for the job.

Sports taught me discipline, resilience, and competition. Operations taught me how organizations function. Marketing taught me how businesses grow.

Put together, those experiences created a foundation for leadership I never would have designed intentionally.

One of the biggest lessons I’ve learned as a CEO is that many leadership lessons can’t be learned through advice alone.

People can explain them to you. You can read about them. But until you experience the consequences yourself, the lesson doesn’t fully stick.

Failure is a powerful teacher.

You see this especially when building teams.

Early in my leadership journey, I wanted to give people opportunities and create an environment where hard work was rewarded. I still believe in that.

But leadership also means making difficult decisions when something isn’t working.

If someone is in the wrong role and the situation goes unresolved, it slowly affects team morale and culture. One person struggling in the wrong seat can quietly influence the entire group around them.

Those decisions are never enjoyable.

But they are necessary if you want to build a healthy organization.

Another lesson is that careers rarely follow the straight path people imagine when they are young.

The times that feel like setbacks often become the times that redirect you toward something better.

If I hadn’t needed Tommy John surgery, I might have stayed focused on baseball much longer.

If the University of Vermont job hadn’t disappeared, I might have built a career inside athletics.

If a friend hadn’t mentioned an opening at Dealer.com, I might never have discovered the world of digital marketing at all.

None of those events felt positive at the time.

But they created the chain of circumstances that eventually led me to where I am today.

That’s something I try to remember when things don’t go according to plan.

Setbacks don’t always close doors.

Sometimes they just redirect you to a path you couldn’t see yet.

And sometimes that unexpected path leads you exactly where you’re supposed to go.