Startup CEO – The Loneliest Job

I’ve long believed that being the CEO of a startup can be one of the loneliest jobs in the world. For the first couple of years of a startup’s life (usually before a seasoned and senior management team is assembled, the CEO is looked upon as the captain of a ship in hurricane waters. Despite the constant onslaught of swells threatening to capsize the boat and send the crew to their watery graves, the CEO must remain stoic and reassure everyone on board that he’ll get them through the storm. Only in a startup, there’s not one storm, but one after another after another.

More often than not though, the CEO has as many doubts and fears as the rest of the team – only he can’t show it – the crew is looking to him for reassurance and comfort. Perhaps the CEO has a spouse or best friend that he can talk to when he’s troubled, but even they usually lack enough context or experience to really be helpful and even if they do, he knows they’re biased in their unwavering support.

Recently, I received an email (along with another board member) from the CEO of a company that I’m on the board of. The very first sentence of the email said “I’m gonna vent – it’s easier than a super composed email or waiting for the perfect time to talk and probably more true to my emotions.” Then, for a few paragraphs, he vented – not with anger – just an emotional discourse on an issue that plagues many startup CEOs. He closed the email with “This is the source of my angst right now. Rant over. Take your time responding – this is chronic, not acute. I’m looking for deep thoughts vs. quick answers.”

So what happened? The three of us brainstormed a bit about the issue and committed to working on it together, and then we went back to work. End of story. No backchannel between me and the other board member, no raised eyebrows, just admiration from both of us for a CEO that has the maturity and wisdom to reach out to his board members in trying to solve a challenging problem.

I think there’s something important to be learned here. First and foremost, this CEO has invested significant time and energy into developing a deep and trusting relationship with myself and the other board member to the point where he feels comfortable sharing all the warts of the business with us. In other words, he trusts that we know how the sausage is made.

In return for his trust and openness, he gets a couple of experienced confidants to share the challenges of growing his startup with, without fear of reproach or recrimination. In fairness, this degree of candidness might not work in every situation.  My advice for startup CEOs is to simply try moving in this direction. Your degree of success and subsequent satisfaction will be predicated on having board members (even just one) that are capable of parsing the difference between typical startup challenges and an ineffective CEO.

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