This week’s guest is Felipe Capella, CEO and co-founder of LoadSmart. After 10 years as a lawyer, Felipe decided to start a company to build something along with his co-founder, Ricardo Salgado. They chose freight transportation since it has a huge total available market, is highly fragmented, and was ripe for technological improvement. They initially started out as a brokerage but over the last ten years they have grown LoadSmart into being a platform that provides, among other things, TMS software as a service, managed transportation, brokerage services, and dynamic algorithmic truckload pricing. Recently, they have added two versions of generative AI to their platform: Co-Pilot which enables plain language querying of a shipper’s data within their TMS and, most recently, Freight Intel AI which makes proactive recommendations on a shipper’s network based on an analysis of their actual transactions. In our conversation, we discuss how the truckload and brokerage market has evolved over the last decade, the importance of context when generating a rate, the growth of algorithmic spot pricing, and where AI should (and should not) be used within supply chains.