Short answer, the $4 options aren't likely to pay off. The $1 options might or might not, but in terms of your personal financial planning you should assume they are worth nothing as well.

Read on for the long answer.

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Let's start with the facts.

First of all your options are contracts obligating someone to sell you stock at a fixed price should you choose. If the stock costs more than that, then your options can be used to make you a profit. If the stock costs less than that, then it makes no sense to exercise your options. If you have 9000 shares at an exercise price of $1.00, then thats not worth $9000, that's an opportunity for you to SPEND $9000 and get something that might or might not be worth more. (Note, there are tax consequences to handing out options at a price different from the valuation of the company, so at the point they are issued the return you can get from exercising them is usually $0.)

Secondly a company is worth today what someone is willing to pay for it. No more, no less. All of the possible potential growth, and future revenue? They only matter in so far as they convince someone that it is worth spending money on. Tomorrow may be a different story, but today it is only worth what you can find a buyer for it.

Thirdly, early stage companies are highly illiquid. Meaning that there is no real market for them, and different people will assign wildly different valuations. Also those valuations can change, fast, as facts change. (Where facts may be as simple as, "there is a different person willing to invest".) A 4x fluctuation is very, very easy to believe. A 4x fluctuation down with new investors tells me that the company could possibly succeed (else where would you find investors?) but the prospects are nowhere near as bright as the company previously thought.

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Now what do these facts mean for you, or any employee?

First, options are not worth the strike price. $150k is not the worth of the options you got in the first round. That is the amount you are allowed to spend at that price for stock that might or might not be worth more. (Hopefully will be worth more.)

Second, as an employee you like low strike prices. The lower it is, the easier it is to be worth a lot later.

Third, options for the future could always wind up worth something, but that is not guaranteed. Your $4 options are only going to be worth something if the company grows to the point where it will be worth a lot. Even if the company is worth less now, it is possible for it to be worth more later. Nobody knows whether that will happen, and your guess is likely to be better informed than mine.

Fourth, the high valuation on your initial options suggests that this is the value that the initial external investor thought it deserved, and maybe invested at. The current valuation is likely to be based on what current investors think it is valued at, and likely that reflects what value their investments were made on the basis of. That means that the initial external investor really believed in the company, and has likely lost a lot of money on paper so far. (But could still make it back if the company succeeds.) As upsetting as this may be for you, it is unlikely that anyone was intentionally trying to cheat you.