Yeah, I have tried to simulate this several times under different conditions. Given zero sum game and random odds, there is always going to be small percentage who have a lot and most will have below what they started with. It is easy to explain as well, if you for example start with $1000 and you have 50% odds of winning 10% every time. If you win and lose 50% you are going to be below what you started.

If you always win after lose and lose after win, then it would go like this:

1. $1000

2. $1100

3. $990

4. $1089

And so on... After 100 turns you would have only around 600 - 700.

But it's a zero sum right. Where does the 300 - 400 go? It goes exponentially to select few who by random chance have more wins than losses.

In fact the longer it goes on, the higher odds of there being outlier with a lot - you might expect that everyone would converge around $1000, but that is not the case.

I did an example run with 10 000 investors, each doing 1000 trades, each trade they bet 10% of their portfolio, with 50% odds of winning.

First investor had 562 wins and 438 losses, with $1,666,061.

Median investor had only $7 left with 500 wins and 500 losses.

Top 10th percentile investor had $364 with 520 wins and 480 losses.

So interestingly even an investor that had 40 wins more than losses, lost 2/3 of portfolio.