The Conversations We’re Afraid to Have with Jerry Colonna

Jerry Colonna CEO of Reboot.IO and former venture capitalist joins us for one of this year’s deepest and most thought provoking conversations about resiliency, our sense of self, and much more. 


  • The keys to developing resiliency
  • Myths about our moment of arrival 
  • Dealing with impostor syndrome 
  • Uncoupling our sense of self from extrinsic 
  • The storm of emotions of that make up life
  • The power of insatiable curiosity and voracious reading
  • Lessons learned from working with Fred Wilson


Books and Resources

Faith by Sharon Salzburg

When Things Fall Apart by Pema Chodron 

The Reboot Podcast 


Whatever capacity I have to see has come from standing on the shoulders of giants.

The fact that I cry and I feel, that’s a superpower. 

I think that we’re afraid of our own feelings. 

How can you be in relationship with someone if you don’t know who you are and you don’t love yourself? 

I used the chase to define myself for such a long that time that when the chase was over who was I? 

The promise of Buddhism is not eternal salvation. The promise of Buddhism is the alleviation of suffering in this lifetime.

Jerry Colonna is an executive coach who uses the skills he learned as a venture capitalist to help entrepreneurs. He draws on his wide variety of experiences to help clients design a more conscious life and make needed changes to their career to improve their performance and satisfaction 

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