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Of course the guy that spreads his bets is going to have a higher chance of being ahead. But he's also going to have a higher chance of being behind. Very simple.
To understand it better -- imagine you're flipping a coin, and you're only going to flip the coin twice. If I bet $1 on both tosses, I have a 25% chance of being ahead, 50% chance of being even, and 25% of being behind. But the guy who bets $1 on one flip and $5 on the other flip, has a 50% chance of being ahead. As long as that $5 bet wins (it could even be a $2 bet for this example), he will be ahead. The other guy needs to win both bets.
"Everyone wants to be rich, but nobody wants to work for it." -Ryan Howard [The Office]
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