While running operations for a large drayage fleet, Larry Cuddy Jr. was on the hunt for a new TMS for his business. He looked at all the usual TMS providers, and he found no one, single system that could meet his specific needs. The lack of a drayage-specific software suite sparked an idea—why not build one? Larry left his position and spent three years rolling up his sleeves and working ‘in the tech’. He landed at three different freight technology firms in the pursuit of pairing his vast drayage industry knowledge with a better understanding of running a tech firm… the ingredients needed to make Digital Drayage a reality.