I think it's public he owns Uber and owned it early. I think it's early to say if that was a "win"; I reckon he got in at a good val but Uber ain't public and w/ a braindrain, 2 lawsuits, likely death of their AI program, ceding China to Didi and public backlash idk if it's got legs.

Chris made a lot of money and he did a lot of interesting things. He's interesting and a lot was luck and a lot was skill. That said, Twitter (if he exited a bit post IPO was the companies big win. You only need one though.

Edit: Forgot about Instagram. He crushed it. Point is more Uber might not be as big, but his track record is amazing compared to other shops