I think 15-40% is a good range. Less than that and they feel like they are just an employee with stock options, but more is dangerously close to equal. You want

I think 15-40% is a good range. Less than that and they feel like they are just an employee with stock options, but more is dangerously close to equal. You want them to always know who's boss :) I'd also get references without asking. If he claims to play golf with someone big, track them down and see if they say the same. Ask around and see what his friends say. Track record is huge. Make sure the measurable successes match the hype. I'd say 2-3 years is good to vest. You'll know by then if the business is failing or not. Things could also change if you get investment. Definitely delay bringing him on board so you can cultivate a friendship and vette his work ethics. Its a lot easier to not hire someone than it is to fire them.I'd say try and spend lots of time together for the next couple months if you just met him. Make him make sacrifices.