I think your employer would find you to be a rather poor employee in that #2 situation.
As an employer, I know that you are working there because you love what you are doing and don't want to be doing anything else. I don't have to worry that you'll move along as soon as someone offers you another $1.50 an hour. And in a startup, I know that if we hit a rough patch we can probably come up with a way to trade you equity for salary. For creative positions, I'd view financial independence as a positive.