CEO brags about dropping $15k twice a year on family vacations to employees living paycheck to paycheck: 'He enjoys taking his kids on separate cruises'

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Ben Weiss • Writer and Editor
Mar 28, 2025 2:00 PM EDT

There are often ways to politely navigate the disconnect between overpaid and underpaid employees within a corporate environment. Most of the time, navigating that territory carefully often involves the higher-up employee at the company staying silent about the privileges of their lifestyle. Unfortunately, it seems that more often than not, the person who makes this dynamic awkward is the more privileged one. What a shocker!

Keep scrolling below for this full story about a CEO who decided that it was a good idea to openly brag about the $15,000 he spends twice a year on separate cruises for his two daughters' birthday festivities.

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    Cheezburger Image 10486896640
    via Unsplash+ (Getty Images)

    The image does not depict the actual subjects of the story. Subjects are models.

  • This dude made the egregious error of oversharing about what his family vacations actually look like in a room that was not exactly full of like-minded individuals. In fact, it was a room filled with underpaid employees, at least one of whom was in her 50s and had recently dealt with overdraft fees as a result of a mistake on her boss's part that delayed her payment. You know there is a serious issue when a middle-aged employee who has put decades into the company has to live paycheck to paycheck after one payment was delayed. You know there is an even bigger issue when one of the higher-ups at the same company gets to spend $30,000 annually on cruise ships alone.

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    "Client VP casually talking on a call about how he enjoys taking his kids on separate cruises. Coworker mentions her account just overdrafted."

    Had to hop on a conference call for client briefings and introductions a while back. One of their vice presidents decides to kick things off with introductions and details how he loves traveling with family and how his 2 kids really seem to enjoy going on annual Disney cruises for their respective
    via Ranier_Wolfnight
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    separate birthdays (the kids nanny also comes). Meanwhile, on a side chat of the call, one of the employees in her 50s mentioned that payroll recently screwed up her direct deposit which caused her bank account to overdraw.
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    So to review, there are those out there that can drop 15K...TWICE A YEAR...on Disney cruises for separate kids birthday occasions. Not including other family vacations and/or events. While others within the same firm are one setback away from living paycheck to paycheck? That was just...some really grim bummer to hear, man. What a kick to the j
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    Illuminator007 - 3 hr. ago The two Disnery Cruises a year with the nanny person just occupies a completely different reality than the overdrawn bank account person.
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    Psychedelic Magic1840 · 2 hr. ago Being in that position know, I've been there. Sitting in meetings with upper management and us, the techies keeping all the facilities running, utilising I skills that took many years of university, and on the job training to learn. Hearing
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    them joking about their holidays and cars, and coming in with coffees and biscuits from the office area only accessible to them, whilst we are not allowed to eat and drink in the meeting
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    rooms. We all lived hand to mouth, worked some brutal hours, and had to sit across from these mouth breathers who barely showed in the office, or had a clue as to what we did. Was glad to leave that job
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    EtherPhreak 2 hr. ago Removing the paycheck aspect which I will cover in a minute, having a boss who likes to brag about all of the cool stuff they are buying, "volunteer" work they are helping with, or vacations they are taking is an instant productivity killer. I have switched positions, and left jobs over this kind of which is not always easy, but can be done.
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    My current employer messed up payroll when they switched to a new company, and I guess they had an issue in the transition. The paycheck landed a day late. There was an apology, a notice they were sending a $300 inconvenience check to EVERYONE, and should there be
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    any additional financial burden on any employee, to please send the details to them so they could reimburse that individual to ensure there were no out of pocket issues to that employee.
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    Cheezburger Image 10486897664
    via Unsplash+ (Getty Images)

    The image does not depict the actual subjects of the story. Subjects are models.

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    AfterVisitSummary - 2 hr. ago I happen to be a VP, and this kind of is absolutely normalized in these "circles". It's infuriating and maddening. I have colleagues in our industry who talk about similar things,
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    brag about how they refuse to fly if they're bumped out of first class, their homes in Paris, etc. while on calls with folks just struggling to make ends meet.
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    It makes me incredibly sad that people have this notion that they're so much "better" than others that they need to bring this stuff up fairly regularly, and it does seem to me in the years I've experienced it that it's really just that - a mechanism for superiority.
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    The obvious correlation is that nearly every time I've experienced someone like this, they're actually terrible at their jobs, have no sense of business strategy (because who with a lick of strategic sense would belittle other humans like that), but continue to get their lifestyle and live that life until their employer realizes it, then they hop to another job.
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    If there's any consolation, any decent person knows they're trash. They're not going to experience real consequences, but my assumption is that they lead sad lives outside of the 9-5. (or 10-2 or whatever they work) Apologies for the rant, just ran into this a few times already today and then saw this post.
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    I TO_TURKEYS 1 hr. ago If you think having a house in Paris that no one lives in is a point of pride, you're just an unappreciative little is contributing to the ongoing global housing that crisis... And bad with money.
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    Like, I like to travel, but given they probably occupy the house 2 months out of the year, even if renting would be $10,000/month, it would take 10+ years to pay off the property. Oh, and there's a 0% chance of squatters being able to take it.
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    RummazKnowsBest 2 hr. ago Urgh. We regularly have calls with the really high ups and they're always describing the fancy holiday they're going on or just returned from. Cheers, mate. Good to know.
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    You_Paid_For_This . 2 hr. ago I can guarantee that the VP does much less work than his employee, both in terms of how many hours he actually spends working at work and also the effort required during those hours. Also he definitely has absolutely no loyalty to the company and would just ship if he was offered a single extra dollar.
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    newforestroadwarrior 2 hr. ago I worked for a European customer who would quite happily ask for deadlines to be brought forwards so they had "something to read" during the August shutdown they had every year. Most European companies think we don't ever take weekends off, never mind holidays.
    via Ranier_Wolfnight
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    akahawkeye 24 min. ago My CEO fights our attempts to raise the pay rate for some of our hourly workers while we sit in meetings she drove to in her Maserati. It's wild.
    via Ranier_Wolfnight

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