You’re not going to hear about all the failures. All the people who took big, crazy risks and failed. You’re mostly going to hear about the success stories. This is otherwise known as survivorship bias.
The amount of skill you have will certainly improve your odds (unless you’re playing strictly a game of chance), but even the skillful who take big risks will fail most of the time. You can afford some small failures, but a big failure can easily ruin you.