Die With Zero: Getting All You Can from Your Money and Your Life

In Chapter 9, Perkins introduces his ninth principle: Individuals should take their greatest risks when they have minimal potential losses. Perkins illustrates this concept through billionaire Mark Cuban’s early career trajectory, noting that Cuban began with modest entrepreneurial ventures like selling trash bags as a child before eventually creating a computer consulting business that he sold for millions. According to Perkins, Cuban never perceived his decisions as particularly risky because he faced situations with asymmetric risk—scenarios in which the potential benefits significantly outweighed the possible drawbacks.

Perkins elaborates on the concept of asymmetric risk, explaining that when potential downsides are negligible, making bold moves becomes logical rather than reckless. He argues that even experiences that do not yield desired outcomes can generate positive memories, or “memory dividends.” These dividends represent lasting psychological benefits that remain valuable regardless of practical outcomes, making them investments in future happiness and contributing to a fulfilled life.

Age plays a crucial role in risk assessment, Perkins maintains. Young people should embrace more significant risks because they possess two advantages: substantial time for recovery if ventures fail and more years to enjoy potential successes. He compares this to poker, suggesting that youth represents a phase when players can repeatedly “reload” after losses.