It’s because he sunk a ton of money into Strike - a company who laid off a massive, massive amount of Bitcoiners because Jack can’t figure out, for the life of him, how to monetize and run his business.  Strike is a shitshow.  Now Samourai (also ten31 funded).  

It sucks to suck.  Some people do it gracefully.  Others do it like Odell lol.