September 8, 2026 at 11:49 am

Billionaire’s Pilot Was Surprised When He Was Asked to Go Grocery Shopping—So He Had Someone Else Do It

by Matthew Gilligan

man on a phone call

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If you’ve ever wondered what it’s like to work for a billionaire, today is your lucky day!

And you might be a bit disappointed that it’s not as glamorous as you thought it might be…

Well, actually it’s probably just like working for anyone else, except they’re a bit more entitled and they boss you around a lot more.

A man who worked as a pilot for a big shot talked about a request he got from his boss that made him shake his head.

Let’s take a look!

What’s the most unreasonable request you’ve received from your boss?

“I used to fly for a self made billionaire.

He was very tight with money most of the time (unless it was for pet projects or basketball games).

At the time we only had one plane. He was out of town with it and his wife had used a chartered plane for her trip.

Since I wasn’t working that day I headed to the gym early so I could beat rush hour traffic.

The boss called with a task…

As I was getting in to my car the boss called. He just rattled off a list of things I needed to go buy and put in their refrigerator for his wife since she’d been gone a few days.

I just said okay then called one of the guys at the hangar and gave them the order.

I want to point out that I was not above doing that.

That’s a bit much…

But between the boss and his wife, they had 5 assistants.

5!

Fetching groceries is not in a pilots job description.

But that’s the way they were. If they were paying you they felt they could ask you to do anything.

We all had their security code and code to garage so that we could drop off items left on the plane or even collect things before a flight. That was no big deal. But asking as to grocery shop was a little over the line.”

Here’s how readers reacted on Reddit.

This person shared a story.

Screenshot 2026 08 08 at 5.20.00 PM Billionaire’s Pilot Was Surprised When He Was Asked to Go Grocery Shopping—So He Had Someone Else Do It

Another individual weighed in.

Screenshot 2026 08 08 at 5.20.10 PM Billionaire’s Pilot Was Surprised When He Was Asked to Go Grocery Shopping—So He Had Someone Else Do It

This Reddit user shared their thoughts.

Screenshot 2026 08 08 at 5.20.50 PM Billionaire’s Pilot Was Surprised When He Was Asked to Go Grocery Shopping—So He Had Someone Else Do It

Another person spoke up.

Screenshot 2026 08 08 at 5.21.12 PM Billionaire’s Pilot Was Surprised When He Was Asked to Go Grocery Shopping—So He Had Someone Else Do It

If you enjoyed this story, check out this post about an employee who was denied a raise for “not being dedicated enough,” but then went on to discover what was really going on behind the scenes.

And this reader weighed in.

Screenshot 2026 08 08 at 5.21.27 PM Billionaire’s Pilot Was Surprised When He Was Asked to Go Grocery Shopping—So He Had Someone Else Do It

He wasn’t about to go shopping for this guy’s wife!

But I’m sure it got done one way or another…

Because rich folks usually get what they want!

Billionaires don’t live on the same planet as the rest of us…

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