The Magic of Dealing With Your Demons

Jessi Hempel from Backchannel just wrote an amazing profile piece on my close friend Jerry Colonna. It’s titled This Man Makes Founders CryMedium estimates that it’s an 18 minute read and I assert that it’s worth every minute.

Jerry Contemplating Something

I’ve known and worked with Jerry since 1996. I now get to call him my neighbor as he moved from New York to Boulder a few years ago. If you want a taste of our relationship, I’ve written a lot about him over the years. Following are a few recent ones.

There are a few people other than Amy and my family who I love. For example, I love my partners. I love Len Fassler, who remains to this day my most influential mentor. And I love Jerry.

There are many choice quotes in the article, but to give you a taste, here are a few.

  • “Jerry?” he responds. “That guy saved my life.” – Bart Lorang, FullContact CEO
  • “There was this moment where you admitted to each other that you were working with him. It’s not an official thing, but there is this almost secret society of people who’ve been coached by Jerry.” – Chad Dickerson, Etsy CEO
  • “Campbell had a testosterone-infused Silicon Valley kind of model. Jerry’s model is more Buddhism and less football.” – Fred Wilson, USV partner
  • “There are a lot of people you can go to who will teach you to be a better manager. Jerry understands the psychology of leadership.” – Alexander Ljung, Soundcloud CEO 
  • “Until we make the unconscious conscious, we will be dictated by it and call it fate.” – Jerry quoting Jung
  • “The Reboot team possesses an otherworldly talent for coaxing authenticity and truth out of people. They can even coax truths out of people who, like myself, have been lying to themselves for years.” – Jacob Chapman Gelt VC partner
  • “Life sucks and it’s okay. Life is great, and it’s okay. Life goes up and it’s okay; life goes down and it’s okay. If we can instill a sense of resilience in people, we mitigate suffering.” – Jerry

Go read the entire article on Jerry. And, if you want more, go listen to the Reboot podcast.

Also published on Medium.

  • jerrycolonna

    Thanks my brother. You’ve been such a profoundly important part of my own journey of healing. I love you and Amy with all my heart.

    • Jerry
      When you ‘heal’ people (crap word but you know what I mean) I assume you’ve often extinguished the crazy / dark / burning edge that made them a great entrepreneur. Better outcome for the human long term of course, but have you ever had vc’s hate you ?

      • jerrycolonna

        Great question in that it’s often the thing entrepreneurs fear. “But wait…doesn’t my crazy ass driven maniacal way of being equate to success? Isn’t that what I need to to WIN???”
        In short: no. That way of being will simply kill you, your colleagues and the people around you. Behind the fear that drives you is a deeper, more powerful set of beliefs. I often refer to it as a “superpower.” The point of radical self-inquiry is to access THAT power. A calm, focused, intense, bright, powerful “warrior-like” stance that creates BOTH drive AND resiliency. There is NOTHING soft about being authentic and real. In fact, it’s fucking harder than being maniacally-driven by fear and paranoia. In fact, facing and working with your demons is harder than building a company. Once you do that, and access the truth of who you really are a leader, the rest is just dumb execution.

        Now SOME VCs (especially those who’ve come to the bootcamps that I, my colleagues at Reboot, and Brad run) get this. But many investors are too plagued by their demons to allow entrepreneurs to succeed. That’s right. Their unprocessed nonsense prevents the entrepreneurs from succeeding. Crazy perverse thinking, eh? Welcome to hanging out with human beings.

        I get tired of people thinking that being real, being authentic, being yourself is some “namaste” soft bullshit. Anyone who thinks so should come to one of our bootcamps. 🙂

        BTW…The VCs who’ve invested in the companies we work with love the results. ‘Cause, as in the case of Bart Lorang, better humans make better CEOs and better CEOS produce better ROI.

        • jerrycolonna

          btw…on a flight now so I’ll likely be offline for a while.

    • I love this post and the profile post. I certainly am not worthy but if you ever need a shoulder reach out.

      You know what makes me happy is making other people successful. You gave me the biggest complement on your Fred Wilson’s post.

      My happiest moment this year was having our Lego Robotics team show third in all of the states out of more than one hundred teams. They were just kids and we invested hundreds of hours in them our return was so much more. Half don’t speak English at home and 40% are girls. I’d post a picture and video but they are 9 to 10 years old, so i will only email one.

      • jerrycolonna

        Ah that is so beautiful. Thanks for the offer of a shoulder. There is no such thing as not being worthy enough to offer love and support. And the offer IS love and support. Thank you. Taking pleasure and delight in other’s being well has been a healing balm for my broken heart. To me, that is the basis of compassion. Be well.

  • Richard

    I’m a little troubled by the endorsement “the guy (jerry) saved my life”. It’s important for people to know that for “entrepreneurs who fear for their lives, there are options that dont necessitate a 5k a month retainer.

  • turns out, when you are real, authentic etc, you wind up NOT walking alone. when you are fake, and all hype, no one really picks up their sword to help you or follow you. You wind up being alone.

  • Gary

    Thanks for posting Brad.

    Everybody’s different but I learn a lot from people when I see how they deal with problems and troubled times. Seeing Jerry make it through and what he learned was inspiring.

    Do you watch Real Sports on HBO? On the current episode, there’s a segment with Cubs manager Joe Maddon. I think you’d really get a kick out of it.

  • Jerry
    When you ‘heal’ people (crap word but you know what I mean) I
    assume you’ve often extinguished the crazy / dark / burning edge that
    made them a great entrepreneur. Better outcome for the human long term
    of course, but have you ever had vc’s hate you ?

  • Myla Mercer

    Your blog is inspiring – thanks for this post!