On failing

Don’t confront me with my failures, I have not forgotten them.

– These Days, J. Browne


Six years ago. I was working on a startup with a bunch of friends, a big idea and one that got me out of bed every morning, excited to go to work. We had raised money from a Name and some amazing venture investors. We were going to be the next Google. My other gig, a venture fund, had just had the exit that put it over the top: one of the portfolio companies had gone public. Me and my two partners–one active and one silent–had made the fund back and then some. I was going to make more than living wage from the eight years of work that portfolio represented. At home, we had finished furnishing the house, our third child was on the way, and my roses were finally getting some traction.

I was out with a good friend recently. He told me an old college buddy of ours was having some trouble with his career, with his marriage. I’ll call him, I said, I should talk to him. No, my friend said, he doesn’t want to talk to you right now. He thinks you wouldn’t understand. Everything’s always worked for you.

Five years ago. Our Name investor had realized that if we stopped trying to grow the business, it would immediately begin making money. This was not what we wanted, we wanted to be the next Google, not a tiny mortgage lead generator. But he wasn’t a venture guy, he wasn’t an investor at all, he was a buyer of assets. He scared away the outside money, starved the business of cash, and forced us to accept a buyout. I had been pushed out of the company I had helped start. In the entrepreneurial community, there aren’t many marks blacker than that.

Meanwhile, my active partner in the venture fund decided that the silent partner should not be paid their share of the fund, contrary to what our contract seemed to my non-lawyer eyes to say, and certainly contrary to what fairness dictated. When I refused to go along with that, he sued me. He also sued the silent partner. The silent partner fought back, and the whole kit-and-kaboodle got locked down. The vast majority of my assets were frozen, being held hostage to some ridiculous legal squabble for some indeterminate period of time.

Not entirely coincidentally, my marriage fell apart at that exact moment.

I had failed, utterly. I had no job, my net liquid assets were approximately zero, my reputation was in tatters, and the one thing in my life I thought was permanent was over. The struts that supported my sense of self all got knocked out pretty much simultaneously. Everything I had, everything I hoped for. Five years ago today.

In what way are you the same person today that you were twenty years ago? There is no atom of matter in you that was there twenty years ago, there is no piece of you that is the same as it was. The pieces of you, the functioning of you, the pattern of you are all different. Why are you you? What is you? What is it that continues? When the Buddha told us to meditate on death this is the question he wanted us to ask ourselves: what were you before you were born, what are you after you die? In what way are you still you even twenty minutes from now?

I’ll tell you an answer, although me telling you no more gives you wisdom than reading a cookbook gives you nourishment: we are a span of links in a chain of causality. My existence now causes my existence a minute from now, and that a minute from then. There is no me except my self causing my next self every tick of the clock. In consequence, I am subject to the Markov property: how I arrived at the current me is irrelevant, every option available to me is embodied in who I am now, not in how I got here.

I’m no saint and failure did a number on me. Someone told me what intense stress would do to my psyche, the stages of irrationality I would go through. Frustratingly, the knowledge of them did not allow me to avoid them. But failure taught me some humility, and being humble forced me to abandon the personas I had built and my arrogance of idealism. And I finally learned that except in how it hobbled me, my failure made no difference–all that mattered was what I did next.

Five years after everything fell apart I have the best portfolio of startup investments in one of the hottest spaces in tech. People I respect and admire recommend me to entrepreneurs. I am allowed to be productive. And I spent Memorial Day with my loved ones and was happy and relaxed and even looking forward to getting back to work after a long weekend. I appreciate it, all of it, every time. I haven’t forgotten I had nothing. I take nothing for granted. But I no longer believe that the past determines the future. The future is determined only by the choices you have now–the ones you can find a way to allow yourself–and what you do with them.

I don’t think saying that everything has always worked for me is wholly accurate. But it may be that it is entirely true.


  1. Thank you for this Jerry, belatedly, this is inspiring and thoughtful. I shared a very small part of that startup’s pain, but given the connections we made there I agree with you that it is something that will end up being net positive in the long run.

  2. Love it.

    I often feel like I’m crushing it and failing at everything all at the same time…all about perspective of the given moment I think…

    My personal trick to keep my spirits up no matter what is going on is to always keep in mind that there are tons of people that would kill to be in my situation (just as there are tons of situations I would kill to be in).

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