I'm not sure why you're being a dick, but I'll bite.
.. they teach you about entrepreneurship is that when you have an idea you should run it past someone with the balls to ask questions and say no and it's clear you never did so.
Evidence? What about posting to this forum? Do the opinions here not count?
I'm asking because you do state that you are the one writing the guides and that the guides are written by experts.
I never said I'm writing the guides. I said "I'm making them for me." Isn't it possible I'm part of a team that shares a common goal?
I think you're enjoying setting up and attacking a straw man instead of constructively critiquing the idea. Even if I was the sole writer on the guides, how do my credentials even matter if the guides are generally better than the free stuff floating on the internet? I'm struggling to understand whether you're against the idea because you don't believe better guides can ever be written or you're against it because you don't have faith in the team behind Waypoint?
Is it the latter? Would displaying my team's accolades help mitigate barriers to adoption and suddenly this becomes a better idea in your mind?