To start winning Bitcoins, you would need to do the same as with fiat.
Invest or gamble.
You can trade your bitcoins, invest them in altcoins, or find a sportsbook/poker site that supports bitcoin.
Lol I was expect that you would say,
"To start winning Bitcoins, you would need to do the same as with fiat.
Work."
OP if you want to make Bitcoin, the answers are the same as making fiat.. offer something that people want, be either your signature space or coding skills or whatever. Just don't expect much from faucets/sig campaigns.