A completely open website, controlled by us, is an amazing outlet to reach "the masses." I have no expertise in how to get the ball rolling to make this happen, but it seems to me that making .win a "destination" website should be the goal. Information and posts from here can be disseminated elsewhere online.
Perhaps some heavy hitters in terms of followers would be people that can help with this.... Ben Garrison, Tom Fitton, maybe even Don Jr.
We could separate humor to a separate tab. Have news be the landing page, and allow the top 2 humor posts show on news tab and vice versa.