Its not as difficult as you'd believe it to be. Not sure if you heard of the show Broad City as I worked with the two stars and asked them how they got their break. They told me about their original programming on YouTube. Each episode was between 3 to 5 minutes just to show the potential. I think they did roughly two years of that and built up a good following and Comedy Central bought the show. They are now going into their 4th season with the network. If you need any insight on cornering the market once you have the basis for something you're going to push as well as the typical process let me know.
Usually, backers or major studios are just looking for proof of concept as they don't want to spend the money anymore. If you can get shorts or episodic releases on YouTube and other forms of social media with a solid following your leverage is already established.
I’ve looked into Broad City, and they did start small indeed.
Thanks for the offer of help down the road, @jacobchamplain. Let’s see how it goes.