What life is all about
The madam of a brothel opened the door to see a well-dressed, dignified man standing at the door. “May I help you?” She asked. “I want to see Penny,” the man replied.
“Well, the madam replied “Penny is one of our most expensive ladies. She charges $1000 per session. Will that be a problem?” “No, I must see Penny,” was the man’s reply.
So Penny comes down and they go up to her room. He gives her the $1000 in cash. After an hour the man calmly leaves.
2. Taxes
3. Being screwed by a lawyer
Not to overthink the joke, but in real life he'd be disbarred and imprisoned for that. Like Michael Avenatti.