Are you working for a startup and don’t know when to quit?
codelathe.com
codelathe.com
Ultimately this can be boiled down to, "If you don't think your company is going anywhere, and you're not being compensated adequately, then it's probably time to look elsewhere." Which is a step closer to reality, but ignores things like the fact that you might simply like it where you work.
I would look at it a little differently; people join companies for many reasons, if you are deciding to leave because of money. You probably already made a few errors; choosing the company, in the hiring process by not getting the salary you deserve and during your yearly review not fighting for more.
Once you joined the company though, you will most likely be working off your balance of intrinsic desire to accomplish everything you can for the company. If at any point your motivation turns to a purely extrinsic (i.e bonuses, cashing out) it is time to leave.
It is a funny thing how different things seem when you are using intrinsic motivation vs. extrinsic motivation. The best way I can explain it is simply: You will walk through hell with seem like heaven when it you are motivated internally vs. even the simplest of task will seem like hell if you are staying to receive a bonus.
- Reallocation of ownership between share classes (substantially diluting the existing common stock).
- Creation of new shares with a high senior liquidation preference.
You might see the reallocation of the pre-money value happen on a "money-in" basis. The valuation itself will obviously depend on how much the company needs the money. When it's all done the existing common stock (founders and employees) could well be worth less than 1% of the company. If you're still at the company you'll probably get new options issued but if you've left you'll just have the old ones worth approximately $0.00.
That said I would focus on whether you're having fun and doing/learning something you think is worthwhile rather than on how much your options might be worth.