Why Most Small Fleets Fail…And How to Beat the Odds | Adam Wingfield on Dri

Adam Wingfield — Founder & Managing Director of Innovative Logistics Group — is on a mission to empower small fleet operators across the country.

In the April 10th episode of Driving Forward, Adam and Nate discuss what it really takes to succeed in today’s freight market and how Adam’s new collaboration with FreightWaves is helping small carriers gain the tools, insights, and data they need through The Playbook.

We explore why small fleets struggle, how to turn information into action, and what every operator needs to understand about compliance and profitability in a volatile industry.

Topics Covered:
00:00:00 Intro
00:06:50 From Driver to Industry Advocate
00:14:00 Why Small Fleets Fail
00:23:00 Mentorship, Legacy, and Leading with Heart
00:26:30 The Power of the Playbook
00:33:00 Audits, Compliance, and Coaching Fleets
00:45:45 Accountability and Real Leadership
00:55:00 Final Reflections & Call to Action

Whether you’re running a single truck or scaling a small fleet, this episode is packed with insights to help you not just survive but thrive.