There's a lot of good in this essay. I'm going to attack the weak point, even though I agree with most of it.
So this is the third counterintuitive thing to remember about startups: starting a startup is where gaming the system stops working. Gaming the system may continue to work if you go to work for a big company. Depending on how broken the company is, you can succeed by sucking up to the right people, giving the impression of productivity, and so on. [2] But that doesn't work with startups. There is no boss to trick, only users, and all users care about is whether your product does what they want.
Then, to his credit, he admits...
The dangerous thing is, faking does work to some degree on investors. If you're super good at sounding like you know what you're talking about, you can fool investors for at least one and perhaps even two rounds of funding. But it's not in your interest to. The company is ultimately doomed. All you're doing is wasting your own time riding it down.
Okay, so we have something to chew on.
First of all, investors are gameable if you're good at social proof arbitrage (that is, lying about competing interest in order to set off a "herd mentality" and become a VC darling). I don't have an ethical problem with social proof arbitrage. It's what you have to do if you want to raise VC and you're not from a very wealthy family.
Is the system gameable? It depends on what your objectives are. You can't build a successful company if you make something no one wants. That's clear. However, let's be cynical and realistic here. Do you care about the success of "the company" or of your own career?
If your investors don't like you but you build a great company, they'll give it (and most of the rewards) to someone they do like. If your investors like you and your company fails, they'll arrange a favorable acqui-hire. This means that you collected $120k for each year that the business was alive, and got a 3x salary bump (plus a 7-figure hiring bonus) in your next job. Or, they might make you a VC.
The part that determines whether your product is Google or Clinkle is difficult, if not impossible, to fake. We don't even understand how many of those random variables work. There's some part that's performance- and skill-related and a large part that's luck, and no one knows where to draw the lines. However, the startup career is immensely gameable, and that's true the whole way to the top (partner-level ranks in VC firms).