Asshole to CEO #7: I Fired Myself As CEO (Why, And What’s Next)

The big reveal from my last post, the thing that enabled us to fix our problems and scale:

I’m no longer the CEO of Book In A Box.

If you read the last post, you know why (and why Zach isn’t the COO): we didn’t do a good enough job being an executive and manager of a fast scaling team. In fact, we did so poorly that we almost screwed up a “can’t miss” idea with a huge market.

The man we hired to replace us is JT McCormick. Most recently he was the President of Headspring Software, based in Austin, and though he did not found that company, he was instrumental in scaling it.

So what’s the story? How did this all happen?

It started in October of last year. At a company off-site, Hal Clifford (our current Head of Book Creation), asked me this question, in front of the whole tribe:

“What are you afraid of?”

It took me by surprise. I gave him the most honest answer I could:

“I’m afraid I’m not the CEO this company needs… I’m afraid I’m not going to be good enough to lead this company where it can go.”

You could have heard a mouse fart. Every single person in the room was shocked.

I think I was even shocked. It was the first time I’d ever admitted this–even to myself.

The reality was that for me, being the CEO of our rocket ship company start-up was terrifying. I was being pushed beyond my level of competence, and I wasn’t confident I was handling the tasks in front of me well.

Even more frightening, I had a team of people that put their faith and trust in me. I was answerable to them, and to their families. And we were on a mission that we believed in, that could genuinely help the world.

That created a recipe for a lot of fear, and that day in October planted the first seed in my mind that led to me seeing the truth about myself.

Because once I admitted it, then I could start the process to learn quick enough to do the job myself–or be replaced by someone who could.

How JT Came On Board

I met JT a few months after the October meeting. He’d been referred to us by another author of ours, and since he was in Austin, I went to his office to talk to him about his book.

His personal story is amazing (and it’s going to be such a good book, which will be out later this year). Towards the end of the conversation, after he signed to do a book with us, I half-jokingly said,

“Man, I’m new to this CEO thing, you gotta help me with this. Our company is doing great, but I’m struggling at my role.”

He laughed and agreed to help me out. I just assumed he was being nice. A few days later, I got a phone call:

JT “Tucker, just got an email from my Publisher. You said you wanted help. How serious were you?”

Tucker “Very serious. I need all the help I can get.”

JT “OK, not everything I tell you is going to be happy sunshine. You wanna to hear the unvarnished truth? Even the stuff that hurts?”

Tucker “Yes, please. As honest as possible, I want to hear.”

JT gave me the most intense breakdown of an email I’d ever heard. He probably spent 30 minutes dissecting it from every angle, explaining how we got it wrong, and then how easily we could have reframed the email to get it right. It was a masterclass in customer service.

And it didn’t stop. From that day forward, after EVERY interaction he had with us, he called me and told me what he thought about it–the bad AND the good (there was plenty of both).

From our call structure, to how we managed expectations, how we presented information, even our payment processing and our invoicing(!), he dissected and evaluated. It was a never-ending flow of deeply informative and immediately actionable critiques, the type of thing you pay a consulting firm hundreds of thousands of dollars for.

I asked him to join the advisory board of my company. He didn’t agree at first:

“Lemme come to your next executive meeting. Lemme see how you guys work. I like your service a lot, but I gotta learn about you guys as people before I say yes.”

At the time the executive team was me, Zach and the GM we had hired to compensate for our lack of management skills (I talked about this in the last post as well).

By the end of this meeting, JT was running it. Had you been watching from the outside, you would’ve just assumed he was CEO already.

But it wasn’t a domineering, talk-over-you, I’m-an-alpha-asshole takeover. There was no selfishness about his energy. He never interrupted anyone, he always listened intently, he never really contradicted, but instead said things like, “Have you guys considered this…,” and most importantly, at no point did you ever think or feel that he was making it about him, or forcing a view, or demanding anything from anyone. He was relentlessly curious and very perceptive, yet gave everyone the space they needed to think and ponder and engage. He just asked questions, exposed issues, and then kept leading us through the questions until we’d thought everything though and come to solutions on our own.

It was nuts how well he did it. It felt like the most natural thing on earth. I’ll give you one a specific example: how he handled my anger.

It was becoming clear that we’d hired the wrong GM. This was a VERY important hire, and she was making all the wrong decisions. But I wasn’t quite ready to admit to myself yet that I had hired the wrong person, and this cognitive dissonance was creating internal emotional friction for me–which came out as anger against others.

I can’t remember what she said, but something triggered me. Maybe a discussion on benefits, whatever it was, it was super clear she was thinking as a big company middle manager, and not as a start-up GM. I started raising my voice, and it turned into an angry, yelling outburst.

Not name calling or anything like that–I just have anger issues. This is ESPECIALLY true when I am mad about something I have not fully accepted to myself; namely, I hired the wrong person, and this was another piece of proof for a fact that I hadn’t admitted to myself.

Then, something happened that I’ve never seen in my life. Ever.

JT totally called me out. But he did it in a way that was so smooth and so calm, not only did he stop me from yelling, he de-escalated the situation, got me to see I was wrong, and to apologize.

Not a few days later. Right there. In the room.

Yet, it felt totally natural and the right thing to do. I never felt bullied or coerced or forced. I was actually happy about it.

Like with all truly emotionally skilled people, I can’t even really describe how he did it. He mainly asked me questions. He was so calm, and all his questions came back to a simple point, “If you act like this, you’re going to destroy what you’re trying to build.” Of course he was right, but he never argued with me, never tried to “prove” me wrong.

It was fucking incredible, I’ve never seen ANYONE handle me like that. My anger can be extremely intimidating, and not only did it not phase him, he handled me like a tiger playing with a ball.

This created two very intense emotions in me:

  1. Deep admiration. This guy was incredible, had what I did not have, and I was in awe of his skill.
  2. Deep shame. NOT because he was right and I was wrong and had to apologize. I’m wrong all the time. I was ashamed because my anger was fucking up something I care so deeply about.He jiu-jitsued my own anger, and flipped it back on me in a way that I couldn’t hide from or argue away or blame anyone else for.

It was also the first time in my life I’d ever really felt Imposter Syndrome. I can remember telling Zach:

“THAT is what a real CEO looks like. Now I see why the good ones get paid so much. I’m not even close.”

I opened up our books to him, so he could see inside the company, and come on board as an advisor. He kept watching us and helping us, and then one day, out of nowhere, I got this call from him.

JT “I got a question for you. Instead of being an advisor, what if I came on as CEO?”

Tucker “What if I was the starting point guard for the Knicks? Let’s live in reality, not fantasy.”

JT “No, I’m serious.”

Tucker “Dude, your salary is almost our gross revenue. I’d love to have you, but we aren’t even close to being able to hire someone like you. We’re still a few years away from getting someone like you.”

JT “Hold on, don’t assume shit. Let’s talk about this. There are things you don’t know.”

I won’t go into the details of his personal situation, but basically we were the exact right opportunity at the exact right time for him. He believed our company had immense potential, and that he was the exact right person to take us to the next level.

I couldn’t believe it. By pure luck, we’d found the CEO this company desperately needed, the one who could work with me, who had all the skills we needed–AND he wanted to join us. He even offered to take the same fucking salary as Zach and I (which was like a 90+% pay cut for him)!

My first thought was suspicion. I couldn’t believe this dude would leave a huge software company to run our small company. Zach and I wondered if he was hustling us! We had conversations gaming out the ways he could potentially be playing us–all we could come up with was that he was going to work hard for a decade so he could get rich with us. It was ridiculous.

We put JT through the interview ringer. We had him talk to almost every advisor we have. I did such a thorough background check on him that I talked to every boss he’d had going back 17 years. It was kind of insane paranoia on my part.

I’ll sum up what we found: he was even more of a baller than we thought. Everyone I talked to loved him. They told me stories about him that were so amazing they seemed made-up (for example, he put a kid through college that wasn’t his).

He was CLEARLY the right hire, at exactly the right time…and yet I was still hesitating.

I told myself it was about doing our due diligence–and that’s correct. We were. I had screwed up the GM hire, and it really set our company back. We couldn’t get it wrong twice, so I was being extra careful.

But the best defense mechanisms are true. If I’m being REALLY emotionally honest, I think it was about something else:

I think it was hard for me to admit to myself that I failed at being CEO, and hiring him was the ultimate admission of this fact.

Yes, I know I said this was my biggest fear at the October meeting, which is admitting it, sort of. Hiring JT was bigger–it was a deep act of humility that was far beyond saying it out loud. It was a full admission of defeat.

Right now, you may be asking the obvious question:

WHY THE HELL DID YOU THINK YOU COULD EXCEL AT SOMETHING YOU’D NEVER DONE OR TRAINED FOR OR HAD ANY EXPERIENCE AT??

You’d be right to ask the question. It’s what my friends asked me. It’s obvious logic.

Brains don’t work on logic.

I’m good at a lot of things. I’m in the top 0.0001% in a few things. When you are that good at something, there is a natural inclination to think you can do ANYTHING well.

Also, I feel into the same trap as a lot of entrepreneurs. Just because we are good at seeing a problem and finding out a way to fix it does NOT mean we are good at taking that solution and turning it into a big company. Starting something and market validating it is totally different than scaling it.

But beyond that, I think this was about my emotional problems. As much work as I’ve done on myself, I still attach a lot of meaning and identity to being successful. Even though I “know” titles like CEO and status symbols like a successful company are silly–I still care about them, at least on a deep unconscious emotional level.

Part of me needed to succeed as a CEO. Not financially, but emotionally. Quite frankly:

I needed to be a successful CEO to prove to myself–again–that I was worthy.

Hiring JT as CEO meant I had to accept, to myself, that I was not a good CEO, which–to my unconscious–symbolized me admitting that I am not worthy. I know that’s foolish logically, but again, that is how brains and emotions work.

The turning point in the decision came in a very unexpected way:

JT “What if I came on board as President and COO. You can stay CEO. I’d be OK with that.”

It was then that I knew I had to not only hire him, but step aside as CEO.

Why?

I mean come on, really? This guy was the definition of a CEO. He was true leader of people, and he was a deeply experienced executive and manager and scaler of companies. Why would he do the actual work of a CEO, yet report to me as if I am the CEO?

That would be a ridiculous fraud. Even if no one else knew, I would know, and I cannot live as a fraud, not in any way, not even just to myself. Either I am succeeding as a CEO or I’m not, and if I’m not, I refuse to pretend that I am. I could not look myself in the mirror if I did that.

I can live with failing far easier than I can live with a lie.

Once I realized that, I stepped aside, we hired him as CEO…and almost immediately, everything in the company that was messed up, turned around.

This is why I did all that emotional work on myself. Spent four years in psychoanalysis, have been meditating for two years, and tons of other emotional work–it all led to this.

I did all that work so I COULD make decisions like this. If I hadn’t done the work, I would’ve refused to see what was obvious to everyone else and made this decision about me and my issues, and I would have held on to the CEO job…and it would have either capped the rise of our company, or killed it altogether.

Simply put, without all the emotional work I’ve done on myself, I would have created the exact thing I feared most.

This is exactly what I’ve done in the past that capped my success, and that is why I had to learn to own my failures.

It’s Not About Me

What’s so funny is that we hired JT for the CEO role when I was several posts into this series, Asshole to CEO. Supreme irony, right? I was writing about how I was learning to become a CEO, as I was firing myself as CEO.

The real insight was when I realized the same goddamn mistake with this series is the one caused me to nearly fuck up my company:

I made it about me.

I solved that problem in my company when I stepped away from the role. That’s when I made it about everyone else, could clearly see the right decision, and made it.

I’m going to make the same decision about this series. I’m ending Asshole to CEO. Instead, I’m going to write about the lessons that JT teaches me and Zach and our team. It will be called “Lessons From Our CEO,” and it will be about what WE learn as a tribe from our CEO, not about me.

The first piece in the series is on Entrepreneur right now. It’s how JT revamped our hiring process.

Every week, I’m going to teach something to you that he taught us (I’ll be posting them all here too, I promise).

You’re going to see how he, and the rest of the tribe, take a company that has done 5 million in sales (as of now) to 50 million+. Starting a business and scaling that business are totally different things, and I’m going to let you in on how we do it.

NOTE: Adding this because some people were confused. OF COURSE I am still part of BIAB. Aside from my family, this is all I do now. I spend most of my time on the two things I am best at: marketing and culture. Just because I’m not the CEO, doesn’t mean I have to leave. I just need to focus all of my time on the things I am one of the best in the world at, and only do those tasks.