Most organizations are adopting AI tools without fully reckoning with what that adoption means for security. In this episode, Kyle Hall sits down with Kyle Gotzman to break down why traditional security models, including role-based access controls and standard detection methods, weren't designed for a world where AI agents can act on behalf of users at machine speed.

They cover the concept of bounded agency, why the MCP layer is becoming the critical choke point in agentic AI environments, and what IT leaders actually need to be thinking about before they hand an AI system the keys to their infrastructure. Whether your organization is deploying Copilot across the company or starting to build agentic workflows, this conversation cuts through the noise and gets practical about where the real risks live.

Managed service providers are often viewed as a way to reduce IT costs, increase coverage, and simplify operations.

But the reality is more nuanced.

In this episode of The RaaP, Kyle Hall and Kyle Gotzman discuss why MSP selection is becoming a more common priority for mid market, enterprise, and private equity backed companies. They break down what MSPs actually provide, where companies misunderstand the economics, why comparing current IT spend to an MSP quote can be misleading, and what makes the selection process so difficult.

The conversation also explores when companies should consider changing providers, how growth and acquisitions can expose MSP limitations, and what good looks like once the right partner is in place.

Most organizations don’t have a shortage of ideas.

They have a prioritization problem.

In a world of infinite options, there are finite resources.

Figuring out how to allocate those resources for maximum impact is where most teams get stuck.

Over time, IT environments drift.

Priorities shift. Vendors stay longer than they should.

What once made sense no longer lines up with where the business is going.

We’re seeing more leadership teams step back and ask a simple question: Are we investing in the right things?

In our latest episode of The RaaP, we break down how we approach that question through what we call an Impact Assessment.

A structured way to evaluate spend, strategy, and execution and bring it back into alignment.

In this episode of #TheRaaP, Kyle Hall and Kyle Gotzman break down the full build buy rent framework and why skipping this step leads to wasted spend, missed differentiation, and frustration across the business.

They walk through:

• Why build vs buy is an incomplete analysis

• How to think about differentiation, durability, and time horizon

• The real costs and risks of building software

• When acquiring a product makes sense and when it does not

• Why renting is often the right answer and when it becomes a trap

• The growing “rent and extend” model most teams are actually using today

The biggest takeaway: there is no universally right answer, but there are very clear wrong ones. The key is intentional, cross functional decision making before the technology choice is ever made.

In this episode of The RaaP, Kyle Hall and Kyle Gotzman strip negotiation back to fundamentals. No games. No manipulation. Just practical rules that consistently produce better outcomes.

They cover:

• How to recognize when you’re already in a negotiation
• Why most bad negotiation is actually bad preparation• How to separate must haves from nice to haves• Why understanding the other side makes you stronger, not weaker• How giving value away silently creates long term problems

Whether you’re negotiating vendor contracts, salary, project scope, or internal priorities, this episode focuses on one thing: clarity with intention.

Most organizations don’t fail because of bad ideas. They fail because execution never truly begins.

In this episode of The RaaP, Kyle Hall and Kyle Gotzman unpack why so many plans stall after the PowerPoint and what actually drives outcomes once the planning phase ends.

The conversation focuses on three execution fundamentals that apply at every level of an organization:

• Building the right team for the outcome

• Creating a bias for action without chaos

• Aligning around a clear, shared desired end state

If you’re responsible for turning strategy into results in January and beyond, this episode is about getting out of ideation mode and into motion.

In this episode of The RaaP, Kyle and Kyle break down the most common—and most costly—pitfalls organizations encounter during the IT sourcing and vendor selection process.

From the ubiquitous “Yes, we can” trap, to hidden-fee mazes, to sales-to-delivery handoff failures, to misleading baseline quotes, to the ticking clock of renewal time bombs, the team walks through how these issues show up in real projects and what buyers can do to avoid them.

They also discuss why vendors aren’t acting maliciously—just operating within their incentives—and why experienced partners can spot these patterns early. The conversation is tactical, practical, and directly rooted in lessons from the field.

In this special episode of #TheRaaP, Kyle Hall and Kyle Gotzman take a step back from their usual topics to reflect on Veterans Day, and what military service continues to mean in business and leadership today.

From the shared trust between veterans to the Marine Corps’ timeless culture and rituals, they explore how strong foundations and shared values enable agility and evolution — both in the military and in modern organizations.

MIT recently reported that 95% of GenAI projects are failing, but not because of the technology itself.

In this episode, Kyle Hall and Kyle Gotzman dig into why so many organizations can’t get their AI pilots out of the lab.

The answer isn’t innovation, it’s foundation. From data quality and process discipline to governance and patience, they explore how companies that mastered the basics years ago are now reaping the rewards of AI, while others struggle to make progress.

They also discuss what it means to “earn the right” to adopt new technology, the difference between moving fast and moving forward, and how preparation, not speed, creates real transformation.

In this episode of #TheRaaP, Kyle Hall and Kyle Gotzman dive into one of the most critical exercises for IT and finance leaders during budget season: assessing external IT services spend.

They break down the foundational steps every organization should take, starting with building a baseline inventory of spend, normalizing vendor data, and questioning long-held assumptions.

From there, they explore how to prioritize opportunities using a practical framework that balances cost, architecture, and security.

Whether it’s identifying stranded services, rationalizing security tools, or grading initiatives based on impact and difficulty, this conversation provides a clear roadmap for finding meaningful savings without losing sight of business outcomes.