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NEWSLETTER BROUGHT TO YOU BY DESCARTES

Every shipment impacts your reputation. Descartes MacroPoint delivers visibility and risk insights you can trust to keep customers confident, freight on-time, and your business growing.

What’s going on, everyone? Man, what a month it’s been! I’m fully in the driver’s seat here on What The Truck?!?, and October did not disappoint. We’ve been hitting it harder than ever with content that’s as real as it gets. Shoutout to production because they have helped deliver all month long.

This month was all about the forces shaping freight today. From technology, automation, market trends, and how operations are evolving across the board. We broke down how carriers and shippers are using data and AI to make faster, smarter decisions, improving delivery accuracy and efficiency while keeping trust and reliability front and center. Visibility across the supply chain, tech that reduces claims, faster payments, and navigating regulatory and economic pressures were all hot topics.

But it wasn’t just about tech. We also dug into the human side of logistics. Driver retention, recruitment, and creating a culture built on authenticity, respect, and education came up again and again. We even touched on sustainability, decarbonization, and how rail and trucking need to work together to keep freight moving efficiently.

The big takeaway? Freight is moving faster than ever, and the people and companies that combine smart tech with strong, people-first leadership are the ones shaping the future. October reminded us why this industry never slows down. And neither do we.

Huge thank you to Descartes Macropoint for making this month come to life. Every shipment impacts your reputation. Descartes MacroPoint delivers visibility and risk insights you can trust to keep customers confident, freight on-time, and your business growing.

Enjoy the recap of these shows, and have a safe and spooky Halloween.

Malcolm “Miggie” Harris

Now on Demand

Cargo Conversations with Mike and Tyler

Malcolm Harris is joined by Michael Hain (Descartes) and Tyler Montgomery (Scout Freight) for a doubleheader on transportation tech and trucking culture. Hain breaks down Descartes’ latest benchmark study — revealing that 81% of companies now see transportation as a competitive weapon — and dives into AI adoption, automation gaps, and fighting fraud with tools like MacroPoint FraudGuard. Montgomery brings heart and humor, sharing lessons from his trucking roots, his vision for Scout Freight, and a wild “What The Truck” story from his first week on the job.

Watch here

Paging Dr. Gracey

Malcolm welcomes Charles Gracey, aka the Dr. Phil of Trucking. FreightWaves’ John Kingston calls in to unpack a major Supreme Court case redefining broker and carrier liability, setting the stage for massive industry impact. Gracey shares his unconventional path — from the Navy to cake decorating to radio fame — and lays out hard truths on driver recruiting, authenticity, and how to fix trucking’s culture from the inside out.

Watch here

Under the Hood: Tech Talk with David and Wes

Malcolm dives into freight tech with David Mendelson (Super Dispatch) and Wesley Montague (ShipItPro). They explore how AI and automation are transforming claims management, payments, and dock operations — turning invisible tech into real-world savings and speed. Plus, Malcolm covers major headlines: FMCSA’s crackdown on non-domiciled CDLs, delivery safety concerns, and Red Sea tensions affecting global supply chains.

Watch here

Market Moves & Smart Dudes

A data-driven powerhouse episode featuring David Spencer (Arrive Logistics), Zach Strickland (SONAR), and Matt McLelland (Covenant). They unpack freight rate volatility, market disruptions, and the balance between profitability and sustainability. McLelland gives an inside look at Covenant’s green initiatives and the “messy middle” of decarbonization, while Malcolm frames it all around staying strategic amid uncertainty.

Watch here

Tracks, Trucks & Tech: Securing the Future of Freight

Malcolm hosts Ian Jefferies (AAR) and Kari Gonzalez (MXV Rail) for a rail-meets-trucking deep dive. Jefferies covers rail safety, policy modernization, and cargo theft prevention, while Gonzalez shares insights on AI-driven derailment prevention, climate resilience, and her rise from intern to CEO. Malcolm also runs through headlines: a million-dollar tequila heist, stolen Nikes, and Craig Fuller’s new book.

Watch here

Storm Watch: Trends, Talent & Tech

Tim Crawford (Tenstreet) and Carly Gumby (Transfix) join Malcolm to talk driver retention, RFP strategy, and AI fatigue. They share insights on why drivers are staying put and how brokers can win in a tight market using automation and human connection. Malcolm wraps with global headlines — from Canada Post strikes to CH Robinson’s tech launch — showing why relationships still drive results in an automated world.

Watch here

Mozzarella, Market Shifts & the Cure for Freight’s Cancer

Malcolm kicks off with John Kingston on a surge of Chapter 11 filings shaking the transportation sector. Then, Beth Young (Velociti) discusses connectivity, AI, and safety systems powering smarter, greener fleets — plus a detour into mozzarella-making and Spanish food. Finally, Trent Tulloh (Forever Freight Broker) shares his mission to educate truckers about brokerage, reshaping trust and transparency in freight.

Watch here

Haul of Fame (F3 Day One)

Malcolm sits down with Alfonso Quijano (Lean Solutions Group), Richard Bubb (Amazon Relay), and Todd Waldron (Truckstop.com) for a “Haul of Fame” lineup. They unpack innovation across carrier experience, relay systems, and tech partnerships, spotlighting leaders redefining freight’s future.

Watch here

Liability, Logistics, and Legends

Malcolm hosts a four-guest freight showdown with Craig Fuller, Craig Leinauer (Travelers), Dan Cicerchi (Descartes MacroPoint), and Mike Beckwith (Odyssey Logistics). Fuller debunks the driver shortage myth, while Leinauer and Cicerchi unpack fraud, liability, and AI-enhanced cargo theft. Beckwith rounds it out with a no-nonsense take on automation, regulation, and carrier agility in today’s market. Packed with insight, energy, and hard truths — this episode lives up to its “Legends” title.

Watch here

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Don’t be a stranger,

Malcolm “Miggie” Harris