Why do so many successful companies eventually fail?
In this episode of Gaining the Technology Leadership Edge, Mike sits down with Sid Mohassib—entrepreneur, investor, and author—to unpack why businesses struggle to evolve, even when they have strong leadership and market position. Drawing on decades of experience advising Fortune 500 executives, Sid explains how ego, profit obsession, and resistance to change quietly erode competitiveness.
Sid reframes business as a series of exchange relationships: with customers, employees, partners, investors, and society. He argues that leaders don’t “empower” people—employees already have power. Instead, effective leaders act as facilitators, creating the conditions where creativity, accountability, and alignment emerge naturally.
The discussion challenges popular assumptions about work-life balance, replacing it with the concept of harmony, and explores why fully remote work can weaken creativity, loyalty, and innovation if relationships are lost. Sid also addresses AI and automation head-on, arguing that the real risk is not job displacement, but failing to mentally evolve as technology reshapes how value is created.
This episode is essential listening for technology leaders who want to build organizations that don’t just survive change—but evolve with it.
