Anyone rich, or not can try again and again, it will just be harder for people who also need to figure out how to pay the bills.
If they play the VC game, returns are still extremely variable.
If they play a bigger game, then they start to be playing the same game as other players that the public can invest in (directly or indirectly) i.e. no advantage.
We see smart investors fail all the time (VC returns are highly variable, even though each VC is diversifying their risk across many investments).
All VCs together as a segment do not make enough return.
And the OP is wrong because you can only make a limited number of investments - because each takes time and most have a minimum stake. E.g. Buffett has so much capital to manage that he doesn’t invest in small businesses even if they might give 1000% return. And it disregards the problem that investors often concentrate their investment e.g. real estate mogul making a billion dollar bet with everything they own, or e.g. mom and pop putting retirement fund into one stock.
If you fail, just get a job, save up more money, then try again.
The more you fail, the more you learn, the greater the likelihood of success the next time around.
If luck regresses to the mean both within and between startups, then it stands to reason that the value of more iterations is limited. I think it's probably more valuable just to be able to recognize which direction you're likely to regress toward.
This means that people with rich families and rich connections can afford to play the game as much as they have a taste for.
If winning means getting 3 heads in a row by flipping 3 coins, and you have 3 coins to flip and someone else has 1,000 coins to flip, the second person is much more likely to win.