That is possible in many areas of life. In case of gambling, you can use beatthebookies.co. This site post an article about an example of bet made and discusses it. This section is focused on soccer and horseracing although the site also gives advice on betting in other sports, roulette and Blackjack.
On the site, there are news about events where you can bet, too. Furthermore, it offers bookmaker reviews and comparison. You can learn betting vocabulary.
One interesting statement on the site is that it is more important how much you bet than the event you bet on.
If you bet everything you have set aside for betting on one event, you can either win a huge prize or lose the whole allowance in no time. So this is not recommendable, especially not with high stakes.
Another strategy, called Martingale system, is to double your stakes whenever you lose to compensate all your previous losses when you do win; only, you cannot be sure when that will happen. Fibonacci is similar but involves lowering your stakes if you are losing multiple times in a row; as the name suggests, you increase the stakes using Fibonacci sequence (1, 1, 2, 3, 5, 8 …). Fibonacci has often been exploited by customers in casinos.
On the other hand, if your stakes remain the same all the time, you are safer but will earn less and slowlier. To both fasten up winning and decrease losses, you should place bets in proportion to the odds. To calculate the exact ammount, use Kelly equation.
None of those strategies is perfect. There is no guarantee ever that you will win. So think carefully how much you want to bet!