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The Trials and Tribulations of being a Founder/CEO
This definitely isn't for everyone
“Entrepreneurship is living a few years of your life like most people won't so you can spend the rest of your life like most people can’t”
I knew from a young age I wanted to be a CEO. I think I just consistently rejected authority, despite being a good student. I was a great worker but resented my managers, who always seemed to have dumb ideas. When I would approach them with better solutions, they didn’t care, which I found infuriating.
I also always inherently understood the basic concept of capitalism, that I produced more value than I consumed. That always bothered me. And the larger the gap, the more frustrated I became. I yearned to own the fruits of my labor. And while that’s not part and parcel of being a CEO, since I’m generally a founder at the same time, it always has been for me.
Certainly, being a Chief Executive is a learning experience. My first time was nothing short of comical. By my 2nd time however, I probably compressed months into days and now during my 3rd time, the job almost seems easy (it’s not). I’m two months into a company I’ve founded with great product/market fit, no need to raise capital, lots of customers, and 85% margins. I talked to a friend the other day asking how in the hell this was possible and, as a kind companion who knows me well, he replied:
“You’re very good at what you do, and you’ve been doing it for 15 years. Realize this didn’t come from nowhere. This is the culmination of decades of experience coming together. Take a breather and enjoy it.”
Perhaps that’s the strangest dichotomy of this job. How much I dearly enjoy it vs some of its worst aspects. I’ll work a 17 hour day and enjoy every second. Just...bliss. There is nothing more empowering and, to me, more masculine than to be in total control of your own destiny, whether it be failure or success. And in my case, not particularly caring which one it is, having long ago learned to just enjoy the ride.
And at the same time, feeling the incredible isolation that comes with the role. No one cares like you do about your company. Not even close. Friends, family...everyone gets very tired of hearing about it quickly. What seem like huge achievements to you get ignored over by even those closest to you. It takes an incredible amount of self-motivation to survive in this role, because you aren’t going to find it from anyone or anywhere else.
Then there’s the responsibility. Most of it doesn’t bother me, but knowing my employees and their families count on me for their livelihoods, health, and children’s education can keep me awake at night. I once had an employee at a previous startup invite me to his house for dinner. He had a four year old daughter who was as sweet as anything. We played all evening. When it came time for dinner, she sat next to me on the bench seat and put her head on my shoulder. When I left, I broke into tears because I didn’t have the cash to make payroll in two days. I made it, but boy was that rough.
The confusion and complex equation of how to keep everyone happy is always a chore. I call it “balancing the three-legged stool.” You have investors, employees, and customers, and they all want something from you. And guess what? They are almost always at odds with each other. During a discussion with a recent CEO friend of a private company, we agreed the right priority is employees, customers, investors, although all too often investors have to come first as they hold the purse strings. As a public company, you’re basically forced into investors, customers, employees, which must feel so unnatural as I deeply value my employees who create the very product that make my company successful in the first place.
Balancing all of these responsibilities can cause a great deal of stress as it’s generally impossible to make everyone happy and sacrifices have to be made. It’s definitely my least favorite aspect of the job.
The latest existential question I’ve had is....why? Why do I do this to myself? I already have most everything I want. I could live comfortably for the rest of my life quite easily. Why work so hard and torture myself? There’s nothing I’m striving for. I’ve proven myself over and over again. So....why?
The only answer I have is to think of George Malloy looking at Mt. Everest and saying, “Because it’s there.”
It’s also the only job that lets me, so to speak, “spread my wings.” Every day I get to dabble in finance, technology, marketing, sales, etc. There’s no way around it, it’s fun. Building a company is like a lego set with a million pieces with no instruction manual. And that’s unbelievably fun! It challenges you on a mental (and interestingly, physical) manner unlike anything else I’ve ever done. I never sleep better than after a long day of work. Nothing is more fulfilling than a hard day as a CEO because you achieve more than in any other role. It’s addicting and once you’ve done it, it’s very hard to go back to, well, the real world.
I have a friend that actually actively avoids responsibility at work and wonders why the heck I do what I do when I actively seek it out. My response to him is I’d rather be the one responsible because the best bet I’ve ever made is on my own ability. We need to not only have unshakable belief in ourselves but also the capacity to feel comfortable with failure and making mistakes. The way a person learns from and recovers from mistakes speaks a tremendous amount about their character and the best CEOs I’ve met are people unafraid to make difficult calls, fail, and push forward completely unshaken, having learned from their error. If you’re afraid of making mistakes, being a CEO isn’t the job for you because trust me, you make them all the time.
And that’s what our job really boils down to, doesn’t it? Making the right call. Steering the ship. Seeing into the future and aiming to where we want to be.
I don’t think being a CEO is for everyone, but I do know I love it, stress, responsibility, isolation and all.
I just wish my hair hadn’t suffered for it.