> standard, comprehensible ways I am not convinced that the problem is exactly the lack of comprehension -- it's that startups going public are a probabilistic

> standard, comprehensible ways I am not convinced that the problem is exactly the lack of comprehension -- it's that startups going public are a probabilistic thing, not a deterministic thing. Given a population you can talk about the distribution of this or that happening, but you can't know if this particular one will get to milestone X. (See also cancer 5 year survival rates.) You could get around this if you could do a ton of startup jobs, because then it starts getting likelier that you actually hit on a winner. But you can't do many in a lifetime, because of the option / tax due on exercise / long pre-IPO / vesting schedule. Even if you could come up with something crystal clear, like "X% chance that you get $Y", and even if you could agree on those probabilities, you still only get to sample that distribution, not enjoy the big-N expected value. I think my best attempt at a solution here probably is forcing the light of public trading onto a company sooner rather than later, via regulation. My understanding is that usually the going public forcing function is the value of assets and the number of shareholders; perhaps some additional constraint on the number of (company-issued) option holders or volume thereof or amount of debt or ... something? as well? (Stupid risk-brain is just inventing loopholes for every rule I can think of.)