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Montekristo Podcast Recap: ITAM, Coaching, AI, and Building Something That Lasts

Author: Jeremy Boerger, The ITAM Coach​

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In this episode of the Montekristo Podcast, host Alex sits down with Jeremy Boerger, CEO and founder of Boerger Consulting, to talk shop on all things ITAM, coaching, AI, and building something that lasts. Jeremy’s a familiar face in the asset management world: author, speaker, consultant, and all-around no-BS advocate for doing ITAM the right way.

Let’s get into the highlights.


From Y2K to Now: The Origin Story

Jeremy’s ITAM journey started back when everyone was panicking about the year 2000. He landed in tech during the Y2K rush, and stuck around after proving he could make sense of a confusing Microsoft Office 98 license. Fast forward to 2017, Jeremy launched Boerger Consulting to help more people than he ever could in a traditional 9-to-5.

“I realized I was solving the same kinds of problems over and over again. Why not help more folks at scale?”

Since then, he’s authored Rethinking Information Technology Asset Management, traveled the country as a speaker, and shaped his consultancy around coaching, not control.


Small Team, Big Expertise

Today, Boerger Consulting runs lean with a three-person team, but don’t mistake that for small-time. Think of them like a specialized medical practice. Each consultant brings deep expertise in specific areas like Oracle licensing, Office software, or data management.

“We’re like a doctor’s office. If we need a specialist, we call them in. But we’ve all got our core strengths.”

This structure helps them stay flexible, scalable, and highly personalized with every client.


Who They Serve

Boerger Consulting works best with organizations that have at least 1,000 employees, though they can support companies with as few as 500. That’s typically the threshold where enterprise licensing agreements start showing up, and things start getting messy.

Their sweet spot: clients with an existing ITAM program who need help taking things from functional to exceptional.

And for practitioners just getting their footing? Jeremy has something new cooking: a learning cohort for up-and-coming ITAM professionals. Perfect for folks with a couple of years under their belt and no clue what to do next.


Marketing That Makes a Difference

Jeremy and team aren’t waiting around for referrals, they’re active. Between speaking engagements, LinkedIn, a thriving newsletter, and events like the ITAM Summit, they’re out there spreading the gospel.


The Value of Coaching Over Control

One of the most refreshing parts of the conversation was how Jeremy approaches client relationships. He’s not here to sweep in and act like he knows everything. His team doesn’t displace internal asset managers or push proprietary tools. They coach. They embed. They educate.  They elevate.

“We’re not trying to replace you. We’re trying to help you avoid the mistakes we’ve already made.”

This coaching-first mindset is part of what makes Boerger Consulting feel different from the pack. Clients feel invested in, not dictated to; and that helps with retention, morale, and long-term success.


Hiring with Intention

If you’re looking to work with Jeremy, bring a good attitude and a thick skin for learning. Skill sets can be taught. Curiosity, not so much.

“I call it the ‘cast iron butt’, you’ve got to be able to sit down, learn, and dig into the details. That’s how you grow.”

That curiosity is the glue that holds Boerger Consulting together. Every contractor is independent but committed to helping the team grow. It’s about collaboration, not ego.


AI and the Misunderstood Buzz

AI is everywhere these days, and Jeremy has thoughts. Spoiler: they’re not what you think.

ITAM pros have been using AI-adjacent methods like data normalization, automated workflows, and predictive modeling long before ChatGPT showed up. It just wasn’t cool enough to talk about until now.

“People are acting like AI just got invented. Asset management has been doing this for years, we just didn’t call it that.”

He’s excited about agent-based AI tools that might automate provisioning or decommissioning in the future. But it only works if the data is clean, which is what ITAM is all about. Otherwise, you’re just teaching your robot to make bad decisions faster.


Where Boerger Consulting is Headed

There’s a second edition of Jeremy’s book coming soon (currently in final review with the publisher), and that learning cohort he mentioned? It’s launching this year.

He’s also working to bring on new clients, not just for growth, but to create more opportunities to coach internal teams. The long-term goal? Keep it small and specialized, scaling only as new client needs emerge.

“We’re not trying to build an empire. We’re trying to build better ITAM teams from the inside out.”


Final Thoughts

If there’s one thing that came through loud and clear, it’s this: Jeremy is passionate about helping ITAM pros avoid the mistakes he’s already lived through. Whether it’s software audits, lifecycle headaches, or the never-ending mess of disconnected data, his team has seen it, and coached teams through it.

If your organization’s ready for better data, smoother processes, and actual clarity across your asset environment, it might be time to call in the coach.


Learn More

  • Visit www.itamcoaches.com

  • Find Jeremy on LinkedIn

  • Pick up Rethinking Information Technology Asset Management on Amazon or wherever books are sold

  • Stay tuned for the new edition, coming soo

Did you miss my exclusive webinar “Future-Proof Your Technology Investments” featuring Kim Master from Netflix?

 

Click here to access the recording.


Your journey to insightful strategies begins now!

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Picture of Jeremy Boerger<br><a class="itam-title">The ITAM Coach</a>

Jeremy Boerger
The ITAM Coach

Jeremy Boerger has over two decades of experience within the Information Technology sector. His signature Pragmatic ITAM Method is used by major manufacturing, healthcare, and global financial institutions. It enables them to Spend Less On Software Without Buying Less Software.

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Buy The Book:

Rethinking Technology Asset Management

If you’re a business leader or an IT
executive who is tired of hearing:
This is just the way ITAM is.
Then this book is for you. Buy here:


Screen Shot 2022-03-31 at 9.31.11 AM
Picture of Jeremy Boerger<br><a class="itam-title">The ITAM Coach</a>

Jeremy Boerger
The ITAM Coach

Jeremy Boerger has over two decades of experience within the Information Technology sector. His signature Pragmatic ITAM Method is used by major manufacturing, healthcare, and global financial institutions. It enables them to Spend Less On Software Without Buying Less Software.

Categories

Categories

Recent Posts

Recent Posts

Subscribe to my blog

Buy The Book:

Rethinking Technology Asset Management

If you’re a business leader or an IT
executive who is tired of hearing:
This is just the way ITAM is.
Then this book is for you. Buy here:


Screen Shot 2022-03-31 at 9.31.11 AM

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