I'm a big film buff with a particular affection for good business movies. Unfortunately, good business movies are as rare as hen's teeth, so I'm forced to include a few TV shows in my list of the "top ten entrepreneur movies" . Here they are in no particular order:

Wall Street

Blue Horseshoe loves Anacott Steel!

I still love this movie after 10 or 15 viewings since 1987. Sure it's a morality play in the second half but the first half showing a young go-getter determined to land a big client is what entrepreneurship is all about. It's about getting the first big sale by not taking "no" for an answer, even after 57 failed attempts. Few movies do a better job of showing what it's like to suddenly have a lot of money coming in very quickly. Michael Douglas's portrayal of corporate raider Gordon Gekko is one of the great performances in cinema, as far I'm concerned. Few scenes in film match the excitement of Bud Fox's first meeting in Gekko's office.

Be honest, wouldn't you want to work for a Wall Street M&A firm--albeit one with an honest boss?



Other People's Money

This film is the perfect second feature for any viewing of Wall Street. If you are curious about how Gordon Gekko and his arch nemesis Sir Larry Wildman made their millions, watch OPM. Danny De Vito plays corporate raider Lawrence Garfield who launches a hostile take-over bid for a small public company, New England Wire & Cable, headed by Gregory Peck. Pay close attention to Garfield's chalkboard explanation of why he wants the company. The two speeches given at the shareholder meeting arguing against and for the takeover tender are brilliantly written and delivered by Peck and De Vito, respectively. This is another movie I own a copy of for annual viewing.

Lord of War

The first time you sell a gun is a lot like the first time you have sex. You have absolutely no idea what you're doing but it is exciting and, in one way or another, it is over way too fast. - Yuri Orlov

This is another great startup movie. Nicholas Cage's character, Yuri Orlov, is the son of a Russian immigrant family operating a greasy spoon diner in Brighton Beach. Yuri wants more out of life. One day he spots an opportunity to get into the arms trade and quickly seizes it. He then embarks on a campaign to break into the big leagues of the arms business after initially being snubbed by the big boys. Fortunately for Yuri he has an uncle who is a general in the Ukrainian military which is holding a fire sale on its Soviet supplied weapons systems after the collapse of the USSR. "Buy 6 helicopter gunships and we throw the 7th one in for free!"



This film does a fine job of portraying the emotional ups and downs and financial pressures of building a fast-growth business and leading the high-roller lifestyle in order to impress others. One memorable scene is about all the expense and trouble Yuri goes to in order impress the girl of his dreams.

If you listen closely, the Yuri character has a lot of quotable lines.

Man Who Would Be King

I can almost hear you asking, "The Man Who Would Be King? What the heck is this doing on your list?" If you don't think that this is a movie about entrepreneurship, you're dead wrong, my friend. This may well be the ultimate entrepreneurial movie.

Ex-British soldiers Daniel Dravot (Sean Connery) and Peachy Carnehan (Michael Caine) have big dreams after retiring from her majesty's service. They want to take over one of the Central Asian kingdoms northwest of India and make themselves its rulers. However, they find themselves in typical entrepreneurial circumstances with next to nothing in terms of a startup budget. So in classic entrepreneurial fashion, the limited financial resources they do have are invested in assets which will bring them the biggest bang for the buck--literally: 16 Martini-Henry repeating rifles.

They then use these rifles to both impress and intimidate the thuggish ruler of a small autonomous tribe on the outskirts of their target country of Kafiristan. This first alliance then becomes the platform from which they launch an M&A campaign to acquire control of additional tribes. Can you say "industry roll-up"? In quick time they acquire enough "assets" to take over the entire kingdom. This is when their real problems begin due to hubris on the part of Daniel.

My only complaint against this classic is that it should have been 20 to 30 minutes longer in order to avoid the abrupt ending. Instead the film has the feel of something lovingly crafted to build to a dramatic high over the first 100 minutes at which point the director realizes, to his horror, that he still has another hour's worth of story to compact into twenty minutes. So he starts tearing out entire pages from the script because he has neither the budget or film time to include them. We therefore miss the great adventure that Peachy must have had in escaping back to India after things fell apart for him and Daniel. The result is a weird ending that feels as if the Starship Enterprise had teleported him back to Rudyard Kipling's office.



However, this classic is still worth watching.

Startup.com

This is the documentary about failed dotcom Govworks and its two founders. I own a copy and watch it annually. If you are thinking about trying to raise venture capital, watch this film first. Its big lesson is that raising capital requires a rare type of personality. Most people simply don't have the right set of traits for it. Kaleil loves schmoozing with the venture capitalists. He's in his element doing presentations. Meanwhile, Tom hates it and just wants to get back to the office to focus on building the website.

(Just out of curiosity, does anyone know what Kaleil and Tom are doing these days?)

The Sopranos

You know, I didn't get around to watching the godfather movies until about 2003 or 2004 due to moral objections. When I was a kid, Life magazine would do these big articles on the Mafia with tons of pictures of dead mobsters lying in pools of blood. Those articles horrified me and I vowed never to read or watch anything that seemingly promoted gangsters. Then after I started running out of movies to watch through NetFlix, a friend recommended that I try TV shows such as The Sopranos which eventually led me to the first two Godfather films. One of these DVDs had an extra feature interview with Francis Ford Coppola who explained that mafia movies are really about capitalism and not about crime. That's when it all started to make sense for me. Mafia movies are about getting a piece of the American Dream when your ethnic group is shut out of the system by the powers that be.

To be honest, I almost didn't make it through the first season of The Sopranos because I found the side stories about Tony's annoying dysfunctional family as well as his visits to the shrink boring. By the second season, I was fast-forwarding through most of them. However, the parts about Tony and his capos building their New Jersey operations while constantly butting heads with the hostile "head office" in New York are top notch entertainment.

Finally, in my humble opinion, the opening credit sequence is the best that I have ever seen. I have never fast-forwarded through it as I do with most TV shows that I rent through Netflix. I even bought a CD with three versions of the opening song to play in the car. (No, I haven't taken up cigar smoking too.)

Tucker

My memory of this movie has almost completely faded since seeing it over twenty years ago. The only thing I can recall about it is having a warm upon leaving the theater. I think this is due to actor Jeff Bridges having done a fine job of conveying Tucker's naiveness. As people will tell you, you can often achieve great things in your twenties simply because you are unaware of what can't be done. As you get older you start understanding why things are impossible and shouldn't even be attempted. Tucker shows an entrepreneur who, although in his mid-thirties, had that all important youthful obliviousness as to why a car company could not be started at home on a shoestring budget.

(Edit: replaced Boiler Room with Pirates of Silicon Valley in mid August.)

Pirates of Silicon Valley

Another good one. Although it's a B-movie shot on a tiny budget it does a fine job of recounting the story of Bill Gates and Steve Jobs in the early days. Watch the Apple crew raid Xerox PARC and "borrow" its best ideas. Then watch Microsoft raid Apple and "borrow" its best ideas. Witness Bill Gates license a software system he doesn't have to IBM. It's all highly entertaining. Read the book afterwards.



Okay, that's still not ten yet but I'm working on it. I did warn you that it's hard coming up with a list of decent business movies.



If you can suggest any other films or TV shows for the list, please do.