It's a serious question. If you were starting today, what strategy would you take?
Go to work at an mid-stage, venture-backed startup where:
* You get lots of options ("lots" being relative to the stage of the company and the % of ownership you'd get at other companies of a similar stage and risk - "lots" can be difficult to determine ; )
* The business is executing well
* Much of the risk has been removed, but this isn't well-understood by the market in general (this is part of why you'll get "lots" of options rather than "very few" options)
* The company is running roughly at break-even, or could be if it dialed-back hiring/marketing a bit
* The company is within a few years of going public
Then, work like crazy, make the place a huge success, and ask for additional options as often as you reasonably can.
Ideally you'll end up with enough options that you'll have $1M soon after IPO.
