Because I am not living in Silicon Valley and not in Hollywood but I am involved in web and film – to some degree here is what I found regarding these two fields of activity which seem different but they are not that much.

Web development and filmmaking have lots in common, as a process.

• Just like a web startup, you can choose your market and genre for a movie.
• Designing the tech spec of a web service/designing the use cases can be equal to writing/rewriting a script in filmmaking.
• Breaking down the tech specs into manageable pieces can be equal to breaking down the movie script into the shooting script.
• Prototyping a website (mockups) can be equal to storyboarding of a movie.
• Choosing your web team can be like casting your actors and choosing the production team to make a movie.
• Coding of the website can be equivalent of shooting a movie.
• Alpha and beta testing of a website can be the test screening/preview screening of a movie.
• Opening a website for the public use is releasing the movie into theaters/TV/DVD/online.
• Marketing of a website (SEO, viral, paid, partnerships, etc) can equal to marketing/distribution of a movie.

The goal for both is to have the audience come and use/enjoy your product. Both are using the team work to reach that goal.

Now, there are some key differences between those two, in my opinion.

First, you are used to iterate and make a better web service while your audience is using it, however, you cannot do that with a movie once it’s released to the public. Once the movie is in the theaters/TV/DVD/online then that’s it. There is not Edit button, unless you are doing a remake 10-20-30 years after. Cross your fingers and hope the public (and maybe the critics) will like it so it will make enough money to allow you to repeat the stunt.That’s why in filmmaking failure is not an option (I don’t think you will ever encounter somebody in the film industry to tell you “fail fast, fail often”).

Nobody will tap your back and say “Don’t worry, you can do it again and again until you get it right. Here’s more money for that.” Blow it 2-3 times in a row and you may never make movies again in Hollywood (you might in another parts of the world maybe).

There were well known directors who blew it not 2-3 times but maybe 1 time and they have hard time getting financed for other movies (Paul Verhoeven, after Showgirls and Starship Troopers or Martin Brest after Meet Joe Black and Gigli – both of them started well with Robocop, Total Recall, Basic instinct or Beverly Hills Cop, Scent of a Woman).

The iteration process occurs in the script phase and sometime during filming, editing, test screenings and editing again. That’s why it takes so long for a script to reach the shooting phase, being written and re-written and re-written over again until only maybe the original idea remains, not the original script. It has to be perfect when the filming starts (of course, not always it happens).

Second, it takes more time to raise money for a film comparing to raising money for a web product. I am sure you will be frustrated by this if you have a mindset of a Silicon Valley/web entrepreneur.This is true especially for first timers (James Cameron or Steven Spielberg wouldn’t have this problem). Not only it takes a lot of time to raise the money, also it takes a lot of money to be raised.

If we compare web and film, you can build a web product or at least a minimum viable product for $25,000, let’s say…what you can do with that money in filmmaking? Not much (unless you want to do a short) – renting a RED camera can empty your pockets of a couple a thousands a week if not more – if you want a quality footage. Also, maybe you can convince your actors to work for free but not all your production team will work for free, unless you alone are your production team. You don’t find too many people willing to work for “equity” that often in the film industry.

For serious moviemaking $25,000 is a drop in a bucket. Low budget movies are measured in at least several hundreds thousands dollars per movie, going to several millions. A medium budget movie goes from several millions to 20-30 millions. A big budget movie is over 50 millions, just like well known Internet companies are raising series C,D financing. But you are raising that kind of money for one single movie and you don’t know yet if it will be successful or not (while when you are raising series C,D or more for a web company you already know that your product is successful).

Third, there is no comparison when it comes to manpower needed to make a movie and to build a startup. A startup starts lean, 2-5 people involved and sometimes only 1-2 people. It’s much easier to manage those people if you are a founder. A low budget movie already has tens of people involved, a medium budget maybe hundreds of people to manage. For a first timer that can be a nightmare, especially that he doesn’t know too much how all these departments and people work together – he may be the director/screenwriter but ne doesn’t necessarily know how the gaffers are working, or what the cinematographer does exactly or the sounds/makeup guys/girls do. He needs help, alot of it from people who alrealdy have experience.

If you are technical in a startup you have a quite good idea how your startup should be working technically, and your partner hopefully knows how the business should be working. You may have some time to learn some business side, your partner may have some time to learn the technical side. Being a director/screenwriter doesn’t give you too much time to learn everything and you will need people to show you the way.

A special attention you have to pay to your actors. If you are not Spielberg or Ridley Scott then they can make or break your movie (bad direction can lead them to bad performances, personality clashes can occur, etc). You may have to take some of flak from them (if you are unexperienced) or to swallow your pride to make things work. Sometime, you may need to be confrontational and that is known it’s not a strong point of someone coming from Silicon Valley. With so many people around be prepared to be “stabbed” in the back (not that in Silicon Valley doesn’t happen but I think it happens less than in Hollywood).

Fourth, while your startup doesn’t need to monetize early on to recoup the money for its investors a movie needs to be monetized right away. That creates tremendous pressure on you to put out there quality work which is monetizable (a bad movie will make less money, if all). You also have to have a strategy for that before finishing the movie (contracts with distributors, TV networks, DVD resales, online distributions – sometime you have to have these even before starting the work at the movie because, sometime, financing depends on these contracts).

In my opinion, moviemaking/filmmaking  is harder than web entrepreneurship.

It takes longer (a movie can be in pre-production — script writing / rewriting, financing, casting, location scouting, etc — for years), put tremendous pressure on being successful right away (and that means making money with the movie or at least win some important festivals), failing is not encouraged and not tolerated too much (because of the investment put into it). It’s a cut throat business and no wonder that Hollywood is called a “crazy” place…

But filmmaking can be also beautiful, have its own rewards.

For one, you can create masterpieces which can live long time (even outlive you sometime) and be seen by millions if not billions of people, just like Intel was created 43 years ago and still going strong (or Microsoft, or Google, or Facebook).

You can create a film which can change lives, set trends, influence generations.

You can travel, see places, meet new people everytime you are making a movie. You will socialize more. And yes, you can become rich in doing so (or, at least, live confortably).

One example I will give here of a Silicon Valley entrepreneur who succeded in Hollywood (albeit, he had lots of money when he went to Hollywood): Jeff Skoll.
He was the first employee and the first president of eBay.com. He remained president of eBay until Meg Whitmann came in 1998. He then went and founded the film production company Participant Media (www.participantmedia.com). Participant Media was and is involved in high profile movie productions like The Beaver, Contagion, Food Inc., The Cove, The Soloist, The Informant, Charlie Wilson’s War, An Inconvenient Truth, Syriana, Good Night and Good Luck and others.

NOTE: This article was published first by me on Quora.com on Feb 23, 2011.

UPDATE

In fact, Silicon Valley seem to be moving towards Hollywood, recently. Or Hollywood seem to take notice what’s going on in Silicon Valley. However you want to take it.
There was  reality TV series “Start-ups: Silicon Valley” by Bravo TV channel which ran with a so-so success (wasn’t renewed for the second season).
There is also a new TV series from HBO “Silicon Valley” which just started (an American sitcom that centers on six programmers who are living together and trying to make it big in Silicon Valley).
There is even a conference named “Hollywood meets Silicon Valley” (a two day conference exploring the growing convergence between Hollywood and Silicon Valley).
If we count the daughter of Larry Ellison (Oracle’s owner and CEO), Megan Ellison and his son, David Ellison – both owners and movie producers through their Annapurna Pictures (Megan) and Skydance Productions (David) – we see that  Silicon Valley is involved also in Hollywood.

Hollywood and Silicon Valley have no other way but to get together and cooperate (Hollywood took some un-popular measures against some Silicon Valley startups which disrupted their business models).
Even Hollywood publications are acknowledging that.