Film

Being Messy

Photo by todd kent on Unsplash

Chanel Miller said her New Year’s resolution for 2020 was to fail as much as possible.

“Making things that are really crappy and undeveloped until maybe they can be good. I’m way too young to confine myself to one lane and lose the ability to openly experiment.”

This is exactly how a the first draft of a film script develops. Characters and ideas float around in your head, and one day, they’re done with the floating and demand to live on the page. The script gets written, and when you’re done… it’s shitty. It’s embarrassing, you don’t want to show it to anyone, and you wonder how on earth your magical characters and ideas amounted to this pile of doodoo on the page.

But, it’s really important to have this first draft. Because as Miller said, yes, it’s crappy and undeveloped, but you need the crappy and undeveloped to have hope for the good and the great.

Struggling, wrangling, failing, crying, working, pushing forward allows your characters and your story to breathe, thrive, and for the bones to slowly emerge from the pile. Experimenting openly, taking the story in unexpected directions, adding or removing key characters, and messing around with no pressure allows the sparks of creativity that makes the script sing.

Every creator needs that messy time.

The same is true for startup creators. Ideas for a product form in your head over time, sometimes over years. Then one day, you’re ready to put it on the “page” — to code something, to craft something. And it may be a sloppy, messy ball of hair, mud, and hope. Don’t clean it up, polish, and shine it in order to raise money too early.

Love your messy stage, because it is so important to relish that stage. You can only do it once for each startup, and it’s when experimentation, ideation, hanging out, and trying weird things is entirely possible. It’s where ugly is awesome.

At some point, a screenwriter will have to share the script with producers. At some point, you have to share your startup with users and, if you want, with investors. If things go well, they love it, and you build an amazing company. Fantastic.

If you’ve grown your company into a wonderfully world-changing one, it’s worth finding ways to go back to being messy. Get into small groups. Make room for experimentation with ugly, creative things that may fail, because that can lead to new lines of growth. If you have the urge to start again, you could start another company and embrace the new ugly ball of mess. Whatever path you follow, the messy part of creation can be the the best part of creation, and the challenge of it makes your ideas and your company better.

Investing in Founders is like Casting Actors

On the set of “Waking Jed”, directing Jessica Chastain. Photo Credit: Anna Kooris

One of my early lessons in screenwriting was to focus on the character—motivations, personality, drives—and not external characteristics. It’s tempting to specify that the leading lady is blonde, petite, or whatever. And it’s okay to envision the character while writing, but we’re taught to avoid specifying detailed external appearance in casting.

The reason is that sometimes, the best casting decision is the one that’s least expected. You might have an image in your head of the character, but the best actor—the person who is most convincing and does an incredible job—might look very different from your mental image. Let’s say your character is written as a seductress, but the best actor for that role could be more of a plain Jane. That adds a lot to the nuance and depth to the story. A more regular-looking person being a seductress is so much more interesting than the hottest person on earth being a seductress. The film Snowpiercer was written for a mild-mannered man in a suit, but Tilda Swinton rocked the role.

During casting sessions, screenwriters and directors need to learn to set aside their mental picture, look at the actors in front of them, and reimagine the story with each person auditioning. That’s the way to cast the best actors.

Similarly, investors sometimes have a mental picture of who will be a good entrepreneur. It’s not based on looks (one hopes), but on the profile — the experiences a person “should” have had to be a great entrepreneur. VCs can sometimes be biased toward someone who’s worked at a hot company that went public, or is an engineer who can build it all, or a name-dropper who seems very connected in the ecosystem.

If investors carry around these biases in our heads, we will miss the best people. Like great actors, great entrepreneurs can come in all shapes and sizes, and from all backgrounds, all levels of work experience, ages, nationalities, and genders.

When casting an actor, the most important things to look for include:

  • Ability to live the character. Do you believe the actor is the character
  • Willingness to take direction. A director should never tell an actor “how” to play the scene, but the director can and should give her guidance on the mood of the scene, how the audience should feel, or the character’s motivation for a certain action. And the actor should be able to take that input and give the director a range of options.

    I remember when I had the chance to direct Jessica Chastain and James Franco. They gave me such a spectacular performance on the first take and then turned around, asked how it was, and whether I wanted to see it another way. My jaw was on the floor — I was blown away by their talent and their humility in asking for input from a student director.
  • Ability to go with the flow. Film production (especially in the indie world) needs to be flexible. Sometimes, a much-desired location might suddenly become available (for free!), and the crew might have to shoot there tomorrow instead of three weeks from now. This means the actor has to be ready for scene 56 instead of scene 18.

Many of those same characteristics apply to ideal founders:

  • Ability to fully inhabit the role of the CEO. This is about vision, tactical capability, ability to hire, and the ability to sell their vision and themselves.
  • Willingness to take input. An investor should never tell a CEO how to do their job, but a big part of the investor’s role is to see around corners, anticipate challenges based on their experience, and give the CEO input and feedback.
  • Ability to go with the flow. Startups need to be flexible. Sometimes, a new competitor might emerge, you might lose a key person on your team, a pandemic might unexpectedly sweep the globe. The best CEOs are those who can adapt and find a way to thrive in the new world.

Just like the success of a film depends on casting the person who is the best actor, the success of an investment depends on casting the best founder. It requires putting aside the mental preconceptions and focusing on the person in the room (or on Zoom). Despite her youth, can she be an amazing CEO? What gives you that confidence? Her knowledge of the space? Ability to be compelling? Authenticity?

The best casting decisions happen when we are open to allowing incredible actors to show us how much better the character can be. In the same way, I try to approach every meeting with a founder with a willingness to be blown away by their vision of the world.

Ignore The Gatekeepers

Photo by Zachary Lisko on Unsplash

Last week, I saw the awesome news that my NYU Grad Film classmates Sarah-Violet Bliss and Charles Rogers are making their next feature. I love their story because it’s so different from what people may consider the “traditional” path in film.

It was the summer of 2012, and most of the class was on draft 63 of their soon-to-be perfect first feature script. But before that, we each planned to submit draft 79 to all the prestigious film labs. There, we would get input from auteurs we admired. Then, we’d make the perfect film, it would open to acclaim at the perfect festival, and get acquired and released nationwide. That was the plan.

That same summer, Charles and Sarah-Violet (SV) had a very different plan. Instead of perfection, they decided to create immediately. They cranked out a feature script. They each borrowed $40K through student loans. Knowing they were on a tight budget, they wrote about a world they knew (deep Brooklyn), with only a small handful of locations (all in NY), and very few characters. They didn’t submit the script to any labs. They didn’t apply for any grants. They did not wait.

They planned the shoot. They cast fantastic actors, some of whom they’d known for years. One of our classmates was the cinematographer.

They shot their feature. They edited their feature.

They did it all on a total of $110K. Tiny, even by indie standards.

One year later, they submitted it to festivals. The movie, Fort Tilden, premiered at SXSW. It won SXSW. And that set SV and Charles on a different trajectory. They were writers on the Netflix show Wet Hot American Summer and now have their own, very successful show on TBS, Search Party.

I share this story to share the power of ignoring gatekeepers. There are a few big steps in making a feature film: write a script, prep and plan the shoot, shoot, edit, release. Every step depends on funding. You could wait for funding at each stage—basically asking for permission from someone else to make your film. Or, you can do what SV and Charles did — make the best movie within the constraint they faced and the funds they were able to access. No waiting, no permission needed.

Don’t get me wrong: this is definitely not an easy or guaranteed path. I spoke with SV recently about her story, and she said, “(Taking out those loans) was still a huge insane risk I wouldn’t exactly recommend for everyone. But it felt right. So I’m always very careful to say, ‘Look, this is how we did it, and it worked out for us. I have some success but I also still have student debt.’ That said, I do NOT regret it. Not everyone would be comfortable with the position I put myself in, but it was right for me. I had a lot of clarity in the process and risking the money didn’t scare me. Waiting years and years to find funding or someone to approve of my voice was a much scarier fate.”

If you follow the SV & Charles model, you will have a real, live product. A product which people can see and enjoy. A product that people can evaluate and say “hey, they won SXSW on a tiny budget.”

Given the choice between being constrained, but still making something, versus waiting for the “ideal” situation, what would you pick? While most of the class was dreaming of the perfect first feature, SV and Charles made their first feature. That was enough to launch them into a world that is very hard to break into.

Breaking into tech is easier because angels and early funders (the gatekeepers) are willing to fund first-time founders. But it’s not always easy to raise your angel or pre-seed round.

Look at the funds and skills that you have. Decide how much risk you want to take — each person has their own comfort level and you should be the one that decides what is best for you. And then, design and build something using your skills and your budget. If you build something people love, you will have a little success. And that little success can propel you onto your next opportunity. And then onto the next opportunity. And each project or startup could get better. The gatekeepers will then come to you (and I say that as a venture investor).

In my film school class, every single person had ambition, most had a great idea. But SV and Charles just did it. And they went from strength to strength. You can, too.

The Necessity Of Vision

Okay, that’s an exaggeration. But in reality, there are hundreds of questions the director has to be able to answer. Many come as they are preparing for the shoot, but things happen, and there are always tradeoffs to be made while they’re on set.

A good director has a point of view on all these questions because she keeps the vision of the film front and center. She knows how every one of these decisions will affect the vision.

Like the director of a film, the CEO is the final arbiter in startup, especially at the early stages. In order to make the multitude of decisions, she needs to have a very clear vision of what she is trying to achieve. Every decision either takes her towards her vision (slightly or bigly) or away from it.

If the vision for what you want to become is muddled, it becomes very hard to make decisions. You always want optionality—to keep all options open, because you don’t know where you are headed.

That is impossible on a film set, because most films are shot in 30 days or less. It’s not impossible in a startup, because you can always defer the decision. But doing so will put the startup at risk of not executing or of muddled execution that leads to failure.

To keep your eyes on the prize, you need to know what the prize looks like and which direction you need to go to find the prize.

Director Ava DuVernay with Cinematographer Bradford Young

You also need to know the fundamental underlying tenets that will help you achieve your goal. For example, at eBay, one unbreakable tenet was always “level playing field”, meaning that every seller, whether a big company or your next-door neighbor, would be subject to the same rules. Another was that eBay would not touch the items, thus keeping it a purely person-to-person marketplace. When opportunities came up, it was easy to evaluate against these (and other core) tenets and determine if they kept us moving towards our vision.

This does not mean that you don’t react to changing circumstances or opportunities. Some of the best scenes or shots on a film set can be the ones where the director decides to improvise on set. She may see an opportunity in a location, in the weather, or in the actors’ mood and try something unscripted. But the reason she can do that is she knows what she wants to achieve and has prepared so well that she has a strong hunch that this improvisation will improve the film.

For a CEO with a big vision, unexpected changes can present an opportunity. With the vision front and center, and all the hard work to understand what moves you towards and away from that vision, you can think of ways to bend and adapt to strengthen the company. Otherwise, you stand the risk of losing what the company is and what it stands for.

Make your vision a touchstone that you come back to often. Make the time to come back to it, refresh it, and let it refresh and reenergize you.

A Whole Lot Of Not Quitting

On Sunday, Carol Dysinger won the Oscar for her short documentary, Learning to Skateboard in a Warzone (If You’re a Girl).

It’s a delightful film that will make you both laugh and cry, but this post isn’t a film review. It’s about a life lesson that I learned from her.

In 1977, when Dysinger was twenty-two years old, she won the coveted Student Academy Award. Frank Capra, famed director of You Can’t Take it with You and Mr. Smith Goes to Washington, presented the award. It was (and is) a big deal — of all the student films made around the world, only one can win. Everyone, including Dysinger, assumed her career would take off like a rocketship from there.

Of course that stuff only happens in the movies. 

Dysinger’s real story was more of a struggle. She has worked in Afghanistan for almost 20 years, making documentaries that won prizes and grants from top festivals. But nothing compared to her early win.

I met Dysinger in 2009 when I joined a grad film program where she was the editing professor. She was working on a film called One Bullet Afghanistan, which, more than twelve years later, she’s still working on.  

It was during this time that Dysinger was asked to make a film about the girls of Skateistan — a school where underprivileged kids learn basic academics and how to skate. She accepted. Then this film, this side project, just took off.

Learning to Skateboard was nominated at major festivals and won at Tribeca and the BAFTAs before winning the Oscar for Documentary Short Subject. 

43 years after Carol Dysinger won the student academy award, she won the grown-up version. 

When I was her student, Dysinger’s favorite piece of advice was that becoming a filmmaker would take “a whole lot of not quitting” — a phrase she repeated during her acceptance speech. 

A whole lot of not quitting. That’s great advice for pretty much anything. Everything takes much, much longer than we think it will. We get frustrated, upset and dejected. After six years or ten, we give up. 

Sometimes quitting is the right choice. But often, those who reach the pinnacle do so not with shortcuts or luck, but because of a whole lot of not quitting. For decades.  

I’m thrilled to see one of the good ones succeed — four long decades after her first taste of success.

Non-obvious choices

My film school classmate Heather shared this video of Henry Thomas’ audition for E.T. Take a look.

What stands out are the choices he made. Before becoming an investor, I spent some years in film. I’ve auditioned children for roles and most of them make the obvious choice – screaming, shouting, being loud. That is likely what most of the kids who auditioned for this role did, too. “NOOOO!!! You can’t take him!!” etc.

But what Henry Thomas did was so unexpected. With such little information, he decided to very quietly cry. He made the creature his friend, he asked how the agent even knows all this. He decided to be extremely vulnerable. These are the choices that got him hired.

I’ve often said that there are a ton of similarities between tech and film1. This is one small example – when you are interviewing candidates, a majority will pick the obvious answers. That’s fine. They could be journeymen in the company. But when there is a candidate who makes an entirely non-obvious choice, something that makes you sit back and think in a new and different way, those are the candidates who can change the trajectory of the company. Hire them.


  1. That’s for another post 

Valuing the struggle

The popular history of science is full of such falsehoods. In the case of evolution, Darwin was a much better geologist than ornithologist, at least in his early years. And while he did notice differences among the birds (and tortoises) on the different islands, he didn’t think them important enough to make a careful analysis. His ideas on evolution did not come from the mythical Galápagos epiphany, but evolved through many years of hard work, long after he had returned from the voyage. (To get an idea of the effort involved in developing his theory, consider this: One byproduct of his research was a 684-page monograph on barnacles.)

The myth of the finches obscures the qualities that were really responsible for Darwin’s success: the grit to formulate his theory and gather evidence for it; the creativity to seek signs of evolution in existing animals, rather than, as others did, in the fossil record; and the open-mindedness to drop his belief in creationism when the evidence against it piled up.

The mythical stories we tell about our heroes are always more romantic and often more palatable than the truth. But in science, at least, they are destructive, in that they promote false conceptions of the evolution of scientific thought.

The mythification of very hard work makes for a good story, but it minimizes the effort that went into it.

The oversimplification of discovery makes science appear far less rich and complex than it really is.

This very good op-ed in the NYTimes is focused on science, but this is true not just for science – it’s true for almost anything. In tech, it’s the pithy “and now it’s a unicorn”. In film, it’s “and it premiered at (insert name of festival)”. The punchline ignores all the decisions and work that went before it.

While you are in the middle of the struggle, it’s easy to be seduced by the thought that others had it easy, that somehow it all came together instantly. But it’s the grind, the perseverance and the hard work that matters, even though it is unglamorous and hard and unreported. It’s the only thing you control.

The myths can seduce one into believing there is an easier path, one that doesn’t require such hard work.
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The Darwin, Newton and Hawking of the myths received that instant gratification. The real scientists did not, and real people seldom do.