He also travels business/first and stays in 5* hotels (clicked something on the Explore tab). My guess is some kind of previous startup that sold well? Maybe his roommate can fill us in.

Had a well paying job for several years and lots of freelancing before that, has roommates so his rent is not absurd so he can afford the great opportunity to travel a lot. :)

You don't need a lot of money to travel.

True, but you should probably take a take a look at the above comment...

No, but given the ballpark for a next day first class fare SFO to Tokyo is in the $10-20,000 one way range, that's not really true in this case.

You need a bit of money to travel to Tokyo on a whim, as detailed in one of his screenshotted chats.

traveling "costs" a lot. what must be given up in order to travel?