Out-of-touch CEO takes new hire out to lunch and insists that employee's expertise could make him a billionaire: 'His words fell flat'

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Ben Weiss • Writer and Editor
Aug 21, 2025 8:00 AM EDT

Most folks don't get the opportunity to have a one-on-one business lunch with their CEO, but be warned: that meeting might not necessarily go as planned. Sometimes, the people in charge can surprise you and turn out to be far better leaders and humans than you could have ever predicted. Other times, they turn out to be exactly what you feared. Perhaps they're even worse than you thought.

In theory, a CEO choosing to take an hour out of their busy schedule to meet with a new hire at the entry level is the kind of hands-on leadership most employees hope for in their workplace environments. A lunch like that could lead to strong first impressions and might even help employees get on their CEO's radar when it comes to promotional opportunities down the road. 

However, there are downsides to this kind of one-on-one interaction as well. What if your personalities do not mesh at all? What if the CEO's true intentions reveal themselves and they end up being not so great a person? In some ways, one could argue that learning the truth about your CEO from the get-go is actually a blessing in disguise. That kind of transparency, for better or for worse, could help clarify where you see yourself in terms of your future in this workplace. If that means that you don't see yourself at all, it might be worth it to start planning your exit sooner rather than later. Sure, it's unfortunate to have that kind of epiphany so early into a new position, but in some ways, it's better to learn the truth about the person in charge from the start than after years of investing your time and energy there.

Keep scrolling below to find out how this business lunch between the author and their CEO went south super quickly!

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  • "Had lunch with the CEO and he basically asked me to make him a billionaire. His words fell flat to me."

    Mature elegant man is making a call in his car while being carried by a driver
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  • When your boss tells you that he wants you to make him a billionaire, that certainly says a lot about who this guy is. It's not like his priorities are for you to become the best that you can be or for the company to become the best that it can be. Instead, this CEO's focus was solely on how he could ascertain more wealth through this new hire's expertise. If that kind of honest admission wouldn't rub you the wrong way, perhaps you should work for this dude.

  • Started a new gig a month ago. I'm a Controller in a PE backed high growth awesome industry. Went out to lunch with the CEO. He was trying to pep talk me and get me excited for the role as their last Controller didn't cut it and k led morale in their accounting and finance department.
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  • He essentially said...'look, you can see the documents. I made 170M in the sale to PE. But I'm still here. I have the drive and determination to exit the next time as a Billionaire. And you're key to getting me there. I hope you're excited'
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  • Was that a weird conversation to anyone else? I wanted to say something but in the end I'm just like 'I'm totally onboard with the mission and your leadership at the organization'
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  • I've heard people gripe about making the rich richer, but he literally asked me to help him do it. Now I really don't want to. Meh. Rant over. Wish I could retire.
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  • Pensive mature man in an elegant suit sits in the back seat of a car.
    via Unsplash+ (Getty Images)

    Image is representative only and does not depict the actual subjects of the story.

  • shapeofthings I know it might have fallen on deaf ears, but imagine if you said to him "why don't you focus on making your employees rich as you are already a multi- millionnaire?
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  • Cat_Impo... I guess he revealed what the company mission was is for him to hoard all of the profits to himself while leaving you dried up. Don't expect a raise anytime soon.
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  • StolenWishes ⚫ They really think making them obscenely rich makes us feel like part of a great cause. The revolution can't come too soon.
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  • Due_Seesaw_2816. Should've asked for a percentage upon completion of this goal.
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  • [deleted] The part that is strange to me is the very wealthy person is motivated by money but somehow they think everyone else in the company should be motivated for other reasons. making someone else money isn't really a motivator this is why we get paid money too.
    via cpaoneday1
  • rap_whats_not_taken. "Have you considered cutting back on avocado toast?"
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  • spiralenator ⚫ I had an interview with a CEO for an engineering role. I asked him about long term strategy for the company and he said "to grow as fast as possible and make as much money as we can"
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  • Talk about weak sauce answers. I went through 7 interviews to talk to this dude whose answers to my questions sounded like cartoon character ceo answers for children. He decided to pass on my candidacy. I was not pleased, but sounds like I dodged a bullet.
    via cpaoneday1
  • Why do these people get paid millions of dollars while giving answers like that when I have to spent 5 hours demonstrating that I can write basic code and do toy system designs that need to scale
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  • to every human on earth being a concurrent user? Why does he get to override every other engineer I spoke with because of his "gut feelings" e.g. unexamined biases? Also why did I have to interview with him at all? Isn't supposed to be busy doing CEO sh and leaving technical hires to technical managers?
    via cpaoneday1
  • [deleted] ⚫ Tell him you will make him a billionaire if he makes you a millionaire.
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  • [deleted] lol WHAT i'm not besties with my ceo but the vibe here is pretty similar, he gets 30% raises every year (in the tens of millions) while we're expected to be excited about stagnant or in some cases cut benefit/wages for the rank and file. but still, the level of blatant insanity of your boss saying this TO YOUR FACE.
    via cpaoneday1
  • "help make me more rich!" like basic common sense would suggest they should stop and think how that would sound to a normal human being.
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  • ed zitron's most recent newsletter had this great line about how certain ceos aren't touched by normal human problems anymore, so we should stop trusting them to solve problems or make business decisions.
    via cpaoneday1

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workplace-stories employee work stories toxic-workplace job work ceo overworked-employees company billionaire money toxic-work-environment
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