He's been an investor for quite a while, he even did a few episodes of Shark Tank.

His work with his company Thorn is really worth checking out. It's a great mission that he's done a ton for.

IIRC he’s been angel investing for quite a while.

Here's him talking at an Airbnb conference: https://www.youtube.com/watch?v=z6vTaiPl6tA (He confronts an Israel protester who comes up on stage at https://youtu.be/z6vTaiPl6tA?t=155.)

He seems like a pretty smart investor.