[foobarkey]

I think there is a sweet spot between risk and expected value, ideally earlier before the IPO looks like an obvious next step. Won’t be retirement levels of money in one go but I would say it is more like 80/20 (success/failure) in that case.

Gambling is only bad thing if the odds are not in your favor.

[boshalfoshal]

The thing is, at that point going to a larger public company would probably net you similar returns and less of the headache (immediately liquid compensation that you can invest into other things, no tail risk of option value suddenly becoming 0, likely better wlb, etc).

Once it an "obvious" choice to join a startup then the valuation of the company is already close to fair, assuming you have about the same edge as VCs do when evaluating these companies. On IPO day it may jump up a bit from its last posted private valuation, but keep in mind once the company IPOs you're typically subjected to a 1-year lockup period, during which the value of the company could change drastically.

[foobarkey]

No, the company is hopefully in high growth stage at that point so ideally you want to join at x and get to IPO at 5x+ (or more) in 4 years. It’s sort of a combination of investing in low cap stocks and swing trading at the same.

Getting the train moving is the hard part but when it is already going it’s about not screwing up and execution, many times better odds (of course evaluate it like you would evaluate stock before buying)

The number of X-s for large cap RSU-s are less likely to be amazing so joining those RSU-s should be pretty much considered at face value (or maybe 10% YoY)