Broadly, I've found that Nassim Nicholas Taleb has the best advice here. I think his "barbell" strategy is perfect. Never invest "moderately," just put most in

Broadly, I've found that Nassim Nicholas Taleb has the best advice here. I think his "barbell" strategy is perfect. Never invest "moderately," just put most in something really safe, and set some aside for big long-shots. (You can also apply this strategy to not just "money," but e.g. jobs and projects)