I am a programmer in Silicon Valley, but I was more interested in philosophy/mathematics when I was young (I was raised and educated on the east coast). I do feel there is a cultural difference -- not sure precisely what it is though.

I guess I share Taleb's problems with models. Even before I read Taleb I would say to myself "the map is not the territory", particularly with regard to software abstractions. I think the space between the model and reality is where you find a lot of interesting things (including the ability to make a lot of money).

I also share Taleb's skepticism with economics. The core problem is that it's not really a predictive science. It's a lot of people talking about stuff. Did those ideas help anyone? You can make a good case that they hurt a lot of people. If they are so smart, why aren't they rich? The Scholes case is a great example of that.

I'm currently reading "The Signal and the Noise" by Nate Silver, which is actually a fantastic complement to Taleb's books. They say very much the same things, in very different ways. The good part is that you will not be turned off by Silver's prose -- he's humble and very readable. I didn't follow 538 at all, and didn't pay all that much attention to the 2012 election, but I can tell that his writing skill was a big reason he became so popular.

To give an example, Taleb talks over and over about "negative knowledge" -- what not to do, what things don't work, etc. And Nate Silver says the same thing. To make accurate predictions and models, you have to be aware of known classes of mistakes, cognitive biases, etc. and not fall into those traps. People often think that they need to improve themselves by learning more. But for a reasonably smart people, the bottleneck to your effectiveness is actually thinking that you know something you don't.

I am also an "ideas" person but I share the utilitarianism and empiricism of Taleb. There has to be "skin in the game", as he says. There are so many ideas out there, and generally most philosophical arguments (and journalism, advocacy, etc.) boil down to confused semantics. So the way to find truth is through actions and experiments. Economics fails these tests for truth.

EDIT: Nate Silver talks about this paper: http://www.plosmedicine.org/article/info:doi/10.1371/journal... This would resonate with Taleb quite a bit. Most ideas are false, including published ones. It would actually violate economic theory if that weren't the case -- if most science was true -- because scientists have bad incentives (something I know from direct experience).