Surviving the Startup Life: Q&A with Jerry Colonna

By December 2, 2014No Comments

At Pioneers Festival 2014, Jerry Colonna had an incredible session on the Academy Stage, where he talked about being a startup CEO: how the frenzied and frenetic life of startups can destroy you, your family and your company. How can you lead yourself and your startup to success without a meltdown? Drawing on his work as a venture capitalist and executive coach, Jerry says the magic happens in the crucible that forms a leader.

Everybody knows we want to care about our families. But that ego who flies from east to the west is somehow stronger – how to beat it?

Jerry: Well I love that you’re referring to my story of flying back and forth to the West Coast from NY in a single day to "prove" how successful I was.

And I think the answer to your question lies in the question itself: The reason I had to do that was that I felt inadequate in my soul. I was trying to close a hole in heart, the source of a sense of worthlessness, by proving how successful I could be. The answer of course is to find another way to address the sense of worthlessness. The answer is to disconnect from external sources of affirmation (such as believing that presenting in a ballroom at the Imperial Palace in Vienna – as I did for the Pioneers Festival – means I’m a good and worthy person. I’m good and worthy because of my humanity.)

The irony of course is that the best parenting I could do would be to model for my children what it’s like to find motivation from intrinsic sources. The best I can do for my children is to teach them to love themselves for themselves and not because of what they’ve done who whether or not they can fly in First Class.

What is a book you advise anyone here to read to be able to resist the fire better?

Jerry: There are a few: David Whyte’s Crossing the Unknown Sea and The Heart Aroused are two beautiful books that explore the existential relationship between the Self and Work. But I also highly, highly recommend Let Your Life Speak, by Parker Palmer.

Parker, who’s become a dear friend, is incredible and looks well at these questions of meaning and work and vocation. Indeed, so profoundly impactful is that book that we use it as a core text in’s bootcamps.

Parker and I are also completing a book a together… one on depression and entrepreneurship. That should be available in a few months.

How can I reduce the time it takes me to take decisions. (Stressful!)

Jerry: This is one of those questions I love. On the surface, it seems to be about productivity and efficiency. But, really, it’s not–and the way I know this is so is because of the addendum: "Stressful!"

So, based on that, I’m going to respond with some assumptions. I assume, for example, that when you’re in the throes of indecision, you feel agony. What is the source of the pain? I imagine it to be fear… fear of making the wrong decision.

Which really is a mask for fear of failure. And this is the root problem.

So if you spend all of your time trying to improve your decision-making process, you’ll not release yourself from the stress. The real problem is that you see each decision as life-threatening. What if, instead, each decision were merely a step in the experiment called "Your company."

What if the process of making a decision and discovering you were wrong were just as valuable as making the right decision?
And, if the entire exercise is merely an experiment, isn’t that the case?

I hate my cofounder for not doing enough. How do I not burst out?

Jerry: Ah, as I often say, hate is really, really interesting. There’s an old Buddhist teaching that goes like this:
Be grateful to everyone, including the people who press your buttons, because they show you where YOU are stuck.

The way to manage your anger, as I’ve often taught, is to become friendly with the fear that drives your anger. The anger is out of control (or barely contained) because you’re not speaking about the ways in which your co-founder’s actions–or non-actions–are scaring you. (For example, you’ve also have a case of Fear of Failure.)

Making matters worse, you and your co-founder have not defined your relationship (with clear, unambiguous language that I would label as Being Fierce–see my videos and blog post on the subject). You’d both do well to come to Reboot’s first Co-Founder bootcamp next Spring.

Lastly, as I often explore in work with clients, and as Parker Palmer analyzes in Let Your Life Speak, the hate that you feel is–in all likelihood–rooted in your own aggression towards yourself. Carl Jung’s concept of the Shadow comes to mind whenever I hear someone speaking of hate. We often hate the things others do because they remind of things about ourselves which we’d rather disown, keep in the Shadow.

To release yourself, consider reading Owning Your Own Shadow by Robert Johnson.

How do you find your stand still activity?

Jerry: Great question. Here’s where my concept of Radical Self-inquiry can be helpful. Really being honest with yourself as you inquire into what makes you happy.

For me, journaling has been my salvation. By journaling I came to know myself quite well, to cut through my own bullshit, and finally to recognize the things that I did that made me feel badly and the things that I did that made me feel good.

So I try to do the things that make me feel good and which don’t hurt others (like sitting in meditation and going to the gym) and do those more often.

When did you most regret not taking a breath before making a decision?

Jerry: Oh my. There are so, so many things I regret. Usually though they have one thing in common: when I act because I can’t stand inaction or uncertainty. Learning to recognize that sometimes I have to wait before deciding is incredibly painful.

My biggest regrets in this area though tend to be around the things I’ve done or said that hurt people. And in looking back, they were always rooted in my poor handling of my own fears.

You refer a lot to religion and spirituality. Isn’t business a means to an end? So not spiritual process?

Jerry: Ah, but I disagree. Let me explain: I think LIFE is a spiritual process.
That is, I define a spiritual process as things that take us closer and closer to our truest, most authentic and most fully-actualized self (in the Maslow sense of self-actualization). Those things that take us there are divine. I know this to be true because it produces a sense of equanimity and well-being (even if there’s sadness) for myself and those closest to me.

My friend Parker Palmer likes to say that his depression is caused by actions that are "cross-wise" with his authentic self. For me, my depression is almost always prompted by what I sense is my own tendency to disassociate from my Self, to leave my Self, and act in a way that is contrary to my Truth.

Therefore those things, which take me back to my Truth, my Self, are divine, spiritual

I firmly believe that work can be a place in which we get to live out our truest Self. Even if your work isn’t "creative" it can be a creative expression of your soul. Even if your work doesn’t appear to be saving the world, it can create a means for your own transformation and emergence as a dear and authentic self.

One of the most full-actualized and beautiful men I ever met was my boss in a job I held as a teenager. Jack Martinez was a Basque. He left school in the sixth grade and traveled the world as a merchant marine. He believed in me even though I was a scrawny clumsy teenager. And when I spent the summers of my youth traveling around the suburbs of NY, fixing school lockers, I learned to use tools, I learned to believe in my capacity to learn to fix anything.
That gift was spiritual. He gave me a chance to grow.

What do your kids think about your philosophies?

Jerry: Ha! I THINK they, for the most part, appreciate them. But they do get sick and tired of me sounding like a coach all the time. Fortunately they have the guts to tell me shut up and to not take myself so seriously.

“Disappearing into the Fire: Surviving the Startup Life” – Jerry Colonna

Watch Jerry Colonna’s session from Pioneers Festival 2014 here:

Download the slide deck of Jerry’s talk here
: "Standing Still while Your Hair’s on Fire". You can also check out THE REBOOT PODCAST here.