What if the amount and quality of industry information you consume could become a competitive advantage?

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.

Key Takeaways

Why media and data consumption can become a competitive differentiator
How Jon's dealership IT experience shaped his entrepreneurial journey
The customer problem that inspired his first SaaS company
What founders can experience after a successful acquisition
Why heavy equipment remains relationship-driven
Why industry information is still fragmented
How Digital Iron Group brings media and data together
Why dealers and OEMs should look beyond their own brands
How better information supports investors and technology companies
Why AI should be evaluated through business cases and ROI

In This Episode:

[00:00] Welcome to Heavy Hitters
[01:42] Jon's path into heavy equipment
[02:31] From dealership IT to entrepreneurship
[06:06] Building a successful SaaS company
[14:02] The impact of an acquisition
[21:18] The industry's information gap
[22:50] The case for centralized intelligence
[34:04] Media vs. data
[36:40] Helping investors and startups
[44:31] Building an audience on LinkedIn
[54:00] Understanding customers and decision-makers
[01:02:52] The right conversation about AI


Notable Quotes


[11:21] "The average service call took 8 minutes... that's 80 minutes in just phone time. That's really, it's a loss of productivity." — Jon Rossi

[21:16] "Your word is your bond, so to speak." — Jon Rossi

[26:19] "Every other industry that there's consolidation happening, people want a single channel. They don't want to go to all these different websites to try and figure out what's going on." — Jon Rossi

[28:13] "I do believe that there is a need for a central solution to get your data from." — Jon Rossi

[01:03:09] "You can't hold AI accountable. You hold people accountable." — Jon Rossi

[01:04:19] "You're a bit of an industry lubricant. What you're providing should make the ease of transacting business in heavy equipment easier, with less friction, with less headwind." — Jay Lucas

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.


Resources and Links

Heavy Hitters Podcast
https://podcasts.apple.com/ca/podcast...

Jay Lucas
Website: https://reputablerecruiting.com/
Linkedin: LinkedIn: jaylucas

Jon Rossi
Digital Iron Group
LinkedIn: LinkedIn: jonrrossi