Hey friends, Kent here with a little story from over a dozen years ago…
When I was studying creative writing at USC, I knew my odds of getting a job in Hollywood after graduating were gonna be slim. Actually, as an English major, getting ANY job was going to be tough. So I figured I better do an internship and try to make some connections.
I applied to every production company that posted on our school’s intern job board, and the only one who gave me a shot was Appian Way Productions, Leonardo DiCaprio’s production company.
When I found out they were giving me an interview, of course I freaked out. Little-21-year-old-me? Working should-to-shoulder with The Aviator himself? This is sure to go poorly.

I promptly went out and bought the cheapest suit I could find. And a fancy leather clipboard thingy to put my resume in, and take notes. Then I did all the research I could on the company and what films they had produced.
My friend drove me to the interview in his beat up pickup truck since I didn’t have a car. There was no AC, and I was drenched in sweat by the time I arrived. I’m pretty sure I was hyperventilating.
This was my first time stepping foot in a Hollywood production company office, and right when I walked in, I suddenly realized 2 things:
This company is much smaller, quieter, and more casual than I expected.
I was way overdressed in my cheap suit.
Well… better overdressed than under-dressed, I figured.
To make a long story short, they brought me on as an intern for the semester. My friend would drive me from USC up to West Hollywood in his truck a couple times a week so I could do (unpaid) grunt work like making lunch runs, sorting fan mail and unsolicited script submissions, writing script coverage that I’m pretty positive nobody read or actually needed, and whatever else needed to be done that day.
I worked under the assistant who ran the front desk, but I got to meet and occasionally chat with all the producers working there. Leo and other actors/directors would sometimes come in too, which was always exciting, if not somewhat nerve-wracking, for me and the other lowly interns.
To disappoint you – I never ended up talking to Leo. But I did talk to his dad for a while, who couldn’t have been nicer.
There were also moments there that made me realize Entourage wasn’t so far off from reality.
But while I saw and learned a lot in those few months, I still only experienced the tip of the iceberg of Hollywood’s machinery. I would have loved to have interned at more places, like a studio, or even an agency.
The real value of my internship experience was getting to observe firsthand how these companies operate and feel. On slow days, I’d visualize myself being in the position of a director coming in for a general meeting. Between that and my constant eavesdropping, I had a pretty good idea what to expect if that day ever actually came.
One eye-opening discovery was learning how much the company valued building and nurturing its network. I’d often be tasked with helping send baskets, gifts, cards, etc to people they had worked with in the past, or wanted to work with soon.
It seemed excessive to me at first, but it makes sense.
In a business where personal relationships and casual word of mouth so often lead to HUGE projects and opportunities coming together, it pays to stay on the right people’s radars. And all across the business side of Hollywood, a lot of effort goes into this behind the scenes.
I think that’s something we should all keep in mind, even on the DIY level of filmmaking. If you want to go far, go together. And little thoughtful gestures leave a lasting impact.
So to leave you with one actionable tip from this story – consider giving little wrap gifts to your whole team after finishing a project. Even if it’s just a handwritten note, it goes a long way.
Favorites this week:
📚 Book: Bird by Bird: Some Instructions on Writing & Life by Anne Lamott
A book about the day-to-day life of a life-long writer. About halfway through it and finding it highly relatable and charming, while also sprinkled with great tips on writing fiction.
📹 Video: Every Airbnb Commercial
If you haven’t seen any of the Almost Friday sketches, you’re missing out. Calling them sketches is doing them a disservice, they’re full-blown short films and feature some of the best storytelling you’ll see anywhere. This one is particularly inspiring because of the low-budget/low-fi style anyone could pull off.
Also because “ghost leash”.
💬 Quote: Don’t put limitations on yourself. Others will do that for you. – James Cameron
That’s it for this week.
Let’s make some movies.
-Kent
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