So, you want to join a startup?
“Victorious warriors win first and then go to war, while defeated warriors go to war first and then seek to win.” This quote is attributed to Sun Tzu and if you understand it deeply, you don’t need to read further.
If you’re reading on, this post attempts to guide the reader on how to decide about joining a startup. If your definition of win is simply to get a role or to get a pay-hike, then you win as soon as you get the desired offer. So the rest of the post might not resonate with you.
However, to those of you who are in the process of deciding to bet their careers when you join a startup, aiming to make it big when the startup makes it big, I have following three suggestions (which are obvious in hindsight). These are the questions you should explore answers to, sincerely, before you take the leap of faith:
1. What kind of world are we building? (internally: What kind of world do you want to live in)
This question needs to be answered by both the sides. Unless you are joining a startup that is simply being built to flip, startups create value for the world in addition to creating value for the shareholders. The purpose of the startup is what will pull you through tough times. It is what your founding team should not compromise on. Also, it keeps the entire organisation aligned to a common cause. A lack of strong sense of purpose in the founding team either indicates incompetence or points to a get rich quick scheme. Additionally, it is important to align the purpose of the organisation to your personal sense of meaning. This lasting sense of satisfaction that you’ll get from working at a startup will come from contributing to a project that was personally meaningful to you. Probabilistically, it is also likely to be the only thing you’ll get out of it.
2. What is your definition of win?
Once you know the direction, it is also important to understand how will you know when you get there. While most early stage founders would want to dodge specific answers around this, it is important to understand the amount of ambition the founding team has. Lack of ambition at the top could manifest itself into lack of resourcefulness and take you towards a sub-optimal outcome. Additionally, some markets are so competitive that until you’re committed to winning wildly, you’ll not get anything out of them. Also, the sincerity of ambition will translate into a winning culture by retaining the focus of your leadership team. A poorly defined win creates a lackadaisical culture leading to a series of compromises eventually navigating to a weak position. A poorly defined win should make you think that the founding team is either not sincere enough or they are more interested in their personal wins.
3. Why is winning personally important to you?
This is the most direct question and it is the one where you should not compromise. This is essentially about understanding the skin in the game. While it is absolutely clear (and absolutely good) that founding teams are largely motivated by financial outcomes, the definition of win must be more inclusive. This is a basic expected difference between the value system of an entrepreneur from that of a banker. Founders who have a more inclusive definition of win could be trusted more. You are less at risk in betting your career with someone whose definition of win isn’t purely about themselves but includes the lives of people they are impacting. This is also why people find it more convincing to work with second time founders. Most of them have already made the money and some of them are looking at making a larger impact on the world. Also, if winning is personally important for the founders, it is more likely to fuel the resourcefulness instead of agreeing on a sub-optimal outcome.
I hope that reflecting on these questions will help you make a better choice. Before you ask these questions, know who is in control. If majority of the company is controlled by an investor, or if it is a ‘startup inside a large organisation’, make sure that you have this discussion with someone who is part of the board or equivalent.
