Well, I grossly oversimplified what Berkshire Hathaway does but yes he had money and kept making really good informed gambling decisions.
There are fewer problems like this in the stock market. However, getting a better model than the players in the market is arguably more difficult. However, with the resources of Berkshire you can do things which a retail investor couldn't dream of, stuff like using satellite imagery to approximate performance. Or paying the CFOs latest squeeze for information (or at least the same but laundered through a 3rd party).
As a layperson, I always wonder: is there some equivalent of the Heisenberg uncertainty principle at play in the market? There is no way to make an observation (in this case, a trade) without altering the very thing your are observing (the market).