Earlier quoted context omitted.
> I had a friend who turned down a job at Facebook in late 2008 because he felt the 15 billion valuation was very high and it limited his upside. He was way off and probably did not ask the recruiter proper questions. Common stock issued to employees is a different class from preferred stock issued to Microsoft.
Well really at the end of the day all that matters is whether this statement (from the video) is true: > Even if you joined Facebook as employee #1000, so you joined it in like 2009, you still made 20 million dollars. I find it hard to believe that it is true, but obviously both you and the speaker know much more about it than I do. However I've also seem people commonly overstate things like this. Some basic math: $…
* typically at that stage those levels of equity are reserved for highly desirable hires that would otherwise be tough to get
* this discounts the effects of dilution that each new investment round (as well as IPO) brings along
I think his point was to provide a ballpark figure to illustrate the main idea - you might have more impact (and receive appropriate compensation) even when joining a late-stage company, so don't dismiss that opportunity without at least considering it.
Taxation rarely plays into such arguments, since by the time the company reaches employee #1000 it's likely to be global, and similar employees with similar compensation packages in California, Washington, Canada or Switzerland are likely to see substantially different after-tax amounts.