In a recent episode of The Freight Pod Podcast, my friend and industry maverick, Jeff Silver, reflected on transformative moments in his career. As he spoke with his son and podcast host, Andrew, I found myself reflecting on my own career and how transformation isn’t just a business concept — it’s deeply personal, too.
Certainly, the metamorphosis of Trailer Bridge during my tenure is evidence of the power of change to grow and sustain a business. Even today, we are amid major technological advancements improving how we show up for our customers and improve our internal processes.
But today, as we close out the first quarter of 2025, I want to share a more personal perspective on transformation with a series of moments that have shaped my approach to leadership.
The Humbling Experience of Building from Scratch
Starting a few businesses from the ground up really humbles the soul.
It’s easy to ride the coattails of an established brand with decades of history, where you can leverage the strength of its reputation. But when you start a business from scratch, you're not just selling a product, you’re selling your own reputation.
My experiences reshaped how I think about leadership. It's not about commanding from the top; it’s about working alongside your team and being there for them. People don’t work for you - you work for them and with them. And when you take care of your people, they take care of your customers and that takes care of the business.
Leadership Is Not Defined by a Title
Looking back, I always wanted to be a CEO but when the first opportunity came over a decade ago, I turned it down. The ‘no’ surprised me as much as it did those around me. At the time, I was able to influence real change at Trailer Bridge without the CEO title simply by caring for the people around me.
Your leadership ability is driven by how you treat people, and the respect you show others. Titles may open doors, but they’re not the foundation of true leadership. That foundation is built on the genuine relationships you create with your team. Your people will respect you, really respect you, because of how you treat them, not because of the title you hold.
The Impact of Family on Leadership
Probably the most profound moments of transformation come from being a dad. Watching my girls grow and become young adults made me a better leader. Why couldn’t I treat those I work with the same way I coach and treat my kids. This is when the word family came into the conversation for me at work.
Some say it’s wrong to use the word family in business, but I call bullshit. Family is about developing a bond through trust, love, and shared experiences—both good and bad. Think about the friends you consider family. It’s not the title they hold; it’s the depth of the connection you share. I want to be the leader that builds those kinds of bonds within the companies I lead.
Transformative moments sometimes are big and loud, but others come in a small quiet moment or in the book you pick up during a layover at the airport (podcast reference, go listen) – be on the lookout for them.
Thank you, Jeff and Andrew, for the inspiring conversation that sparked a moment of reflection for me. Hopefully, this note from me will inspire someone else to pause and reflect on their journey.
- Mitch
