It sounds like a no-brainer: already has paying customers, has enough cash to be offering a Real Salary, and the founders have prior successes. But the family

It sounds like a no-brainer: already has paying customers, has enough cash to be offering a Real Salary, and the founders have prior successes. But the family one is a huge issue. You're probably looking at longer hours, with more uncertainty, and possibly a drop in quality of the health care plan/general benefits. If the home front can't buy into that for the potential upside of a happier + possible bonus-enhanced you, then it's going to be a very stressful situation. Also, be sure it's a product / technology you like to work on. Every hiring manager I know will tell you you're going to have a lot of "freedom, input into the direction of the product, and the process" - even the several I know at IBM & Microsoft. The caveat to that is, "within the bounds of what we feel are appropriate." If you're making this change just for the freedom, look for something where you're a founder and the technical lead. If you're doing this for a change of pace from the bank and the potential upside/startup experience, then I'd say consider it strongly :-)