Reboot

Jerry Colonna's journey to founding Reboot began not with ambition but with desperation. Despite outward success as a hotshot venture capitalist and co-founder of Flatiron Partners—one of the most successful early-stage investment funds in the world—he found himself profoundly depressed and suicidal in his late 30s. He realized that all the trappings of success—the money, the status, the accomplishments—had not delivered the promise he'd internalized since childhood: that success would make him happy and safe. This painful truth became his North Star. Colonna recognized that he, like many entrepreneurs and leaders, had been chasing a mirage, what he calls "the pursuit of lemon drops." Growing up in financial chaos, he'd associated his grandfather's endless supply of lemon drops with safety and stability. Decades later, despite having actual wealth, he still didn't feel safe. This realization sparked a deeper question: how could he help other leaders avoid the same trap?

Colonna didn't set out to build a company immediately. Instead, he began experimenting with a model grounded in what he calls "radical self-inquiry"—the practice of asking uncomfortable questions about our deepest beliefs and the stories we tell ourselves. Working with his co-founder Allie Schultz, they designed what became known as CEO Boot Camp. The original iteration was deceptively simple: they would market practical skills to first-time CEOs, then use what Colonna describes as a "bait and switch" to ask the real questions. "Who would you be without the story of who you are?" "Tell me about your father." "What's your relationship to money?"

They also formalized an equation that became central to Reboot's philosophy: Practical Skills + Radical Self-Inquiry + Shared Experiences = Enhanced Leadership + Greater Resilience. The breakthrough was understanding that when leaders gathered in circles where they could tell the truth—where their companies weren't always "moving up and to the right" and their products weren't always "working"—transformation happened. This shared vulnerability created space for authentic growth.

The early adopters were first-time CEOs who were already experiencing some form of crisis or dissatisfaction despite their success. Word-of-mouth became the primary driver as leaders who attended boot camp shared their experiences with peers. Colonna's credibility as a former VC partner and his willingness to be radically honest about his own depression gave the offering immediate authenticity. He wasn't selling another productivity hack or leadership framework; he was offering a path to becoming more human while leading.

What worked was the counter-intuitive nature of the offering. In an entrepreneurial culture obsessed with growth and optimization, Reboot asked the opposite questions: What are you not saying that you need to say? How have you been complicit in creating the conditions you say you don't want? What would happen if your self-worth wasn't attached to your outcomes? These questions terrified people—which meant they were working. Colonna discovered that the most powerful coaching happens when questions "take your breath away."

The model also worked because it addressed a real blind spot in the startup and executive world. Everyone was talking about building great companies, but no one was talking about building great humans—and the catastrophic cost of pursuing success at the expense of mental health and authentic relationships. By creating spaces where leaders could acknowledge their depression, anxiety, and existential doubts without judgment, Reboot filled a critical gap.

More than 25 years into his coaching practice, Colonna has become one of the most respected voices in executive development. He's authored two books—*Reboot* and *Reunion*—and continues to lead a thriving coaching and development firm. He's also leveraged AI tools like ChatGPT and Claude as thinking partners, uploading his own 10+ years of journals to reflect on blind spots and patterns. Importantly, he's maintained his beginner's mind, holding his own frameworks loosely and continuing to ask the hard questions of himself. His message has only grown more urgent in what he describes as a chaotic and unsettling time: the world needs leaders who are kind, present, and willing to do their own internal work. At 62, Colonna is focused on his legacy—not as a businessman, but as an ancestor and a voice of sanity in an increasingly fragmented world.