When first filling out the Risks and Challenges section your first inclination will probably be to prove how there are no risks and no challenges. Instead of taking this path, be open about what you feel the risks are and your plan for minimizing them. Talk about the challenges you currently are facing and how you've solved other challenges in the past. If I'm going to sail out to sea with you on this voyage you'll be more likely to convince me you know how to handle a storm than to tell me there won't be any storms at all.

What you suggest is another, different, and also valuable blog post. His choice:

  Pro tip: if I, who know your business as well as I know the
  feeding habits of the Springbok Antelope, can come up with
  more risks than you can, you’re not doing it right.

It's disdainful, sure, and not to my taste, but it's memorable and cuts right to the issue. He's trying to be George Carlin. There's some value overall in a reasoned argument, and some value overall in a certain amount of hip hectoring if the author can piggyback wisdom on entertainment.