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Why Stressed-Out Control Freaks Make Insanely Great Entrepreneurs

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“I drive myself too hard.” “I sometimes push others too far.” “When I want something badly, I don’t know when to stop.” “When I’m stressed I sometimes take it out on my team.” “The ends justify the means.”

If any of these statements sound like you, join the club. The bad news is you’re a stress monster control freak who makes everyone around you miserable. The good news is you’re likely to be very successful. And you’re in very good company.

I, for one, have put myself and probably half the people who have ever worked for me, worked alongside me, or even lived with me through the same meat grinder since day one. So be it. And it’s absolutely a big reason for my success. And I’m not alone.

Not to compare myself with any of the greats but the truth is Steve Jobs was known for the same thing. So were Bill Gates and Larry Ellison. So are Elon Musk and Mark Zuckerberg. They expect great things of themselves and others. That’s who they are. That’s how they roll.

I keep reading that we should lighten up and quit being so competitive. That we shouldn’t be perfectionists. That we should cut ourselves and others some slack. That we shouldn’t set the bar quite so high. That’s the popular wisdom of the day, is it not?

I don’t know how to tell you this, but that’s an incredibly slippery slope. It sounds great on paper, but, in reality, it’s impossible to manage. You either want to accomplish great things or you don’t. If you don’t expect and push for it, you don’t get it. It’s pretty black and white.

But, hey, that doesn’t mean you have to be an insane jerk about it just because some of us are. If you can somehow manage to pull off being nice and not flying off the handle when people make commitments and let you down, go for it. Be my guest. More power to you. But that’s a pretty tight strait to navigate, I can tell you that. You pretty much have to be the Magellan of management.

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One story in particular sticks in my mind. I use it to coach people all the time. I think you’ll get a lot out of it or at least enjoy it in a “misery loves company” sort of way.

My company was planning its IPO, and we had our first daylong due diligence meeting with all the investment bankers and their analysts and lawyers. I was the company’s senior veep of marketing and sales. It was my job to stand up, present our business and have all the answers to a million and one questions as the pros picked apart every last detail.  

Due diligence is a tough process. No stone is left unturned. I knew that and that was fine. I’d been there before. I could do this. I just needed my team to spend a couple of weeks filling in all the missing pieces we’d previously waved our arms about and said, “We’ll figure that out later.” Well, this was later. Later was now.

It’s the big day of the big presentation. As usual, everything’s down to the wire. It was nail-biting time but that was cool. I understood. I held my breath and told my CEO I had everything under control even though I didn’t. But that’s what a good boss does, right? Shoulders the stress while his team does the heavy lifting. I did that. I had faith in them.

I sat in the lobby of Silicon Valley’s biggest corporate law firm and waited for the last guy to show up with a thumb drive of the only charts I was missing. Minutes before the meeting begins he pulls up, gets out of his car, walks breathlessly into the lobby and hands me the thumb drive.

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For a second or two, I’m relieved. I can feel my confidence surging. Then the guy sort of looks at me in a funny way and I know something bad is coming. I can feel all the blood drain from my face as he says, “Um … there are still a few gaps in the forecast.”

I did one of those double take -- you know, where you blink your eyes a bunch of times, shake your head a bit and hope you heard wrong. I said, “What do you mean there are some gaps in the forecast?” I’m sure it came out sounding like Jack Nicholson from “The Shining.” I really didn’t mean to freeze the guy in his tracks but what can I say? I was stunned.  

Look, I don’t want to get into the gory details here but let’s just say the guy didn’t have a butt left when he scurried out of the building and back to our headquarters, leaving me to face an enormous conference room full of hungry bankers, analysts and lawyers with unexplained gaps in a revenue forecast that our entire business plan rested upon.

Long story short, I fudged my way through the meeting. Over the coming months we got our S-1 prospectus and roadshow pitch done and approved. Of course, that’s exactly when the dot-com bubble burst, putting off our IPO by, oh, about four years. But we did eventually go out and today the company has a $1 billion plus valuation.

In case you’re wondering, that employee survived the episode. I think it surprised both of us but he made the cut. Years later he told me over beers that, while he was terrified of me – perhaps more of letting me down than anything – he was all the better for it, learned a lot and all that good stuff.

Meanwhile, after 20-something years of corporate craziness, I quit “the life” more than a decade ago and operate in a somewhat lower gear these days. Sure, I still hold myself to the highest standards, but I no longer strike fear into the hearts of those around me. And that’s a good thing.

But I wouldn’t change one minute of all those previous years. It was, after all, the genuine me and some great things came of it. If it’s the genuine you, don’t second-guess yourself. Do what you have to do. Life is long. You’ll have time to tone it down later, as I did. Just be true to yourself and everything will work out fine.     

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