One of the very first VCs of the Internet Era, and especially the NYC tech ecosystem, Jerry Colonna reflects on his journey from growing up in New York to becoming a successful journalist and venture capitalist. Jerry discusses his transition to venture capital, the founding of Flatiron with Fred Wilson, and the challe

Radical self-inquiry begins by asking yourself tough questions, such as "How am I complicit in the circumstances I say I don't want?" Honest self-reflection is a crucial step in improving as a leader. In today's episode, Jerry Colonna, CEO of Reboot.io, executive leadership coach, and bestselling author, discusses lead

How do we navigate seismic shifts in our industries and our lives while striving to remain true to ourselves and those we care about? In this episode, Jerry sits down with Randy Goodman, recently retired Chairman and CEO of Sony Music Nashville, to reflect on a career arc that spans decades of change, challenge, and pr

Jerry Colonna is a world-renowned executive coach, a former venture capitalist, and the co-founder and CEO of Reboot, an executive coaching firm that combines practical leadership development with deeper self-inquiry. With over 27 years of coaching experience, he has guided countless leaders through the challenges of s

Former American venture capitalist and once named a “Prince of New York” by New York Magazine, Jerry Colonna faced a profound depression that compelled him to confront his inner demons through what he calls “radical self-inquiry.” This transformative process led him to Buddhism and leadership coaching. Now a certified

In episode 17 of season 2, we sit down with Jerry Colonna, the CEO of Reboot.IO and author of Reunion: Leadership and the Longing to Belong. Jerry is known for his radical approach to leadership and self-inquiry, and in this episode, he shares his insights on how leaders can create conditions of belonging within their