Most trucking companies don’t fail.
They just keep running the same business at a larger scale — until it finally breaks.
If you’re running a fleet with 20 to 80 trucks, you’re no longer in the startup phase. You’ve entered the design phase of your business — whether you realize it or not.
In this episode of Driven for Success, we step back from day-to-day operations and talk about what really changes as fleets grow:
- Why your role shifts from doing the work to designing the work
- Why strategy isn’t a plan — it’s a set of decisions
- How complexity quietly creeps in and starts draining margin and morale
- Why the best-run mid-size fleets intentionally make things boring
- How to move from firefighter to executive without losing control
This episode isn’t about payroll, dispatch, or compliance specifically.
It’s about asking the question most growing fleet owners never slow down enough to ask:
What are we actually building?
If you want a trucking company that:
- runs without heroics
- survives scrutiny
- attracts good people
- and doesn’t rely on you holding everything together
this conversation is for you.
🎧 Driven for Success is the podcast for owners and executives of mid-size trucking fleets who want fewer headaches, better drivers, cleaner systems, and a whole lot less chaos in their business.