I think some of it is relative. If someone is risking 500k on an idea, then I'm impressed... but that's because my net worth is negative. Some of these invest

I think some of it is relative. If someone is risking 500k on an idea, then I'm impressed... but that's because my net worth is negative. Some of these investors, and especially investor groups, have hundreds of millions, if not billions of dollars and have access to lawyers and analysts who know how to hedge their risks. So to say that they're taking more of a risk with their investment based just on numbers ignores the fact that the risk to their actual well-being and wealth is actually quite low. For the generic employee of these startups, few people have the resources to evaluate the companies financials and the reputations of the owners/investors, etc. You're essentially given the same pitches that all other investors get and yet don't have the same resources to evaluate the credibility. Now you said it, employee risks joining eventual-failure company A instead of eventual-unicorn company B or risks giving up years of a higher salary for the potential of windfall stock options. Looking at just the numbers, losing 20-30k/yr in salary over 2-5 years is 40-150k loss, nowhere near the 500k single investment... yet comparing the net worth of these individuals you realize the investor risks a small percentage of their net worth, while the employee risks a much more significant portion. This isn't even taking into account the emotional investments that employees make, which are almost always higher than those of investors. The main point being (and I hope I'm making it decently) is that how you have compared risks between individual employees and investor groups is not exactly fair.