The “$20 Trick” has spread around the internet as the best way to get a nearly free upgrade at any hotel. Popularized by the book“Heads in Beds: A Reckless Memoir of Hotels, Hustles, and So-Called Hospitality” by Jacob Tomsky, this idea has spread like wildfire and has resulted in an unrealistic expectation of nearly free upgrades. For those who have tried it, they seem to have varying success. Many front desk agents will not accept the money; others will only accept it if they like the person. Some people have even paid the bribe but have been given a room that was less expensive than the bribe itself.
I am not a fan of this trick, have never used it, and will never encourage it. There is a difference between a tip and a bribe. In most cases, it can get a staff member fired if they are caught. Front desks often have cameras pointed at them, and catching an employee taking a bribe is grounds for termination at most hotels, especially higher-end ones. Obviously, this is a loss of revenue for a hotel. That upgrade is no longer available for sale, and the hotel makes no additional profit from the use of that room. Yes, the decision to take the bribe rests on the employee, but I would rather not be the guest to cause them to make that mistake.
I have, on many occasions, tipped a front desk staffer because they helped me solve a guest issue, they made changes for me, they printed documents for me, etc. But I have never bribed one.
Mr. Tomsky’s book does have a number of good pieces of advice, which you can explore in an abbreviated version linked below, but his experience is only with very high-end properties and, realistically, only two. One is in New Orleans, and one is in New York. This is a very small number of properties, and it’s only one type of property. There’s a lot of information and experience missing from this behind-the-scenes account of the hotel industry. While I do highly recommend the book, and Jacob Tomsky is a very fun writer, I recommend doing some additional research on his tips and deciding for yourself which ones are appropriate to follow.
For those of you who haven’t read the book, you can read a summary of Tomsky’s key points HERE.
If you’re curious about my opinions of the tips in the article above, here are some brief reactions to Mr. Tomsky’s suggestions.
- Hotels are raking it in.
Sort of. Turning a room often costs about $40, but at some hotels where the staff-to-guest ratio is extremely high, the turnover cost could be upwards of $100 or more to cover those extra staff members. Hotels have huge expenses other than their simple turning costs that are not accounted for in Mr. Tomsky’s math. Just like any business, they have insurance costs, repairs, maintenance, etc., and most hotels reinvest a lot of their profits into new properties, upgrades to their existing property, multi-million dollar renovations, etc. Yes, there are people at the top who make large amounts of money, the Hilton family, for example, but, again, that’s true of all large companies. Smaller properties with only one, maybe two locations will have much lower profit margins and can suffer significant losses with practices such as the $20 trick. - Staying for just one night? You might get “Walked.”
This is true, and from my experience, Mr. Tomsky’s reasons a guest would be walked are correct. There are times when many guests need to be walked that these criteria would not be followed. Click here for some of my experiences with walking guests. - Smart complainers win.
This is true, but please don’t do this unless there is a real problem. If you have a problem, YES! Tell someone! Come to them with a solution, be polite, and ask to speak directly to the person who can solve it.
But please don’t do this just to get something from the hotel that you don’t need or deserve. There are lots of real problems already being solved, and we don’t need your attempts to get amenities and upgrades to get in the way. - There’s a better way to case a pillow.
I’ve honestly never tried this one, but I do AirB&B my house when I’m away, so I’m going to try it! - Enjoy your lemony fresh glasses.
I have never experienced the “lemon aftertaste” Mr. Tomsky refers to here. I’m sure this is the case at some hotels, and if you’re concerned about it, take a quick sniff before you fill the glass. If it smells lemony fresh, just wash the glass in the sink with the provided body wash or bar soap. All soap is pretty much the same, anyway. - Never, ever pay for the minibar.
This is just dishonest. You can choose what kind of person you want to be, and I choose not to be this kind. - Book on a discount site, get a discount experience.
This is usually true. Be super polite when you get to the front desk, and they may give you a better room, but overall, you’re going to get what you pay for. That being said, I often use discount booking sites for personal travel, and I often have a great experience. There’s nothing wrong with it, just know that you won’t be given the best room on the resort because someone else paid more than you did. If you want a better room, just book a better room. - Bellman hate your suitcase – but not because it’s heavy.
Another one I completely agree with. His job is to help you get your stuff to your room. Just let him do it.
Bellman can be your most valuable asset when you’re on a resort. Have $2 – $5 on-hand for them, and let them carry your stuff. When you need a taxi, need help explaining to a taxi driver where you want to go in the local language, need change in USD, need help finding something on the resort, need a ride in a golf cart, etc., guess who’s got your back? - Front desk agents can also be agents of karma.
True! Keys can be deactivated remotely. While it’s kind of rude for a desk agent to do, it does happen.
Another thing to keep in mind is how much power a desk agent has. Be nice to them so they’ll stay in your corner. - There’s one surefire way to get an upgrade.
As discussed, this is not “surefire” and is a good way to get a well-meaning front desk agent fired. While it does sometimes work, I don’t condone it. Just ask nicely if there’s a good view available or pay for the upgrade.
