Overthinking it and worrying about all that can go wrong is the biggest reason for failure, you fail the most by not trying.
As for a ton of money, I can’t say. But I am pretty sure it is an inverse of what I said above. Ra’s Al Ghul said it best: "The training is nothing, will is everything. The will to act."
You may think it is cheesy to pick a movie quote and you'll also probably see quotes like that in your social media feed by people who share them without really understanding them and observing them in the world. You’ll know what I mean when you meet people with immense potential, skills and resources that are still utter failures. Then and there, you'll know and understand, that “will is everything”.