Driving Forward Podcast

Selling, Succeeding & Staying Independent: Doug Grawe of The Grawe Group

August 21, 2026·1h 2m
Episode Description from the Publisher

You know what your trucks, equipment, and customers are worth. But is the rest of your business ready for someone to look under the hood?Growth, profitability, legal exposure, technology, customer expectations, and changing regulations all compete for attention. The decisions made in one area often create consequences somewhere else in the business.This week on Driving Forward, Nate Johnson sits down with Doug Grawe, Owner & CEO of The Grawe Group and former General Counsel at Dart Transit — one of the nation's largest owner-operator fleets.Doug has spent two decades helping family-owned trucking companies navigate the legal decisions that make or break them, and he's opening up the playbook:🔷 How to get your company ready for a sale (and what kills deals in diligence)🔷How to bring the next generation into the family business without blowing it up🔷What the DOL's latest independent contractor rule changes mean for owner-operator programs🔷The contract clauses carriers should never sign blind🔷Why those dusty bylaws and operating agreements might be the most important papers in your buildingFor transportation owners and executives thinking about growth, transition, risk, or long-term business value, tune in for a look at how the decisions made today can shape what comes next.

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