I wonder why his choice is limited to 1) seeking to have a lucrative career at a big company, and 2) apparently seeking to hit a home run with a start up. A third choice would be to immigrate to a country which still has cheap land and, as a single man, perform whatever is work necessary, for a few years, to buy and own a homestead outright. This could be done in about five years if he was frugal enough. Then... just…
Wouldn't you want to have a good contact who knew something about homesteading for this?