As someone who did the Ivy thing, and got a Ph.D: If he can get an internship with a well known high-tech company, that will have some impact on college admissions, but much greater impact on job prospects when he hits the market. When it comes to getting a Ph.D., unless he's a superstar, jobs prospects in academia are pretty sparse. Depending on the field, they are very sparse outside of academia as well. High tech is littered with Ph.D.s that are working at the same level of seniority as people who spent those years working, earning money, and avoiding the stress of the graduate student life. To be very clear, the only valid reason in my mind to get a Ph.D. is that you are absolutely in love with the field, and would consider it worthwhile even if you had to start a career from scratch when you finished. A passion that burns. If you do it in the hopes of getting a job, you will be disappointed.