I originally wrote this as an answer to a question on Quora.
I joined a startup founded by ex-Google people in 2010 as the third engineer. I worked there for 2 years, had a great time, learned a ton, got my first patent out of the process, and the experience is one of the best I’ve ever had. I wouldn’t trade it for anything.
The only reason I didn’t stay is because California wasn’t for me, but the startup is still going, and it feels like my shares are a pocket full of scratch-off lottery tickets. They could end up failing, but they won’t.
1-year-old is probably the best time to join a startup with solid backing, and even though being ex-Google doesn’t necessarily make you smarter or more likely to succeed than anyone else, it sure makes it easier to get funded.
In the worst scenario, they’ll run out of money and he’ll have to spend three or four weeks looking for a job. If he has any skill and/or motivation, he’ll be so much smarter and better for the experience that it’ll be really hard to NOT get hired for something new.
That’s the big fear fallacy with startups — that they’ll fail and you won’t be able to get a job. But all of the things you go through in making a serious go of building a startup make you so much better at what you do that there’s nothing to fear. I like to think of the experience factor as being 2 to 1. If you spend 2 years in a startup it’s a similar learning experience to spending 4 years at a stable company.
The fatigue factor is also similar. I feel like software can be a very mentally taxing and draining endeavor, so a 6-month sabbatical every 5 years is almost a must unless you’re in a perfect environment. Being in a startup shortens that “wear out” time, so you might need to take a break every 2-3 years in order to remain healthy and sane.
The most important thing to do if you’re considering joining a startup is to make sure the people running it are somewhat-well-adjusted grownups, or at least likely to become so in the near future.