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I wish I had followed that advice at 25.
Your friend's young. He has plenty of time to accomplish everything he wants to (and what he wants to accomplish will change over time). Freedom comes from within. It's important that he realises that he's already enjoying his freedom to have a stable and settled life, start a family and invest in its future by buying a house and growing his 401k.
Maybe he needs to start putting a little money by every month towards a sabbatical fund so that, a few years down the line, he can afford to take 6 or 12 months off work and do the stuff he doesn't feel free to do now.
Perhaps your friend would feel some accomplishment by:
* Mentoring new startups
* Mentoring disadvantaged youth
* Religion
* Community service/projects
* Becoming involved in local government service
* Horticulture
* Woodwork/old car restoration/old computer restoration
* Adopt an elderly neighbor as a "grandparent", that he goes and speaks with on a regular (at least weekly) basis
* Read the works of the greats, genre open
* Pick up painting or other artistic ventures
* Set a goal that's a lot of fun. For example, I know of a friend who has a life goal to hike each US state's highest peak or point. He's made it about 15 in, and has a lot left to go.
* Get involved with the local Boy Scouts/Girl Scouts program (related to mentoring), if Boy Scouts go through Woodbadge (extensive leadership training)
* Join a nonprofit board
Each of these points are kind of getting at a main point: live for something. Work and career are certainly intended to be a vocation, but they aren't always going to be an avocation. When avocation and vocation conflict, I believe a lot of people get dissatisfied.
Of course, I could also be completely wrong and a therapist is advisable. But it's something to consider.
He doesn't understand how to be happy or satisfied. He needs a therapist. I think most people do, they underestimate the value of having an independent sounding board to help work through these kinds of feelings. His expectations are either unrealistic, or he's surrounded by people who are always doing better, despite him doing well, which makes him seem like a failure. He has the luxury of those feelings. Silicon Va…
Your brain, like your teeth or your car, needs regular servicing by a professional if you want optimal performance and want to avoid costly repairs.
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.