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Rich said, losers are people who think that losing is bad. Losers cannot afford to lose and often acid losing at all costs. Many losers bet only on sure things such as job security, a steady paycheck, a guaranteed person and interest from a bank account. Losers keep losing and winners keep winning simply because winners know that losing is part of winning.
If we knew we could win a million dollars and the risk reward ratio was 1:100 in single bills and work our strategy to bet our only dollar 100 times. After we won once, we would go back to paying the same odds because the odds rarely change. We might increase our bets but only if we could survive losing 99 out of 100 times.
That was his simply way of training us to think in terms of risk and reward instead of right and wrong, risk or safe. Rich did not like gambling not did encourage us to gamble. He simply was training his son and to think in terms of risk and rewards.