The obvious answers are that you need more eyeballs on screens - both for advertising to be profitable and for PPV to be profitable.
I think there might be potential in a 'freemium' type of bundle.
Check out the website creativelive.com. It's geared towards creatives. They are making a lot of money (albeit with a larger audience than pool) by offering the first run content free live and then if you like what you're watching you can purchase the 'extras' and access to the video to download, watch streaming, etc... This works well for seminar type content.
It could be that having some of the pool hucksters on there talking about their method like TOO (or whatever the heck it is

) for free. And then people can upgrade to get the course materials (like diagrams and hypnotic tapes etc...) and then be able to download and re-watch whenever they like. Maybe even another upgrade with a 1 -hour Skype lesson or something.
Then split with the promoter. So for example, if CJ came on and talking about 'the web is the teacher' people could watch his entire seminar for free. While it's going on. Then if they were willing to pay $59.99 they get all of his PDF diagrams, audio tapes and can rematch the course as much as they want. If they pay $99.99 they get all the above plus a hardcopy of his book. If they pay $199.99 they get all the above, plus an ugly sweater and a 1-hour Skype lesson with him.
All the revenue is split between CJ and the streamer.
For competition it's tougher because people don't want anything but to see the action. That's why a PPV is probably the best way to go so far. If TAR had free matches and tried to rely on add-ons they would probably have less revenue than they did. Maybe things like watch for cheaper and then upgrade and get the VOD + bonus footage interview with the players + autographed TAR t-shirt. If you can bundle things then people are usually willing to try and justify the expense. Maybe they wouldn't spend $22 on a signed t-shirt, but they would spend $79 on a signed t-shirt + VOD + Bonus material + annotated analysis of key shots and games by the players themselves. (A pdf with key shots diagrammed and notes about what they player was thinking or why they took X shot over Y Shot. Possibly even analysis by other pool experts with suggestions for tips or drills on how to get proficient at that particular maneuver.)
Even with ALL that pool still doesn't get enough eyeballs on the screen to really make it worthwhile.
IMO Justin has an enormous amount of talent and reputation and a good persona - he will be able to find a way to leverage that into something big that will reward him very well financially. I think what he and Chad did with TAR is nothing short of amazing. I remember when they first started talking about it on AZB and I was so impressed that they talked...and then they did it. And they did it in a big way.
Heck, he may want to approach creativeLive to do a seminar on how to handle streaming live events and the ins and outs of lining up talent. Could put a little $$ in his pocket for the next thing.