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Host Thomas Wasson sits down with Drew Farwell, Chief Operating Officer at Midwest Carriers, live from the Barkcast booth at Trimble Insight 2026. Drew breaks down the operational philosophy behind his whitepaper, "The Next Generation TMS: From Load-Centric to Network-Centric Intelligence," and why traditional transportation management systems fall short in today’s complex trucking landscape.
In this episode, they discuss:
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In this episode of Loaded and Rolling, host Thomas Wasson sits down with Greg Akselrod, Chief Technology Officer at Outpost. They dive deep into the often-overlooked world of yard management, exploring how modern technology, AI, and computer vision are revolutionizing traditional gate operations and check-in workflows.
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In this episode of Loaded and Rolling, host Thomas Wasson is joined by Sean Dehan, Vice President of Strategy and Corporate Development at Truckstop. Together, they dive deep into the changing landscape of the freight industry, exploring how brokers and carriers can navigate a post-Montgomery world, fight rising freight fraud, and adapt to shifting market dynamics.
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In this episode of Loaded and Rolling, host Thomas Wasson sits down with David Blackwell and Akshaya Kumar from EROAD to discuss the evolution of the “Truck Whisperer”—the art of transforming overwhelming fleet data into meaningful business outcomes.
As modern commercial vehicles generate upwards of 50,000 data points per day, many fleet managers find themselves suffering from “alert fatigue” rather than gaining operational control. David and Akshaya break down how to cut through this digital noise to find the “juicy nuggets” of actionable signal.
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On this episode of Loaded and Rolling, host Thomas Wasson sits down with Steve Oliver of Taylor and Martin to unpack how shifting freight rates, tariff uncertainty, and lower diesel prices are reshaping the new and used truck markets. They explore how auction activity offers real-time insight into freight trends, why equipment scarcity is driving values higher, and how small and midsize fleets are positioning themselves for growth as optimism returns. Oliver also shares details on Taylor and Martin’s expanding auction footprint, major fleet dispersals, and a newly launched engine protection plan designed to give buyers added confidence in today’s evolving market.
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Trucking isn’t just a job—it’s a craft, a culture, and a way of life. In this episode of Loaded and Rolling, host Thomas Watson sits down with journalist and lifelong trucker Gord McGill to unpack how deregulation, automation, government policy, and the “driver shortage” narrative have transformed trucking over the past few decades—and not for the better. Drawing from McGill’s upcoming book End of the Road: Inside the War on Truckers, the conversation explores declining wages, rising safety risks, forced churn, and the erosion of driver skill and pride. It’s a candid, sometimes uncomfortable look at what’s gone wrong in trucking—and what it will take to fix it.
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At Trimble Insight 2025 in New Orleans, FreightWaves’ Thomas Wasson sits down with Brian Mulshine, Senior Director of Product Management at Trimble, to unpack how AI, integrations, and real-time data are reshaping fleet maintenance. From AI-powered road call agents and automated invoice processing to predictive maintenance, OEM deep-linking, and tire failure trends, this conversation dives into how fleets can reduce downtime, slash administrative work, and keep trucks rolling in a tight freight market. A must-watch for fleet operators, maintenance leaders, and anyone focused on keeping equipment profitable.
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Recorded live at Trimble Insight 2025 in New Orleans, FreightWaves’ Thomas Wasson sits down with Jonah McIntire, Chief Platform Officer at Trimble Transportation, for a wide-ranging and refreshingly candid conversation about AI, software, and the future of logistics work.
Jonah breaks down how Trimble operates at the “plumbing layer” of the supply chain, why tools like PC*MILER are still the industry’s ground truth, and why many past tech hype cycles—blockchain, visibility, buzzword AI—missed the mark. He doesn’t shy away from the hard truth: AI will eliminate back-office jobs, even as it radically increases productivity and reshapes how logistics companies scale.
The conversation dives deep into AI-written code, self-connecting systems, rewriting legacy software in days instead of months, and why Trimble is betting on AI colleagues—not just AI features. From creative destruction to AI agents interviewing for dispatcher roles, this episode offers a rare, inside look at how one of the largest supply-chain software companies is rebuilding for the next decade.
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At Trimble Insight 2025, Thomas Wasson talks with Trimble’s Rishi Mehra about the rapid evolution of fleet technology. They explore how AI is transforming route optimization, driver navigation, fuel planning, order intake, and back-office workflows—without replacing human expertise. From capturing dispatcher tribal knowledge to enabling voice-driven, in-cab AI copilots, this episode breaks down what’s real, what’s coming, and how fleets can unlock immediate ROI in a tight freight market.
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Fleet operations are moving faster than ever — and legacy systems can’t keep up. In this interview from the Trimble Insights Conference, Trimble CEO Rob Painter explains how cloud-based TMS platforms, agentic AI, and connected workflows are helping fleets cut hours of manual work down to minutes.
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