Asshole to CEO #1: The Start

I’m writing again.

About myself, obviously, but a very different side of myself.

This time, I’m not writing about being an asshole up to my knees in crap, at least not in the way you might have come to expect from my fratire books (I retired from fratire in 2012).

I’m still up to my knees in poop, but this time it’s baby poop; yes, I have a wife and an 18 month old son (). Don’t worry–I WILL NOT be writing about my family. I love and cherish them, but quite frankly, my home life is boring (in the best way). Plus, I actually care about parenting my son. I don’t care about “playing the role of cool dad” for stories in a book.

Instead, my new writing will be on a very important theme to me, but one I haven’t talked much about publicly:

My ongoing journey from Asshole to CEO.

What am I the CEO of? My co-founder and I started a company called Book In A Box. We turned writing and publishing a book into a service. We’ve been around for 18 months, have 10 full time employees, 100+ freelancers (we’re hiring more BTW), multi-millions in revenue, hundreds of clients, high growth rate, etc, etc. The origin story is here.

But this series won’t be stories about my company per se. That’s the backdrop. I’m going to focus on what I’ve had to learn to succeed in business, and more importantly, the deep personal and emotional changes I’ve had to make (and am still making) in order to be an effective founder and CEO.

The Shift From Asshole Author To Entrepreneur & CEO

This transition started many years ago, when I was still writing my fratire books. I assumed I could crush any business endeavor I attempted, because I’m awesome at everything, so of course I’ll be awesome at business, right?

Wrong. I failed. Repeatedly.

Stupid Halo Effect. I was determined to figure out what I was doing wrong. I dove into learning about starting and running businesses, and read every fucking business book I could:

I definitely learned a shit load.

Mainly, I learned that the vast majority of business books are fucking stupid. At best, they’re abstract strategy totally disconnected from the reality of capitalism and commerce. Quite often, they’re just objectively wrong.

A small minority are amazing of course, and those are the ones that taught me a shit load (part of this series will be about which ones I think are great, what I learned from them, and how I apply it in my company).

The good news is that learning how to successfully start a business is easy. And learning how to build and run a business is not easy, but it’s doable.

Once I got the base of knowledge I needed, I figured it would solve my business problems.

Except it didn’t. I kept failing.

I actually got good at starting businesses–but I SUCKED at running them. How? How could I know so much, and still not get results?

So talked to the smartest and most experienced business people I knew. They all said the same thing, and it blew my mind. I’m paraphrasing them:

“The fundamental point you’re missing is that running a business has very little to do with knowing business. Running a business is about understanding people. Most business theory assumes that human nature and emotions either don’t exist, or are just a minor variable. They don’t understand human beings and human psychology.”

From uber-successful public company CEOs, to start-up founders, to venture capitalists, to consultants, to famous business writers–the smartest business people I know ALL all privately acknowledged this core truth.

As soon as you think about it, it makes total sense. Most people have no understanding of themselves and their issues, and refuse to even explore them, and this causes most of their problems.

The problem is that NO ONE TALKS ABOUT THIS, especially how it applies to business. All business and start-up education assumes that people are basically sane and rational. This is total nonsense. People are fucking crazy.

Armed with this realization, I looked at my business problems fresh. The truth was clear:

My business problems were almost ALL caused by my people problems–with myself and others.

This series will take you on my (still on-going) journey to understand and fix these issues, especially in the context of how it applies to starting, building and running a serious company.

This Is A Big Change

This is obviously very different than my old writing. Since there are not going to be any hilarious stories about me puking on myself, many of you won’t care. That’s cool.

Why should you care? What will you get out of reading this?

I’m not quite sure. I’ll tell you what my three personal goals are for writing this are:

  1. I want to have deep, connected relationships with the people I love and care about–work or personal. I think I’m doing OK, but I have a lot more work to go, and writing about my issues helps me be clear (with myself) about them.
  2. I want to be in a tribe of great people that makes meaningful contributions to the world. Our company is already on that path, but we can do way more, and writing about our issues will help us solve them.
  3. I want to be a great leader–in all parts of my life. I’m not even close right now. At my best, I have small flashes of greatness, but most of the time, I’m mediocre. At my worst, I’m destructive and counterproductive. Writing about my leadership problems will help me solve them.

So, I want to be a great leader, who does great things, with great people…and I’m going to tell you how I make it happen in my life.

If you want to read about that, because you have similar goals, then this series will be for you.

I can’t promise these stories will make you achieve these goals. I can’t even promise what works for me will work for you.

But I can promise that I’m going to be as raw and honest and open as I always am. I’m going to tell you what issues I’m facing, tell you what I do to try to resolve them, show you where I succeed and fail, and let you into my thinking about all of it.

And if this helps you too, then that’s awesome, and I’d love to hear about it.

I can tell you what this will NOT be:

-No entrepreneur porn.

-No clickbait and listicles.

-No lies about how everything always works out.

-No lifestyle business nonsense and posts from beaches.

-No bullshit.

Zach and I and everyone at Book In A Box are trying to build something awesome, something real, and something meaningful. We’re trying to build a real company, and that takes hard, hard work. This series will be about the journey. We’ve only just begun.

The first post is already out. I thought the best place to start was to go back through my entrepreneurial history, evaluate it as harshly as I could, and own all of it. Taking responsibility for what you is the first step to getting past your problems.

Owning Up To My Business Failures (Asshole To CEO #1)


NOTE: I released that piece last week, and some people thought I was saying that I was already CEO #1. That made me laugh, a lot, but no, not my point at all. It was just the first post in this series. I’m going to label them all that way. If we were ranking CEO’s, I’m unranked right now.