Answer by Jason M. Lemkin:
you absolutely should not start something unless it's 100.0000% clear to you this is absolutely the best thing in the world to do, for you.
TechCrunch, YCombinator, The Social Network, and all that have over-glamorized entrepreneurship:
- First, your start-up will almost certainly fail, and while that's OK, you won't really get any credit for it. No one cares about your failed start-up that got no traction and that no one ever heard of. They won't judge you. But they won't care.
- Second, the risk-adjusted economics s**k. If you are smart and driven, then risk-adjusted, you'll make more money joining, staying, and getting promoted at a top web company. While the comp delta between a start-up and BigCo doesn't seem huge at non-leadership levels, it really grows if you get promoted, and get into management.
- Third, even if you want to do a start-up, you're far better off joining an existing rockstar/super-strong team. Great start-ups need great teams, which are rare. Better to join one than try to start one from scratch, which is close to impossible.
- Fourth, it's far far harder than you can imagine. The highs are higher, for sure, but the lows are so low. Most people really aren't up for that, the lows, and can't handle them properly, if at all. E.g., are you OK signing a full recourse $750,000 promissory note to fund payroll, like I did at my first start-up, when all the funding fell through?
And yes, while you will have more "freedom" doing a start-up, it's so all-consuming hard work, you probably won't appreciate it, at least not enough, at least not while you are going through it. It's hard to appreciate the view when you're glued to the screen.
Having said that, if it's a calling, go for it. I did. But that's the only logical reason. Since it is illogical.
You have to both see something the rest of the world doesn't see, be so confident in it that you don't see all the risk, AND have nothing in the end "better"/higher ROI (all things considered) than doing a start-up. IMHO.