Field notes from the road, kept like a journal.

№ 02

May 19, 2026

MSPGeekCon 2026 · Orlando, FL

This deck reframes the entire AI conversation for MSPs around a simple shift: you don’t sell AI, you operationalize it. The core insight is that clients are already using AI without structure or oversight, often running multiple unsanctioned tools in the background. The opportunity isn’t introducing AI, it’s stepping in to manage the chaos. Just like previous waves like cloud and cybersecurity, the pattern repeats. Fear shows up first, but the MSPs who lean in early expand their role and capture more value. The document makes it clear that most current approaches are broken. Custom AI projects and “AI readiness” engagements are framed as consulting work that doesn’t scale, serving a small percentage of clients with high effort and little compounding value. This leads to what’s called the “trough of no value,” where licenses are purchased and money is spent, but there is no training, governance, or real adoption. The result is predictable: customers feel the cost immediately, but the value remains invisible, creating pressure from leadership asking where the ROI actually is. The path forward is operationalization as a managed service. This means moving from one-time projects to a recurring motion built on governance, training, and measurable outcomes. The shift from “AI ready” to “AI enabled” is central. Ready is a future state and a project, while enabled is something that happens now and is sustained over time. By establishing policies, enabling users, driving adoption through cadences like QBRs, and continuously improving workflows, MSPs turn AI into a repeatable, scalable service that delivers visible ROI and compounds over time.

№ 01

May 18, 2026

MSPGeekCon 2026 · Orlando, FL

Your professional growth depends less on linear moves and more on the intentional collection of diverse experiences. This session explores how compounding curiosity transforms a standard technical path into a resilient, high-value career. Learn to identify the hidden patterns in your work history that signal when to pivot and how to deepen your expertise.