I hope it works for him. If someone could pull together an honest to goodness high school level website that really explored the entire scope in Wisconsin, there would be a lot of happy people. The only drawback is that it's going to be an enormous undertaking to get stringers working with him, for virtually every conference, and sport, in state. It will almost certainly end up with younger people manning those positions, and they have to be dependable. People want to see content in a timely manner.
I wish him well. It's a vast undertaking, and it will probably take some time for him to gain enough traction to make it profitable enough to say he's making an income.
What he has going for him is that Wisconsinites, even when they move, seem to have an awful lot of loyalty to their schools.