Why Creatives Will Win by Thinking Small

In 2024, the path to success has been turned upside down

A few weeks ago, 35 of the biggest names in Hollywood collaborated on a business venture. Can you guess what it is?

I’ll help by providing a list of the participants. Here they are in alphabetical order, to avoid wounding any of the huge egos involved:

J.J. Abrams, Judd Apatow, Damien Chazelle, Chris Columbus, Ryan Coogler, Bradley Cooper, Alfonso Cuarón, Jonathan Dayton, Guillermo del Toro, Valerie Faris, Hannah Fidell, Alejandro González Iñárritu, James Gunn, Sian Heder, Rian Johnson, Gil Kenan, Karyn Kusama, Justin Lin, Phil Lord, David Lowery, Christopher McQuarrie, Chris Miller, Christopher Nolan, Alexander Payne, Todd Phillips, Gina Prince-Bythewood, Jason Reitman, Jay Roach, Seth Rogen, Emma Seligman, Brad Silberling, Steven Spielberg, Emma Thomas, Denis Villeneuve, Lulu Wang and Chloé Zhao.

What are these movie titans up to?

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Maybe they want to make a film together? Or perhaps they’re thinking bigger—planning to launch their own production company or even a movie studio?

Nope. They weren’t thinking big. They were thinking small—very small.

“Even the gatekeepers are sick of dealing with gatekeepers.”

These heavy hitters got together to buy a 93-year-old building.

They now own the Westwood Village theater at 945 Boxton near the UCLA campus. I went there to see films when I was in high school and it was old even back then. At some point it stopped being old, and became historic and vintage. (Maybe if I live long enough this will happen to me too.)

Movie premiere at the Westwood Village theater (Wikimedia Commons)

But these 35 investors aren’t just interested in preserving a quaint old building. They want to own a place where they can show quality movies to a flesh-and-blood audience without anybody getting in their way.

We’ve reached a point where even the people in power at the top of the industry want to bypass the system. Even the gatekeepers are sick of dealing with gatekeepers.

That’s how bad it’s gotten.

And this isn’t an isolated incident. Quentin Tarantino bought the Vista in Los Feliz in 2021. This cinema, built in 1923, has two theaters—a large one seating 400 people, and a small 21-seat micro-screening room.

The Vista Theater, now owned by Quentin Tarantino (Wikimedia Commons)

Once again, the obvious question is why a director who has millions of fans would want to reach 400 random people on any given night. But it’s not hard to figure out that Tarantino also wants to bypass the system.

This is happening everywhere—although it’s not getting much media coverage.

• Just today I heard from the people behind the Pico Union Project. They want to transform the the community by operating a 375-seat sanctuary/theater.

• In San Francisco, an organization called CounterPulse bought a building in the Tenderloin, and is pursuing its own vision of smallscale outreach.

• In my own favorite field, jazz, the Louis Armstrong House Museum recently opened an expanded facility—run out of the trumpeter’s 1,954-square-foot former home in Queens.

I could give many more examples.

But even the huge successes in the culture right now are following a similar strategy—let’s call it direct-to-flesh marketing. Just consider Taylor Swift’s triumph with her world-beating Eras Tour, the most impactful music project of the digital age—but bypassing the digital platforms.

The dollars involved here are much larger than the above examples—this tour has generated more than a billion dollars in revenue. But Taylor Swift did it in the exact same way, namely by bypassing the dominant platforms and bringing her music directly to flesh-and-blood fans via 152 concerts on 5 continents.

Taylor Swift also distrusts the system. I know that for certain—just look at her fierce battle with the music business in recent years.

And, of course, the same thing is happening in publishing. Not long ago, almost everything I wrote had to go through gatekeepers (almost always sitting in an office in New York) before a single reader saw it. Then I decided to bypass the system too.

What’s going on here? Is the system in trouble?

Or are we just damn fools for trying to bypass it? After all, the system is huge and we are small.

The odds against us must be enormous, no?

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I rarely pay much attention to management gurus, but in the early 1990s I heard a prediction from business guru Peter Drucker that shook me up. In the aftermath, my thinking changed about many things—including how I handled my own career as a writer.

Business guru Peter Drucker changed my thinking on how writers should manage their careers (Wikimedia Commons)

Drucker grew up in an era when the most successful businesses dominated through their manufacturing power and cenntralized staff. But he now predicted that this was going to change—in fact, it would reverse completely  

In the future, he claimed, control over distribution would become more important than manufacturing or marketing or research.

What was Peter Drucker smoking? This prediction made no sense in the early 1990s, before the rise of the Internet.

When I was a student at Stanford’s Graduate School of Business, I was taught that distribution is an ugly business, with low margins and few defenses against competitors. I still remember my first consulting project after graduation, when I saw how distributors struggled to survive.

You need to own the factory, not the warehouse.

Drucker said this was going to change because smart businesses needed to get closer to the user of their products. The most powerful distribution model of them all was finding a pathway directly to the consumer, or as close as you could get.

If you have a strong connection with the end user, all your other business problems will go away. That was the essence of Drucker’s prediction.

In the old days John Rockefeller got rich by owning Standard Oil, but in the future you didn’t need oil wells and huge refineries. You wanted to have a relationship with customers pumping gas in their cars.

Back in the 1990s, I was shocked by Drucker’s reasoning, but I took it seriously. As it turned out, he was even more accurate than he could have envisioned.

When Netflix launched as a mail-order DVD distributor in 1997, nobody could imagine that it would eventually become more powerful than the biggest Hollywood movie studios.

After all, Netflix was just a distributor.

But guess what? That’s exactly why Netflix rose to the top of the entertainment business. It didn’t start worrying about creativity or artistry until it had figured out the optimal distribution model.

Netflix was already flourishing before it shifted its emphasis to online streaming. That’s because Drucker was correct. As the world gets older and stodgier and more bureaucratic, the wisest strategy is to bypass the system and connect directly with users.

But after the rise of the Internet, the power of this approach increased tenfold. To win in this new environment, you don’t want to own the factory, you don’t want to build Sears Tower.

In fact, Sears Tower (now known as Willis Tower) is a symbol and case study of the mistake you must avoid. Sears was the largest retailer in the world when it decided to build the largest building in the world—emblematic of a huge enterprise that was growing more centralized and out-of-touch with each passing year.

Willis Tower (formerly Sears Tower)

If I wanted to pinpoint the moment when Sears started to crumble, I’d cite September 9, 1973—the day the company bosses started moving into the tallest tower on the planet.

In the new world order, the execs in the looming towers think they control everything they see below. But they are kidding themselves. The real power is now on the ground level.

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That’s why artists and other creatives have a realistic advantage versus the power brokers and gatekeepers. In fact, their advantage is growing over time, not shrinking.

But the way to do this is to think small.

That’s why the single most important move I made as a writer happened in July 2007 when I decided—for the first time in my career—that I would self-publish an article on the Internet instead of submitting it to an editor.

At this point I had already published articles in famous periodicals and released books with prestigious imprints. But even though I had the benefit of an impressive track record, I didn’t trust the system. I felt that it was slow and sluggish, and sometimes even hostile.

So I went off on my own.

I eventually launched six of my own websites, just so I could have a place to publish my writings. I put out more than 400 essays on these homemade platforms over the next decade. (Those essays are now in The Vault on my Substack, available to premium subscribers.)  

By any measure, this was career suicide.

Nobody paid me for any of these articles. My homemade websites had no prestige or subscribers or sweet search engine placement. I had no sponsors. I had no marketing budget and no advertising.

I didn’t even have a Twitter account to promote these articles until 2009, and my presence on social media grew very slowly. At the start of 2011, I still had fewer than 70 Twitter followers.

Why was I doing this? Despite the overwhelming odds against me, I felt I was making the right choice.

I had four reasons for bypassing the system 15 years ago:

1. I had more confidence in myself, and the courage of my convictions, than I did in the system;

2. I wanted freedom to write in my own way about the subjects that mattered to me—and the system would fight me at every step unless I took matters into my own hands;

3. I knew I could operate much faster and more fearlessly if I were my own boss; and

4. I wanted to have direct contact with my reader, with nobody standing between us.

It helped that Peter Drucker had advised entrepreneurs to do precisely that back in the early 1990s, and I had seen amazing success stories among people who had taken his advice.

I suspect that the movie moguls who bought the Village Theater in Westwood a few days ago have similar motives.

And if the insiders are now starting to think small in the same way I did, something has changed in the culture. The power at the center must be hollow inside. The only thing flourishing is the energy at the fringes.

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I know that some people point to me as a Substack success story. Some people even tell me to my face that I am some sort of a fluke—I got lucky on Substack.

And I don’t rule out luck as a force in human affairs. But there’s a larger story here.

I was able to thrive on Substack because it was the culmination of almost 15 years of learning how to reach directly to readers. I’d gained some skills along the way. Even more, I came to Substack totally committed to this way of operating.

I like thinking small. I like thinking of my reader as an individual.

And even if I did this out of sheer stubbornness at first, I’ve come to think this is exactly the strategy for creatives in the current moment.

There are now so many tools for people who want to bypass the system. Almost none of them existed when I started my lonely path as a one-person publishing business back in 2007. I wish they had been available then. But they are here now, and more are available all the time.

My overnight success took fifteen years. Consider that before saying that I am speaking from an advantageous situation. It certainly didn’t feel advantageous back in 2010 or even 2020.

The key thing is that the Drucker strategy is the right one for creatives.

Stop worrying about what happens in some gatekeeper’s office in New York. The action right now is happening at the grass roots level. And even if you make that decision to get down and dirty in the grass right now, you’re still getting in early.

Here’s what I tell writers, and musicians, and other creatives:

The system is formidable, but growing weaker with each passing year—sometimes it feels like each passing week. Somebody is going to benefit as the insiders falter, and it might as well be you.  

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