The CEOs who sabotage their own companies, and keep their workers from being successful

(written by lawrence krubner, however indented passages are often quotes). You can contact lawrence at: lawrence@krubner.com, or follow me on Twitter.

It is surprising how common this kind of self-sabotage is among CEOs:

There is a version of the story of this company in which idealistic journalists, unconcerned with profit, are posed against ruthless business-doers, concerned about profit above all else. That would be a convenient story, pitching me and my colleagues and friends as people who just care too much about The Truth to yield before the gale-force winds of Capitalism, but it wouldn’t be a true one.

The real and less romantic story is this: The journalists at Deadspin and its sister sites, like most journalists I know, are eager to do work that makes money; we are even willing to compromise for it, knowing that our jobs and futures rest on it. An ever-growing number of media owners, meanwhile, are so exceedingly unwilling to reckon with the particulars of their own business that they refuse to accept our eagerness to help them make money. They’re speaking a language no one else does, proud of their own inability not just to not fail, but to not understand the terms on which they’re failing. The tragedy of digital media isn’t that it’s run by ruthless, profiteering guys in ill-fitting suits; it’s that the people posing as the experts know less about how to make money than their employees, to whom they won’t listen.

This is basically the same story that I tell in my book, How To Destroy A Tech Startup In Three Easy Steps:

Again, a CEO who needs the help of certain employees seems determined to drive such employees away, to the ruin of the company.

In the case of Deadspin, there is also the angle that the CEO seems to hate the business that he just bought, and that his buddies from 20 years ago are the ones who can fix the current situation:

The richest men in digital media sometimes show they are not the adults in the room in the pettiest ways. The beginning of the end of my time here came when Spanfeller, my boss’s boss, threw a tantrum in an email to the entire company over a story our staff was reporting on his hiring practices, management style, and threats to editorial independence. He accused us of biased journalism based on the fact that we had sent an early draft to our media lawyer, which is standard journalistic practice. He accused me and a 26-year-old reporter who works for me—a wildly talented reporter who has as much integrity as anyone I’ve ever worked with—of trying to “shame and discredit others in our community” by reporting a story. When another colleague suggested in an all-staff meeting that his email was itself an attempt to publicly shame and discredit his employees, he doubled down, saying he is a transparent guy who says what he thinks. The story—which was damning only in that it was a true recitation of facts—was published anyway, not because our bosses “allowed” it to be, but because Gawker Media journalists are not and will never be intimidated by bullying.

After I submitted my resignation, explaining that the ongoing undermining from my bosses made it impossible for me to continue to succeed in my job, and that I believed I was putting my staff at risk by staying, the CEO threw a tinier tantrum. When I passed Spanfeller in the office a week after I put in notice, he let out a cruel barking laugh, as if he was disgusted to be in my presence. I said “you can speak to me, you know,” and he responded in a tone familiar to anyone who was ever bullied in middle school. “I don’t want to,” he sneered.

This man is not the adult in the room at the former Gawker Media, just as Kendall Roy was not the adult in the room at Vaulter and Alden Global Capital executives are not the adult in the room at any of the 100 newspapers they are destroying. Sending a copied-and-pasted company handbook, issuing vague edicts about becoming sites for “enthusiasts,” and making inexplicable changes for the sake of making changes are the professional equivalent of a small boy dressing up in his father’s suit: He is role-playing, deluding himself but no one else.

The editors and writers and video producers and artists and sales reps and product managers and so on—the people who made this a successful company while also making it the best place I can imagine working—are its actual leaders, and the reason that, despite it all, these websites will continue writing things the rest of us want to read. But none of those people are the richest person here, which means they will keep succeeding despite—not because of—the man who is. He doesn’t know what they know; he doesn’t have to know. No one like him does.

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