I went through grad school once (PhD, dropped out, left with a MSc), am now doing the startup thing, and intend to go back for a PhD because I do love some things in research and academia (and I have some R&D-type ideas I'd like to work full-time on which require me to be in an university setting).
What I suggest to friends asking me for advice re:grad school is to go to grad school IF AND ONLY IF they get an assistantship of some sorts (those usually come with a tuition waiver).
When I applied to grad schools, I didn't get in my top 2 programs of choice; I did get in decent programs, but which wouldn't pay me (or not enough to cover my various expenses). I ended up choosing a lesser program, but one that gave me full tuition waiver + a teaching (and later, research) assistantship.
Grad school is a great experience, and I believe most people will get something from it. But it's not worth getting in debt for it (even if it's your top choice- you wouldn't pay Google/Apple/[insert your favorite company here] to go work for them).
Now of course, this advice is easier to follow for the scientific fields; but I have friends who got into liberal arts programs with full tuition waiver + a decent assistantship. The bar is just much higher for these (as it should be).