Asshole To CEO #3: How I Learned To Own My Failures

“Evil isn’t done so often by evil people, but by good people who do not know themselves.”
-Reinhold Niebuhr

My first post in this series was about my start-up and business failures.

When I was done, I felt proud of myself. I was proud of my honesty and vulnerability, because  five years ago–maybe even one year ago–that post doesn’t get written. I would have hid my problems or argue them away, claiming the failures were other people’s faults, not mine, and I was proud that I wasn’t doing that anymore.

I should know this by now; as soon as I feel prideful, the fall is coming. The very first email response:

“That article was revealing, but missing something. How did you come to understand these flaws in yourself? You just tell us what your mistakes were, and not how you got to that insight, which is what I really want to know, so maybe I can do this for myself.”

Gut punch.

Publicly owning my failures wasn’t hard. That was easy, actually.

What was hard was getting to the point where I could actually own my failures to myself, and I didn’t really explain how I did that at all.

I wrote about the result of that work, which is, at its core, just me showing off.

That’s the dirty little secret of the fetishization of failure in Silicon Valley. It’s by and large a high-status excuse to show off. You tell everyone how many businesses you’ve started and how much money you raised, and how you are a better person through humility. You are competing to see who can be more humble. No one dives into how they actually learned from their failures, because they didn’t. It’s entrepreneur porn.

I hate when people do that…yet it’s exactly what I did.

That’s bullshit. If I want to write for me, it’s totally fine, I just need to keep that shit in my fucking diary. If I’m going to publish it, it has to be for other people, to help them.

That’s what this post is. A deep dive into how I actually learned to own my failures to myself. I’m writing and publishing this so that, by seeing my process, you can help yourself do something similar.

When My Perception Of Identity Was Fucked Up
Like I said, I already wrote a whole post about my start-up and business failures, but the one thing I did not do in that post was get deeply into how I screwed up. So I’ll dive into one example of a big failure, probably my biggest and most personal ever:

 

 

 

 

 

 

 

 

The movie about my life failed. And it failed mainly because of my bad decisions, and all of those decisions were ultimately driven by my deep identity and emotional issues.

I had an immense amount invested in this movie. Not money–I actually had zero money invested in it. But I had my entire identity and emotional state invested in its creative and commercial outcome.

If it succeeded, then I was a success. It was, at least in my subconscious, nothing less than a referendum on me as a person. Valid or not valid. Good or bad. Worthy or unworthy. Everything about who I was rode on the success of that movie, and every decision I made was deeply and unconsciously impacted by that.

The full story of that movie could be it’s own movie, but some quick, easy examples of how this emotional identity issue impacted my decision making:

  1. We had the wrong director. You know who picked him? Me.
  2. Very smart people told me I was wrong, and gave great reasons to not select this director. I ignored them. Why? My deep need to show everyone that I was right about MY decision. I made it about me.
  3. We had the wrong production company. You know who picked them? Me.
  4. Very smart people told me I was making a mistake. We even had a HUGE offer from the best studio in Hollywood. I turned them down. Why? Because, again deep down, I wanted to prove I could beat the Hollywood system by making an indie movie that I owned and I controlled. I made it about me.
  5. We still could have made a good movie–even with a bad director and the wrong production company. But the shoot sucked. You know why? I made the whole thing about me.
  6. Why? My need to show how smart and important I was became so manifestly important to my identity, that it sent my controlling side into overdrive. Nobody knew my life better than me. Nobody knew me better than me. So only I could make certain decisions. I screamed at a lot of people. Not because I hated them, but because their ideas about the character and the world of the movie so threatened my perception of myself that I couldn’t allow words or concepts that I disagreed with to even leave their lips. I emotionally and spiritually crushed everyone on that movie set, all because of my own emotional issues I would not face.

I could go on and on with examples like this. You get the point.

I can remember the night I knew the movie wasn’t going to do well. It was possibly the hardest night of my entire life. I cried more than I had ever cried in my life. I felt the worst I’d ever felt about myself. The emotional pain was so intense, so real, it became literal physical pain.

I wasn’t suicidal, but I honestly felt like I wanted to die. I’d spent the previous seven years scratching and clawing and fighting to get to this moment. I’d run through walls, over people, around obstacles, all for this? To feel this way?

I’d never felt so alone, so crushed, so utterly defeated. I had not failed at something. I felt like, in a very real emotional sense, that I was a failure as a human being.

Believe me, I FULLY recognize the self-indulgent absurdity of this scene: here I was, a rich and famous white guy, who someone gave millions of dollars and creative control to make a movie about his life based on his #1 New York Times bestselling book, crying because it didn’t do 50 million dollars its first weekend? Boo fucking hoo.

But emotions and identity and self-perception are not about objective facts (talk to any Trump fan to see proof of that). This is about the emotional reality of my life, and it was this moment–where I felt like my entire personhood was a failure and invalid–that set me on the journey I am on today.

That was my emotional bottom. From that moment, I knew I had to get help. I knew the way I looked at the world, and at myself, was broken, and it would break me completely if I didn’t change it. I didn’t know why, and I wasn’t sure how, but I knew it was my reality.

A few months later I moved to Austin and started psychoanalysis. I also started angel investing at the same time. It was a coincidence, but those two things together taught me how to take responsibility for my actions and own my failures.

How Therapy Helped Me Shift My Identity Problems
It might be hard to understand how identity and the unconscious works. I can’t begin to give a full explanation of it, even in a long piece like this. One of my favorite blogs on the internet had a great explanation about how this works:

“The unconscious doesn’t care about happiness, or sadness, or gifts, or bullets. It has one single goal, protect the ego, protect status quo. Do not change and you will not die. It will allow you to go to college across the country to escape your parents, but turn up the volume of their pre-recorded soundbites when you get there. It will trick you into thinking you’re making a huge life change, moving to this new city or marrying that great guy, even as everyone else around you can see what you can’t, that Boulder is exactly like Oakland and he is just like the last guys. And all the missed opportunities–maybe I shouldn’t, and he probably already has a girlfriend, and I can’t change careers at 44, and do I really deserve this?– all of that is maintenance of the status quo, the ego.”

If you want to learn more quickly, Paul Graham has a great essay about separating your identity from the results of your actions, called “Keep Your Identity Small.” There are so many books and research papers about this idea, the problem is that they all have different names and different conclusions (quick start on background: a research paper showing people literally can’t do math when it goes against their identity, and a good book intro to this is Mindset).

The best tradition I’ve read to deeply understand this issue is actually the oldest: Buddhism (the actual Buddha called this problem in people “The Hungry Ghost”). In fact, you could say that this insight is the key insight of Buddhism: all the suffering of humanity is caused by the attachment to an identity or a result.

It’s even enshrined in their primary dicta, the Four Noble Truths:

[Don't worry, I won't lecture you about Buddhism, I promise]
[Don’t worry, I won’t lecture you about Buddhism, I promise]
How you define and see yourself and the results you strive for creates the suffering you endure. In essence, the less you are attached to things, and the more you just experience them, the better off your life is (I also included some basic reading lists for Buddhism at the end as well).

Simple to say, but hard and complicated to apply to your own life. I tried to learn this by just doing psychoanalysis and reading a lot about it. I have a large dent in my checking account and an even larger collection of flagged and annotated books as testaments to that effort. Eventually I got it “intellectually.”

But getting something in your conscious brain is VERY different than getting it deep in the unconscious. I only learned HOW to apply this concept (divorcing your identity from your results) to my unconscious—-to my own thinking and my own emotions–from the time I spent angel investing.

Lemme walk you through how that that process worked for me, maybe that will explain better.

How Angel Investing Taught Me To See Entrepreneurs’ Issues
When I was first starting my own companies, I was emotionally attached to each of my ideas,  and attached to their success. Not in the sense that because I worked hard on them, I really wanted them to happen. That’s normal. I was attached in the way that the ideas and the success became part of my identity.

When I say “became part of my identity” I mean this as literally as possible. I would, at least unconsciously, think that if my business idea succeeded, then I was a success. And if the business idea failed, then I was a failure.

I couldn’t look at my ideas or my companies objectively, with any kind of detachment, because they represented, in a very real way, a judgment of myself as a person. Their success was, in my mind, nothing less than a judgment of my validity as a human. Just like on the movie.

Being so attached to results was a problem. It prevented me from honestly and critically looking at my ideas and their results–even if they weren’t working. Especially then. It was too painful to see they weren’t working, because that made me feel bad about myself as a person. So I would lie to myself or convince myself that something stupid was smart (if you’re familiar with western psychology, this is basic rationalization and projection, and I did 100 times on the movie).

If you do this in a relationship, that’s not good. But it’s just about the very worst thing you can do as an entrepreneur (or a creative). Facts are facts, whether you like them or not, and if you are making emotionally-driven decisions about factual situations in start-ups, then you are going to make bad, bad business decisions.

Here’s where angel investing helped me: I wasn’t evaluating my own decisions or identity. I was looking at other people and their decisions.

My job as an angel investor was very simple: I bet money (through buying equity) on my ability to correctly assess three things: 1. the entrepreneurs who pitched, 2. the product-market fit of their start-up, and 3. the market they were competing in.

If I did it right, I made millions. Wrong, I’d lose millions. Even though I’ve stopped, I made millions.

The reason I did so well is because when I evaluated other people’s start-up ideas, I didn’t have any attachment to them. It meant nothing to my identity if they were good or bad, so I could be completely objective. I could look at the facts with clear eyes. I could ask hard questions. I could see other alternatives. I wasn’t tied to any ideas I had about myself, because these weren’t my ideas.

You know the feeling where you can see all the relationship problems all of your friends have with total clarity, but you can’t figure your own stuff out at all. It’s the same concept (there’s an entire business built around this ironic tension–it’s called ‘life coaching’).

What I found out was that when I wasn’t unconsciously worried about defending my identity from failure in business, and I let my ability loose in evaluating OTHER entrepreneurs’ companies, it worked great. I was really, really good at evaluating founders, start-ups, business plans–all of it.

The funniest thing is that I started to become an true expert at calling out the entrepreneurs who were just like me!

The entrepreneurs who were so tied to their start-up idea or their success were super easy for me to spot. Just like former drug addicts are the best at seeing the tricks of other addicts, I could see them performing all the mental gymnastics I used to do to avoid admitting clear facts that might make them see themselves in a way that hurt their ego and identity.

Simply put, I paired up the insights I got in therapy (being able to see how much I tied my identity and self-esteem to my fame and success) with the insights I got from my angel investing (seeing how other founders delude themselves in the same way I used to and how it affected their business decisions), and it showed me where I was making emotionally-driven identity decisions in business–so I could stop doing that.

Except, to make it REALLY work, I had to do something really hard: I had to turn this new super power on myself.

 

How I Combined These Insights To Own My Failures

“We do not learn by experience, but our capacity for experience.”
-Buddha

I turned that super-power on myself in a very specific way. It may not work for you, but I’ll list out the process to make it easier to find your way:

  1. For each business I’ve ever been involved in (and I included books and movies as businesses), I wrote down everything that happened. The objective facts. You can see most of them listed here, things like revenue, time, result, etc. I got all the facts (that mattered) out of my head onto a piece of paper, as many as I could think of.
  1. Then I did something really weird (I learned this from a doctor who treats OCD patients): I pretended that I was talking to a different entrepreneur about THEIR business, and then evaluated the facts of that person’s business.

I didn’t just pretend. I actually changed the name at the top of the page to a different company and a different person for each company. Of course I knew it was me, but this little mental sleight of hand was enough to free me up to dissect this company and “this guy” objectively, because it was a “different” person. It took MY identity out of the equation.

  1. Because it “wasn’t me” anymore, I was totally free to let go of any assumptions and just approach every problem with a fresh, beginner’s mind. I listed out, in detail, every mistake, every reason that every mistake was made, what other things the entrepreneur could have done better, anything I could think of. I went at each company like I would as an angel investor–razor sharp analysis and totally fucking brutal.
  1. Once I had all the facts and decisions out on paper, then I started to analyze them. For EVERY decision, especially the bad ones, I asked myself this simple question:

Why would “he” make that decision?

Usually the first few answers were rationalizations or excuses. So I kept asking the question, with small variations, over and over and over…until I got to a reason that “he” would make that decision that was not driven by facts or reason or logic or business sense, but was driven by emotions or identity or status. Just like I did with other entrepreneurs, I was relentless in digging until I found the real reasons for decision.

Those were the decisions I was looking for–the ones that had deep underlying unconscious motives that I wasn’t admitting it to myself.

THAT is how I was able to write the post so brutally and precisely dissecting my own failures in business. Once I had that angel investor perspective working, I turned it on myself, and my decisions–and I kept dissecting them until was able to see them for what they really were.

 

You Gotta Own It
There is one more part to this, one more key to the HOW of really digging into your failures. I left it to last, because it’s the hardest part, and no one ever wants to hear this:

This only works if you’re willing to take complete and full responsibility for everything in your life.

When you ask these “why” questions, when you really dig into your decisions, you are trying to find the place where you can own the mistake or failure or decision. If you don’t, then you aren’t really owning your failure–you’re just re-assigning the blame to someone or something else.

EVERY TIME I answered a “why” question and the blame fell on someone else, I asked a deeper why question, until I got to something I did or I thought that caused the problem. Only then would I let myself stop (and even then, I often had to go another level or two up to get deeper).

Here’s a great general example:

We all know that one person who says they keep dating crazy men/women, and they can’t figure out why. They go on and on about their multiple insane exes, and all of their problems…yet they never stop and make the obvious and simple observation that they’re the ONLY constant among all of those exes.

Obviously they’re making decisions that are either attracting those people, or allowing those crazy people into their life. Once is an accident, twice is a concern, and three times is a pattern. They will NEVER change until they admit that to themselves–that THEY are the cause of the pattern, at some core level–and then go about figuring out why and answering the fundamental question: what emotional need is being met by having crazy people as partners?

It’s not different in business. I did this for EVERY GODDAMN DECISION I MADE in this piece. It really fucking sucked.

I am not telling you that everything bad that happens to you is your fault. HELL NO. Even natural disasters aside, people have bad luck and shitty people do things to you that you did not deserve. God knows I’ve had those things happen–but did you notice I left pretty much all of that out of my failure list?

NOTE: Owning the decisions you made that led to your failures is not about beating yourself up, and it’s not about making yourself feel like shit. Don’t do that. Being honest with yourself does not mean you have to be mean to yourself.

Taking responsibility and owning failures is about clearly seeing where you are making bad decisions, and understanding why you are making them–so you can stop.

Taking Responsibility SUCKS
Make no mistake about it: that was really, really, fucking hard. It’s incredibly painful to honestly look at your mistakes and really fully own them, in all their glorious awfulness. To turn into that pain, instead of running from it, it about an unfun as life gets.

But it’s also incredibly liberating. Once I embraced the idea that I didn’t have to (and shouldn’t) judge myself by my successes, but that instead I could create a very small identity, and then see my businesses as things I did rather than things I was–then I was totally free to deeply critique them.

And once I did that, I could clearly see why I was making so many bad decisions–they were rationalizations for deep seated emotional issues. Not actual business decisions. And then, I could STOP MAKING THOSE STUPID ASS DECISIONS!

I honestly believe this identity shift in my mindset is responsible for why my current company is doing so well. Obviously, we are also hitting the three essential elements of start-up success out of the park, but Movie Tucker probably would have torn that all down, and all because he didn’t understand his issues, or even accept that they exist.

It’s not that I don’t have any more emotional issues. Please–just ask anyone on the Book In A Box team, they’ll tell you I have issues (we even talk about them in our meetings, like we do with everyone on the team). It’s that now I know where they are (at least most of the big ones), I can account for them, and I am open to talking about them and working to fix them. I understand that this is a process, not a result, and every day is about working the process.

The problems you know you have are almost never the problems that sink you. It’s the problems you don’t know you have (or won’t admit) that destroy you.

And that is why owning your failures is both so hard and so important–it’s the only way to improve and grow and change.


Buddhism Reading List:

There are so many places to start to learn about Buddhism. Maybe the easiest for many people is this book: 10% Happier by Dan Harris. It’s about how a person with SERIOUS identity issues found meditation.

But probably the best into Buddhism for Westerners, I think Zen In The Art Of Archery is also amazing. What both this book and 10% Happier have is an emotionally honest recounting of the way the mind works through these issues at the beginning.

That’s only a start though. From there, my favorite reading on Buddhism is pretty much all the books by Mark Epstein. I think his best is The Trauma Of Everyday Life, which is a psychoanalytic reading the Buddha’s life. Sounds really wonky, and to some extent it is, but it changed my life. Possibly a better place to start is Thoughts Without A Thinker or possibly Psychotherapy Without The Self. Or, if you want to go really deep, try After Buddhism by Stephen Bachelor.

I don’t feel qualified to give you any more of a list beyond that, because there is SO MUCH, and most of it is really contextual. What will deeply move one person is gibberish to another. And in fact, what was gibberish to me at one stage of my life, deeply moved me at a later one.

The only way to know you’re walking the right path is to walk that path yourself.

 

[This post is the first in a series called “Asshole To CEO” where I write about my transition from fratire author to start-up CEO. The rest of the posts can be read here.]