What I've learned burning through about 5 co-founding relationships over the years is that, whatever you do, you need to have a 3-month probationary period wher

What I've learned burning through about 5 co-founding relationships over the years is that, whatever you do, you need to have a 3-month probationary period where both parties understand they can leave with minimal loss and no hard feelings. Moonlighting is fine over this period (see the point about minimal loss). If he's good and really sees value in your idea, he'll get a LOT done over evenings and weekends, if not, he's not co-founder material, period. A cofounder needs to be ridiculously motivated, self-aware, and hard working. 95% of people who would make good employees wouldn't make a good co-founder. Another tip: if someone is hesitant about sales, he is not for sales. Good sales requires genuine enthusiasm and persistence. Especially in the early stages, where it's all about winning hearts, and less about "sales playbooks" or established processes. I heard Dharmesh Shah (CTO at HubSpot) describe early stage sales pipelines with two words: non existent.