There’s not just one way to break into Hollywood. You can write a couple of specs and submit them to write for an existing series, you can sell an original, or you can make your own film/show/web series. The key is to get someone to notice your work.
Short films are unique in that they’re more or less like a joke: set-up, punchline. But they should also have a surprise twist ending. A short is anything under 60 minutes so there’s a lot of room to play. If you’re going to produce it yourself, keep it simple: one room, maybe even one scene with a couple of actors so it’s really easy and cheap to produce. If you have a more complex idea, you could get funding or sell it to a producer. You won’t get much money for it if any, so your top priority in selling it should be to make sure it’ll get made, it’ll be made well and get shown in festivals. So many shorts never get finished. There’s also nothing wrong with YouTube videos to showcase your work.
These are a lot harder than you think. There’s a lot of ‘competition’ out there now and they’re getting quite sophisticated. Keep it simple so budgets stay low and it’s quick and easy to shoot. If it’s more complicated, you’ll need to get funding, so your concept needs to be solid and your episodes short. Episodes are best kept to five minutes or so. I’ve seen some series that were shot like a half-hour TV episode but released two minutes at a time. They were well done, but tedious to watch. Another series had half-hour episodes, which was way too long not just to serve the story, but too long to maintain interest. It would have helped if they chunked it down to ten minute segments. Don’t think that just because you’re producing it for the Internet that you can skimp on quality. This is your chance to showcase your work, make it stand out. Watch a few to see the differences in quality. Would someone choose to tune into your web series regularly over watching something made by pros?
Personally, I don’t think there’s a lot of value in shooting a trailer unless it’s top-notch. It needs to look pretty close to the finished product and that typically requires money and professionals. Your concept should be strong enough to pitch without a trailer, but if you’re going to do one, do it well. One of the biggest mistakes independent filmmakers make is cutting a trailer that looks great but says nothing or looks terrible so no one pays attention. A trailer is not the same as a teaser. A trailer shows scenes taken from the actual film, a teaser is mostly text or voice over with snippets of visuals to give a hint of what it’s about. If done really well, you can get a lot out of a teaser, but it should tell the viewer the message you need to convey about your project, which is tough when you’re not showcasing your work in the same way as a trailer. You can also make a short film version of your feature, but in my opinion, if you’re going to raise money to make a short version, why not raise more and make a feature?
You can produce your pilot yourself and hope a broadcaster picks it up. It’s not a bad idea if your show is reality-based or talk/variety, even a sitcom, but once you get into complicated shows with a lot of cast and locations, you’re better off finding a producer to do it right. On the other hand, you could produce it deliberately on the cheap, like It’s Always Sunny in Philadelphia where that’s the visual style. You could get it shown on cable access channels; you won’t get paid for it, but you’ll have a show on TV that might get attention from bigger broadcasters. It does happen.
These days you can produce a feature for very little money provided you know what you’re doing. Don’t overstretch yourself with too many characters and locations or special effects and fight scenes. The less complicated your script, the more time and money you can put into the quality of your production. Horror sells well on the indie market, but even then there’s not a lot of money in it unless you score big with a film like Paranormal Activity. Aim to keep your budget under $50,000 or so. Hire the best cast and crew you can for no money. Don’t spend money on people with little to no experience. You can get professionals to work for free provided you feed them, you finish the film and they’re passionate about the project. Typically these people are trying to make a career transition either to a different role or go from TV to features.
Always keep in mind your desired outcome. Why are you producing this? Is it to get into festivals, to raise money, to put online, to get attention? That will help guide you in the right direction.