As a hardcore hodler you know the market is in despair when your mental attitude switches from "*hark* *hark* all those cheap coins, come to daddy!" to "oh crap better sell some now this thing could actually go down, better save than sorry". 
This is going to be the longest down trend in history, those private keys will have to be pried from my cold dead hands.
I had my "oh crap" moment at the end of 2012, and I can't imagine any futurist investors investing big thinking it may be a good idea to be overextended to Bitcoin, my bet is they're in it to the end.
I'm watching Silbert, when he gets squirmish, I'll know the tide is about to turn.
It'd definitely be nice to see some libertarian, futurist billionaires invest large amounts into it because they are supportive of the concept.