Startups have a seductive call, a promise of a big impact, great wealth, and control of your destiny.
The reality is somewhat different. The common view of startups suffers from selection bias. When we look out at the startup world, we tend to laud the successes and ignore the failures. We glorify the struggle and skip over the pain.
If you join a startup, you should make sure to do it for the right reasons.
The wrong reason is to get rich. Very few startups make positive returns for their investors, not to mention we founders and employees who are the last in line for the spoils. The reality is that most people working at a startup will take a significant cut in pay and benefits, work over their evenings and weekends in an obsessive fight for success, and then find their ownership stake worthless in the end.
The right reason to join a startup is to learn. There is no experience like doing a startup. Everything is your responsibility. If it is going to get done, someone on your small team will have to do it.
That means you will get experiences you never would in a larger company. The variety is stunning. One moment you will be working on low-level networking issues to keep your systems running, another moment you will be talking to the press. One morning you'll fearfully be rearchitecting your database backup, hoping against hope the system doesn't go down while you are vulnerable, that afternoon you will be reviewing legal documents or planning marketing strategy.
It is an incredible education that will serve you well for the rest of your career.
But, even if you do everything right, and that is very unlikely, even if you have a strong team that also manages to do everything right, which also is unlikely, the overwhelmingly most common outcome is failure.
A startup is a tiny ship sailing on a great ocean. Timing, lucky networking encounters, and fortunate business deals count for a lot. You can position yourself well, work hard, be ready for what is to come, and still find yourself swamped in the next storm, crushed beneath the bow of a giant competitor, or just stuck in doldrums far from any refuge.
This is all fine if it matches your expectations. If you go into a startup planning on learning, then you will succeed no matter what happens. The remarkable experience you had will echo throughout the rest of your career. The journey will be your reward.