Obviously I like the idea of having money, but more than anything I want to make my own choices, and I don't think I'll be able to do it at this place.
Is this a stupid whiney thing to think about? Or is it something worth actually doing?
More specifically, Time that I can spend doing whatever I want, with enough income to do it.
The plan is to do it with a small pile of SaaS products that don't take a lot of maintenance to keep alive and attract customers who don't need much hand holding. Naturally, the target is to have as high an income as possible with the least amount of time spent "working".
It's taken a while to get it all off the grand, but it's started to pay off in the last year or so.
I have a well paying job now, but would drop it once my startup launches even though I have no plans or real ideas for pulling in revenue (income). But I have faith that the more people I help, eventually money will come.
I agree with your thinking. Do what you feel is right... there will always be startups of 10+ people for you to join later on if you so desire. If you join now, you will always be wondering "what if..."
Do it because you love what you do and are passionate about it. Too many people failed trying to chase money. Don't make the mistake of doing a startup for the wrong reason.