Do you think some of these issues could be ameliorated by setting out guidelines in the very beginning such as sticking to a simple business model, saying you won’t scale past a small size, and outsourcing business-related work to 3rd party services? Many engineers probably identify with your quotes about “building something no one else has” and “freedom to work on what I want.”

I think many of us would find guidelines like that useful! Because to a corporate engineer drone like myself, starting something small like Pinboard sounds rewarding.