Choose wars based on strengths & battled based on weaknesses
blog.thestartuptoolkit.com
blog.thestartuptoolkit.com
Also, I would argue there's much more to consider before offhandedly determining anything you don't know "is the riskiest part of your business". The real answer probably lies in the question: Can I hire somebody to do this, or is it important enough to distract us from other goals? If yes then do it, otherwise reconsider when resources free up.