In this wide-ranging and deeply thoughtful conversation, Joey Pinz sits down with Jason Magee, former CEO of ConnectWise and current CEO of Cynet, to unpack what leadership really looks like when the stakes are high and the noise is constant.

Jason shares his personal journey through a major health challenge, a high-profile CEO transition, and the mindset shift required when moving from leading a global platform company to scaling a fast-growing cybersecurity organization. Together, they explore the difference between leaders and managers, how to spot real growth versus empty visibility, and why disciplined decision-making matters more than ever.

The conversation dives deep into AI, automation, cybersecurity, and the realities MSPs face today—from talent shortages to increasing threat pressure and consolidation. Jason also opens up about motivation, legacy, burnout avoidance, and how leaders can stay grounded while navigating complexity.

This episode is a masterclass in modern leadership, focus, and long-term thinking—for CEOs, founders, MSPs, and anyone responsible for building teams, platforms, and trust in a rapidly evolving industry.

🌟 Top 3 Highlights:

🧠 Leadership vs. Management — why titles don’t define influence

🔐 Cybersecurity + AI Reality Check — separating signal from hype

🧭 Sustainable Growth — how leaders stay proactive instead of reactive