Since you said he's always working on some startup to become the next millionare I'm assuming he is surrounding himself in that culture. Wouldn't he also be on

Since you said he's always working on some startup to become the next millionare I'm assuming he is surrounding himself in that culture. Wouldn't he also be on HN? Anyway, although it's hard to sympathize for someone that seems financially stable with a wife AND a newborn to not have a purpose in life, try surrounding him with friends and activities. What are his hobbies (besides startup life)? Tell him to watch some TED talks discussing this same thing. Hell, volunteer! The culture shock of helping those in need should make one self aware of their luck and privileges vs. immersing yourself around people who strive for the next big thing.