Conversation with a very technical friend of mine about filling positions in my bootstrapping company:
HIM - you need a technical cofounder
ME - don't I know it ... perhaps you could learn objective C and not only work with me but have tons of high paying freelance work available
HIM - that's a huge time investment. Maybe you should learn objective C and then you wouldn't have this problem any more.
ME - I would genuinely enjoy that. But then who will go out and talk to bands (my first target customer) not to mention doing all this design work, architecture for the product, finding more staff, managing projects, marketing the product ...
HIM - Lot's of people can go talk to bands. Get a college kid to go talk to bands. Developers are what's hard to find.
The thing is, he's probably right ... but there is a structural problem in how we make these decisions about working with other people ... it is nearly impossible to assess expertise in something that you are not knowledgable about. So we often either massively overvalue stuff other people do; i.e. "set up a C corp" is quite a small undertaking and isn't how I would evaluate a business cofounder, or undervalue it "anybody can go talk to bands" displays a lack of specific understanding of the music industry.
