The correct answer to this open question is the following.
The five questions that I would ask Christopher Columbus if he asked me to finance his first voyage to Asia would be the following.
1.- Why is the purpose of your trip if already exists some navigation routes?
2.- How many ships do you need to take on this new adventure?
3.- How many people or crew are needed to support this exploration?
4.- Is there any kind of certainty that makes me think there are any chances of success?
5.- How much money do you need and how I am going to recover that investment?