Projects fail for all sort of business reasons that have nothing to do with programming. However, that doens't mean that projects never fail because technical folks are not aligned with the business interests.
Sure, if you're just a worker bee, you can be selfish and milk these poorly organised start-ups for all they're worth, but if you wanna step up into those senior roles and actually have a chance of making something of those options, you need to weed out folks who don't care about delivery.
I'm not saying the guy definitely doesn't deliver but there are a number of indicators that suggest that he's not actually suffering from imposter syndrome but is actually just self aware to the point that he knows the companies hiring him are not getting value for money.
Even if that is true, he himself can hardly be blamed for taking the money. Whilst I try to deliver value to my clients, I also bill them as much as I can get away with.
