Please don't ask founders existential questions

Imagine your life is going smoothly. You have a well-paying job, friends, and overall feeling of satisfaction. One day, you happen to meet one of your college friends who is still obsessed with some version of some crazy startup idea. You, for some reason, do not really believe in his idea. You, with some self-righteous zeal, also want to save your friend from some tragic failure.

So, being a nice friend, you try to save this friend from losing big time. You tell your friend hundreds of ways how what they are doing is not cool, or won’t work, or how your friend is not aware of the competition, etc. Then, you, sir are being a jerk. You are not doing anyone any good. You are doing a disservice. Please do not!

Let’s say your friend is obsessed with building a new search-engine. When you ask them why do they believe they can do better than Google, you are literally telling them that they shouldn’t be doing this since if it was ‘correct’ or possible or profitable, then Google would have already done that. This is bad.

It is almost certain that if someone is smart enough to build a search engine while living off of ramen, they also know more about what Google is capable of. Your attempt to question them is not helpful to anyone. If anything, you’re totally denying the fundamental aspect of innovation and entrepreneurs throughout history who have established that one or ten person team can conquer many a Goliaths, or bring to the world something entirely new.

You don’t have to lie either. You can just be quiet i.e. not share the same enthusiasm and excitement they have. Or you can be more specific, and hence more constructive. Here are some better framed questions:

  • How will you get your first x users? (instead of You can’t get any customers like this!)
  • Why did you decide to work on this idea? (instead of A lot of people have worked on this and failed.)
  • What is the competition missing that you think you got? Why? (instead of You’re competing with a 100x million dollar company with 100 people, you stand no chance.)
  • I think your UI is not good (instead of No search engine will take off without a good UI)

Building a successful startup is hard, and a zero-to-one startup is an order magnitude harder. There are so many unknown answers, and the founder(s) work on a lot of assumptions. It is safe to assume that majority of founders will have extreme but still a limited capacity for taking nay-sayers. Founders are obsessed with what they are working on, and they are working on the assumption that if they are correct, they will make a big positive impact in the world. Individuals obsessed with working on hard problems are very rare, so please don’t be a jerk to them. This impact could be way worse, especially, if you are a close friend, or someone they admire, or someone they trusted as a co-founder or early employee.

There is already enough knowledge about startups. As a matter of fact it seems that there are more startup experts than startups themselves. If there is one thing I am very sure about startups, personally, is that I have read most startup books, tried and failed like three times, and I am only sure about one thing- there is no single theory of startups. The motivation and confidence of founders, I believe, do correlate with their success. Asking existential questions to founders, thus, is a net loss for everyone.

Some interesting essays that seemed to me to me to support my take here were Fierce Nerds, Be Good, and The Hardest Lessons for Startups to Learn.