I generally look for folks with totally different experiences from my own these days -- domain experts, folks who have made investments in themselves in a way I haven't (e.g. my current co-founder is a neuro interventional radiologist).

Focus on the part of the idea most likely to fail first. In terms of the business itself, as a leader, I always am looking for a way to displace my own role and hire folks who can do a better job at my current responsibilities.

I guess me being remembered isn't as important to me as the impact I'm able to have. After selling my first business, I choose to move into healthcare to try to impact a field with pretty poor tech available to it. I hope I'm able to positively improve physicians experience with technology and in doing so their ability to have a great impact on the individuals they care for.