🚀 What separates companies that simply grow from those that create lasting impact?

In this episode of Joey Pinz Discipline Conversations, Joey sits down with technology executive, private equity partner, and former ConnectWise COO Santo Cannone for a deep conversation on leadership, company culture, entrepreneurship, mentorship, and building organizations that endure.

With nearly five decades in technology, Santo shares lessons from helping scale ConnectWise during its formative years, serving on multiple technology company boards, mentoring startups through Tampa Bay Wave, and volunteering with foster children. His perspective extends far beyond business—covering service, curiosity, listening, humility, and what truly defines success.

Whether you’re an entrepreneur, executive, investor, MSP leader, or someone focused on personal growth, this conversation delivers practical leadership wisdom rooted in decades of real-world experience.

🌟 Top 3 Highlights:

✅ Why culture is built from the bottom up—not the executive suite.

✅ The leadership principles that helped ConnectWise become an industry icon.

✅ How serving others, asking better questions, and listening first creates long-term success.

If you’re building a company, leading a team, mentoring others, or preparing for your next stage of growth, this episode offers timeless lessons from one of the most respected leaders in the technology community.