It's interesting to read this with Taleb's "The Black Swan" in mind (which I just reread this weekend), specifically because it made me think of Taleb's "barbel

It's interesting to read this with Taleb's "The Black Swan" in mind (which I just reread this weekend), specifically because it made me think of Taleb's "barbell strategy": "... your strategy is to be as hyperconservative and hyperaggressive as you can be instead of being mildly aggressive or conservative. Instead of putting your money in 'medium risk' investments, you need to put a portion, say 85 to 90 percent, in extremely safe instruments, like Treasury bills—as safe a class of instruments as you can manage to find on this planet. The remaining 10 to 15 percent you put in extremely speculative bets, as leveraged as possible (like options), preferably venture capital-style portfolios." It seems that going to work for a startup is the exact opposite of this. I.e., it would be better to be an investor in many startups rather than working solely on/for one startup.