You wrote a good post. It reminded me of 'The Origins of Wealth' by Beinhocker. He spends a lot of time exploring why most companies spend most of their time playing it safe and why so little is spent on exploring new markets/business models.

He also makes the point that most companies don't survive very long. I don't think tech is especially unique in this regard.

People probably don't leave the hedge funds because they are in a great situation. Hedge funds managers get to play the heads I win tails I get a management fee game. People, once they have wealth, can be surprisingly risk averse and don't want to risk substantial portions of their own wealth as capital in a new venture.