Microsoft stock option backdating

I often talk to startups that claim that their compensation package has a higher expected value than the equivalent package at a place like Facebook, Google, Twitter, or Snapchat.

One thing I don’t understand about this claim is, if the claim is true, why shouldn’t the startup go to an investor, sell their options for what they claim their options to be worth, and then pay me in cash?

Like most people, extra income gives me diminishing utility, but VCs have an arguably nearly linear utility in income.

Moreover, even if VCs shared my risk function, because VCs hold a diversified portfolio of investments, the same options would be worth more to them than they are to me because they can diversify away downside risk much more effectively than I can.

The preferred stock VCs get usually has a 1x liquidation preference.

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