If you lend a poker player $20,000, you will always get your money back.
But if you lend him $20, you'll never see it again.
That truism popped into my head the other night when several people around the table started talking about lending money to other poker players. Over the years, I have lent money to a few friends in casinos and, fortunately, I've always been repaid in full. I had one guy who stiffed me for a couple hundred bucks for several months -- the fact that he owed me money didn't stop him from buying in to games when he knew I wasn't around -- but even that eventually came home. Since then, I've only handed over some cash to people who I absolutely know are good for it and will return it within a reasonable amount of time.
The other thing that occurs to me every time the topic comes up is this joke. I don't know who originated it, so I can't give attribution, but present it for your enjoyment nonetheless.
A homeless guy walks up to a man on the street and asks if he can spare a few dollars. The man rebuffs him, saying, "Neither a borrower nor a lender be. That's Shakespeare." To which the homeless guy replies, "Oh, yeah? Fuck you! That's David Mamet!"
There's also my all-time favorite true story about lending money to a poker player, which I told in a post called "The Borrower," which Anna Boden and Ryan Fleck liked so much they used in their gambling movie "Mississippi Grind." Read it here.