We’re not talking about how to tip your waitress, or your mait’r'e d. If you don’t know how to do that, you need a lot more help than this site can give you. We’re talking about how to tip in situations where tipping isn’t customary, where the small incentive of paper currency can help get what you want.
This technique involves slipping a $20, $50, or $100 dollar bill in the hands of a patron with the hopes of getting something in return. I have personally used this technique in three situations that have all worked phenomenally:
1.) Getting into a club where I didn’t know the doorman.
2.) Getting an upgraded hotel room from the concierge.
3.) Ensuring my luggage gets on a plane when I arrived 20 minutes before takeoff
There is a great thread talking about the success of slipping a $20 here.

A smile and a Jackson can soften anyone up
The trick with tipping in this manner is understanding the needs and wishes of the people you tip. You can’t just go around waving a Franklin and expecting better service. Often times they have a supervisor nearby, the establishment’s policy discourages tips, they may not feel comfortable accepting a tip in front of their coworkers. Understanding this you will need to be discrete. You need to help them help you.
How To Tip Properly
We discourage blatantly saying you will tip the patron, flashing money, or dropping a $20 on a counter- this is rude, shocking, and crass. Instead state your request, and ask for their help. Then repeat these magic words:
“If you take care of me, I will take care of you.”
Pulling out your wallet or casually placing your wallet on the counter will help reinforce what “take care of” truly means to you. If they accept:
1.) Grab the bill or bills and fold it in your hand

Fold the bill in your hand and tip discretely
2.) Shake their hand
3.) Exchange the money
Here are a few conversations I have had in the past, the patrons objections, and what I have done to overcome them.
At a club:

Dealing with Bouncers
Bouncer: Are you on the list?
Me: No, I am not.
Bouncer: ::Looking at me and my party of 6:: Ok it’s going to be $20 each.
Me: Is there anyway you could hook us up?
Bouncer: Sorry, you’re all going to have to pay.
Me: Are you sure? If you take care of me, I will take care of you. ::Pulls out wallet::
Bouncer: ::Softening up:: No.. you still have to pay
Me: I’d much rather pay you, then her ::referring to cashier- while opening wallet::
Bouncer: ::Thinks for a second:: Ok, go ahead. ::Opens velvet rope, tells cashier that we’re all ok to go in::
Me: ::Slips the bouncer a $20, escort my group in, enjoy the rest of the night with a smirk on my face::
This was an actual conversation at a Miami club. It was as simple as that. My whole party was escorted in like we owned the place, we saved $100 between the 6 of us, I solidified my reputation amongst my friends for being able to get in anywhere, and we all had a great time.
At a Hotel:

Bellagio Front Desk
What a lot of people don’t realize is that concierges and booking agents have unbelievable power when it comes to giving away goodies- from room upgrades, meal comps, drink tickets, and club passes. Because of this power, this technique works even better at hotels.
First
Research the hotel you are staying at. Familiarize yourself with the different suite upgrades they have available. Then call the front desk ahead of time, ask a few questions, find out if the person you are speaking with will be working when you check in. If they will not be working, call back until you find someone who will. Then ask for their name.
Next
When you arrive for check in, go directly to the guy (keyword- guy) you spoke with on the phone. Remind him of the conversation you had on the phone. When he remembers you, make sure you keep using his name throughout the conversation (this develops a good repoire).
Ask him “Busy Day?”
Service industry people love this question, because it’s a refreshing change of pace to see someone care about their feelings rather than worrying about everyone else’s.
After you soften him up a little bit ask directly which suite upgrade you would like by name.
They will usually quote the standard upgrade price. This is what you will do next.
Here is an actual conversation I had with a concierge in Vegas.
At a Hotel:
Concierge: “Ok sir, if you would like to upgrade your room that will be an extra $165/night”
Me: Please, call me (my name). (Insert his name here) Is there anything else we can do to make this upgrade happen. “If you take care of me, I will take care of you.” ::places wallet on counter::
Concierge: ::looks at the wallet, then pretends to crunch a few numbers in his computer:: Ok (my name), you have just been upgraded to (Inset fancy name here) suite, complimentarily.
Me: Why thank you (insert name here). Do you mind helping me up to my room with my bags?
They always oblige (customer service is always number one in any decent hotel). I then use this time to further increase my relationship with the concierge, pick his brain for any great shows, clubs, attractions, that I must see. He tells me to come back down and he will get me some free passes to everything he can.
I never let him actually carry my luggage, I tell him “don’t worry about it, I just didn’t want to tip you in front of your boss, I know how it works- I used to work the front desk in (insert Miami hotel here).” I then slip him some decent bank roll.
Because of this I was able to stay in a penthouse suite for an entire weekend which would have cost me over a grand for less than $200 a night, including the tip.
You can skimp and get away with slipping a bouncer a $20, or even a $10 if you’re really bold, because by the time he accepts the cash, you and your crew are already half-way through the entrance. But, with a concierge, I would tip generously. They will remember you throughout the weekend and continue to give you great advice, comps, and service.
Last Minute Tips:
-Black guys tend to hook it up the most
-Asian ladies tend to hook it up the least
-Generally guys will hook it up more than women will
And that’s it. Feel free to use this technique at any number of places:
1.) Ticket collectors at sporting events
2.) Baggage handlers
3.) A host at your favorite restaurant
4.) Yacht rental clubs
5.) Rent-A-Car locations
The sky is the limit. You never know what you can get away. It doesn’t hurt to ask. Good luck, and happy hunting.