I think your sports analogy is close, but not quite there. Most writers write for smaller publications, build connections with editors, and then as one is brought up to the big leagues, they pull the other with them. Eventually, they pull their squad together to go build a new team that competes with the rest. Bill Simmons started off with his own blog while bartending until he moved up to Page 2 on ESPN.com. By building connections there, he was able to start building Grantland, and now The Ringer.

I wonder if the monetization problem has already been solved through HBO’s contract with Simmons. Similar to how HBO can make money through product placements on their shows, The Ringer could make money by writing about HBO’s shows (like they did at Grantland), which encourages people to seek out those shows (and HBO) without a single banner ad being displayed or footnote text.