
The Playbook: A Collaborative Resource for Small Trucking Companies and Owner Operators
FreightWaves has partnered with Adam Wingfield to co-create The Playbook – a community that empowers owner-operators and small fleet owners with the tools and knowledge needed to succeed.
As a passionate advocate and educator for small trucking companies, Wingfield understands the unique challenges owner-operators face. The Playbook combines FreightWaves’ industry expertise with Wingfield’s real-world strategies to deliver a comprehensive, actionable resource designed to help small fleets navigate compliance, improve profitability, and do business the right way.
From insightful masterclasses, podcasts, data tools, calculators, templates and quarterly almanacs to events tailored for every stage of your journey, The Playbook equips its community with practical guidance to tackle the complexities of running a trucking business.
Whether you’re starting out or scaling up, this collaborative effort ensures you have access to the best data and actionable insights to take your business to the next level.
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Meet The Host

Adam Wingfield
Founder, Innovative Logistics Group & The Playbook Host, FreightWaves
Adam Wingfield is a distinguished expert in the trucking industry, renowned for his innovative approach to small carriers and transportation management. With a career spanning over two decades, he’s made significant contributions to the field by blending deep operational knowledge with strategic insights that drive growth in the trucking sector.
As host of FreightWaves’ show and newsletter, The Playbook, Wingfield brings his passion and insights to the owner-operator and small fleet community each week. Sign up today at freightwaves.com/subscribe.