I watched the game last night and still can’t name one player on Baylor or Gonzaga. I don’t think I can name one NCAA player in the tournament. I kid you not that I know nothing about this sport. I bet purely out of trying to win money with zero interest in the outcome emotionally.

Last night if Baylor won, I would win $192 dollars in a pool (I’d win 0 if they lost). This concept comes up all the time not only in sports gambling, but life. You have a bet that hasn’t quite paid off and you have options. These decisions dictate who you are as a person. Here are 3 examples of how to look at my scenario last night.

  1. I’m happy with the chance to win $192 dollars in a pool. Why would I want to bet on the game?
  2. I can guarantee I win some money by forfeiting a bit of my winnings if Baylor wins, and put some money on Gonzaga, so I win money no matter who wins.
  3. I’m confident in my selection and I’m going to let it ride and also bet on Baylor.

I’d recommend 3 unless the money is substantial. For me, $192 does nothing. If it was $1,920, I’d probably put $500 on Gonzaga, just to win something. If it was $19,200, I’d lean towards more on Gonzaga and eating some ML juice. If you’re hedging for $192 dollars, you’re doing it wrong.

I like the concept of going down with the ship. Clearly with Baylor being 4.5 dogs, you wouldn’t think they should have won the tournament. Here’s what I know about Vegas, and I truly believe this concept no matter how much you may disagree, almost every bet is 50-50. So in my spot last night, it was possible if I took Gonzaga minus the points, they win by 3, and I lose principal. Which means I’d have to go ML, which completely eats into the profit. Instead I decided that the 50-50 is good enough for me and I backed up my bracket pick with the +4.5 and would earn the spoils if they won outright (or cover) which they did.

This is what happens to me in golf and I’ve lost a lot of money. My player with opening tourney odds starts out well and his odds decrease as he picks up steam. I keep hammering him if he’s up on the leaderboard. Then it gets to the final round and I’ve bet my guy 10 times because I’m that sure he’s going to win and I want to get a payday. It rarely happens for me like that but I’m not going to say that it’s the wrong strategy. If you believe in your convictions, I say double down, don’t hedge like a pussy.

This goes doubly for stocks. If you think the stock was a good deal at one price and it goes lower, don’t be afraid to buy the dip. Dollar cost averaging is how you make money when you’re right. Humans have been conditioned to be pussies and life is too short not to take risks. Own it.