Episode Highlights
In this episode of Heavy Hitters, host Jay Lucas sits down with Jon Rossi, founder of Digital Iron Group, to explore the growing power of media, data, and industry intelligence in heavy equipment.
Jon shares his journey from dealership IT to entrepreneurship, including how he built a SaaS company that solved a practical communication problem for equipment dealers before eventually being acquired. After the acquisition, he returned to the industry with a new mission: make heavy equipment information easier to find, consume, and understand.
The conversation explores why industry information remains fragmented and why Jon believes a centralized, searchable platform can help dealers, OEMs, investors, and technology companies make better decisions. They also discuss looking beyond your own brand, building reach through LinkedIn, and understanding buying decisions.
The episode closes with AI. Jon explains why companies should not adopt AI simply because it is available, but should first understand the problem, build a business case, define ROI, and establish what success looks like.

Our Guest
Jon Rossi is the founder of Digital Iron Group, a new media and data platform on a mission to become the definitive source of information for the heavy equipment industry. Jon is a serial entrepreneur with deep experience at the intersection of equipment and technology. He spent a decade at a Komatsu dealership, where he rose from IT admin to Director of IT & Operations. He then founded a SaaS company designed to improve dealership-customer communication which was later acquired by a Fortune 100 OEM. Now, Jon is building Dig to aggregate industry news, data, and insights, providing a “Bloomberg-like” resource for dealers, OEMs, investors, and entrepreneurs.



