A friend asked me for advice: startup or big company

This may not be quite what you're looking for, but bear with me...

There is an unwritten tradition in Judaism that a non-Jew will not be considered for conversion until after his first 3 requests have been turned down. Why? The thinking is that it is so hard to be Jewish that only those who want it badly enough will succeed. They must show that desire by continuing to come back until they get a yes.

That same thinking probably applies to starting a business. It's hard. Unless you're fiercely determined to succeed, you probably won't.

Tell your friend to go with the big company. A startup is just too hard. (You'll be telling him the truth.) His reaction may tell you a lot about his desire.

Seems pretty sensible. Good listening resulted in good advice.

Most of the time when people come to me for advice I just ask them a lot of questions and let them tell me the answer. It's usually obvious that they really want one answer rather than the other but just find it difficult to choose between two good choices because they might lose out.