Outsourcing is a learned skill, definitely. I didn't start with outsourcing a full blown startup project. I started with small admin tasks using a virtual assis

Outsourcing is a learned skill, definitely. I didn't start with outsourcing a full blown startup project. I started with small admin tasks using a virtual assistant I'd pay $5 / hour. It helped me understand how to be clearer via emails, what processes to use to gain visibility on progress without micromanaging. Also I am a seasoned traveller and I think it helped me understand cultural sensitivities. An Eastern European contractor usually behaves differently than a Filiino or an Indian. They tend to be more direct in their communication style, to the point of sounding rude sometimes. Once you know that, it is easier to tolerate it :)