First, welcome back to Owner to Owner—a newsletter for 1,200+ small business owners and operators who want to become better leaders and design the next chapter of their companies.

This month, we hosted a very special guest: former Chicago Bears player, Desmond Clark. Before Desmond became the owner of Bear Down Logistics, he spent 12 seasons in the NFL, beginning with the Denver Broncos after being drafted out of Wake Forest in 1999.

He later spent a season with the Miami Dolphins before building the bulk of his pro career with the Chicago Bears, where he became part of the team’s 2006 Super Bowl run.  

But what stands out most in Desmond’s story is not just the length of his playing career; it’s the mindset that carried him through it: resilience, self-belief, and a refusal to let circumstances define him.

Those same traits show up all throughout his approach to business today, making his journey from NFL veteran to business owner feel less like a reinvention and more like a continuation of who he has always been.

For me, the transition wasn’t really about leaving football; it was about figuring out what lane I wanted to build in next. I went from real estate to medical devices, where I co-founded a company that failed, then into financial services and insurance, and after that, I wrote a book and was planning to speak full time before the pandemic crushed that plan.

I found logistics in 2021 through a guy named Brian Rice, who reached out to me on LinkedIn and asked if I had ever thought about doing anything in the space. At first, I told him straight up, “I don’t even know what logistics is.” But the more time I spent in Chicago learning the business, sitting in his office, studying the systems and the process, the more I started thinking, “I could build something here.”

When I started the company, I said I wanted to build a $100 million company, and I meant it. I had learned that the average gross profit margin in the industry was around 15%, and I set that marker because I wanted to challenge myself: Could I make more in one year than I made in my entire 12-year NFL career?

In football, I made $15 million, and for me, this wasn’t about ego or proving something to the world; it was a challenge to myself. I’ve always said I’m more than a football player, so this business became a way to test that belief in a real, measurable way. I wasn’t asking, “Can I do it?” because to me, that already brings doubt into the picture; it was, “Let’s go do it.”

One of the first big lessons I learned was that growth can fool you if you don’t understand what’s actually driving it. We went seven months with just a small team, and then in those last three months, we started making a profit, and I thought, “Oh, just hire more people.” That was the wrong move, and I almost crashed the company within the first year because I got too fat on overhead too early.

What that experience taught me was that you can’t build just because you finally see a little momentum; you have to understand the model underneath it. It also forced me to get a lot clearer on what kind of people I actually wanted in the business and what structure would really work. Sometimes an owner’s biggest lesson comes from realizing that more activity is not the same thing as a stronger business.

The biggest shift came when I stopped trying to build a company that could do a little bit of everything and got clear on who we were. One of the most important hires I made was Louis Santana, who is now my VP and business partner, and he brought deep experience in heavy haul and oversized dimensional freight. I didn’t know anything about that world at first, but I liked his vision for the business, and I could see the opportunity in what he was building.

Within a few months, that became the identity of Bear Down Logistics; we became known as a heavy haul, oversized freight brokerage, and that focus changed everything. Once we found that niche, we started growing exponentially because we weren’t showing up as just another generalist anymore; people knew exactly why they should come to us.

The biggest thing I’d say is to get clear on your identity, but don’t confuse that with your title or your company. Your business is a vehicle; it’s not who you are. I also think owners need to be honest about what they actually want, because once you know that, your thoughts, emotions, and actions all need to line up with it.

In business, that shows up in really practical ways: the people you hire, the lane you choose, the way you handle setbacks, and whether you stay committed when the circumstances change. If you don’t know what you’re building toward, you’ll get distracted by every opportunity and every problem. But if you do know, then you can build with conviction and make decisions that actually move your company forward.

Our conversation with Desmond was one that stuck with us. There’s a level of conviction and self-awareness that shows up in how he approaches both growth and identity. As we stepped back from the conversation, three themes stood out:

This conversation brought a different kind of energy, one rooted in conviction, self-reflection, and a willingness to learn in real time. We’re grateful for the chance to step into Desmond’s journey and share a bit of what he’s building with Bear Down Logistics.  

If something here sparked a thought, a question, or a story of your own, just reply—we read every note. And if you’d like to be a part of a future issue, say the word.

Until next month, wishing you a strong week ahead. We’ll see you soon.

— Victor & Brian

P.S. Hit reply and tell us anything on your mind about life or business.

This is a private email for owners of B2B businesses in the US. Hosted by two longtime business owners, Brian O'Connor and Victor Saad of NextGen Growth Partners, we share personal interviews, honest lessons, and draw connections back to your work and life. Glad you're here.