I think you should ask him what he wants to do and talk to him about tradeoffs with each option. What he wants is more important than any advice from me or anyo

I think you should ask him what he wants to do and talk to him about tradeoffs with each option. What he wants is more important than any advice from me or anyone else online (including Naval). Life's gonna throw challenges at him whatever he decides, at least let him enjoy the journey.