Part of founders’ job is to empower investors with sufficient knowledge about their business, so the investors don’t ask dumb questions.
In most cases, VCs won’t invest in companies where they find themselves asking dumb questions. Because it means they’re not familiar with the industry; also, no one wants to look stupid, especially VCs with top school degrees and a giant ego.
One time I got pitched on an inland salmon farming business (don’t ask me why, because I don’t know either.) The kind of questions I was asking after the pitch were laughably basic, like those questions a third grader would have asked — “What do salmon eat?”, “Won’t salmon die if the water temperature gets too hot?”, etc. Clearly, I knew nothing about fish farming, and it showed.
If an investor (who otherwise has a great track record) starts asking really dumb questions, you either chose a wrong investor (someone who’s not familiar with, and therefore probably won’t invest in, your industry), or didn’t empower the VC with sufficient knowledge and data in advance.
Conversely, if your investor asks penetrating, highly relevant questions, it’s a sure sign that you found the right investor. Now, you can only deliver and win 🙂