"What would you do? Would you just support him blindly or would you advise him to do something else?"
Regardless of the idea, I would advise setting a squeal point in advance, a condition such as [cash < $20k] that will immediately trigger the action of giving up and looking for a job.
Aside from that caveat, I would give much the same advice as others have given here: focus on the needs of your users, keep your burn rate low, and code like a madman.
Common advice for new Go players is "lose your first 100 games as quickly as possible." Players who follow this advice invariably win their first game long before playing 100 games.
