What exactly does he define "vicariously living the startup life" as ? It seems that the answer to this might give you a lot more insight.
Yea, we've been wondering that ourselves. :) We've already gone through the DD process with him and his lawyer, and a new shareholder's agreement has been drafted. It has verbiage in it that basically allows him to come on as a voting shareholder, with the ability to ascend to a director once he feels "he is ready". His readiness is mostly contingent on industry knowledge. We're in a space that is largely unknown to…
Thus far, the potential investor has shown himself to be uninterested in direct interactions that would let you get more comfortable with each other, and nothing in his behavior provides reason to expect he'll suddenly become helpful and acquire a deep understanding of your business once he's your partner.