Nobody Is Crying For You When You Are Worth Billions

I like characterizing the investment in a startup for preferred stock as a bond with an out of the money option. That is certainly the sort of expectation I hear about from investors. Sort of a "well we'll get our money back at $X, may money at $Y, and kill it at $Z" sorts of things.

I don't know that I agree with hiding your valuation. Like it or not those big valuations lend a certain credibility to a company when it knocks on the door of an established entity. If 'some startup' wants to talk to a city about how its regulation of the livery business is not good for its citizens, it might not get the time of day, but if a $2B company comes calling? Sometimes it seems like that is the difference between them taking the meeting or not.

I could certainly see this as solid advice if you're just beavering away at a killer product company, but if part of your strategy is going to require influencing the public or a market segment, then sometimes this sort of 'validation' can be very helpful.