Failure Has Limited Value

I think this article is trying to get at a supposed culture of failure worship that exists in the Valley but I don't think that the point is clearly made that anyone is that obsessed with failure. Everyone wants to be successful and nobody regards a 3x failed entrepreneur as being as reputable as a 3x successful entrepreneur. People don't make a point of reading into the details behind success and failure.

I think it is more accurate to say that Silicon Valley has a culture of failure tolerance that is far above the ordinary level of failure tolerance one would expect in other societies. And that is a good thing. In fact, it is probably not high enough, which encourages entrepreneurs to chase quick flips so they can write "(2x exit)" next to their name rather than give a huge, risky idea a chance.

That said, I see the point that failure doesn't feel great. If the author is really trying to say "don't chase failure" then I wholeheartedly agree. Failing sucks and it feels awful, but I think anyone who has been through a failure knows that there is no way you can put a gloss on it. After the first failure you don't need someone to tell you how bad it is, you need someone to encourage you to try again.

  Maybe I only had to make 1 or 2 angel investments (and not 5) to learn what I did?

That bullet point stood out because it reminded me of a passage from "Reminiscences of a Stock Operator":

  It cost me millions to learn that another dangerous enemy to
  a trader is his susceptibility to the urgings of a magnetic personality when 
  plausibly expressed by a brilliant mind. It has always seemed to me, however, 
  that I might have learned my lesson quite as well if the cost had been only one 
  million. But Fate does not always let you fix the tuition fee. She delivers the 
  educational wallop and presents her own bill, knowing you have to pay it, 
  no matter what the amount may be.Having learned what folly I was capable of, 
  I closed that particular incident.

Sometimes you just have to pay your tuition.

Edit: Formatting