I never play for money - I toured with bands for a number of years in the same circuit, and played a lot of tournaments during my down time (during the day) when there was nothing else to do. I got a mild reputation for being a decent player - people get to remember you and look forward to challenging you, especially if you trounced them the last time you were there. Playing for money and soundly beating the local pool sharp is a sure-fire way to get your head kicked in with some of patrons that frequent the places I performed at back in the day.
Fun story - my buddy was the musical director for the Cirque du Soleil show "Eau" for a year in Vegas. My wife and I went to visit him, and we caught the afternoon performance and then got the "royal backstage tour" which was excellent. We were hanging out in the green room (performer's lounge) and chatting before we were leaving, and one of the main acrobats came in to chill. There was a pool table there, and he was banging the balls around a bit. My buddy introduced us to him (knowing that I was a player), and we got to chatting. During the conversation he mentioned that when he got too old for acrobatics, he was intending to take up a professional competition pool playing career.
"Oh, you like to play? Let's play a few."
I trounced him at least 3 games straight - I remember more, but my wife says it was 3... I have my good days and my crappy days, but I can hold my own usually!