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How One CEO’s Demand For a Special Out of Office Reply Led to a $300k Disaster

by Believe Johnson
January 20, 2026
in Social Issues

A powerful CEO with a big ego learns the hard way that tech systems and arrogance don’t mix. When Mr. Bigwig, the CEO of a major automobile sales company, insisted on having his out-of-office reply feature customized to his demands, he never imagined the chaos that would follow.

His outlandish request came with an attitude that his status should give him carte blanche to make his own rules, until it backfired, costing him and his company $300k in lost revenue.

What seemed like a small inconvenience for him turned into a catastrophic email loop that brought his communication system, and those of the top CEOs and politicians he worked with, to a halt. His tech team’s compliance with his demands led to the unthinkable: a backlog of 150,000 undelivered emails, making him the laughing stock of his business circles.

What happens when you push for your own way without understanding the consequences? This story is a perfect example of how entitlement can cost even the most powerful players dearly.

Now, read the full story:

How One CEO’s Demand For a Special Out of Office Reply Led to a $300k Disaster
Not the actual photo

'"Everybody must know when I am out of office."?'

So yeah, a couple of years ago I was working for an IT company which also provided server management and general domain and E-Mail services.

We had some really big companies as clients, so we were used to some really idiotic demands,

but most of the time we could convince the people whose main job seemingly was "to be in charge" to listen to our expertise. Not so Mr. Bigwig.

Mr. Bigwig was the CEO of a large automobile sales company.

He also was the type of guy who prided himself with being a "great negotiator" and "thinking so far ahead, regular people can't follow".

And he was a complete ass to everyone.. ​

Mr. Bigwig went on a holiday once and set up an automatic out of office reply in his mail account,

but - as is the technical standard - everybody who wrote him during that time only received the reply just one single time.

When Mr. Bigwig returned from his vacation this infuriated him a lot so he called our support line and yelled and cussed his way up our hierarchy until he had...

I tried to tell him that this was working as intended and tried to explain why, but Mr. Bigwig wouldn't have any of it.

This went all the way to our CTO who sent him a waiver to sign, stating that we would deactivate this limitation, but not be liable for any consequences (in...

Then he told me to make the changes to MBs account. I tried to object, but the CTO just smiled, shrugged and went into his office.

Mr. Bigwig was happy. He won and booked this as his latest negotiating victory.. ​

Now let us jump to December the 29th of the same year. I get a phone call. From Mr. Bigwig. He is not happy.

He is not happy because he is blacklisted on about every blacklist in existence. He is also not happy because he can't receive or send any email.

And he is not happy because he can't find any mail he received during the Christmas holidays or near them.

He can't find them because the nice number in brackets besides his inbox folder, that indicates the amount of unread mails he has, reads 50,000.

A quick look around the server logs tells me there are indeed some mails he did not receive. 150,000 to be exact.

They are still pending delivery because his inbox is full.. ​. He is also not happy because he is the laughing stock of everybody he ever respected.. ​

Now let me guide you as the reader to the bottom of this. What you don't know and we also did not know at the time is:

Mr. Bigwig was member of a very exclusive group of business owners, CEOs and high ranking politicians around the globe.

The kind of people you would imagine sitting around a large oak table, smoking cigars, drinking 200€ whiskey and discussing world dominance.. ​.

This group had a mailing list. A s__tty, basic mailing list.. ​. It went something like this:. ​

Bigwig: (Out of Office Reply) Hey, thank you for you mail, but I am on holiday! I will reply later.. Somerandomdude @mailinglist: Merry Christmas!.

Mailinglist @everybody: Hey guys, Somerandomdude is wishing you Merry Christmas..

Bigwig @mailinglist: Thanks for telling me, but I am on holiday! I will reply later..

Mailinglist @everybody: Hey guys, Mr. Bigwig is on holiday, he will reply later..

Bigwig @mailinglist: Thanks for telling me, but I am on holiday! I will reply later..

Mailinglist @F__KING EVERYBODY: Hey guys, Mr. Bigwig is on holiday, he will reply later..

Bigwig @mailinglist: Thanks for telling me, but I am on holiday! I will reply later..

Mailinglist @F__KING EVERYBODY: Hey guys, Mr. Bigwig is on holiday, he will reply later..

Bigwig @mailinglist: Thanks for telling me, but I am on holiday! I will reply later..

Mailinglist @F__KING EVERYBODY: Hey guys, Mr. Bigwig is on holiday, he will reply later.. ...repeat until the servers give out.. ​

So B-Diddy was not the only one who had thousands and thousands of mails in his folder. All his fancy pants networking contacts had too.

Mr. Bigwig raged hard at everyone who was brave enough to get on the phone with him, threatened to sue us for millions of Euros and to "end us as...

We finally put him through to our founder, who listened to his rant and told him he would send him a solution within the next ten minutes.

He sent two documents: A scan of the signed waiver, in which the consequences of disabling the out of office message restriction were outlined in detail,

and a service contract, allowing us to fix the problem to our abilities without any financial budget limitations, but with a really nice (read: enormous) estimated budget.. ​.

It was a good year for the company, with an unexpected spike in revenue, just before new years eve.. ​

//Edit: Thank you kind stranger for Reddit Premium! I have no idea what to do with it, but knowing somebody liked this enough to gild me with it makes me...This story is a reminder of how appearances can be deceiving and how assumptions can have costly consequences. Mr. Bigwig’s experience with the Cadillac dealership highlights the damaging impact of superficial judgments, especially in high-stakes business environments.

It’s fascinating that such a small oversight, ignoring a potential customer because of how he looked, could cost a business so much. It also speaks to the larger issue of entitlement and the arrogance some people hold when they think their status grants them special privileges. While Mr. Bigwig’s behavior was certainly over the top, it’s hard to ignore the fact that the dealership’s failure to treat him with respect was equally shortsighted.

In the end, it was the customer’s lesson in humility, while the dealership learned the hard way that every potential sale counts, no matter how a person is dressed. It’s a perfect example of why you should never judge a book by its cover.

Judging customers based on their appearance is a dangerous practice, especially in industries where customer service and sales interactions are key to success. Mr. Bigwig’s story serves as a cautionary tale, showing how a car dealership’s failure to see past a customer’s modest appearance resulted in the loss of hundreds of thousands of dollars.

According to business expert and consultant, Paul Smith, “In customer-facing businesses, the ability to connect with people from all walks of life is essential. The assumption that wealth and success are visible through clothing or demeanor is not only outdated, it’s dangerous.”

Customer service experts emphasize the importance of treating every customer with the same level of respect, regardless of their outward appearance. Mr. Bigwig’s treatment, or rather the lack of attention he received, directly resulted from his casual clothing and beat-up truck.

In an ideal customer service model, businesses should prioritize engaging with customers who walk through the door without any preconceived notions about their worth or potential. According to a report by Harvard Business Review, businesses that train employees to treat all customers equally are more likely to see higher customer retention rates and increased revenue.

The dealership’s misstep of not acknowledging Mr. Bigwig for 45 minutes turned a potential sale into a lost opportunity. As Smith points out, “It’s not just about making the sale, it’s about cultivating long-term relationships with clients. A single bad interaction can tarnish a brand’s reputation, and it can have consequences that ripple far beyond that one interaction.”

Mr. Bigwig’s desire to teach the dealership a lesson is understandable, but it also underscores a more significant issue: entitlement. His belief that he should be treated differently due to his status in the business world led to a rash decision, but it also highlighted the dealership’s own lack of awareness. The concept of customer loyalty is increasingly difficult to cultivate in a world where businesses are driven by quick sales and short-term results.

Yet, companies like the one Mr. Bigwig chose to work with understood the importance of relationship-building and went the extra mile to cater to his needs. According to a report by Forbes, loyal customers are likely to bring in a revenue boost of anywhere between 25% and 95%, a strong reason for companies to avoid making assumptions based on appearances.

The dealership’s failure wasn’t just about missed sales—it was about their inability to manage a customer interaction that could have been transformative. If they had taken the time to engage Mr. Bigwig properly, the story might have ended differently. The dealership could have easily avoided the mistake by following basic customer service principles: greeting the customer promptly, asking the right questions, and making the client feel valued.

For businesses, the key takeaway here is that customer service training must be an ongoing process, focusing not only on technical knowledge but also on emotional intelligence and understanding the subtle cues that clients give off. Training should include strategies for engaging all types of customers, from the humble-looking ones to the more ostentatious ones. Additionally, businesses must recognize that their employees’ behaviors and attitudes directly impact their bottom line.

Mr. Bigwig’s experience reminds us of the importance of treating every customer as a valuable opportunity, regardless of how they appear or their perceived status. Businesses must always be vigilant about not letting biases influence their interactions with potential clients. The story’s lesson isn’t just about the mistake the dealership made, it’s about how businesses can make the effort to engage respectfully with all customers, creating positive relationships that are built to last. This is the key to achieving success and fostering long-term loyalty.

Check out how the community responded:

Redditors were largely in support of Mr. Bigwig’s actions, calling his revenge satisfying and well-deserved. They also highlighted how the dealership’s failure to engage with him was both foolish and shortsighted.

LyndyDM - THIS is why I read this! :) thedangerman007 - Similar thing happened to a friend's son. He inherited money and wanted a Subaru WRX.

Went to a dealership with cash, they wouldn't give him the time of day, much less a test drive.

Other users appreciated the payback aspect of the story, seeing Mr. Bigwig’s decision to buy from a competitor as a form of teaching the dealership a hard lesson.

Geminii27 - Founder and CTO reeled that one in. High f**kin' five to them.

now_you_see - Your founders way of dealing with this is perfection 👌

Some users focused on the real lesson here, which was the failure of the dealership’s staff to treat Mr. Bigwig with respect in the first place.

showmedogvideos - Listen to the people who know what the f**k they are talking about!

00Dan - A tip/fyi for those that need more replies than the standard one time only Exchange does- https://www.symprex.com/out-of-office-extender

In the end, Mr. Bigwig’s story isn’t just about petty revenge, it’s a reminder of how the smallest misstep can lead to major consequences. The dealership’s failure to engage with him, simply because of how he looked, cost them a fortune.

It’s also a reflection of how important it is to treat every potential customer with respect, regardless of their outward appearance. As many Redditors pointed out, appearances can be deceiving, and the person who seems like an unlikely customer may be your best buyer.

What do you think? Was Mr. Bigwig’s revenge too much, or was it a fitting response to the dealership’s poor customer service? Would you have done the same thing, or would you have handled it differently?

WHAT DO YOU THINK OF THIS STORY?

WHAT DO YOU THINK OF THIS STORY?

OP Is Not The AH (NTA) 0/0 votes | 0%
OP Is Definitely The AH (YTA) 0/0 votes | 0%
No One Is The AH Here (NAH) 0/0 votes | 0%
Everybody Sucks Here (ESH) 0/0 votes | 0%
Need More INFO (INFO) 0/0 votes | 0%

Believe Johnson

Believe Johnson

Believe Johnson - a dedicated full-time writer specializing in entertainment and news writing. Her experience in various jobs related to movies and TV show news enhances her understanding of the industry, making her an indispensable team member.

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