“When you bet on a winner, diversifying is likely to be a case of you selling the winner to buy the loser.”

Well yeah, that assumes you know the winner. The point of diversifying is that you don’t know the winner. So, it’s better to make a few guess with a chance of making up losses than likely backing a total loser.

Maybe I’m missing Saylor’s main point?

“If you look at most industries, you get one clear winner, one guy that treads water, and a shit ton of losers.”

OK, stop the interview right here. This statement is true only when you cherry-pick. The clear winner changes very quickly, even quarterly.

Isn't diversification usually more along the lines of different sectors and asset classes? Trying to hedge your bet in Apple by buying Samsung doesn't seem like a sensible strategy, since many things could happen that adversely affect that whole sector. but then again I am far from an expert here.