I see Taleb's ideas more and and more frequently applied to software development e.g. by authors such as Kjell Jorgen Hole in his "Anti-Fragile ICT Systems", and Michael T. Nygard in his "Release It!: Design and Deploy Production-Ready Software" (2nd Edition).
I think it's a little risky to transfer concepts from one domain to another, without taking into account the working assumptions and the surrounding context. For example something as fundamental as the definition of the concept of 'Black Swan' à la Taleb, is a tricky one, let alone its application to the world of software development. Maybe the best we can do so far is to take this in a very broad sense, and interpret it as a general principle: "first, avoid ruin". But, almost by definition, the events outside the control of a software development/project team can be so extreme that it might render the practical application of the principle almost meaningless. (Think about it: what does it really mean in the context of creating a software product really?)
There are of course meaningful principles that apply to creating investment portfolios, strategies, etc.; do they really apply to software development? Are we using similar data sets and statistics for software development and combination of financial instruments? Can we? That's something I can't say "yes" immediately.
