without a doubt, he should go to HBS, it's a much better MBA program than MIT's, even aside from the alumni network and connections he will make there, which are priceless
if he wants to work in high tech, he should then enroll in an M.S. program at Stanford after graduation if he thnks he still needs the skills or credential
those two together would be ideal, rather than the dual degree from MIT
the two summers in between starting and first/second years, he should come out to CA and work in Silicon Valley at any one the Paypal mafia start-up's and get to know the players and interview at Stanford for the MS program while he's out here
p.s. what was the last successful company started by an MIT alum in the last 10 years??? I can't name one either