Once you’ve got that kind of money, I’m sure you have millions squirreled away here and there.
That’s kind of right. He likely has liquid funds stuffed away in all kinds of places, possibly in different currencies on different continents. The only way to put someone like this in the poorhouse is to bankrupt every single one of his investments, while simultaneously freezing all his funds internationally.
From a finance perspective, a billionaire is a few orders of magnitude beyond “escape velocity” from ever being poor. I think most of us would need a few tens-of-millions USD in cash to even consider achieving such a thing.
Another way to look at it is that the billions in “net worth” he has accumulated are just ablative armor for real spendable wealth. Consider the move he made with Twitter: the objective was controlling the platform and discourse on it, full stop. Losing tens of billions didn’t matter - it wasn’t real money in the first place (mostly stock) and wasn’t spendable in the conventional sense. DOGE is a similar play in that the kinds of unfair advantages being gained are worth at least what he’s losing.
Now, or when he was alive?