This is a "cool factor" splurge. Spending ~100k cash for a bootstrapped startup on something rather superficial is enough to question their future decision making. To me this shows a bit of immaturity and irresponsibility. What future shinny objects will they splurge on instead of focusing on investments that have more substance?
But seriously, as brilliant of a songwriter and musician he was, it's hard to not suspect he had ulterior motives here. He's been wanting his content off streaming platforms for a while (he's done it before, citing music quality as the supposed reason). This latest stunt vs Rogan/Spotify was a great opportunity for him to earn social brownie points while moving to stream his music on his own platform. Win-win.
He is totally free to do that of course, just as Spotify is free to not be held hostage by his ultimatum.
Great, let's nickle and dime the single mother selling arts and crafts on Etsy while the mega corps get away with billions.
This was buried in the same legislation supposedly drafted to help the poor. But of course, the fattest handouts were all to big banks and the rest of too big to fail corporate America.
OP is taking way too much on himself. I understand, and to a point respect the personal responsibility he takes, but he's going way overboard here. Perfectionism is the enemy of growth sometimes.
And to reiterate what many have already said, this perpetual growth and scale mentality is so so toxic.