If you start a company, only do so if you have an idea you're in love with. If you fail at an idea you loved and could have been great, you're unlikely to regret it, and people won't hold it against you. Failing at a me-too copycat startup is worse. Startups are a 6-10 year commitment—wait for the right one.

If you join a company, join one on a breakout trajectory. You might get 1/10th of the equity of a tiny startup, but at 1/100th or 1/1000th of the risk. You'll work with very good people, learn what success looks like, and get a W on your record.

Don't let salary be a factor. The author watched someone turn down a breakout company because Microsoft offered $30k more—a terrible decision. In a few years, when it's time for something new, the options in front of him will be much worse than they could have been.

No matter what you choose, build stuff and be around smart people. Sitting around talking with your friends about how you guys really should build a website together does not count.

Working at an already-massively-successful company means you will learn much less, and probably work with less impressive people. Spending years at a company that fails has path consequences—the breakout-trajectory company is the sweet spot.

Keep your personal burn rate low and minimize your commitments. A lot of people miss great opportunities because they couldn't afford a salary cut, couldn't move, or didn't have the time.

Becoming a VC young is usually a mistake—the best way to become a VC is not to grind up from junior associate. Start or join a startup and get partner offers at 28. Good founders want investors with operational experience.