Military Leadership Lessons Applied to Freight Brokerage and Team Building

Rob Skelton didn't come to freight brokerage through the traditional path. He came through the military. And in this episode of The Journey Podcast, Will Jenkins sits down with Rob — CEO of Third Coast Logistics — to talk about what service taught him about leadership, team dynamics, and the kind of resilience that lets you build a freight brokerage through market cycles that would break organizations built on flimsier foundations.

Rob talks about the specific lessons he carried from military service into freight: the clarity about mission, the non-negotiable accountability, and the understanding that ego is a liability in high-pressure environments. In freight brokerage, where market conditions can swing fast and team performance directly determines survival, those lessons translate directly. He shares what it looked like to apply them in a business context and where the translation required adaptation.

The conversation covers the early challenges of building Third Coast Logistics — the financial management realities of running a freight brokerage, how to navigate the cash flow dynamics of a tight market, and what leadership looks like when you're making hard decisions with incomplete information. Rob is honest about the mistakes he made and what they cost him, and equally clear about what they taught him.

He also talks about what it takes to build a freight team worth working for — the culture, the communication, and the specific behaviors that make talented freight professionals want to stay.

For freight brokerage operators building their teams, explore Journey's contingent recruiting or learn about freight consulting services.