He also doesn’t engage with the fact that this company required funding from y combinator to get to that point

Which is something that is not an option for most people.

Look at where y combinator founders come from. It’s 99% people from elite institutions

That is a core part of AOC’s point

Getting a startup funded is just not something that is possible for most people. They just aren’t in the right circles. Does not matter how good of an idea you have

However, if you’re in the right circle, you’ll get shitloads of chances even after repeatedly failing. Just look at how many of these founders that “made it” drove multiple companies into the ground before making it. It’s a lot easier to find “good fortune” when you have a lot of chances than when you have 0 chances

What AOC actually said was (linked in the essay): "You can’t earn a billion dollars. You just can’t earn that." That is a strong claim - a claim of universal impossibility - but it's the claim she chose to make. Because she made a universal claim, an N=1 anecdote is enough to disprove it by counterexample.

You can disprove an absolute statement with n=1

That's an argument for AOC to make. This post is about PG responding to the argument she actually did make.

She has made vague, handwavy, and (depressingly) oft-repeated statements that "there are no ethical billionaires" and that "it's impossible to earn a billion dollars," but she has rarely supported with these statements with any facts or evidence whatsoever.

He is probably the actual billionaire in question, but doesn't want to highlight that point given the populist backlash against billionaires.

In my view, there is no such thing as free market capitalism without regulation. The only thing that could create anything resembling a "free market" in the first place is regulation. The whole point of the endeavor is to enact regulations that essentially play whack-a-mole in making every means of profit illegal, except for means that serve the greater good, i.e. producing, serving, innovating, and/or lowering prices, or investing in those that do.

Without regulations (just a fancy word for "laws"), few people would bother to do any of these things. As it would be much more profitable to simply sabotage competitors, form cabals or monopolies, oppress and steal from the populace, conquer and loot your neighbors, lie and deceive and trick your partners, etc. And even if it weren't, anyone who did want to truly innovate or produce something useful would be discouraged by the fact that, due to others engaging in the above activities, they wouldn't see any profit.

So, to answer your question…

> How often does this actually happen?

All the time! Hundreds of thousands of times per year! Because we don't live in an unregulated free market, because there's no such thing and the concept is absurd on its face.

There are plenty of gaps and inefficiencies where new businesses can provide value to customers at scale who will happily part with their money in return.

Not to mention the fact that the constant march of technology (as well as changes in policy, culture, environment, knowledge, etc.) are constantly tearing open new holes in the market.