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In this episode, we sit down with Dan Brink, Chief Revenue Officer at Fleet Owl, to discuss how mid-sized fleets are navigating the complex intersection of tradition and technology. As a third-generation trucker, Dan brings a unique perspective on why the "freight recession" is hitting hard and how operational AI is becoming the secret weapon for survival in 2026. We dive deep into the rising threat of cargo fraud—including the infamous "lobster heist"—and explain how modern TMS (Transportation Management Systems) are moving beyond simple data entry to become proactive security and profitability tools. In this episode, you’ll learn: How to differentiate between AI "hype" and actual operational tools. Strategies for mid-sized fleets to maintain margins during a market downturn. Why legacy systems are leaving your cargo vulnerable to sophisticated fraud. The future of port logistics and the role of Navy-grade efficiency in trucking. FleetOwl is a logistics technology company reshaping how businesses manage fleets, dispatching, shipments, and end-to-end transportation operations. The company helps optimize fleet operations through innovative software and technology. FleetOwl is an all-in-one trucking management platform built to help carriers, dispatchers, and owner-operators run more efficiently. From route planning and tracking to driver performance and settlements, every FleetOwl solution is designed to reduce manual work, cut costs, and maximize profit, powered by real-time data and AI-driven automation. FleetOwl Website: https://fleetowl.com/ FleetOwl LinkedIn: https://www.linkedin.com/company/flee... Daniel Brink LinkedIn: / danbrink4 TIMESTAMPS: 0:00 - Introduction: The State of Trucking in 2026 0:45 - Dan Brink’s Journey: From 3rd Gen Trucker to Tech Leader 03:12 - Why Mid-Sized Fleets are Feeling the Squeeze 06:40 - AI vs. The Hype: What "Operational AI" Actually Means 10:15 - The $400K Lobster Theft: How Cargo Fraud is Evolving 14:50 - Legacy TMS vs. Modern Tech: Why Your Software is a Liability 19:30 - Navigating the Freight Recession: Practical Survival Tips 24:05 - The Future of Fleet Owl and Port Logistics Efficiency 28:45 - Closing Thoughts: Keeping the Industry Human in a Digital Age Subscribe for more insights into the future of freight and logistics! #Trucking #Logistics #FleetManagement #AI #CargoFraud #TMS #FleetOwl #SupplyChain