From Trailer Park to $25 Million: The Casey Neistat Story

When your dream job doesn’t exist, you make it up.
From Trailer Park to $25 Million: The Casey Neistat Story
From Trailer Park to $25 Million: The Casey Neistat Story

The path that Casey Neistat took to success is not one that was laid out for him. It’s not something he learned in a book or from a course. It’s nothing that could even be taught since the way he became successful didn’t even exist before he made it. That's what’s earned him millions of views and dollars—his commitment to creating his own path. When there was no model for a filmmaker to become a daily YouTube vlogger, he created it. No success story of a vlogger starting a social media company, he lived it. And he did it all even though, from his earliest years, no one thought he would succeed at all. 

It's not surprising. There wasn’t a lot in Neistat’s early years that would have inspired confidence in people. In some ways, he did everything exactly wrong. Before moving to New York where he started his filmmaking in earnest, Neistat was a teenage father on welfare living in a trailer park in Connecticut and washing dishes for work.

No one would have predicted he would find his way from obscurity to success, even before that. As a child he was always getting in trouble—not because he didn't respect authority, but because he didn't agree with it, and had no problem acting on that feeling. Neistat remembers getting suspended in high school for riding his skateboard in the school. The principal told him if he expected to skate through hallways for the rest of his life, he had another thing coming.

Fast-forward a couple decades and Neistat built a half-pipe in his office to do exactly that. And the only way that Neistat was able to have the success that gave him that freedom was because of that same instinct to ignore the rules and follow his own way. That insistence has led to a life of constant expansion, blazing a path into the unknown that has made him an inspiration for millions.

But the story only makes sense looking backward.

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Meant to Be In Motion

Neistat was born in Gales Ferry, Connecticut, where he described himself as the “other” sibling—not the oldest, not the youngest and not the girl. It gave him a personality of being the loudest and always trying to get attention. Even today, he has an uncontainable energy that leaks into his videos where he's always in motion—running or skateboarding or doing something physical; trying to use the relentless energy that’s been in him from an early age. 

The way Neistat uses that energy—for action instead of thinking—is something he credits for his success in life. There is a piece of advice he gives to all people in creative fields: “Overthinking the process will kill any career in the creative space. You just have to do, not think.”

But while that mindset might be what makes Neistat a self-made success today, it’s the one that almost derailed him before he got started.

In high school, after years of struggling with authority, Neistat's boundless energy gave him the gumption to do something about his frustration—run away from home.  At the age of 15, Neistat left home and moved in with two girls, quickly getting one pregnant.

Then, at 16, he dropped out of school. To this day, he doesn't seem to think he missed much. “I would describe so much of what I experienced and so much of the guidance I was given, right up until my teenage years, as straight to the middle,” Neistat told Reddit in 2015. “Like...if you want an average job and an average life, here’s an instruction manual to do it. If you don’t follow these rules, you are wrong. And I didn’t believe in that, I didn’t subscribe to that.”

The most dangerous thing you can do in life is play it safe. — Casey Neistat

Much as he might have disagreed, when Neistat dropped out of school, it’s not as if he had a better plan. He was just reacting. His girlfriend gave birth to a son two weeks after Neistat’s 17th birthday, and suddenly he had a baby at home and was on welfare getting free milk and diapers from the state. Then even that life came crashing down around him when his son's mother dumped him two years later—in Neistat’s words, “for all the right reasons.”

Finding a New Direction

But as so many self-made greats have done, Neistat took that struggle as a chance to reinvent himself. Suddenly, nothing was keeping him in Connecticut, and he took it as a chance to finally do something about a fascination for New York that had been with him since his childhood.

Around the same time, his older brother had introduced him to video editing, and Neistat began experimenting with making films on one of those colorful, old iMacs. In editing those films, he had discovered a way to share the ideas that he’d always had in his head. So when Neistat found himself with a desire to do something more and nothing holding him in place any longer, he put those interests together and started forging his own path. 

Neistat packed up what he owned—a duffel bag in one hand and his iMac in the other—and hopped on a train to New York City. He moved into a 300-square-foot sublet with a stranger. His space was so small that the futon he slept on couldn’t even be laid flat all the way.

In a city with no friends, still working in restaurants just to make the ends meet, he poured all of his time and energy into making films, sitting and editing at home all night on his iMac.

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Bennett Raglin/Getty

Making His Own Luck

Within a year, Neistat got his first taste of real work when his films caught the eye of artist Tom Sachs, who hired Neistat and his older brother Van to create films for him, in spite of their lack of any formal training. Then, in 2003, Neistat created a film called iPod’s Dirty Secret about the lack of replaceable batteries in iPods. The film went viral before social media was a thing.

Something was starting to click in his life. It would be years before where this was all leading would become clear, but his restlessness and refusal to follow the paths of others spurred him to do things in a new way—and it was starting to make him stand out.

For the next four years, Neistat continued his zig-zag path as a filmmaker, jumping from one project to the next. Then, in 2008, he turned his hops between projects into a giant leap forward. Having worked hard to build their profiles as filmmakers, he and his brother Van sold an eight-episode show on their life to HBO for $2 million. Suddenly, Neistat’s career kicked into a whole other gear. 

Going Off the Beaten Path

By 2011, he was “making it” by anyone else’s definition of success. His film, Daddy Long Legs premiered at Sundance and internationally at Cannes, and won him an Independent Spirit Award.

But, flying home alone with his award and recently split from working with his brother, Neistat had an epiphany that this was not the path for him. “I had this moment, it was a ‘What am I doing?’ moment. I call it a Jesus moment, even though I’m Jewish…I wasn’t really happy trying to be this big-deal Hollywood producer type…I thought if I’m going to be unhappy in my career, fuck it, I’ll go back to Connecticut and wash dishes.” So he left the path of success that many would have pursued and, as he has done his entire life, started forging a different path of his own. 

He started making films on YouTube. In his mind, it wasn’t a compromise or a step down from being some big-name producer. It was the most egalitarian platform there was—anyone could make it as a filmmaker there. It was all about the content he created.

It didn’t take him long to become one of the ones who found success. He created a film called Bike Lanes where he careened into obstacles in bike lanes throughout New York City in response to a cop giving him a ticket for once riding out of the lane.

It took off—and was named one of Time’s Top 10 creative videos of the year in 2011.


Defining a New Style

His adventurous edits and honest style started to build him an audience, which got Nike calling in 2012 with his biggest opportunity yet. They wanted an ad for the Nike Fuel Band.

But rather than make them a commercial, Neistat again took the option that wasn’t even on the menu. He took all the money for the commercial and traveled around the world with a friend until they went broke, creating a film that has now been viewed more than 30 million times, and made him as famous as the Fuel band. 

After that, the pace of Neistat's reinvention only accelerated. In 2015, he started making daily vlogs on YouTube, and launched a new video social media app the same year called Beme.

Then, in 2016, he changed his path again, ending the vlog that had earned him 5 million subscribers and more than a billion views over 500 episodes. He also sold Beme to CNN. For $25 million. 

Since then, he’s made films for some of the biggest names in advertising, from Samsung to Mercedes to Google. But he’s always done them on his own terms, with a unique way of staying true to his own brand. Like taking money from Mercedes to create videos making fun of the process of making car commercials.  Or using his Samsung spot during the 89th Oscars to highlight the maker spirit that’s become part of his identity.

It’s a path that no one would have foreseen for a disruptive high school dropout living in a trailer park. But when the rest of the world didn't expect his life to go anywhere—even when Neistat didn't know where he wanted it to go himself—he just kept moving.

And as he moved, he learned what all truly great self-made people know: that ideas on their own aren’t worth anything. The only ones who ever truly become anything are those who execute. And Neistat does that better than almost anyone, chasing his inspiration wherever it leads, and inspiring millions to follow in his footsteps of walking a path that has never been defined before.