Jerry Colonna — Leadership, Fear, and the Inner Work of Building Companies

What if the hardest part of building a great company isn’t strategy, fundraising, or product—but confronting yourself?

In this episode of Human Unicorn, we sit down with Jerry Colonna—executive coach to some of Silicon Valley’s most iconic founders, former VC, and author of Reboot—to explore the inner lives of leaders. Jerry shares hard-won lessons from decades of coaching CEOs through growth, breakdowns, and breakthroughs, revealing why unresolved fear, shame, and identity often shape business outcomes more than market forces.

We talk about the myth of the heroic founder, why “bringing your whole self to work” is both necessary and terrifying, and how true leadership begins with radical self-inquiry. This is a conversation about power, vulnerability, and what it really means to build companies—and lives—worth being proud of.

If you’re a founder, operator, or leader navigating pressure, uncertainty, or success that feels strangely hollow, this episode will challenge how you think about ambition, culture, and yourself.

Topics covered:

• Why leadership is an inside job
• The emotional cost of scaling companies
• Coaching founders through fear, ego, and failure
• Redefining success beyond metrics and exits
• How compassion becomes a competitive advantage