The most difficult question for some founders is “why do you want to spend 10 years of your life working on solving this problem.” Whoa, 10 years? Who said anything about 10 years?
Yeah 10 years is a long time. And that’s the point. Most startups won’t make it 10 years and the question doesn’t necessarily assume the founders will be in the same roles the entire journey. But my bet is the stronger your flinch to the question, the shorter the roadmap you have in your head and the smaller, less urgent, less valuable the problem you’re trying to solve.
(1) Hunter Walk’s question is pure genius. If he asked “Are you doing something valuable, and are you committed to it?”, every entrepreneur would simply answer “Yes, and yes”. Instead, he avoids the pitfall of asking a multiple choice question, in this case a direct question with a yes/no answer. So he probes the value of the problem you’re trying to solve and your commitment indirectly, with an open-ended question: “Why do you want to spend 10 years of your life on this?”
(2) Hunter is a VC; he uses this question to assess the founders of companies he’s considering investing in. The question is equally important for founders to ask themselves.
(3) Cf. Is your company truly disruptive? Try this simple litmus test, and the questions asked by Ben Horowitz for determining whether to sell your company.