There's a less know book written by him:
Weinberg on Writing: The Fieldstone Method
It's the only book I've found that teaches you how to steal like an writer, which the book Steal Like an Artist advocates but doesn't get into how to actually do it.
The talk is about how Damien quit his job to hack on open source software. It shows his struggle and doubt while embarking on the project and then finally invented CouchDB. It's a passionate and human account of the process of creating something significant. I recommend every hacker watch this.
+1 for Taleb's books. His Black Swan book actually inspired me to pursue a startup. However, his ideas are not actually that original (which is not a bad thing). One might get similar level of knowledge(albeit takes more time) from reading stoic philosophy, Popper's philosophy of science, tacit knowledge (Michael Polanyi) and complex system sciences.