I've read Black Swan and heard Antifragile was quite good as well think I'll pick that up instead. Liking these recommendations a lot. Here are a few that are "similar" since I asked you for some recommendations.

I really enjoyed The 48 Laws of Power and a few other titles by Greene. Some of Malcolm Gladwell's books are interesting although they are a tad popsci. Recently finished Zero to One which was good, but if you listen to Thiel often there wasn't much new material. Lords of Finance is a NYTBS that is really well done and reminiscent of Taleb so you might like that.

Thanks.