[Spoiler alerts for The Dark Knight Rises contained within]
I couldn't read Sarah Lacy's The Acqui-hire Scourge: Whatever Happened to Failure in Silicon Valley? without thinking of that prison scene from The Dark Knight Rises when, after a few failed attempts by Bruce Wayne at climbing out of that prison, that blind guy explains to Wayne why he keeps failing to make the leap to that final ledge near the top:
Blind guy: You do not fear death.
Bruce Wayne: I do fear death. I fear dying in here while my city burns.
Blind guy: Then make the climb.
Bruce Wayne: How?
Blind guy: As the child did. Without the rope. Then fear will find you again.
Bruce Wayne: You couldn't have told me that before I jumped and missed a few times and nearly snapped by back in half at the end of that rope?
[Okay, I made that last line up. Also, there was room to get a running start to jump and catch the other ledge, how come everyone seemed content to just try to do a standing jump? Oh, never mind.]
In The Dark Knight Rises, Bruce Wayne, flush with wealth from Wayne Enterprises, spends hundreds of millions of dollars trying to develop a clean energy source, then goes bankrupt when Bane takes his fingerprints and makes some crazy options trades (a la Mat Honan with GMail, apparently Wayne had not turned on two-factor authentication on his ETrade account).
In real life, Elon Musk, who had plenty of money from PayPal, nearly bankrupted himself launching and financing an electric car company. Most people who obtain a lot of wealth walk away from the blackjack table, but Musk put all of his chips back out in play, and not on sure things. Building cars is inherently a high capital, high risk enterprise, and building electric cars are even more so. But that wasn't enough risk for Musk so he also started a space exploration company. There are entrepreneurs, and then there are Entrepreneurs, and then there are entrepreneurs' Entrepreneurs, and Musk is the latter. If his parents had been gunned down in an alley by a criminal while he was just a child, Mustk might be spending his evenings in a batsuit, fighting crime in the Tenderloin in San Francisco.