If you’re going to take a career risk, do it now. Screw the student loans. There will always be some huge financial responsibility you can use later on as an excuse to hold yourself back like a mortgage or YOUR kids college tuition.
Right now you have time on your side, and a lot of energy. Don’t get sidetracked by the light-weight benefit plan of a startup, or a boss who happens to be the same age as you. Go for it! This is a great opportunity to put your fingerprint on the company culture and witness an entrepreneurial endeavor first hand.
If it doesn’t pan out, you’ll be that much richer in experience. From your vantage point (“I’ve already done a startup”) you will smell the duck coming long before you see it waddling and quacking. Plus, you’ll have an awesome story for the next group of co-workers at the “BYOB” water cooler.