The Free Press makes $15M in annual revenue and sold for $150M - that's a 10x revenue multiple. That's not a business outcome, that's an ideological bailout. Ellison didn't buy this as a media investment, he bought it to install Weiss at CBS. The early VCs (Andreessen, Sacks, etc.) weren't making business bets either - they were funding ideology and got rewarded for it when a fellow billionaire needed to acquire the vehicle to legitimize his hire (but still nowhere near the type of exit they would seek for their non-ideological bets).

Also, since when is "built a business" the qualification for editor-in-chief of CBS News? That's an _editorial_ position at a major news organization. The relevant qualifications are journalism credentials and editorial judgment - you know, the things Weiss notably lacks. She came up through opinion pages, not the news side, and as Oliver documented, her publication has repeatedly published poorly fact-checked stories that fell apart under scrutiny. But sure, she can raise money from right-wing billionaires, so let's put her in charge of 60 Minutes.