Your startup seems to be doing pretty well (I would call it "profitable-able in a pinch") and you have a mini safety net with your wife's academic employment sh

Your startup seems to be doing pretty well (I would call it "profitable-able in a pinch") and you have a mini safety net with your wife's academic employment should provide health insurance indefinitely if you do take the jump. Also, with your experience you will also likely find job in industry if your startup folds, so you have fallback options, assuming you are OK with working for a corporation. That said, I would personally still take your "one more year" option as it gives you an extra year to get your startup to profit without officially resigning. This seems to be a very valuable freebie. Did I misread your web post about this option or are you reluctant to take this for other reasons? And finally, on your startup -- I would steer it to become profitable ASAP; for example if and when you are deciding between hiring a fifth employee (to grow faster) or getting profitable sooner I would take the second path. My 2c. And good luck whichever option you choose!