In my opinion, getting a technical cofounder would have been a great asset in helping him make the right decision in the first place. Unfortunately I don’t think he have learned that because the last time I check he was still doing something similar. It has to de with the thinking and respect he has for developers in general. I think his frame of mind is still in the era in which it was widely believed outsourcing could solve all problems. My take is if you want to build a tech company, you MUST have a tech cofounder to avoid dangerous pitfalls.