There's a moment in the CWT episode with Ezra Klein, where Klein talks about his perspective of Silicon Valley. He explains that the Silicon Valley model is about coming up with 20 ideas knowing only two of them will work. Klein doesn't favor this approach (always), opting for a better understanding of the problem before generating solutions (I lean this way too). In explaining his thoughts, Klein mentions Chesteron's Fence without further explanation. I had no idea what Chesterton's Fence was, so I followed the link to learn more.
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