What if the preferred stock has a liquidation preference and the amount is smaller than their investment? There are some cases where the preferred shareholders can get paid and not the common right?
Obviously you weren't talking about that sort of acquisition, but it does highlight the point that common stock would be worth somewhat less than preferred due to that potential unless I misunderstand something.
I believe that "lottery ticket" thinking is really dangerous.
It leads to making really awful financial decisions. At many companies, people don't do enough math to realize how little their options are worth. And so slog it out for years thinking it is a good deal.
And many companies will argue that paying below market is justified because they're giving you options. If you do the math, you might find out that the lottery ticket, spread out over 4 years, diluted by liquidity preferences and successive rounds don't come close to the aggregate bonuses from a 'regular' job.
True story:
At my last startup, as I was leaving, I created a spreadsheet that took everything into account (liq. pref., multiple rounds, etc.) so you could plug in the options you had and an acquisition price and see what you'd make.
I went and showed it to some folks to make sure I'd done all of the crazy math right. It turns out that
I'd like to hear more about exercising options early. I had no idea that could be done. Not that I'll ever be in that situation, but I'm just curious how that happens. Sounds like a bit of a legal hack. Did you mean with the 83b form?
I did exactly this when I joined justin.tv - it's not very difficult to arrange. The hardest part was actually finding a CPA who had any availability to work with me, and who I felt I could trust (he came recommended by a friend).
It's obviously important to keep in mind that to exercise your options you'll need some cash. If your share is big and the company has been well funded already, you might need a lot of cash. And you need to be prepared to lose it all if the company fails.
Obviously you weren't talking about that sort of acquisition, but it does highlight the point that common stock would be worth somewhat less than preferred due to that potential unless I misunderstand something.