How exactly would you be racking up debt as a computer science Ph.D student? You don't pay for tuition, you get paid a pretty decent stipend + health insurance and you probably will do many industry/research internships (where you get paid very well). I say this with experience, as I am a CS Ph.D student and make more than enough to live on with a modest lifestyle and I have no debt. Plus if you get an outside fellowship, which most successful students do, you'll essentially be able to work on just about anything you want (I don't think this can be said for a random Google employee, however this is probably true for a YC founder). The Ph.D lifestyle is pretty great imho...at least in CS (non-CS, that's a whole other story).
Google pays a decent salary- not the highest, but fair when considering the cost of buying a home and living in a city near a Google office. I have never heard of a Grad student getting a stipend in the amount someone who studied CS for 6-8 years should be able to get outside of academia.
I'm not saying doing a CS Phd program is not worthwhile- it still is. But, if you have an existing offer at Google or YCombinator its like going to the NBA straight out of high school. Certainly there are good reasons to go to college. But at the end of the day, if the NBA is where you're trying to get to- you take the chance when the opportunity presents itself. Grad school will always be there.
Get paid a pretty decent stipend + health insurance?
Most Ph.D student got less than $2000/month before tax, even less than $1500/month and should pay for health insurance by themselves. OK, decent, how to define decent.
The NSF GRFP provides ~3k/month plus tuition and health insurance are covered. If you do a 3-month internship each summer on top of that you can get an extra $20k-30k easy. I am not saying you'll have the same lifestyle as a Google employee but I think it's hard to argue that you will go into debt. Maybe I live a more modest lifestyle than others. Also all the schools I got into when I applied to grad school would pay health care/tuition, that's standard.
If I may, I found the NSF GRFP process unsatisfactory. For example, I was rejected for two reasons: 1) because I did not publish prior to applying, and 2) because the reviewers thought that my research, although it had intellectual merit, did not have broader impacts (i.e., "the potential to benefit society and contribute to the achievement of specific, desired societal outcomes").
I proposed research on how to improve upon string searching, which according to the reviewers, did not benefit society (??).
The reviewers all have PhDs, I believe. But somehow, I do not feel they are qualified to review the applications. They are looking for specific things cross the check-boxes.
The second point is that stipends are taxed. So, $3k looks like a lot, but post-taxes, it's trimmed. Also, if you look at the OP's posting, $300k for ~5 years for a student. That does not mean the student receives $60k/year for living.
The third point is that someone immediately out of undergrad at 20 might find PhD / below poverty level stipends enticing, but once you make 150k+, you really don't want to hand control of your life over to your advisor's whims.
The fourth point (which is a corollary to the third) is that I know quite a few miserable PhD students, whose advisors control large aspects of their life. For example, a few of them were house-sitting their advisor's newly purchased mansion overnight in sleeping bags. These were foreign students.
