[argonaut]

As a side note, there is nothing wrong with asking for a reasonable raise from your current employer. Have a chat with your boss, and tell him/her that you think a fair salary for someone with your experience, is, say, 130k.

[michaelochurch]

If he wants to be a startup founder, he should push for investor contact so he can start building a network in the VC community. I doubt he'll get it right now, but it needs to be his goal.

Without VC contacts, it's going to take 12+ months of bootstrapping, with substantial traction and press coverage, to get funding. They'll take forever to make decisions, dilly-dally while they compare notes with other investors, etc. So you blow a year of savings, in a high-COL area, working so hard (60 hpw is not atypical) that you'll be exhausted at the end of it, and probably need a month off before starting your next job.

With VC, if you have some genuine allies on the inside, it doesn't mean they'll fund an idea they dislike, because their job is to make money. It does mean they won't waste your time in deliberation, will treat you as more of a social equal-- making horrid liquidation preferences and management concessions less common-- and will actually say "no" if they're not interested and try to help you find a way to something they'd actually fund. Finally, having allies in VC means you get an EIR gig or an associate position to fall back into if the company doesn't pan out.

If I were him and wanted to be a founder in 5 years, I'd ask for investor contact, point-blank.

If they say no, that's fine. This is called "door in the face". People talk about getting a "foot in the door" (a small request, granted, to prime for a larger request) but, given the employer/employee power relationship, that rarely is as powerful as the "door in the face" (a large request, rejected, that leaves the person more likely to grant small favors). When you have a mutual but asymmetric power relationship, "foot in the door" makes you seem demanding while "door in the face" techniques are more natural; they have more power but you have some, so they'll deny one request but are unlikely to turn down two orthogonal requests in a row. Yes, they have more power, but they can't turn down all your requests.

He probably won't get investor contact, but then he can ask for a paltry 15k raise, more challenging assignments ("if I'm going to be making that much, I ought to be earning it; are there openings on the X team?") and possibly a more favorable reporting structure.