I'm sorry, but I find the underlying point hard to swallow:
"Later, when [the company] did work, I realized that moment, while locking the front door that night, was when the company turned around. When we went from being in crisis mode to being a winner, for one very simple reason. I tried to visualize failure, and couldn't do it."
So, because you were unable to imagine yourself failing, you succeeded?
Doesn't this smell distinctly of self-actualization and other hocus-pocus? Especially since the article leads with:
" One night I was leaving the office and I knew the next morning I was going to lay off a quarter of the company and cut the salaries of everyone else in half."
So, you were able to recognize that you failed to provide one quarter of the company jobs which you presumably offered them and also failed to live up to paying the salaries of everybody else but you were, at that very moment, unable to imagine a situation where... you failed to save the company?
Maybe I'm oversimplifying, but this is, in the words of Winer "really convoluted and it's really wrong."
People who say "failure is not an option" are hopeless pollyannas. Success does not happen because you refused to accept failure as a possible outcome. Success is a product of hard work, talent, timing and luck in varying measures.
I've failed in 9 out of 10 projects I began on the web since 1995. I have been fortunate that the 1-in-10 successes have enabled me to continue trying new ventures. If I refused to acknowledge failure, would 10 out of 10 projects I launched be a success? It would be foolish to think so.
Embracing failure is a good way to fail and also a good way to succeed.
If succeeding in business was as easy as following a mantra we'd all be millionaires. Time has told us that Winer made arguably the right decision, but time has not told us whether Google made the right decision to kill wave.
If either philosophy was right all of the time YC would just put a checkbox with "Embrace Failure?" on the application and be done with it.
Wisdom is knowing when to apply the right knowledge.
Is success also not be an option if you haven't visualized it?
If you don't have a plan for revenue much less profitability or acquisition, I'd say that you haven't 'visualized success' the way you would do so for failure in this parable — on the basis of not dying, not traction.
Given the (IMO, correct) disdain for business plans and worship of 'making something people want', there seems to be a big inconsistency here.
I never thought I'd see Dave Winer and Jason Fried singing from the same hymn-sheet. Dave has a lot of experience through running his businesses over the years and it's a shame he doesn't share his evergreen wisdom on these matters in this way more often.
"Later, when [the company] did work, I realized that moment, while locking the front door that night, was when the company turned around. When we went from being in crisis mode to being a winner, for one very simple reason. I tried to visualize failure, and couldn't do it."
So, because you were unable to imagine yourself failing, you succeeded?
Doesn't this smell distinctly of self-actualization and other hocus-pocus? Especially since the article leads with:
" One night I was leaving the office and I knew the next morning I was going to lay off a quarter of the company and cut the salaries of everyone else in half."
So, you were able to recognize that you failed to provide one quarter of the company jobs which you presumably offered them and also failed to live up to paying the salaries of everybody else but you were, at that very moment, unable to imagine a situation where... you failed to save the company?
Maybe I'm oversimplifying, but this is, in the words of Winer "really convoluted and it's really wrong."