I got a call from someone who asked me “you work with a lot of startups, what should I think about before joining a startup?” I asked him to clarify if they were asking him to come on as a co-founder or an employee and he said that they had funding and were looking to hire him as an early employee. He wanted to understand what were the key questions he should be asking about “position, compensation, exit strategy, layoff chances?” It was his first startup and while he was excited by romance he wanted to know what the practical realities of the marriage might look like.

My answer was that these were the first three questions he needed to be able to answer before digging into finances etc..

  1. Do you like your boss and look forward to working for him?
  2. Do you like your team and look forward to working with them?
  3. Is the problem the firm is solving for it’s customers compelling for you to work on.

I advised him that these questions are no different than ones I would ask for any job. Picking who to found a company with probably changes #1 to “Have you worked with this person before and do you have confidence in his integrity and ability to deliver?” But I think two and three are the same. I told him that on a statistical basis the probability that you will get rich is very low, so make sure you are going to learn something, working with and for people you like and respect, and that the problem you are helping to solve is compelling for you.