Upside Investing Helps You Build a Living Standard Floor and Invest in a Manner that Should Entail Only Upside Risk to Your Living Standard.
Upside Investing treats investing in the stock market like playing the casino. When you are running the program in Upside Investing mode, you tell the program how much you currently have invested in stocks, how much you intend to add to your stock holdings through time, and when you expect to start and stop converting your stocks to safe assets.
The program then sets your living standard floor assuming that all your current and future investments in the stock market are entirely lost. But the program also runs simulations to show you the chances of different upsides -- different living standards above the floor -- once you start converting your stocks into safe assets.
Upside Investing is heavily influenced by the work of Boston University economist, Zvi Bodie. His book, Worry Free Investing, calls for building a living standard floor with TIPS (Treasury Inflation Securities) and using stocks, options, and other risky investments to provide an upside to our future incomes.
Bodie's "safety-first investing" also requires safety-first spending, namely not spending out of risky assets until they have been converted to safe assets. In short, leave your wallet at home when you go gambling and don't spend your winnings at the Casino while you are still playing craps. Upside Investing incorporates both dictums -- invest only a share of your resources in risky securities and treat them as totally lost in terms of your spending until any winnings have been converted to safe assets.