Fascinating conversation. I see opportunity for media properties to have a variety of entrances, as opposed to worrying about front versus side doors. Jason Hirschhorn has me nailed down as a loyalist for his awesome MediaRedef property, but I never go in through the front door. He had me with his newsletter (which I will admit was his front door for a while), and even now that he has an app, I still rely on his email newsletter and Twitter feed to land in his media world.
Same goes with Medium. Very rare for me to type medium.com or open the app unprompted. The Daily Digest or story recommends/shares are my entry points, and my immersion in the site can be described as shallow once I am there. But I am most certainly a hardcore Medium loyalist.
As an about to launch media property, myself and my aKoma co-founder are considering the question of what types of doors or windows do we create for entry into the site. We most definitely know we have to have as many as possible, in addition to great content and experience.