I haven't read his books, but I am familiar with Black Swan theory and (from what I've gleaned) the arguments he makes are sound. Building a "robust society" that can withstand these kinds of things is easier said than done, though. I acknowledge that part of the problem with a libertarian state is that it lacks the resources and efficiency to quickly confront these kinds of crises when they arise. In order to deal with Black Swan events in the long term, we have to rethink the basics of how our hierarchies operate.
I recommend you read the Thaler & Sunstein book about Libertarian paternalism. Like most of Sunstein’s work, it is pretty interesting but kind of mind numbing. It solves that problem in a way no other Libertarian school of thought really has.