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Dont think it does work always but... for me it increased the odds by alot!
After lowering myself to a point where going all in WOULD bankrupt me and then winning (thank you strong bad), the next hand (where I had more chips than any other NPC could match) I went all-in and the achievement popped.
So I guess the best way to try to get it, is to go for a situation where you win an all-in that would otherwise eliminate you, then immediately go all-in the next hand.
So go for the "all in at the beginning" strategy when you are neither small nor big blind for two rounds in a row!
(I know the post is outdated, but it did help)