Elon isn't paying for this out of his own pocket. He's not transferring it to some perpetual trust a la the Guardian and the Scott Trust. He's taking it private but there will still be pressure from everyone he's raised money from to make sure they make good.
Mostly, I think this is going to end up being one of the most expensive acts of individual hubris in history. It's strange from someone whose other notable projects have such clear goals. "Moar free speech lmao" doesn't sound measureable, let alone achievable while also making bank.
Bloomberg mentioned two loans to cover the shortfall in his equity swap (one external and one drawn on his Tesla stock), with annual interest payments in the ballpark of $1B each. So Twitter's take home pay just lost $2B of the $4B it nets annually. Losing further market share by re-engineering retweet algorithms to be kinder/gentler looks like a better bet to bury Twitter than raise it.
But mature media giants are supposed to lose money, right?
Mostly, I think this is going to end up being one of the most expensive acts of individual hubris in history. It's strange from someone whose other notable projects have such clear goals. "Moar free speech lmao" doesn't sound measureable, let alone achievable while also making bank.