Things Regular People Overheard Rich People Say

Author image for Eric Lund
Eric Lund
Apr 30, 2021 1:00 PM EDT

There are a few crucial points when regular folks get access to the conversations of the obscenely wealthy. People like chauffeurs, golf caddies and caterers get to enjoy the wild, out-of-touch and interesting things these people have to say. It's a complete shock to see someone do something like spend 30 thousand dollars on flowers, which is why tales like these absurdly expensive things people witnessed and cases of out-of-touch wealthy people are as frustrating as they are a circus-like spectacle.

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  • 01
    Font - letsryan 16 hours ago · edited 16 hours ago 2 2 About 25 years ago I had a summer job at a very tony country club. Six figure joining fee, five figure continuing membership dues, and that got you nothing but the privilege of paying top dollar for rounds, food, etc. I was a porter some of the time, as we had cottages on club grounds for members to stay and make a weekend of it. One of my duties was driving members to and from airports - usually private airports for private jets. One time I
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  • 02
    Font - MastadonBob 14 hours ago Friend of mine worked for an upscale concierge chauffeur service. His most memorable moment came when he lost Marie Osmond. Fairly simple gig, go to airport and pick up Marie Osmond, who was to be the featured entertainer at a private event. Plane comes in, he meets her, she has carryon bag but her checked suitcase, containing her stage dresses and makeup, is missing. She is unflappable, though...asks to be taken to the nearest upscale mall. He does as instructed,
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  • 03
    Font - Chauffeur buddy is in mini-panic mode now, running wildly around the store asking random customers "Have you seen Marie Osmond? Have you seen Marie Osmond?" Store security is summoned and he is asked to leave the premises right NOW, He calls his employer and tells them he has lost Marie Osmond. The employer doesn't have her cell phone number but has her agent's number and he is not accepting calls. She has in the meantime taken a cab to the gig, thinking she has been forgotten. Lots of ap
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  • 04
    Font - WatchTheBoom 20 hours ago 2 2 Not a chauffeur, but seemed like a good chance to remind people of the story of John Boehner (At the time, Speaker of the US House of Representatives, 3rd in line for the US Presidency) not knowing how to use Uber. As the story goes, one of his aides downloaded the app onto his phone and showed him how to use it. Unknown to him, he'd been stuck on the carpooling option, uber- pool. That's what he used for years. There are all sorts of tales of commuters hoppi
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  • 05
    Font - pursuitoffruit 17 hours ago S Not a chauffeur, and I was a participant in this conversation. I used to tutor an oligarch's daughter in Rublevka, the wealthy suburb outside Moscow. One day she mentioned that she likes to ski. I asked her which kind of skiing she preferred (downhill is more popular where I'm from, but cross-country is quite popular in Russia; it's even part of some schools' curricula). Her answer? "My favorite kind of skiing is the type where you jump out of a helicopter."
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  • 06
    Font - prailock 18 hours ago 2 Drove L.I.M.O. at Marquette University during undergrad and grad school. Some of the students that went there were obscenely wealthy. Limos are the vans that drive drunk students anywhere on campus and a few blocks outside of campus. Couple things I remember randomly from it: 1. Drunk guy leaves his wallet on a van and another driver calls it in so me and another supervisor can take it to campus police. We pick up the wallet from the driver and open it to get the s
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  • 07
    Font - SayNoToStim 15 hours ago S I used to know a Chauffeur, he ended up driving around some big stars. He was big dude, like 6'8" and super muscular. His best story was when he was driving around a few WWE (WWF back then) stars, and they awkwardly asked him to not get out and open the door for them because he'd make them look smaller.
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  • 08
    Font - nanocurious 14 hours ago Not a chauffeur but worked as a caterer for private jets and the insane folks who owned them. Had a huge order from what I knew to be a smaller jet so I really wondered about it. When one of the owner's handlers was training a new flight crew, he ordered $12k of meals for a flight that didn't exist just so the new flight attendants could practice the fine points of checking in a catering order. I listened outside after the food drop as the handler started explaini
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  • 09
    Font - whoreychan 13 hours ago Wasn't exactly a chauffeur but I did have the distinguished privilege of working with a multimillionaire one time for a couple days and I was just astounded at how out of touch he was with реople. One conversation he was talking about how he hated all the new homes they were building and he liked old castles so he was having a castle in scotland disassembled and reassembled here in the US piece by piece. On another occasion he asked me why I wasn't in college yet (
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  • 10
    Font - dog_superiority 13 hours ago This is not a limo story, but this thread reminded me of a rich guy story. My daughter played soccer for many years and at one practice, a guy drove up in a Ferrari, got out, and started talking to another of the dads on the team. After a few minutes, the guy left and another of the dads went over there and asked him who that guy was. He replied that the guy was his lawyer or something. I come to find out years later, that that guy in the Ferrari was a multi-m
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  • 11
    Font - kry1212 18 hours ago · edited 18 hours ago I was driving as Uber and I picked up two business men in an industrial park. They were building developers. The man who was clearly the boss spoke to me as if I were a man and I was always the driver who picked him up. Although they were clearly from the middle east, they chose to speak English. Maybe they thought it was rude not to, being in the US? But if that would have been rude I'm not sure what the rest of the conversation was... They spok
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  • 12
    Font - satanismymaster 17 hours ago Not a driver, but I used to caddy at a fairly exclusive country club in Massachusetts. It's the kind of place where, no matter how rich you are, you can't buy a membership. You're either born into it or you marry a member. As a result, a lot of the members like to show off their influence by inviting guests who would otherwise be unable to play at the club. Someone invited Mitt Romney. We were given a heads up that the governor (he wasn't a senator yet) would
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  • 13
    Font - LifeWithAdd 15 hours ago · edited 11 hours ago Not a chauffeur but I work in high end real estate so I'm in the homes of the affluent a lot. Once I was in a home selling for over 10 million with two Bentleys in the garage. I over hear the homeowner talking to her friend in the next room. "These new tax laws are killing us in the middle class, we had to open another trust just to save more money this year" insane that this woman really believes that she's the middle class. Another time in
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  • 14
    Font - AustinSomething 13 hours ago I am late to the party but I can absolutely contribute to this thread. Used to work for a private transportation company, started my own chauffeur business last year. Couple things right off the top of my head that come to mind: 1. had a really snobby family from another mountainous state come to our state and the entire ride to their destination was spent talking about how much better their state was. Towards the end of the ride, the mother started CUTTING HE
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  • 15
    Font - hotpocketsinitiative 13 hours ago I drove the Chancellor for a large University around and was told to actively forget everything I heard in the car. Throughout my undergrad career I constantly heard about massive cuts to the Humanities and Fine Arts budgets because we simply didn't have the money. Multiple buildings worth of people were forced to share a single, outdated building during 5 year long renovations. Graduate students and University staff were criminally underpaid and underfun
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  • 16
    Font - pokemonhegemon 16 hours ago Just had to share this. A coworker of mine was telling how on his side gig as an uber driver, he had picked up one of the receivers for our local NFL team. He complained that he had driven this man for a half hour and didn't even get a tip or a good rating. "That assh le just signed a six million dollar contract and he couldn't even tip me"! Then he added how he trash talked the NFL guys abilities during the whole ride. Sometimes like gives us reasons to smile!
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  • 17
    Font - Careless_State_3908 14 hours ago This happened to my roommate , been years ago . Living in NY. He worked part time as a chauffeur. He was all ways picking up rich people. One night his boss told him to pick up LT Lawrence Taylor of the Giants. He was going to a party up town. So he picks him up. Very nice to him . Had two other him. He takes him to this party going on . Limousines guys with parked all over. LT gets out and says wait on me. So he waited for like 2 maybe 3 hours. LT comes o
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  • 18
    Font - wyzzzzzard 11 hours ago Professional Chauffeur here, I've never heard anything in my many years of driving. 542 Reply Share Report Save sensesmaybenumbed 11 hours ago The real professional, right here.
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