201 karma · joined March 13, 2014
Syncing is the single biggest technical issue and currently not easy since most platforms don't allow access to the point where we could really time-sync. Still looking at a few options, though.
I am confident that the trend away from broadcast towards on-demand is working in our favor.
Not sure if the attempts are comparable and if the same problems apply. Finding the integration (or other route) that helps generate enough traction is one of the top tasks on the business side of this.
Monetization can happen through partnerships with content creators/publishers (even white label solutions), timed advertising or affiliate links (think "I love the dress Claire is wearing – here's the link" or "Meet 'The Mountain' at ComicCon – link").
For examples with some activity, check out House of Cards Season 2 or Game of Thrones Season 4.
This number from some relatively recent Game of Thrones ratings that admitted on not counting a lot of on-demand (as well as pirating, of course)