I very occasionally scroll through my Instagram feed. It’s not friends’ photos anymore. Most of it is junk. There’s a very specific genre I’ve seen pop up lately of AI-generated well-coiffed late middle aged and older characters spilling ‘old money secrets’. And then there’s this, which purports to combine the ‘secrets of the wealthy’ with ‘travel’ that I’m clearly coded for in their system. And it is… special: “7 Unwritten Travel Rules Every Billionaire Follows”
I bet the person who did this video has never actually met a billionaire? The video claims:
- They never check luggage. True, there are billionaires who fly commercial! But not checking a bag, because they get lost and they take time to collect isn’t a ‘billionaire secret’.
- “They dress for the destination before they arrive, no sweat pants on the plane you never know who’s sitting next to you or who’s picking you up.’ If you are a billionaire you do not need to impress randos in the seat next to you when you fly commercial. This sounds like LinkedIn striver advice, not ‘things I learned from billionaires’.
- “They tip before the service not after, $100 at check-in gets you the room they don’t advertise.” I’ve tipped at check-in in Vegas. It got me a five bathroom penthouse suite at Bellagio. But if you’re a billionaire, you have an assistant boooking the room you want, you aren’t tipping at check-in hoping for an upgrade.
And tipping ‘before service’ is something I saw earlier on one of the AI old money videos. Tell me why the guy is giving this advice about flying commercial and seeking upgrades in front of a private jet?
This video seems to be from the ‘luxury travel channel’ of a… men’s polo shirt brand? And they’re full of questionable advice:
[Hotel upgrades] “go to the highest expected value guest… you gotta look like you tip big… the front guest is making a split-second decision, is this person worth giving a $500 upgrade to?”
Upgrades are generally assigned to reservations before the guest arrives. There may still be room inventory, but much of it has already gone to guests with status or other priority (meetings, Virtuoso, etc.) – so contra the claim that hotel status doesn’t work, at many properties it’s doing most of the work.
Hotels don’t set up upgrade decisions to encourage tipping the front desk. That would be called a principal-agent problem, where the money goes to the employee making the decision rather than the asset owner. Tipping can work in some cases, but most front desk agents don’t get tipped and don’t expect to be tipped anyway, so wearing “Blazer. Clean shoes.” isn’t going to change their expectation.
If you want tipping to influence your upgrade chances, you aren’t trying to signal that you’re going to tip with your clothing. You need to signal it with your money. Stick a $100 bill under your credit card, with the amount clearly visible as you slide over the card and make your ask explicit, “I was wondering if you have any upgrades available, I’d love one of those [view/penthouse/specialty] suites.”
It’s not hard to know what ‘billionaires’ think but it’s odd to be getting hotel upgrade advice on a channel where the word billionare pops up over and over. I heard recently that Instagram is where people pretend to be wealthy, while twitter is where wealthy people pretend to be normal.
They used to say that Facebook was where you’d lie to your friends, but Twitter was where you’d speak truth to strangers. Twitter is now X, and Facebook is no longer about friends anymore, so I guess I’m just old.
I’m not quite a billionaire. But, if I was I’d know the person picking me up doesn’t care what I wear. I’m pretty sure being a billionaire means you can do whatever the f■ck you want.
Great points Gary.
If one needs to watch videos on how to behave, get rich, get what you want or act like you have money, then the game is already over. The loser is still the loser and everyone else moves on.
@This comes to mind — No, being a billionaire should not mean you can break laws without consequence… *cough* Epstein class *cough* …but, sure, wear a silly outfit, if you wish.
You nailed it. This is so opposite how actual billionaires act- and yes- I know a few.
My experience is that people in suits don;t have the money, they are trying to impress. It’s the guy in baggy cargo pants and a Mets jersey (and I say this even though I am a Phillies fan, lol).
Once you get to $10million +, you don’t care what people think. Yeah, they will wear a sports jacket, and there are some random exceptions, but for the most part, they want to be normal and blend in.
-Jon
Guy obviously never saw Billions. The difference between billionaires and millionaires is that billionaires have wheels up private jets. Millionaires have shared private jets or fly commercial.
Chuckling. As a meetings consultant for nearly 50 years, I flew commercial using miles to upgrade. Hotel upgrades were a waste on someone who needs an accessible room and wants all with in easy reach. Amenities too: site inspection 1 or 2 nights. Don’t waste on me. And traveling with clients? THEY get hotel upgrades. I will never be a million- or billionaire. I’d like to fly on a private jet as only passenger for a trip in peace. Ahhhhhhh.
I know quite a few 9-digits millionaires and some billionaires, most of them Europeans, to be honest. You will be amazed how they travel. Since they usually travel quite a lot they will “blend in” as much as possible:
– Most of them, probably 90%, fly with regular airlines. And they do not book business, unless on long haul flights.
– They will never ask for extras. They will often even skip the “VIP” line and early boarding. Privacy and Anonymity are valued more.
– That’s also why they will seldomly wear any expensive jewelry or watches. Men usually wear a Swatch or no watch at all. The wife might wear a simple Cartier watch. Unless it is the second, younger wife or the mistress, of course.
– You will still see high-end luggage – still a lot of the old Rimowa collection – and you can expect an expensive handbag – with no logo and subtle colors.
– Same for clothing: Men wear Loro Piana as an example, but you will not recognize it easily. It is the part of the collection you do not see advertised.
– They will always, always be very nice and kind to the service staff. But they will not tipp while traveling.