It is very interesting for me, because there are few programmers in the Hollywood and YouTube communities, so there are a lot of interesting opportunities available.
I literally just today turned my head towards building the most entertaining thing I possibly can. My thought on it is a site that is super branded for entertainment like break.com or collegehumor.com or smosh.com. And combine that with a big YouTube channel, just like those websites do.
But at the same time, it is necessary to see where the eyeballs are currently heading. I think reddit is a wonderful example of a modern entertainment site which can be seen in its huge growth. I would be nice to combine the usability of a site like reddit with the targeted branding of a site like collegehumor.
The super interesting thing to me is that a project like this is much more of a lifestyle business than a venture business. BUT THAT is currently a huge difference between Hollywood and Silicon Valley. I see LA as the land of the cash businesses and Silicon Valley as the land of the VC businesses. All of my professional YouTube friends are making straight cash and building large audiences, but will never have a public exit or a huge windfall.
It seems to me Hollywood's culture about cash business verse Silicon Valley's culture, is an advantage for Hollywood in creating entertainment properties. Entertainment properties require a careful and focused branding for a focused demographic and audience, you can make millions off something like this, but it is hard to IPO.