This is the problem solved by ETFs. Small amounts of money buying lots of diversification.
Is this really true — from a rational perspective, and not one where someone idolizes wealth or being able to purchase "whatever they want?"
The utility of anything — including money — diminishes as you have more of it. The utility of the next hundred million dollars is less than the first hundred million.
So I don't think a rational actor would take the gamble.
So if one idolizes wealth then clearly they have assigned high utility to money in a non-diminishing returns sense. It is then rational for them to match their utility curve. Life is full of threshold systems. Given that, it would be very unusual for utility curves to not be deformed by them.
It's easy to construct a few scenarios with locally convex curves:
* You're in debt to the mafia and you will die if you don't pay them your $100k debt. You have $10k dollars. Do you spend the $10k to try a long shot of making $100k?
* You're poor and make $15/hr. If you save you will have an extra $1000 a year in savings. You will never own a home. You will never have time to study for a better job. The magic of compound interest with contributions is in the regularity, not so much in the amount. Put $1000/yr in a calculator and $998/yr in a calculator (assume it compounds 3% every year) and see the difference you get over 60 years. It is insignificant on a 60 year horizon. $2 will buy you a powerball ticket, and maybe out of this life.
* You're an immigrant. You need a few million dollars for your investor visa. Your current visa runs out next year and then you return to a slum.
I tend to agree with your point for larger sums like a billion dollars, but maybe you're really passionate about the potential for EVs to positively impact our growing climate problem and need an enormous pile of cash to get that off the ground. People are complicated.
The net expected value of the dollar doesn't have to be positive. Losing $2000 over 80 years of your life is certainly worth is a non-factor for many.
Add in the fact that RH has reduced barriers to entry to investing. It's way easier to get RH and buy VOOG than to get Vanguard set up. I have enough in both to know.