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Hollywood story

Audio version

Listen to this article on Spotify or use the audio player below. Recorded by Listle.

It begins with a question

As a kid, I had a curious thought: What if breaking into Hollywood was much easier than it sounded? What if it was "hard" because it attracted incompetent people — and those were the people reporting back to the rest of us that the odds were insurmountable?

Here's my tale of breaking into Hollywood to become a major film director.

After college, I journeyed to Los Angeles. It was the only time in my life I detoured from startups.

The first thing I did was pitch a large film site to let me host a film show for them.

I shot sample footage in which a friend and I riffed on the Marvel Cinematic Universe. It was great. He was a fantastic co-host.

The film news site responded, "Heck yes. Let's do this."

The show became my baby. I spent months producing it.

We commissioned a gorgeous, hand-built set. We booked a theater to shoot the pilot. We had a crew of our college friends. 

All we were missing was a celebrity — so we could end the show with an interview.

Somehow, I got one.

Our pilot episode's guest was Morgan Spurlock — the man behind Super Size Me and other films.

At the same time I was producing this show, I was trying to get in touch with the writer-producer behind one of my favorite comedy films: the first Harold & Kumar.

There was little chance. I didn't know him, and it's exceptionally difficult to meet Hollywood directors. Let alone get a 1-on-1 lunch. It's what everyone wants.

But I got the lunch. Using a well-penned Facebook message. (Back then, you could message anyone. And people would read it.)

Back to the film show for a moment: The edit was shaping up. We spent 200 hours crafting an epic opening sequence. The set looked regal. The Morgan Spurlock interview was solid. I asked good questions; he gave great answers.

All that was left was releasing the show to the film site's 3,500,000 monthly visitors.

Now back to the Hollywood director story: While editing the show, I was simultaneously becoming a part-time assistant-to-the-assistant for the Harold & Kumar co-director, Jon Hurwitz — one of the kindest and most gracious people I've met. A gentleman whose willingness to meet over lunch in Beverly Hills sparked a fire in me that's remained lit to this day.

Because, here's the thing: Assisting a director — even in the peripheral capacity I was in — is the most efficient path to launching a career in film. Many major film directors got their start because they pulled off what I did here.

And assisting a director is especially effective when becoming a screenwriter. Because the director's agents can read your scripts. This means you bypass slogging through the outskirts of Hollywood doing set assistant work and so forth while praying you bump into a legit producer willing to listen. Which rarely happens.

Anyway, we released the film show I had been tirelessly editing. It was three hard and fun months in the making.

It instantly BOMBED.

Not no one watched it bombed.

I'm talking EVERYONE watched it but violently HATED it bombed.

Why? Because, before the closing Spurlock interview, we had an opinion piece where my co-host and I argued that some old films have inflated IMDb scores. As in, some of them are overrated.

Two 21-year-olds throwing shade on classic films was not a good look to the film site's late-30's cinema enthusiasts.

This is "no sh!#, Sherlock" in hindsight. But, in the moment, I thought we were saying what everyone wanted to say but was too politically correct to. 

I thought I was film woke.

To make matters worse, I thoroughly lacked on-screen charisma that day. I was anxious. Stiff. (For the record, I'm normally charming 😃.)

So two, anxious 21-year-olds spitting on classic films. On a major film news site. Meaning, we're supposed to be qualified. Meaning, we "took" the job from other armchair film experts who daydreamed of the opportunity we were wasting.

To put this in context, let's cut to the comment section beneath our pilot episode: One person said "absolute charisma vacuums." It was a brilliant remark, but man did it hurt. Another said something like, "So, so bad. Jesus Christ."

It got worse. Quickly.

Because people ragging on you in a comments section is merely a footnote. That's just the Internet.

But also having two dozen leading film critics — from L.A. Times to Ebert's successor — suddenly hate-follow you on Twitter is suddenly a headline. Not just a footnote.

These critics wanted to see what stupid thing I'd say next.

To put this in perspective: In 2012, around a quarter of all reviewers on Rotten Tomatoes were following me on Twitter.

And the hate-train kept chugging. 

A couple other major film news sites covered the bombing of the show.


Shock turned to crippling embarrassment. The vocal Twittersphere of film critics and aficionados was ripping me a new hole.

I wanted to be part of that community. Not the laughingstock of it.

Online transitioned to offline: I was embarrassed to walk around Los Angeles. I remember going to the grocery store on Sunset Boulevard being worried that someone would recognize my face. Paranoid? Probably. But I was truly ashamed.

Thankfully, I'm not prone to depression. But I bumped up against what it must feel like for nearly three months.

I felt I had shut the door to being taken seriously in film. Why would any studio want to produce a screenplay from someone who every critic is predisposed to hate?

Pursuing film is the thing I've wanted most since I was 12 years old — when I picked up a camera for the first time. Nothing brought me as much creative fulfillment as shooting documentaries.

And here I was in Hollywood making my childhood dream a reality. On an accelerated timeline. I had only been out of college for 5 months. Most other college grads my age were dragging their feet unsure of how to get started in film.

Meanwhile, I was the producer and co-host of a film show on one of the biggest film news sites. And I was in with a major director. At age 21.

Speaking of which, let's return to the work I was doing for the director. Thank the flying spaghetti monster for that. Because, yes, the film show couldn't have failed worse, but the relationship with the director remained solid. 

I don't even think he knew about the show.

Plus, working for the director was a straighter path toward doing what I wanted: screenwrite.

So I focused on that! Right?

I started to move on — with sights set on becoming the director's right-hand man.

Until two weeks later, that is. 

I got an unexpected notice in the mail.

The U.S. Government was booting me out the country. Effective immediately.

It turned out my post-college visa was expiring (I'm Canadian), and my attempt to switch visas failed for standard, bureaucratic reasons. But it was still a surprise.

I was given 30 days to leave the country.

That's 30 days to vacate my apartment, 30 days to abandon my friends in California, and 30 days to renounce the life I had set up. Because I wasn't allowed to return to the U.S. for 6 months.

Worst of all, it was 30 days to leave the film industry. Because, I'm not breaking into Hollywood from hundreds of miles away. Let's be real.

Closing the door also helped me move past this blow-up of an anticlimactic journey.


And so I returned to tech, startups, and coding. The hobbies I always toyed with. And enjoyed very much.

I haven't worked on film in any capacity since the day I got that notice in the mail.

And I think everything I've worked on in tech since then has been a legitimate success: I released an open source library used by hundreds of millions of web visitors. Maybe a billion people — because it's used by Twitter, Microsoft, Samsung, WhatsApp and many others.

I started a domain name company, which got lots of press, and made okay money.

Then I broke into growth marketing. I built possibly (?) the best-known agency in Silicon Valley. We've worked with some of the biggest startups. We've grown some to tens of millions in revenue. (Here's a recent interview on my growth marketing work.)

And, most dear to me, I began writing at Julian.com, which has been read by a couple million people and has built a name for myself. Based on my passing interactions, many startup entrepreneurs have read my work or listened to my interviews. That means nothing unto itself, but it may be a proxy for how much of an impact one's had.

And, I got my green card. I'm forever back in the state I love most.

Re-examining the film experience, here's where I netted out: As of today — seven years later — the film blow-up is mostly inconsequential. None of the film people from my old Twitter handle would recognize me from that time. Or know my name. 

Most importantly, I'm no longer deterred by the experience. Time alone heals wounds.

In fact, my interest in screenwriting is richer than ever. It's also clearer than ever. I now know why I love it. When I'm divorced from its short-term glamor, I can focus on its long-term fulfillment: telling stories that I want to hear myself.

I think the lesson to all this is that sometimes you need to wholly embrace your detours in life: sometimes you need to accept your plan B when plan A is slapping you in the face over and over. And over.

By rejecting film — my plan A — I had purity of purpose. Focus. Because I no longer had one foot in B and one in A. For the first time, it was 100% B. 

I was 100% startups.

And that's why B worked out well.

Later in life, once you've achieved happiness from plan B, you can revisit your plan A when it's not all-or-nothing. Because you have something to fall back on. This means you can pursue A more methodically, more patiently, and more earnestly.

There are optimal times in your life to chase each thing you care about. As long as you don't become jaded from bad experiences, when old opportunities pop back up, you can wholeheartedly embrace them again.

The skill to develop is knowing when to stubbornly pursue each plan, but also knowing when to ease off your plan A.

So, is it perhaps time to move onto your plan B?

And now for some pictures of the film show.

The Spurlock interview. That part went well. (I'm on the right.)
Our college film crew putting the set together. My co-host is on the right.
A still from the final cut. Featuring my co-host.

And below is a companion podcast that dives deeper into the story. I'm joined by the show's director of photography.


I originally wrote this story as a Facebook post. I then shared it with the Harold & Kumar director on Twitter. I hadn't spoken to him in 7 years.

Do him a favor and don't bug him about becoming an assistant. It's been years since he had the opening, and I'm sure he's as busy as ever 😎

You're good to go  ⚡ Say hello on Twitter.

Who's Julian Shapiro?

I try to simplify complex topics.

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What to work on

Choosing your big projects

Stress of competition

How to handle competitors

On being annoyed

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My Hollywood story

I broke into the film industry

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Running an agency

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