It's fairly common for options to expire shortly after leaving employment, regardless of vesting: you have to either buy them out or lose them.
Options are not shares. They are a contract that allows you to buy shares. When options vest over time, you become eligible to buy actual shares. In your case it seems that the options do have actually vested: but you still need to pay $150k out of pocket to own real shares in the company.
This is not an issue when the company gets acquired, because you can buy the shares and then sell them on immediately, pocketing the difference.
In summary this means that your choices are:
1. Stay employed with the company until it gets acquired or goes public. If the final valuation is over $30m, you can at best earn (X-$30m)*0.005. For example, at a $40m sale, you could make up to $50k (minus taxes, or the investors' preferred share payouts). If the company is sold for less than $30m, the options are worthless.
2. Leave now, and just before that spend $150k of cash to exercise the options, buying shares. The profit calculation is still the same, but in addition you have to risk actual cash.
3. Leave now, and don't exercise the options.
The second choice is extremely risky, especially when you don't have $150k to blow on investments, or when you don't believe that the company's value has increased far above $30m.
Options are not shares. They are a contract that allows you to buy shares. When options vest over time, you become eligible to buy actual shares. In your case it seems that the options do have actually vested: but you still need to pay $150k out of pocket to own real shares in the company.
This is not an issue when the company gets acquired, because you can buy the shares and then sell them on immediately, pocketing the difference.
In summary this means that your choices are:
1. Stay employed with the company until it gets acquired or goes public. If the final valuation is over $30m, you can at best earn (X-$30m)*0.005. For example, at a $40m sale, you could make up to $50k (minus taxes, or the investors' preferred share payouts). If the company is sold for less than $30m, the options are worthless.
2. Leave now, and just before that spend $150k of cash to exercise the options, buying shares. The profit calculation is still the same, but in addition you have to risk actual cash.
3. Leave now, and don't exercise the options.
The second choice is extremely risky, especially when you don't have $150k to blow on investments, or when you don't believe that the company's value has increased far above $30m.