I'm on the other side of the fence now. Yes, it's much harder, and much more stressful, but it's on my terms.
There's a lot more to this story, but I've decided to draw this out over a couple posts.
Funny you mention being risk averse. I've talked about this with my cofounder, and we don't see doing this as being risky. We see taking jobs as being risky, because we feel like we are losing out on doing something we like more and wasting our lives.