Sure, what has changed over the last 10 or so years is that winning the startup lottery pays close to nothing incremental over working at a large company since most of the equity is now held by founders and late stage investors and most of the stock growth happens before a company goes public.

I'm not saying you can't get rich off of gas station scratch tickets, but it's not the best option.

i.e. you can join a startup that is already successful (the winner has been picked, Amazon, Google, Uber, ...) and safely with less variance expect to gain more expected value than you'll on average get from trying to pick the next winner. If you say "but startups are win win" then I'll say "but he's saying monopolists are win win win"

Microsoft was already an OS monopoly by 1990, but after that is when it really started to make real money, and for a lot more people than had worked there in the 80's. Because monopolizing a niche industry is nothing compared to growing the monopoly to mainstream acceptance.

you don't have to agree with his assessment; I'm just trying to clarify that he is saying something, not just selecting a point on a gaussian.