So here is the scenario - you are smart, talented and ambitious. You abhor the corporate world. You have tons of creative ideas and obnoxious energy. You love tackling world-changing projects. You thrive in unstructured environments. Your risk tolerance is high and you handle uncertainty well.
You don’t yet have your own world-changing idea, but you’ve figured out that you want to join a startup.
Now all you need to do is decide which startup to join.
When thinking about this incredibly important decision, consider three things (in this order):
First and most definitely foremost, consider the people involved. Do you absolutely LOVE the people? Do you trust, respect and admire them? Do they inspire you? Are they smarter than you and will you learn from them?
If you answer no to any of these questions, you should probably stop now and move on to the next opportunity. Startups are 99.9% about the people. Great people adapt to the inevitable zigs and zags of startup existence to find and capture opportunity. Great people *will* their companies to succeed. Less than great people are unlikely to adapt, evolve and overcome challenges necessary to find success.
Never, ever, ever compromise on this issue. If you do not love, trust, respect and admire the people you work for and with, run away because the company will fail.
Assuming the people involved rock your world, you should then consider the company and your role within it.
Do you believe in the mission of the company? Is the product or service solving a real world pain? Has the product or service been architected intelligently? Is the market opportunity massive?
If you don’t believe in what the company is doing, you should not be there. Period. And don’t outsource this assessment to others, you need to go with your own gut. Either the mission and product/service resonates with you or it doesn’t. If it does, great - you will join and come to work everyday with burning passion knowing that you are working on something special. If it does not - run away, the company will probably fail anyway.
One (highly theoretical) downside of working at a startup is the lack of brand value for your resume (unless, of course, the startup goes gangbusters and becomes a huge success). You have to be completely willing to sacrifice this if you intend to work at a startup. What you should not sacrifice, however, is loving what you do.
A huge benefit of working at a startup is that you should have the opportunity to impact the outcome of the company. Teams are small, bureaucracy is nonexistent (and if it exists, run), and everything that is done accrues value to the company and helps it inch closer to achieving its goals. This does not mean that all the work is sexy - to the contrary, in startup world you have to be willing to role up your sleeves and GSD. Sometimes this involves sexy work, but often it doesn’t.
Regardless of whether or not the work is sexy, you have to love what you do. If you are truly inspired by your role as a important contributor, you will be bring energy and passion to work everyday. If you don’t enjoy the way in which you are contributing, your passion will wane, your energy will dissipate, and you will do a shitty job.
Remember, startups are insanely risky when everything is 100% perfect. Going into an environment where you are not confident in the team, company and your role just adds unnecessary risk to what is already innately risky.
Hold yourself to a high standard, trust your instincts and intellect and don’t compromise on these issues. And when you find a company that meets these criteria, attack the opportunity with all your energy and passion because you are probably on to something special.