Brain Crusher: How Do You Make A Lopsided Bet? Learning from Errors

Table Tennis Players

Thinking Outside the BOX

You bet a group of hustlers/bettors that if there is enough prize money–$500,000 or more, you will play the winner of this match in a two-out-of-three match in games to twenty-one.  You have only played twice before against your little sister and lost. You win $500,000 or you lose $500,000.  However, you get to choose how you will play the game of table tennis (ping pong). Both of you are under the same rules/equipment and you must abide by the rules of table tennis—hit the ball over the net, one bounce, no touching the net, etc.

You have 15 days to prepare. What are you gonna do? This story comes from a true story of a famous proposition gambler.

If you lose, then these guys will help you pay: Your career is over.

Table Tennis

Please don’t post the answer if you know the true story behind this bet. Otherwise, try your hand and win a prize.

I hate the term, “Thinking Outside the Box” but I provide this puzzle/quandary as a way for you to think about investing in an unusual way. GOOD LUCK!

The most powerful mind is the quiet mind. It is the mind that is present, reflective, mindful of its thoughts and its state. It doesn’t often multitask, and when it does, it does so with a purpose.

Improving As an Investor

Lecture_01_Sanjay Bakshi_Improving as an investor

31 responses to “Brain Crusher: How Do You Make A Lopsided Bet? Learning from Errors

  1. Great book! If I remember correctly, he had a bit more time to prepare…

  2. was thinking about how to hedge bets with a bookie based on the most probable outcomes, ie bet against my self so at least I don’t lose any money, with tiny bet on myself in the miracle case that I win.

    It seems the investing correlation would be not to lose money, don’t play a game where there is no margin of safety or edge, stay within circle of competence.

    If betting against myself isn’t on the right track then another clue would be good.

  3. OK, Kevin. Hint 1: The trick is not to play basketball against Michael Jordan, but chose a game he can’t play, but you can. Don’t trade against high frequency traders in a well-know big cap stock, go where you are the smart money (smarter money) and have a longer time frame than most.

    Hint 2: is in the post.

  4. Something along the lines of you have to play with your non-dominant hand, while you train your non-dominant hand. OR the racket, equipment, etc. you are using is something that almost dumbs down the game to a point where you are at equal competition?

  5. You could request that the game be played in total darkness. That way neither player has an advantage since neither player could see the ball…???

    • You’re on the right track, but in this case you would both playing on a level playing field. You’re getting warmer though and are approaching your analysis from the right angle….

    • Ok, but where is YOUR advantage. NEVER play a fair game if you are a professional gambler or an investor. You want the UNFAIR advantage. If life is unfair, then be on the side of favor.

  6. Ask your opponent to play the opposite hand.If he is right handed player, ask him to play the left hand. In the post i see the man playing in left hand (Hint No.2).

    • The Hint is the Rackets.

      If you ask your opponent to play with their off-hand–they can require you to do the same. Check-mate!

      • It seems like people are coming up with ideas that, at best, give you an equal chance of winning. Unless you’re getting odds better than 1:1 there is no reason a risk adverse player would really want to take that bet.

  7. Thanks Scott for not spilling the beans.

    I will post the answer this weekend. This is a tough one. An amazing story about an old Texan gambler who first cleaned up through out the American SW playing pool, moving onto poker and prop. bets like this one.

    Boy, I would not want to be on the other side of a bet from him.

  8. Each player can only hit the ball once and you let the other person start first.

  9. If the answer is to play with a king size racket, I’ve tried it and its no use! Maybe it gives slightly better odds but it still won’t be enough. It prevents you from being nimble in a fast paced game.

  10. Since my last answer was incorrect and I don’t know if this is allowed, but if allowed, I would setup the table up in the right angle in the L shape, so that the opponent would be playing against him/herself.

  11. If you’re both right handed: Make a rule that requires the paddle to stay in the hand closest to the right side of the table. You’ll have the paddle in your right hand and theirs will be in their left hand.

    If you’re both left handed: Require that the paddle stay in the hand closest to the left side of the table.

    If you’re right handed and they’re left handed: Make a rule that paddles must be in players’ right hand

    If you’re left handed and they’re right handed: Make a rule that paddles must be in players’ left hand.

  12. John,

    Thank you very much for your hard work, I learn a lot from reading your site.
    You do a wonderful job.

    A few guesses:

    (i) Maybe he put a magnet in his racket and some iron powder in the ball so he only had to face it at the right angle and more or less the right location to hit the ball back across the table?

    Or maybe even a stronger magnet that will attract the ball to his racket once it crosses the net?

    (ii) He electrified the handle of the opponents racket? Made it slippery?

    Hope I am not going too far with this..

    • Thanks, but you both have to have the same table, racket, shoes, etc as the opponent.

      Don’t despair, this is a tough one. Wait until I post the answer …………..

      • Here’s my take: you both have to use the same equipment etc (you have access to the same resources). But what I would do is choose a piece of equipment I’m most confident with, or choose equipment that I can get good with in 15 days. Being a former highschool and college athlete, I’d make us both use baseball bats or hockey sticks – maybe even play with skates on. We used to do drills like this in college (hitting ping ping balls back and forth with a partner using bats). Wierd? Yes. But I know I can ‘bunt’ the ping pong ball over the net, and odds are my opponent didn’t do the same drills I did in college, so I will take my chances.

  13. Play with something else besides a standard paddle — sufficiently enough that would eliminate the skill edge

  14. do we both get to practice also.. or i have to declare my rule/strategy on the day of game..


    “(1) you get to choose how you will play the game of table tennis (ping pong). (2) Both of you are under the same rules/equipment and you (3) must abide by the rules of table tennis”

    My bet is that there is a problem with the question itself.


  16. 1) Bribe the other player.

  17. The symmetry of rules and equipment indicates that the asymmetric advantage lies in the initial and environmental conditions; the “how to choose to play”. Therefore I choose to focus on an area where I am confident our table tennis champion will fare poorer at – computer programming. 15 days seems a bit tight but I could rig up 1 robotic arm with camera for each player that will swing at the ball in full compliance with the rules of the game. The trick is that the computer must operate the arm; the player must use their own skill to program the computer before the game. I am a programmer with mechatronics experience so this suits me personally.

  18. Nope. The question is fine.

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