> the odds of becoming a billionaire are low, but it doesn’t matter if you only consider the conditional probabilities. [...] The bet sounds insane to begin with, but at each step you’re taking on a very reasonable level of risk.

I'm still not convinced that it makes self-interested sense to do the risky thing and spin the billionaire roulette wheel i.e. leave a steady well-paying job and try my luck with a start-up. (Ignoring that some people just prefer being in a start-up, and some prefer not being in a start-up.)

The most likely outcome is a significantly reduced personal wealth. There's a vanishingly small probability of vastly increased personal wealth, but as the article acknowledges, this suffers from diminishing returns. It's a question of what statisticians call 'expected value', and it seems unlikely to me that spinning the wheel improves the expected value of the sum of my happiness and life-satisfaction numbers. Even if I increase the expected value of my wealth, the non-linearity will presumably easily outweigh this.