Well, you would still have certain data points to make a decision from. If you've been part of an industry for a while you'll start understanding it.

Second, if you already have a ton of money, you might take on the additional risk to get 2x instead of 1x. Say you have $20mm in the bank, generating 10% a year, then getting a $10mm payout instead of a $5mm is probably worth it, since an extra $5mm won't change your life.

If however, you have $100k in the bank, then you should probably take the $5mm.

Exactly. Two people can face at the same choice with the same facts and same assumptions and come to different conclusions because of their individual risk preferences. Neither is necessarily wrong.