Stories from the Trenches #4: The Operator vs. The CEO Who Couldn’t Operate
Some stories are sent to us. Others are whispered through back channels. This one? It was yelled across the war room table before the whole thing blew up.
This is the fourth entry in our Stories from the Trenches series, where readers share real-life corporate battles, founder betrayals, and operational warzones—all names changed, all bullshit preserved.
Let’s meet the players.
The Protagonist: The Operator with No Off Switch
Mid-30s. Former founder. Former COO. The kind of guy who doesn't ask for permission, just clears the path with a machete.
He had the receipts:
Turned a bleeding D2C service business into a 25% net margin machine by the end of 2024.
Built and exited a successful restaurant venture years prior.
Co-led a $16M VC raise in his late 20s.
Helped scale a hyper-growth company from $100M to $15B in just 21 months.
He was known for three things:
Speed—always going 100 mph.
Conviction—he didn’t just “believe in leadership,” he bled for it.
Bluntness—if something sucked, he’d say it… even if it was the CEO.
And that’s exactly what happened.
The Villain: Greg, the CEO Who Should’ve Stayed in Finance
Greg, mid-50s, white-collar white male. Fancy resume. No spine.
He liked to call himself a “visionary,” but mostly just micromanaged the hell out of everyone. One of those CEOs who read Good to Great and thought the “hedgehog concept” meant firing everyone who disagreed with him.
Control was his love language. Delegation? Never heard of her.
Greg had no clue how to operate, so he did what most non-operator CEOs do:
Got in the way
Blamed everyone else
Replaced high performers with yes-men who eventually quit too
The Final Straw: One Meeting, One Truth Bomb
It was the end-of-year leadership meeting. The kind where everyone pretends to be strategic while doing mental math on how many PTO days they can squeeze out before January 1.
Greg stood in front of the exec team and said:
“Let’s be honest. If there’s something we need to fix going into next year, now’s the time to say it.”
Our guy didn’t need an invitation twice. He’d been waiting.
He locked eyes with Greg and said:
“You want honesty? You’re the company’s biggest blocker. You micromanage, you confuse vision with noise, and you don’t know how to lead. You’re the reason we stall.”
The room froze. You could hear the head of HR’s soul try to exit her body.
Greg laughed. One of those tight, corporate laughs that says “you’re dead to me.”
Three months later? The COO was out.
But That Wasn’t the Only Red Flag
This story didn’t start at that meeting. The rot had been festering for years.
Let’s look at the highlight reel of Greg’s Greatest Hits™:
1. The Cancer Incident
A mid-level manager’s cancer returned.
Greg—our noble leader—didn’t want her using the company’s insurance.
“It’ll raise premiums,” he said. “We should eliminate the role.”
The COO pushed back, hard. But Greg overruled him and fired her, disguising it as a “restructure.” He even had HR draft the script.
The COO, disgusted, paid her three months severance out of his own department’s budget.
2. The CMO Revolving Door
Over 10 months, the company burned through three Heads of Marketing.
Each one brought in by Greg. Each one scapegoated.
He’d set unrealistic expectations, ignore strategy input, then toss them when numbers didn’t skyrocket in 30 days.
By the time the third one quit, the running joke inside the company was:
“Marketing’s real job is surviving the quarter.”
3. The Fear Culture
Employees would DM the COO privately:
“Can you talk to Greg for me? He’s not listening again.”
People were walking on eggshells. Strategy meetings felt like political debates.
Nobody knew where decisions were made—only that Greg wanted to be the smartest guy in the room, even if he was the only one who didn’t understand the math.
The Operator’s Quiet Exit
He knew speaking his mind would get him canned. He did it anyway.
Because unlike Greg, he gave a damn.
He gave a damn about teams that actually execute.
He gave a damn about employees too scared to speak up.
He gave a damn about the company surviving despite its leadership, not because of it.
Was he perfect? Hell no. He was intense, stubborn, and impatient.
But he got results. He turned red ink black. And Greg couldn't handle that.
Lessons from the Trenches
🔹 Culture isn't what you write on a poster. It's what happens when power gets threatened.
🔹 Real leadership invites friction. Greg? He preferred flattery.
🔹 Operators aren’t disposable. They’re the ones making sure the machine doesn’t blow up while the CEO’s busy filming a new thought-leadership podcast.
🔹 Speaking truth to power is a gamble. And sometimes, the truth costs you your job.
Closing Thought
To the operator who walked away: You didn’t lose. You walked out with your integrity intact.
To Greg: May your next “vision meeting” go uninterrupted by reality.
And to the rest of you in the trenches, remember:
If your honesty threatens your position, you weren’t working with leaders. You were babysitting egos.
Want your story told anonymously?
Reply to this post or email us at ops.anarchy@gmail.com
We’ll handle the rest—names changed, receipts included.
Ops Anarchy: where the bullshit ends and the stories begin.