[coherentpony]

Even with a 30% tax bill in the worst case, the effective gain is infinite%.

[khuey]

No, it's not, because you have to pay the tax bill whether or not you ever see any returns.

[compiler-guy]

If the company fails, I get to write the taxed valuation off as a loss on my future taxes.

So this comes down to "Do I have enough capital and time to see it through?"

[cbanek]

That's true, but it may take a while for the company to fail, and in the meantime, perhaps no one wants to buy your stocks. I think there might be some way to give them back to the company if they want to, but not being able to sell them, even for a loss, keeps the loss from being realized and therefore deducted as a capital loss.