"No work of art can every really testify to the scale of its own impossibility."
I responded that I thought it meant that no work of art can ever convey how difficult it was to make (Wachowski's version is more poetic, to be sure). Wachowski's quote reminded me of something my film school professor Rory Kelly used to tell us all the time our first year in the directing program. I don't remember the quote by heart, but to paraphrase: the universe conspires against your movie.
That's what it feels like, especially as a student filmmaker. The universe is fighting you every step of the way. It doesn't want to see your movie. It doesn't even want to see it completed.
Two important lessons in that idea. One is not to get down when things go wrong during pre-production or production. That's just the universe's dark sense of humor, and every filmmaker before you has gone through it time and time again. Secondly, and perhaps more importantly, it takes the prodigious and insatiable will of the filmmaker to overcome these forces and bring the movie into existence.
The psychological profiles of successful filmmakers and entrepreneurs overlap in many ways. They work in a field where success is more probabilistic than anyone would like to admit, but they must believe it is deterministic. Failure in a probabilistic endeavor should be much less of a verdict on one's capabilities than in a deterministic endeavor, and so successful entrepreneurs and filmmakers should brush off failure more easily than the average person for whom one strike can by psychologically crippling.
That's just for the individual, though. The one great difference between Silicon Valley and Hollywood is that Silicon Valley is far more tolerant of failure. The returns to a successfully funded startup are so outsized that tech investors are very comfortable with a portfolio with one massive winner and dozens of failures. It's like playing roulette. You just don't see many movie studios with that type of power law distribution of successes. A run like that gets studio heads fired.