25 Cringe-worthy CEO Fails That Show Just How Detached They Can Be

When it comes to running a company, a CEO’s decisions can mean the difference between success and disaster. But some leaders take mismanagement to new heights, leaving employees and customers stunned. A Reddit thread posed the question, “What’s the fastest way you’ve seen a CEO ruin a company?” The responses poured in, revealing jaw-dropping tales of incompetence, ego, and short-sightedness.

#1

Image source: VampireHunterAlex

Jaguar in recent days: Why pander to an audience who don’t drive and can’t even afford the product?

#2

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Sears paid Amazon to make their website.

Amazon finishes.

Sears execs say it’s pointless. Internet is a fad.

They give their blessings to Amazon to use the website.

How’s Sears doing?

#3

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Eddie Lampert at Sears. It took him a few years to do it, but he managed to destroy two 100 year old companies. Sears and Kmart.

#4

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Not nearly as high profile as a lot of what was posted here but:

A couple of years back, I works for a small, single product manufacturer who were trying to get approval for it to be used as a medicine.

6 months into my Contract (I was a contractor – this is outside the US) it was surprisingly bought out by a US based mid-sized food manufacturer.

We met our new owners and one of them shook me by the hand telling me how much we’d all be needed over the next years as the bought the product to market.

Next day they terminated my contract as ‘non-essential staff’. On the one hand I was a contractor and s**t like that can happen. One the other, f**k those guys a month before Christmas.

2 months later the site was shut down with the loss of about 60 jobs. Why? Because the idiots had no idea of the regulatory process of bringing an API (Active Pharmaceutical Product) to market.

That was easily $200 million straight down the drain.

#5

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Last year our new CEO decided prices were too low. He jacked them by about 70% and customers completely stopped buying. The entire sales team (7 people) quit or was fired. I’m told the company expects to close less than 50% of the revenue it did in the previous year. Major blunder.

#6

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He tried to run a nonprofit library wholesaler like a car dealership. Because he was a car dealership guy who knew f**k-all about libraries.

Most of the senior staff retired and he fired the rest. Then implemented policies that treated us all like children, such as having to put our phones in a box at the front office when we got into work in the morning. Hired a bunch of rando high level positions who also knew f**k-all about libraries.

Then he talked some s**t about people who ‘couldn’t handle change’ because they’d quit. Refused to allow us to order inventory so libraries couldn’t get extra copies when a book unexpectedly blew up.

Anyway, I quit when I was handed a coworker’s entire job with no extra compensation (or, you know, choice in the matter) and the 60+ year old company was dead within about a year, year and a half of him becoming CEO.

#7

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How about Chainsaw Al Dunlap. They called him Chainsaw because he’d take over a company and cut it up into pieces. He took over Sunbeam and bankrupted it in an elaborate accounting scandal. He’s on the list of worst CEO’s of all time. Look him up. It’s an interesting read.

#8

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Just saw on the news a Texas logistics company CFO was sentenced to 51 months in prison for wire fraud for transferring company funds to his bank account and destroying the company causing it to shut down and lay everyone off.

The kicker is, he was convicted of the same felony in 1994 so second time he’d done it.

#9

That guy at Blockbuster who turned down Netflix’s offer.

Image source: stcrIight

#10

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The CEO of Hoover? Decided on a ridiculous giveaway with the purchase of a new vacuum.

They were giving away airline tickets worth more than the price of the vacuum- everyone told him it was going to flop and cost the company millions more than the revenue it would bring in. He stuck to his guns then tried to cancel the whole thing at the last minute.

This was in 1992 in UK and if one spent 200 British pounds of Hoover stuff they would get an airline ticket worth 600 pounds.

#11

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Bob Chapek’s takeover of Disney in 2019.

He immediately hired finance buddies into creative positions, prioritized making money via their parks, and had a *quantity over quality* approach with their movies. He had a hand green-lighting an insane amount of projects which lead to overworked staff, bad quality production, and as a result: disliked projects and failing entertainment properties (mainly Marvel).

#12

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He bought Twitter.

No-Comment-00:

Must have been one of the fasted destructions of company value. Insane, sure he and his state actor ‘investors’ didn’t buy it solely for financial gain but also political influence, but I think Elon actually thought his changes were great ‘business wise’. Instead he destroyed everything that made twitter so popular and the company profitable.

#13

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The most classic example is a guy called Gerald Ratner who was ceo of his family’s jewellery business

The shops and products were popular despite being tacky

He gave a speech in 1991 where he said:

We also do cut-glass sherry decanters complete with six glasses on a silver-plated tray that your butler can serve you drinks on, all for £4.95. People say, “How can you sell this for such a low price?”, I say, “because it’s total c**p.”

After the speech, the value of the Ratner group plummeted by around £500 million, which very nearly resulted in the group’s collapse.

#14

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Took a job at a tech startup in the 90s with the promise of fast growth and opportunity.

Things really took off in the second year and we opened up several more branches in different states while I was promoted to production manager. The company hired a young CEO who was only a couple of years older than me. Sometimes he would stay at our location for a couple of weeks at a time and he started driving really nice sports cars to work. When he would leave to other cities he would leave his cars in the parking lot of our branch. There were corvettes, porsches, audis, and more.

After the second year of promising growth, the business suddenly stopped while the owners visited and yelled at the entire crew for not managing our money and told us that they were in debt by over a million dollars. We were all given the task of dismantling the equipment and preparing it to be sold and shipped before being let go.

On our last day when the building was empty we all noticed that the row of sports cars was still there and the owner had placed for sale signs on them. It turned out that they were all bought as company vehicles and the CEO had done this at each business location.

We all still were yelled at in a furious rage by this CEO and owner for not being responsible people.

#15

For me, It is Michelle Gass, former CEO of Kohl’s.

Before her, Kohls was a fun place to work, everyone got along, sales were booming and black fridays were huge events.

Then she said she didn’t want stores to carry large amounts of inventory, which is fair, but they overdid it. There were large empty spaces at most stores and noting in the stock rooms.

Then, came the Amazon deal. Kohls would take in Amazon returns in the hope of increasing sales. They gave every person that returned Amazon items an in-store coupon. However. People who shop Amazon don’t care about Kohls. They can get it cheaper on Amazon.

Part of this deal was that Kohls used its distribution system to ship Amazon packages back to amazon…. the sales didn’t even make up a part of the expenses.

Amazon, really won that one.

Then, during covid, she cut 90% of the loss prevention staff. Which, you guessed it, resulted in record inventory losses. It wasn’t unheard of for 10% inventory losses compared to sales. I had a few stores that hit over a million dollars in lost inventory.

What did they do with the remaining Loss prevention staff? They made them door greeters. Which resulted in people leaving the company.

Then, throughout covid, Kohls was one of those companies that should have profited massively. They had a large distribution chain and online sales. Yet. They closed down store ability for online sales and only used specific stores.

Kohls is now in the beginning stages of becoming Sears.

Image source: dGaOmDn

#16

That CEO who removed dislike counter on YouTube. And brought a million ads.

Image source: StewartConan

#17

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Not CEO but President and especially Vice president of the company.

BIG MOTOR.

President of the company placed his son as vice president and profits skyrocketed, but only because as it turned out, new vice president forced dealerships to commit insurance fraud, regular fraud, abused and humiliated the staff, killed all the plant life around dealership. After it got out, reputation of the company was completely destroyed, despite them being the biggest and most trusted dealership before that.

#18

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A CIO came in and started his tenure off with telling everyone his second week there on a Friday that starting Monday, there was absolutely no wfh. Nada. Zilch. No excuses. HR got involved and made it even clearer.

This was before Covid and it was wfh 3 days/week. Some people had moved 2+ hours away, would come in to town Monday morning, stay the night, work Tuesday, and go home to work until the next Monday.

Well in IT it’s not very prudent to not have your guys be able to hop on to fix a problem. So the CIO would try to make the exemption in special cases and no one would budge. So the few times some people went in, a 10m fix would run them 3-4 hours.

This CIO also had a knack of yelling at people in public and just being a huge dumbfuck and not knowledgeable about anything. He took a 15 year secretary and made her an enterprise backend developer… that she never wanted. He took an amazing developer and assigned them to 1 of 58 sites for a pet project where we could start pulling data without the site’s permission. The site told them to f**k off when they realized what was going on after a few months. The thinly spread developer led to a site getting hacked and held for ransom, literally.

And that’s just before I left. In 2 years the place had a 50%+ turnover. The old timers who wrote the old a*s code keeping the place running took early retirement. Middle careers like myself f****d off. Everyone else was just new looking for experience or holding on for early retirement. The place cratered.

From some colleagues who stayed I heard people were often crying in the hallways. They had to hire a moral boosting position that did jack s**t. Federal requirements were falling through left and right and the agency was getting sanctioned repeatedly.

Eventually the board wiped out the entire top brass of about 10 people (in a 200 person agency). But the damage was done and to this day s**t still hasn’t recovered. I know people who took 40k pay cuts for other jobs just to get tf out of that place.

#19

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A construction company near me was pulling $100-$200 million in revenue every year and growing constantly, then the owner died and his fratbro failson was handed the reins.

Within a month a quarter the employees had either been fired or quit. After four months the rental companies were showing up and repoing lifts and cranes/carrydecks in the middle of the day because they weren’t being paid. Almost 3/4ths of the employees had quit by this point because paychecks kept bouncing. Before six months had passed, what was left was sold for a pittance to another company that just wanted what was left of the maintenance contracts.

So like six months to bomb the company he’d been groomed to take over since he was a teenager to rubble and p**s on the ashes.

#20

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Randall Stephenson: AT&T

He bought DirectTV and Warner Brothers (including DC Comics, CNN, HBO and so on) for only $175B dollars between 2015 and 2018. When everyone was moving to stream services, he thought it was a good idea to buy a cable company that was losing customers by millions and a struggling media company.

Me and thousands of people lost their job because of it. Including Randall, with a $64 million retirement package.

#21

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My personal experience was a new manager that stopped all overtime. I was trying to keep customers happy and he was not for it. The overtime is an indication that we needed more people. He couldn’t see it. I left and they folded.

#22

Segway brought in a new CEO who promptly decimated the stock value when he died riding a Segway off a cliff.

Image source: Sexyturtletime

#23

The guy that ran a lottery on a live stream, then didn’t give the winner a PC because he said she had too few subscribes.

ShawnyMcKnight:

Had to look up the company; Artesian Builds.
It’s crazy how in a promotion to improve your reach you absolutely destroyed it. If they set the rules up front that you had to have X number of subscribers no one would care, it makes sense. They want people with influence to use their product. Crazy how badly they shot themselves in the foot.

Image source: RoseWould

#24

There was the whole Walgreens theranos debacle. Fun fact: the ceo who basically ruined Walgreens became the CEO of Joann Fabrics and basically drove them into bankruptcy too.

Image source: liblairian

#25

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Good old “Big Jim”

Came in on the promise to shareholders he would double the profits in less than a year. And that he did.

First: Forced “retirements” for anyone there over 15 years. Get rid of those high salaries. ( and institutionalized knowledge, but who cares about that)

Second: Cancel all capital projects. Why build out when customers are kinda forced to buy from us anyway?

Third: RTO all around! Even said in a teams meeting ( from his comfy home office of course) “If you don’t like it, leave.”

35% of us left. Company is barely hanging on and it’s well known they are positioning themselves to get sold.