What if scaling your fleet meant skipping the load board altogether?
In this episode of Miles and Mentors: A Trucking Podcast, Roy Craigen, founder and president of Transcom Fleet Services, delivers decades of wisdom from the cab to the C-suite. Raised in the industry and seasoned through transforming trucking companies across North America, Roy explains why most startups fail and how to build lasting, compliant, and efficient operations instead.
From managing small fleets to overseeing 200 terminals, Roy shares tactical, real-world insights on fleet structure, compliance risks, and the power of direct customer relationships. Whether you're running one truck or twenty, this episode is packed with mentorship gold for trucking entrepreneurs ready to grow the right way.
Like what you hear? Be sure to like, subscribe, and share the show with others in the trucking world.
🎧 Episode Timestamps
📍 00:00:00 – Meet Roy Craigen, President of Transcom Fleet Services
📍 00:01:04 – Roy’s start: born into trucking and driving trucks at age six
📍 00:04:05 – From pulling A-trains to managing national fleets
📍 00:07:30 – The story behind Transcom and what sets them apart
📍 00:09:00 – Why Transcom gets behind management, not in front
📍 00:11:01 – Helping small and massive fleets, from 6 vans to 200 terminals
📍 00:13:35 – Why 90% of new fleets fail and how to prevent it
📍 00:15:57 – Hidden compliance costs and fines every operator should know
📍 00:17:52 – The dangers of scaling without structure
📍 00:20:12 – Why Roy never used load boards, even when scaling to $150M
📍 00:22:09 – Build local customer relationships, not broker dependency
📍 00:26:01 – Key advice for launching a fleet today
📍 00:27:06 – The hidden value in reading trade publications, including the ads
📍 00:28:10 – "Float the boat" and how to reduce equipment wear and fuel waste
📍 00:29:25 – The moral duty of every driver on the road
📍 00:30:33 – How to contact Roy and learn more about Transcom
🎙 About Our Guest
Roy Craigen is the President and Founder of Transcom Fleet Services (https://transcomfleetservices.com), a hands-on operational consulting firm serving trucking fleets across North America. With over 20 years of leadership in award-winning logistics operations, Roy helps companies, from small local outfits to multinational carriers, build better systems, stay compliant, and avoid costly missteps.
LinkedIn (Roy): https://www.linkedin.com/in/transcom-fleet-services-inc-6095576a/
Website: https://transcomfleetservices.com
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Miles and Mentors isn’t just a podcast. It’s a movement built on real stories, tactical insights, and mentorship that fuels the next generation of trucking leaders.
Reach out: milesandmentors@gmail.com
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