How much will a $20 dollar tip given to the right person in NYC get you? That’s what this author attempted to find out:
A twenty should not be a ticket so much as a solution. You have a problem, you need something from the back room, you don’t want to wait, you whip out the twenty.
I could have stood in line at the airport cabstand for fifteen minutes like every other mook in the world, freezing my balls off, but such is not the way of the twenty-dollar millionaire. I walked straight to the front of the line and offered a woman twenty bucks for her spot. She took it with a shrug. Behind her, people crackled. “Hey! Ho!” they shouted. I knew exactly what that meant. It wasn’t good. I needed to get in a cab soon. One of the guys flagging cabs pointed me to the back of the line. That’s when I grabbed him by the elbow, pulled him close, and shook his hand, passing the next twenty. I was now down forty dollars for a twenty-dollar cab ride. He tilted his head and nodded to his partner. I peeled another twenty and they let me climb in. As we pulled away, someone in the line threw a half-empty cup of coffee against my window.
That whole event had been too public, too visible. Another lesson learned: The bigger the favor–which is to say, the more visible the favor–the more discreet the pass should be. A security guy elbows his way through the crowd to get you up against the stage at a concert and you slip him the twenty quietly, at belt level. Conversely, the smaller the favor, the bigger the flourish. The bellman brings you a bottle of seltzer on a rainy afternoon, you pass that twenty as if the world were watching.
A few months later he tried the same $20 trick in other cities.