In Silicon Valley with a tech background it's rarely a very stark choice, though. If you have good tech skills, a the default/fallback option is a pretty nice one, materially speaking: a low 6-figure programming job at a big company. There is very little chance of ending up unemployed-and-homeless, given how much companies are scrambling to hire technical people.

In that context, it makes more sense to me to encourage people to think about something other than money as their main/only goal. It is indeed something you can only afford to do if you're privileged enough to have the option, but being a tech person in Silicon Valley means there's a high probability that you do have the option, because if you "fail", you can always fail back to the 6-figure corporate job, which is a pretty soft landing. So given that you can live a materially comfortable life just taking the default route, what else do you want to do?