[perl4ever]

All else being equal, given that you turned $100 into $100K, you're much more likely to have $100K that you can afford to lose.

Saying that the history of your investing shouldn't impact your choices is saying that your total wealth shouldn't affect your choices.

But if I borrowed $100K against my home and it gets foreclosed and I'm homeless, that's very different from if I gambled $100 and got $100K whose loss will be no worse for me than losing the original $100.

[ALittleLight]

That's exactly the fallacy I was describing. Whether or not you can afford to lose money is completely independent of how much your initial investments cost. You will tend to make more money, provided you have some ability to predict, if you do what you predict is best based on the present and the future, compared to changing your decisions based on the origins of your money.

[perl4ever]

  A = Bob has $1M in bitcoin.
  B = Bob can afford to lose $1M.

It appears to me you think P(B) = P(B|A). I think obviously P(B) < P(B|A).

How about:

  A = Bob has $1M in bitcoin which he paid $100 for.
  B = Bob has $1M in bitcoin which he paid $1M for.
  C = Bob can afford to lose $1M.

It appears to me you believe P(C|A) = P(C|B) = P(C). I'd expect P(C|A) > P(C|B).