9 Things Every Entrepreneur Needs to Learn From Woody Allen


Editor’s note: James Altucher is an investor, programmer, author, and entrepreneur. He is Managing Director of Formula Capital and has written 6 books on investing. His latest book is I Was Blind But Now I SeeYou can follow him @jaltucher.

I hate Woody Allen. Here’s why. Because if you’re Jewish and a little neurotic then it has become a cliché that nerdy neurotic Jewish people describe themselves as “Woody Allen-esque” thinking it will attract women. They do this on dating services. The idea is that they will then attract some waif-like Mia Farrow-ish  (or the 17-year-old Mariel Hemingway in Manhattan) blonde who will love all of their neuroses and want to have sex all the time and will, in the ideal case (the 17-year-old Mariel Hemingway in Manhattan, the 21-year-old Juliette Lewis in Husbands & Wives), be the most mature  in the movie and yet still be madly in love with the 30-year-older Allen.

This only happens in Woody Allen movies. And power to him. He made the movies. He can do whatever the hell he wants in them. If Mariel Hemingway wants to have sex with him all the time then no problem. He wrote the movie! It’s up to you whether you believe it or not.

And people believed it. Manhattan is considered one of his greats – shot in black and white, skyscapes of Manhattan in every direction which are actually shot from Allen’s penthouse apartment. It was beautiful and makes you fall in love with Manhattan.

(Mariel Hemingway in Manhattan when Woody Allen is breaking up with her)

Allen puts out a new movie or two every year. None of them will compete with Star Wars or Harry Potter in terms of gross dollars. But it seems like his studio gives him $10 million, his movie will make $20 million, and everyone is happy and he gets to keep doing what he’s doing.

So he’s built up a substantial body of work that we can learn from. Why learn? Because clearly he is a genius, regardless of what other opinions anyone might have of him (and I only know him through his work. I don’t know his personal life at all). It is interesting to see how he, as an artist and creator, has evolved. To see how his idiosyncratic humor has changed,  how he twists reality further to stretch our imagination. He always stands out and stays ahead of the other innovators. And for other people who seek the same, he is worth observing.

(Juliette Lewis in Husbands & Wives)

Here’s some of the things I’ve learned from him:

1. Failure. Some of his movies are just awful. He admits it. In a 1976 interview in Rolling Stone he says, “I would like to fail a little for the public…What I want to do is go onto some areas that I’m insecure about and not so good at.”

He elaborates further. He admits he could be like the Marx Brothers and make the same comic film every year. But he didn’t want to do it. It was important for him to evolve. To risk failure. To risk failure in front of everyone. And his movies did that, going from the early slapstick humor of Sleeper to the darker Crimes and Misdemeanors and Match Point.

One of my earliest memories is having a babysitter while my parents went to a movie. Then when they got home I asked them what they saw and they described a movie where a man falls asleep and wakes up in the future where a giant Nose ruled the world. Woody Allen has been there since the beginning for me. And just the other day I watched Midnight in Paris with Owen Wilson (who, despite looking very un-Woody Allen-esque, plays the virtual “Woody Allen” role very well. The movie explores the history of art and how no art form exists by itself but is always influenced by generation after generation of artists before it, dating back hundreds if not thousands of years).

(Scarlett Johansson in Match Point, one of Allen’s best movies)

Woody Allen has also failed spectacularly, in every way we can imagine – personally, professionally, etc. And yet he’s always pushed forward, trying to surprise us again and again, and largely succeeding rather than giving up.

2. Prophetic. In a Washington Post interview in 1977 he states, “We’re probably living at the end of an era. I think it’s only a matter of time until home viewing is as easy and economical as desirable.” In the past three days I’ve watched three Woody Allen movies on my ipad. I don’t know if this changed the way he made his movies. But it’s clear he never got himself stuck in one particular form or style that would eventually fail to cater to the tastes of the average audience.

3. Flexible. We admire the entrepreneurs who quickly recognize mistakes and then transition their business accordingly (the catch-phrase lately is that these entrepreneurs know how to “pivot”). Allen typically starts off with a broad outline, a sort of script, but it changes throughout the movie. Specifically he states, “To me a film grows organically. I write the script and then it changes organically.I see people come in and then I decide…it changes here. It changes if Keaton doesn’t want to do these lines and I don’t want to do these- we shift around. It changes for a million reasons.”

(Winona Ryder in Allen’s “Celebrity”)

The entrepreneur, the entre-ployee. Relationships in general, all shift and change. You set out in life wanting certain things – the college degree, the house with the white fence, the promotions, the family – but things become different. You have to adapt and be flexible. To say only the lines you are comfortable with and evolve into.

4. Productivity. To put out a movie every year or so, plus plays, magazine stories, books. you would think Woody Allen works around the clock. From a 1980 interview, “If you work only three to five hours a day you become very productive. It’s the steadiness of it that counts. Getting to the typewriter every day is what makes productivity.”

He states later in the interview that when he was younger he liked to get things out in one impulsive burst but he learned that was a “bad habit” and that he likes to wake up early, do his work, and then set it aside for the next day.

Probably the most productive schedule is to wake up early – do your work before people stop showing up at your doorstep, on your phone, in your inbox, etc, and leave off at the point right when you are most excited to continue. Then you know it will be easy to start off the next day.

I read in a recent interview that it takes Allen a month to write a comedy and three months to write a drama. On three to five hours a day it shows me he writes every day, he’s consistent, and he doesn’t waste time with distractions (going to parties, staying out late, etc)

5. Avoid outside stimulus. Every day right now I make a huge mistake. I start off with the loop: email, twitter, facebook, my amazon rank, my blog stats, my blog comments. My wife Claudia asks me: “did you finish the loop yet?” And I think it will only take a few seconds but it actually takes about twenty minutes. I probably do it ten times a day. That’s 200 minutes! 3 hours and 20 minutes! Ugh.

Here’s Allen’s description of when he won an Oscar for Annie Hall. First off, he didn’t go to the Oscars. Why get on a plane (8 hours door to door), and go to a party where he would feel uncomfortable, to win an award he probably didn’t care much about (although it magnified his prestige in Hollywood, the city that paid his bills):

In a 1982 interview with the Washington Post he states that he went to Michael’s Pub to do his weekly jazz clarinet playing although he says “I probably would not have watched anyway” just to see everyone he knows hunched down in the audience waiting for hours to see who would win. He states that he had “a very nice time” at Michael’s. So for him his pleasure came first. Rather than the anxious watching and waiting.

But then, when he got home, he didn’t even care. He went out the back way of Michael’s so he skipped all the photographers, went home by midnight, had “milk and cookies,”  went to sleep. And then he TOOK THE PHONE OFF THE HOOK. Who even does that now? In an age where we (or, I should say, “I”) literally sleep with my iPad and phone in the bed. He took the phone off the hook on Oscar’s night, went to sleep. In the morning made his coffee and toast. Got the NY Times, and then finally opened it up to the entertainment section where he saw he won the Oscar. It’s in this way that his productivity (compared with the lack of productivity many of us suffer now because of the constant influx of outstide social stimulants) was kept at a very high point.

(Penelope Cruz in Vicky Cristy Barcelona)

6. Imperfection. Allen has stated many times that none of his films were exactly what he wanted. That they were constantly imperfect. It’s almost like he’s the imperfect perfectionist. He wants things just right and he tries very hard to get it that way. But he knows it will never happen.

That said, he doesn’t give up. He states in 1986, “we go out and shoot…again…and again…and again if necessary. And even at that rate, all the pictures come up imperfect. Even at that meticulous rate of shooting them over and over again, they still come out flawed. None of them is close to being perfect.” Ultimately, he says, all his movies prove to be “great disappointments”.

And yet, knowing that he will always experience the same thing, he goes out, stretches his boundaries of where he’s comfortable failing, and does it again. And again. Knowing nothing he will do will be the masterpiece he initially conceived.

Nothing comes out exactly how we want it. But we have to learn to roll with it and move to the next work.

7. Confidence. I watched Husbands & Wives the other day. It wasn’t a funny movie. It wasn’t a pretty movie. I watched it with Claudia and by the end we were thinking, ugh, I hope that doesn’t happen to us in ten years. Meanwhile, the movie itself was jarring. Instead of being shot traditionally it was shot with a hand-held camera. It was edited with lots of jump-edits, where you’re looking at a character and suddenly she’s an inch over because some small piece of film was cut out. The editing itself became part of the jolting and jarring in the story. It was as if the story was not just being told with the acting and the writing but with the way it was shot and edited.

It reminded me of something Kurt Vonnegut once said. He’s usually considered an experimental author. But, he said, to be experimental, first you have to know how to use all the rules of grammar. You have to be an expert first in tradition. It also reminds me of Andy Warhol, who was a highly paid, very straightforward, commercial artist, before he went experimental and started the pop art phenomenon.

Allen says about Husbands and Wives in a 1994 interview (note: Husbands and Wives was his 20th movie): “Confidence that comes with experience enables you to do many things that you wouldn’t have done in earlier films. You tend to become bolder…you let your instincts operate more freely and you don’t worry about the niceties.”

In other words: master the form you want to operate in, get experience, be willing to be imperfect, and then develop the confidence to play within that form, to develop your own style. You see this in Kurt Vonnegut too as he transformed from the more traditional “Player Piano” in the early 50s to “Slaughterhouse Five” a novel about World War II that includes aliens who can time travel.

8. Showing up. As Allen famously stated: 80% of success is “showing up”. Nothing more really needs to be added there except it might be changed to “99% of success for the entrepreneur is showing up”. What do you have to show up for: you have to find the investors, you have to manage development, you have to find the first customers, You have to find the buyers. They don’t show up at your door. You show up at their door. Otherwise your business will just not work out. Let’s take Microsoft as one example among many: Bill Gates tracked down the guy in New Mexico to build BASIC. Bill Gates put himself in the middle when IBM wanted to license an operating system. He just kept showing up while everyone else was skiing.

9. The medium becomes the message. I mentioned this in the point above but it deserves further elaboration. The jump-cutting, the hand-held camera, every aspect of the film became woven in with the story. Allen states: “I wanted it to be more dissonant, because the internal emotional and mental states of the characters are more dissonant. I wanted the audience to feel there was a jagged and nervous feeling.” In this he shows not only his own evolution as a filmmaker but what he’s borrowed from the artists before him – not only Godard and Bergman who did their own experimentations, but musicians like Profokiev where the dissonance itself is so tightly wound with the music it becomes a part of the music, as opposed to just the notes being played. This is underlined in his latest movie, Midnight in Paris, very highly where Owen Wilson, the main character, pinpoints the roots of his own art by going back further and further in time.

My takeaway – study the history of the form you want to master. Study every nuance. If you want to write – read not only all of your contemporaries, but the influences of those contemporaries, and their influences. Additionally, draw inspiration from other art forms. From music, art, and again, go back to the influences of your inspirations, and go back to their influences, and so on. (See also, “Steal and Get Rich”)

The facets that resonate with time, even if it’s hundreds of years old, will resonate with your work as well. It’s like a law of the universe.

(Rachel McAdams in Midnight in Paris)

In today’s day and age, we want to transform decades of work into years or even months. Allen built up his career over five decades and kept at it persistently, even when scandal, or a bad movie, or a bad article, would cast gloom over his entire career. But he shrugged it off.

So what can we learn from Woody Allen?

  • Wake up early
  • Avoid distractions
  • Work three to five hours a day and then enjoy the rest of the day
  • Be as perfectionist as you can, knowing that imperfection will still rule
  • Have the confidence to be magical and stretch the boundaries of your medium.
  • Combine the tools of the medium itself with the message you want to convey
  • Don’t get stuck in the same rut – move forward, experiment, but with the confidence built up over experience.

The same can be said for successful entrepreneurs. Or for people who are successful in any aspect of life. Is Woody Allen a happy man? Who knows? But he’s done what he set out to do. He’s made movies. He’s told stories. He’s lived the dream, even when it bordered on nightmare.  I can only be so lucky.

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