Jeremiah – I feel the same way as you after going through dozens of these cases, and I think your points are all spot on. Once again, as we’ve heard mentioned in class, it’s easier to connect the dots in reverse for both failure and success by picking out anecdotes selectively.
I guess Williams kept putting himself in a position where success was possible, even if the odds were minuscule in the toughest times. He never removed himself from a situation where things could turn around, and he did everything in his power to keep the ball moving forward at least a little bit. The vast majority of the people never show up to play the game or they give up early, so by default they can’t “win” the way Williams did.
Still, it’s pretty risky and not necessarily the best path to follow as you all have pointed out.
Failing well in these cases seems especially difficult, as your post and some of these comments outline nicely. I think once you are a unicorn company/founder, there is an “air of inevitability” that everyone begins to treat you with. You might be a billionaire on paper, and maybe you gave last year’s commencement at your alma mater. It seems even more likely to me that in this case the founder will hang onto the company to the very end and risk making bad (destructive) decisions during the failure process.
On the other hand, failing an early stage company that never gained traction seems easy in comparison!
Dino, great post – will you be following this advice for your own startup? I imagine it is easy for these ultra wealthy founders to have more confidence in their own abilities to predict success than for other people, including investors. So, that might be the temptation to ignore signaling and pour your fortune into something foolhardy.