#72 – From the Trenches: Mentor-Driven MSP Growth & Practical AI Automation (Kevin Kahn)

In this From the Trenches episode, Kevin Kahn joins Josh Peterson for a candid conversation about what actually drives durable MSP growth: the mentors who changed your trajectory, the relationships that compound over decades, and the operational discipline required to scale without losing your soul. Kevin shares how an early “bankroll-and-belief” mentor helped him buy out a partner, survive near-collapse moments, and build an 80-person MSP that still prioritizes customer connection over transactional delivery. Along the way, Josh connects the dots to execution systems and measurement—reinforcing the importance of the Vision operating system, why structured peer learning matters, and how mature MSPs think about agreements and accountability in the real world (see peer teams and the impact of MSP SLAs on pricing).

The discussion then turns to what’s changing fast in 2025: AI, automation, and the growing reality that clients are already being approached by specialized “AI outcomes” firms—forcing MSPs to learn and deploy automation internally before they can credibly advise externally. Kevin explains his pragmatic stance: adopt AI where it truly removes friction, protect the customer experience, and keep humans at the center when empathy is required—because when everything is broken, clients still want a real person. Josh and Kevin also unpack tooling choices and reporting maturity (including Halo’s evolution), the risks of tool-switching, the shifting role of the modern technician, and why long-term success still comes down to trust, operational efficiency, and leadership that keeps paying it forward.

For MSP leaders looking to strengthen execution and long-term performance, explore related resources from Bering McKinley: the impact of MSP SLAs on your pricing structure, peer teams: why bother, and how MSPs ensure 99.9% uptime through infrastructure management.

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Episode Highlights

• 00:00:16 – Kevin’s origin story: from accounting detour to building an MSP from the ground up.
• 00:02:47 – The mentor moment that changed everything—and why paying it forward still matters.
• 00:05:26 – “All you can eat” helpdesk billing: getting the model right, then fixing pricing over time.
• 00:08:08 – Switching PSA/RMM: why it’s painful, when it’s justified, and what Halo changed for visibility.
• 00:20:56 – The 2025 outlook: security, AI, automation, and the relentless push toward efficiency.
• 00:23:46 – It’s already happening: AI advisory firms knocking on client doors—and how MSPs can respond.
• 00:31:01 – The human edge: AI won’t replace empathy—especially when clients need reassurance under pressure.

About the Guest

Kevin Kahn is an MSP owner and operator based in Baltimore and the leader behind Intellicomp. With nearly three decades in IT, Kevin has built a relationship-driven organization that grew organically for years before formalizing sales—while navigating major client losses, scaling challenges, and the constant evolution of tools and delivery models. Today, he’s focused on practical AI adoption, operational efficiency, and keeping human connection at the center of client experience as automation accelerates across the industry.

🌐 Connect with Kevin on LinkedIn →

About the Host

Josh Peterson is the CEO of Bering McKinley and host of the BMK Vision Podcast. Through the From the Trenches series, Josh speaks candidly with MSP owners and operators about growth, execution, and the realities of building sustainable service businesses.

🔗 Connect with Josh on LinkedIn →