The special relationship between CEOs

I met with a fellow CEO last night for a quick get-to-know-you beer.

I enjoyed it very much as we covered a wide range of topics and were very candid with each other.

At the very end, as we were saying goodbyes, I encouraged him to attend some of the CEO group events that I attend in the community.

I said: “You know how at the end of an NFL game, the quarterbacks who should despise each other, end up hugging it out? There is the NFL Starting QB fraternity? It’s like that with CEOs.”

He responded: “Exactly. You just don’t know until you know.”

And that’s the thing. As much as you can try to write about it or describe it, it’s difficult to put in words.

But experienced CEOs know, because they have been through the shit – and the shit is just fucking hard.

(and for clarity – I use the term CEO for simplicity. But it applies to anyone who is in charge of an entire organization where they are the sole, accountable individual)

I recently reached out to a first time CEO to offer a helping hand, or just someone to talk to. He dismissed me, confident that he knew exactly what he was doing.

I was disappointed. I have been leading companies all of my adult life. All I learn, every single day, is how much I still have to learn.

So I just shook my head, and thought to myself – “he’ll learn soon enough how hard the job is.”

Because eventually, you will learn about all things that fellow CEOs have had to deal with, and hopefully will learn from their experiences and hardships.

They have had to made a tough decision on cutting a product line.

They have had to deal with an irrational investor’s baseless legal threats.

They have had to deal with sudden deaths on the leadership team.

They have had to deal with attempts by board members to oust them.

They have had to deal with brilliant jerks that Monday Morning Quarterback every decision.

They have had to deal with their spouses and family members lacking empathy for the emotional strain of the job.

They have had to deal with the difficulty of turning over leadership teams to get to the next level of scale.

They have had to deal with intra-office marital affairs.

They have had to deal with investors turning them down too many times to count.

They have had to deal with random people on Twitter trolling their personal profiles and attacking them.

They have had to deal with the press attacking their company for no good reason.

They have had to deal with failed product launches, product recalls and massive product flops.

They have had to deal with hackers actually attacking their company.

They have had to deal with fist-fights and verbal abuse on their own teams.

They have had to fire executives, but not been able to disclose to their employees why.

They have been in the red in their business and personal bank accounts, not knowing if they were going to make payroll.

They have personally collected giant receivables from customers using techniques not exactly sanctioned by their legal departments.

They have incurred giant liens on their homes to fund the business.

They have withstood the day to day scrutiny of an enormous number of people noticing every movement they make, facial expression they make, piece of clothing they wear, action they take and every word they speak.

They have had to fire a co-founder because the corporate organism was rejecting her.

They have had to file bankruptcy and tell the investors that they lost all their money.

They have withstood the board inquiries that seem like Spanish Inquisitions or “Torture the CEO” events instead of productive, healthy discourse.

They have experienced the “whispers of doom” in the community when underperforming, fired employees talk shit about the company.

They have had to deal with co-founders conspiring against them.

They have had to deal with competitors badmouthing them to the press.

They have had to deal with divorces inside their company.

They have had to deal with sexual harassment and discrimination – real and perceived.

They have had to deal with baseless threats of lawsuits – or actual lawsuits – again and again and again.

They have had to deal with embezzlement.

They have had to deal with employees dying of fucking cancer.

They have to deal with the endless emails from recruiters and people “just wanting to grab coffee.”

They have had to deal with workplace violence.

They have had to fight with personal bouts of severe depression while trying to lead their organizations.

They have had to deal with macro-economic collapses.

They have had to lay off 90% of the company to rebuild.

They have had to deal with nonsensical tax laws and audits.

They have had to deal with everyone assuming the CEO doesn’t work at all and has it easy (not realizing the exact
opposite is true)

They have to recapitalize, only to wipe out the vast majority of shareholders.

They have had to deal with everyone expecting they have all the answers for every problem.

They have had to deal with the outsized expectations of their role – by almost everyone.

They have to take all the blame for a company’s failures, deserved or not.

But, it’s not all bad.

They also get to see individuals flourish and grow.

They get to see teams accomplish more than they possibly imagined.

They get to meet with happy, satisfied customers.

They get invited to weddings and meet their employees parents – and have parents thank them for all they have done.

They get to watch their teams laugh, and play and have fun together.

They get to feel the immense sense of pride inside when the company accomplishes something truly great.

Most importantly, they get to help build something in this life.

And somehow, those good things about the job outweigh the bad, and that makes it all worth it.

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  • Bart, I love you, man. But what’s with those pants you’re wearing? Also, you’ll be hearing from my lawyer.

  • wow! thanks for this! its scary how many of these i have actually had to deal with!

    • Yep, I find that the anxieties we keep hidden from each other are always more common than we think – both with CEOs – and other humans in general!

  • Roger Anderson

    I work with startups and I tell every one of the potential company leaders to join a group. No one underrstands what you go through and you cannot always talk to investors, friends, or collegues without causing a panic in your team. Great list. I have been through about 90% of those and I only ran small companies.

    • That’s great advice. Amazing, isn’t it?

  • Bart,
    this is refreshingly honest. As a newbie entrepreneur who works with leadership teams I see these pains and strains all the time and I’m always taken by how rare it is to find those willing to speak about what it ACTUALLY takes to lead a company – personally and organizationally. Thanks for paving the way – leadership with heart. That’s one of a kind.

  • Kevin McLaughlin

    Bart – thanks so much for posting – I’ve lived about 1/2 of those in the last 10 years. I’d love to post my favorite to the “good” side: Helping an employee beat fucking cancer by pushing our healthcare provider.Never felt more worthwhile in my life. Love your posts.

    • thanks Kevin. That’s fucking awesome. I’ll add that.

  • Bart, amazing post, I am wondering if you’ve been trolling my email or you have my phone bugged! Awesome, awesome, awesome. I love seeing QBs (or other players and in other sports) chatting it up after a game. So much to learn from eachother.

    • Thanks Kevin – I appreciate that 😉

      No Trolling – just amazing how more in common we are than we all think!

  • yup. loneliest job in the world. well composted post Bart! was talking to someone yesterday about how you have to get your head around the fact that no matter what you do, you can’t satisfy everyone. you can expend _all_ of your energy trying, but, in the end you can’t guarantee a smile on ever face. so, you have to get to a point of realization that… all you can do is be yourself. consequences be damned.

    • Thanks, Jud. That’s a really good point. You really can’t please all the of the people all of the time, so the only way through is to be authentic. You can’t be You if You’re Trying to Be Someone Else!

  • Julian

    This post inspired me to start a global Slack channel for CEO’s. For me it’d be a great way to learn a little from people that have a little more experience with all of this – I’m trying to learn as much as I can but there’s just so much and I think a little peer-to-peer advice can really help out!

    If any CEO here would like to join, please reach out and perhaps we can make it a nice global community of CEO’s where rookies can learn and veterans can reminisce & find support!

  • David DuPont

    Amazing post, Bart. You need a few more “get to’s” to balance things out, though. 🙂

  • Gennady Shenker

    Bart this is just superb, a great continuation to Ben Norowitz’s Hard Things About Hard Things. Thank you!

    As always happens with deep though provoking pieces, I have an idea. Why not create a compendium with each issue as a chapter and allow C-level people to share their experiences in each … possibly anonymously?

  • Bart, this was a great read. I found it very inspiring and your words were very relate-able. I’m about to embark upon the journey of starting my first company, do you have any other resources or outlets of information you could recommend?

  • David Mandell