This piece is a cover story from Creator Mag.3 — physical editions are available now.

It’s a 50-minute drive through the hills as we make our way up to a small ice cream shop in Burbank, California.

Decades of movies and television have iconized this mecca of the entertainment world, the famed Hollywood Sign overlooking the bustling industry it’s spawned like a caring grandmother. Yet even with the countless images of celebrated studios and sidewalk stars that have seeped into my pop cultural subconscious, I still can’t help but take note of every sight and sound we pass by along the way.

Our Uber driver narrates this odyssey north, pausing infrequently as we stop and go in a sea of trademark traffic. He’s lived in Los Angeles for most of his life, he tells us, and this is actually his first day working for the rideshare app. He recently suffered a minor workplace injury, and the Tesla we find ourselves in arrived while he’s been recovering. So, instead of lounging around the house until he’s ready to go back to work, he decided to give the new car a whirl, and we’re one of his first customers.

When we arrive at our destination, both the driver and I are collectively puzzled. “You sure this is the right spot?” he says out loud, verbalizing the confusion that’s slowly dawning on us. Don’t ask me, I think to myself. I was provided with the address only two hours prior; now, it’s 3:50, and we’re slated to meet with our interviewee in just 10 minutes.

We inch our way up the street until we find it, it being a rundown, ‘50s-style joint serving burgers and milkshakes amidst corporate buildings and a sprawling neighborhood (in a bizarre fashion, Cartoon Network’s offices are located a mere block away). The driver drops us off in the parking lot before speeding away, back to his newfound life as a proud Tesla owner.

Listen along to the story here!

I call Steezy Kane, the YouTuber with over 3.6 million subscribers who I’m here to write a cover story on, to let him know we’re here. Describing him as just a YouTuber feels akin to labeling Donald Glover — one of the creator’s biggest inspirations — solely an actor. Steezy is a multi-hyphenate in every sense of the term, an outgoing prankster one day and a reserved graphic designer the next, writing, directing, and editing every project he takes on. His filmmaking dreams have found him right in the heart of Tinseltown; YouTube just happens to be the avenue which he took to get here.

“You guys are already there?” Steezy responds on the phone. “Okay, we’ll meet you around 4:45. We’re just finishing up a drone shot right now.”

It’s not often you meet a multi-hyphenate accused of doing too little.

The blacktop hits a little harder on this steamy April day, so we walk a couple blocks around the neighborhood and settle for a cold drink at a nearby Starbucks. By the time we make our way back to the parking lot serving as today’s set, Steezy and his team have arrived, and the show is about to begin.

The premise of the video they’re shooting is pretty cut-and-dry, Steezy tells me. In the last month, gas prices have shot up in a major way. So, his team rented a U-Haul, filled up containers of nearly 100 gallons at a nearby Shell, and drove their mobile station to Burbank, along with a sign reading “FREE GA$$.” In total, the gas cost “around $600,” Steezy says. “$1,000 counting the containers.”

The team in question consists of Steezy; two videographers, Josh and Max; and Rody, who tells me he’s Steezy’s “business partner” for the day. I ask them several questions here and there, but mostly try to stay out of the way as they set up, and within 15 minutes, their first “customer” has arrived.

While the ice cream shop looks like it’s seen better days, there are several patrons ordering from the takeout window and eating at the accompanying tables. Steezy didn’t plan for this. Along with serving as on-air talent and production manager, the creator was fulfilling his duties as location scout for the video, and it turns out that this lot wasn’t abandoned like he’d previously thought. But at this point, his team is too committed to turn back, so they usher the sedan into a spot and start to fill their tank for free.

It’s hard to claim that Steezy knows exactly what he’s doing; after all, he’s not exactly a veteran of the oil industry. Nonetheless, from our vantage point behind the scenes, it’s immediately obvious just how comfortable he is in putting himself in uncomfortable situations.

Steezy and his team putting up a sign for their new venture (Photo by Andrew Fenichel)

As Rody continues to wave their makeshift sign from the sidewalk, encouraging passing cars to stop by, Steezy plays it cool, confidently explaining to each curious customer that no, this is not a ruse — they’re really there to give away gas. He’s keeping a straight face for the cameras, though I notice him silently directing the shoot. His eyes dart around, observing the ridiculous scene unfolding in front of us, stitching each possible shot and every potential angle together while he edits the eventual video in his head.

It helps that the people showing up make for great characters in their own right, too. One woman tells us she moved from Armenia to Los Angeles when she was 5 and grew up chasing Hollywood dreams. She was just on her commute home from a movie set, and she excitedly shows us a photo she took with “Eva Mendes’ brother,” the presumed star of the film she just landed a role in. Upon realizing who Steezy is, she starts posting to her Instagram story and tagging him, telling her followers to come pick up some free gas.

Another man was in the car with his sister when they stopped by — “Call my baby mama and tell her to come, too!” he exclaims to her. The pair expresses their appreciation for Steezy, labeling the recent hike in gas prices as “ridiculous”; the woman drives from Burbank to L.A. for work every day, and given she fills up 2 times per week, she’s now spending upwards of $550 a month. When I tell them I’m writing a profile piece about the creator, the man says, “Shit, you should write about me too! I’m a rapper from Long Beach” (I unfortunately didn’t catch his SoundCloud).

Over the course of a half hour, I count 10 cars that turn into the makeshift station and reap the benefits. Number 11, however, is a different story: the owner of the ice cream shop arrives, and she says she’s going to call the police if Steezy and his team don’t leave now.

So, while the creator scrambles to pack up the U-Haul with Rody, we hitch a ride with the camera crew towards the next location, a nearby Whole Foods.

I’m curious to hear how one ends up shooting a gig like this, so I ask. Max, who’s driving, is an aspiring documentary filmmaker who’s currently a sophomore studying broadcast journalism at Chapman University. He’s made the nearly two-hour trek from Orange County to film with Steezy “about four to five times,” and he skipped his media law and ethics class to be here today, claiming he usually learns more about the modern industry from these projects anyway.

On the other hand, Josh tells me he got into freelance video work after he “met a guy at a 7-Eleven.” I ask him to elaborate, to which he explains that he was introduced to his current business partner through a mutual friend; a 7-Eleven just so happened to be the venue where the interaction occurred. “I just want to make an honest living…I love shooting something and bringing it home and putting it together,” Josh says regarding his career goals. “Like, that’s my favorite thing to do, compared to hearing someone tell me, ‘Oh, flip a burger’ or ‘punch some numbers on a computer.’”

By the end of the trip, I realize something: Max and Josh have never met each other before. Even as both capture every interaction from today's shoot on camera and work as a team, they’ve been brought here, together, unified by the vision of one 22-year-old YouTube creator.

But to really get to know Steezy Kane, first, you need to understand the person behind the greatest character he’s ever crafted: himself.

"This is where David Dobrik lived when he first moved to L.A.," Steezy tells us as we walk through his apartment building in Hollywood the following day.

The creator is noticeably tired. After wrapping the shoot the previous night, he spent most of today with his mom, as she's in town to celebrate her birthday. Somehow, he still has the energy to invite us over at 11 p.m. for a sit-down interview and photoshoot. When I ask him what time he needs us out by, he responds, "As long as you leave by 3 a.m., we should be good."

His real name is Isaiah Shepard. The main reason we're here is to pull back the curtain and get to know who Isaiah is when he's not playing Steezy. Still, it's apparent from the jump that the two lives he leads are blending into each other, sometimes even indistinguishable from one another. His apartment – which appears in many of his videos – looks more or less how you would expect a creator's living space to look, with camera equipment, boxes of merch, and props such as a mannequin hanging around the main room.

In between photos, he mentions that he recently attended South by Southwest in his hometown of Austin, Texas. He was invited to attend a screening of the upcoming documentary about the aforementioned Dobrik, "Under the Influence," which was directed by one of his favorite creators, Casey Neistat.

Isaiah actually got to meet the legendary filmmaker after the screening and talked to him for a couple of minutes, describing the experience as surreal. It's not the first time I've heard members of our generation speak on the impact and influence Casey had on their lives and careers.

"His style [of creating] is amateur a little bit…he writes his title cards on cardboard," Isaiah notes. "So, his videos really speak to you subconsciously. Like, 'You can do this, too.'"

Steezy at his apartment in Hollywood (Photo by Andrew Fenichel)

Once we've sat down, we dive more into how that influence manifested in Isaiah's own journey navigating YouTube. Born and raised in Austin, he started his first channel when he was 8 years old and made three more before launching the current iteration in 2016. Along with this early love for photography and filmmaking instilled in him by his dad, he was an avid skateboarder growing up.

It's where the name "Steezy" came from. Skateboarding slang short for "style with ease," Isaiah paired the popular phrase with his middle name, Kane, and a new alias was born. He just had no way of expecting how big that alias would become.

"When I made Steezy Kane, I was expecting people to call me Kane," Isaiah laughs. "But everybody called me Steezy, and a lot of people think that's my real name."

If you watched his early videos, you'd see an outgoing teen exuding confidence, singing songs in public and joking with strangers around town. In reality, he describes himself as an introvert, the type of kid who rarely ever spoke during class. The Steezy character came out of a desire to fit the immature prankster mold that was becoming popular in the mid-2010s, and given how steeped the creator was in YouTube culture from an early age, it made sense to stick with what worked.

"I was so desperate to be successful in high school," Isaiah says. "I kind of created this alter ego [as a way] to start doing outrageous, crazy things."

To match that drive, he'd bring his laptop to the school cafeteria, quietly editing away at his videos towards the end of the table. He was always a firm believer in working hard and lives his life by the "law of attraction," which states that whatever you think controls your reality. "I was always cocky in my head," Isaiah says. "I never said it to other people, but I knew where I was going and I knew I was going to get it. And I knew that mindset was going to give me that."

Still, upon graduating in 2018, Isaiah didn't have much of a plan past working on his YouTube channel. He decided not to go to college and was living at home, having recently quit his job.

"I was really broke…I was applying to be a security guard because I was running out of money," Isaiah recalls. "Then I learned that in order to start the security job, I would need to buy my own boots and black pants, which I couldn't afford. I had, like, five bucks."

Little did he know that a trip to Santa Monica would change things forever.

At least, not immediately.

That summer, Isaiah went to the Santa Monica Pier to film with some friends. He played the Steezy character per usual, filming his interactions with strangers as he explored the area. Eventually, he made a bet with a girl he’d just met: If I jump off the pier and into the water, can I get your number?

She agreed, and the Pier Jump was born.

He posted the clip on his Instagram and the full vlog on his channel in June. “It didn’t really do anything on YouTube…I mean, it got like 2,000 views at first,” Isaiah recalls.

The creator then sent the video to WorldStar HipHop (@worldstar), the uber-popular website and aggregator that shares viral content with tens of millions of followers across social media. Two weeks later, WorldStar posted it.

The clip got seven million views on Instagram alone.

Over the next two days, Isaiah’s own account went from 4,000 followers to 25k. This newfound audience was highly interactive, sharing his content across channels. Meme pages started picking up the Pier Jump, and it soon went viral on Twitter. Facebook wasn’t far after, with the clip watched over 20 million times on the platform. “I had co-workers at my old job texting me that it was popping up on their news feed,” Isaiah says.

The thumbnail from the now-famous "Pier Jump" (Photo Illustration via Steezy Kane)

He then uploaded a video where he loudly sang Juice WRLD’s diamond-certified track “Lucid Dreams” in public to YouTube, followed by Travis Scott’s “SICKO MODE” in the same format. By the end of September, he’d grown his subscriber count from 2,000 to half a million, which allowed him to start monetizing the channel via ads for the first time.

“My first-ever AdSense check came in…$17,000,” Isaiah says. “I was broke before September and then all of a sudden, the most money I’ve ever seen in my life.”

He continues. “I don’t remember how I felt. I couldn’t process it. It just happened too quickly. I didn’t understand it, but it was all I ever wanted as a kid…to be a YouTuber.”

During that period of rapid growth, Isaiah didn’t upload anything new. The pressure to live up to viewers’ expectations was at the forefront of his mind, and he didn’t want to disappoint them. So eventually, playing it safe, he posted a video answering questions from fans.

“I was so nervous, and then I upload a Q&A video,” Isaiah laughs. “Everyone’s watching, like, ‘What’s he gonna do next? Oh my god, this guy is so crazy!’ Then he drops a boring Q&A video.”

By February, his channel had passed 1 million subscribers, and he began to experiment with different styles of content. In pursuing a career in the film industry, he aspired to break out of the “YouTuber” label and the negative stigma he perceived to come with it. So, he started producing projects with other Austin creatives and shooting more scripted sketches. Some videos — such as “The AirPod™ Curse” — even mixed his classic prank show style with cast members acting out scenes written by Isaiah.

Throughout 2019, though, it became apparent what his audience wanted: more Steezy, more of the time. People had fallen in love with the boisterous character belting songs in parks and crosswalks, making them laugh just as much as he made them cringe. Steezy stood for something tangible, a lifestyle, a carefree swagger showing viewers that they too could break out of their shell and push themselves out of their comfort zones.

In the beginning, Isaiah didn’t notice anything wrong with this dual identity that was developing. After all, he’d reached the mountain top, doing this thing he’d been chasing his whole life — working full-time as a creator — in front of an audience of millions. Steezy was the reason he was turning his childhood dreams into a reality.

But the alter ego slowly begun to take on a life of its own, gnawing away at the creative potential Isaiah aimed to fulfill. “I have fans come up to me like, ‘Yo, do some Steezy shit!’” he says. “‘Yo, can you jump off a pier? Go pick up some bitches!’ And I feel like they’re talking to the wrong person.”

He pauses before resuming. “I could play [the character] for a few years, but eventually, it caught up to me. And I kind of realized I don’t like doing pranks, that this isn’t me.”

When January of 2020 rolled around, Isaiah appeared in a video with a friend and fellow creator, SNEAKO, a video in which he calmly proclaimed something he’d previously kept private:

“I don’t want to be doing YouTube in 5 years.”

During the early days of the pandemic, Isaiah packed his bags and left his hometown. Though a July video in 2020 titled “I Moved to LA” claimed that he’d wanted to live here since he was 15, in his words, it wasn’t driven by a desire to collaborate with bigger players or any of the other myriad of reasons why creators flock here in droves.

He tells me that while he’ll always love Austin — and plans on buying a house there one day — he’s not a big fan of the Texas summers and simply wanted a change of pace. “I hate how hot and humid it gets there,” he says.

From left to right: Isaiah Shepard, Alejandro Colosio, and Fil Gelabert (Photo via Pullout Podcast)

When he first came out to Los Angeles, Isaiah lived with two friends, Fil Gelabert and Alejandro Colosio. The trio had met each other through various creative projects over the years; upon moving, the arrangement was that Fil would operate as Isaiah’s manager, with Alejandro in a production role.

While the creator would continue to upload content and work with brands like Converse and Hulu, over the course of the next year, his relationships with Fil and Alejandro became strained. Some of it was caused by the common friction between any creator yearning to produce what they want to and the management team tasked with keeping their business afloat. Another reason Isaiah points out was that given they were all roommates, it was difficult to keep their work from seeping into their personal lives.

Nevertheless, in October of 2021, Fil and Alejandro left amicably, returning to Austin. Another one of their friends, Deniss Armijo — often referred to as “Russian Deniss” in videos — moved in with Isaiah, but he wound up leaving about six months later.

“You know, it was the best for everybody,” Isaiah says. “But I don’t regret working with them. They taught me a lot of things. I taught them a lot of things, hopefully…and yeah, we’re still really great friends. It was a cool era.”

However, balancing commerce with art hasn’t always been easy, with or without a team behind him. Some of Isaiah’s most-watched uploads began to receive copyright strikes, particularly given the use of popular songs in his “Singing in Public” series. His AdSense subsequently cratered, dropping from five-figure checks to just $500 a month, and he almost got evicted from his apartment.

“After that, I was just trying to figure out how to make money,” Isaiah opens up. When thinking about his journey, he says that “there’s not really been a true point of, like, amazing financial growth…my income and expenses have always been really close.”

Over time, he’s been able to supplement the loss in advertising revenue with a renewed focus on brand deals and merch drops. Yet given the uber-public nature of life as a creator — as well as a growing-yet-overall-lackluster amount of education centered around turning YouTube into a career — fans’ perspective on his success is often drastically skewed.

“When I had a million subscribers and I’m making $500 a month, there’s people coming up to me on the street saying, ‘I can’t believe I’m meeting a millionaire!’” Isaiah laughs. “They think I’m a millionaire. Not even close.”

He repeats himself, this time with an added expletive. “Not even fucking close.”

Between managing messy relationships and constantly iterating in an ever-changing industry, Isaiah has seen it all in the last four years. Those lived experiences are exactly how, in his words, he plans to “get out of the whole YouTube bubble.”

Inspired by vignette-driven shows like FX’s Atlanta and Dave, he began to develop his own project centered on the creator economy, dubbed Views. Unlike “cliché influencer shows” that portray a luxurious lifestyle in the hills — such as the recent Hype House spinoff on Netflix — he envisions a scripted narrative about creators who move to Los Angeles and struggle financially, rooming with each other and delivering food while trying to film prank videos on the side.

“When I first came to L.A., before I lived here, I had to sleep in a car,” Isaiah says. “We showered at the UCLA gyms. And you know, I want to make a show about those moments.

“I want to show the real shit in the industry, someone trying to socially navigate and meet other creators…basically the whole internet culture life,” he continues. “Everyone’s trying to do it but nobody’s doing it right. Because all of these other showrunners aren’t creators.”

Isaiah's mockup for "Views" — you can check out the show bible at viewstvshow.com (Photo Illustration via Isaiah Shepard)

By the time our interview nears its conclusion, it’s 2 a.m., and everyone’s pretty exhausted. When I stop recording, though, Isaiah’s excitement picks up upon getting the chance to talk about his show. “Wanna see the pitch deck I’ve been working on?” he says, with a gleam in his eye.

As he scrolls through his “show bible,” articulating the overarching plot points and some of the scenes he’s already shot, I can tell just how much Views means to him. He’s not treating it like a lackadaisical side project, either — he recently met with some folks at Disney, the parent company of FX, where he thinks the show would slot in seamlessly.

“What Disney said in the meeting…they were like, this is the first time somebody came to us that is actually a creator, that has the skills and is writing and putting in the effort,” Isaiah recaps.

He’s been developing the show here, by himself, in his apartment, putting his heart and soul into this passion project that he believes will help him transcend the platform that launched his career. He says he feels isolated at times, but he thinks that’s “really important.”

“I finally have time alone to work on this TV show,” the creator says. “Basically, it’s the only thing I see right now…and if it doesn’t get picked up, I’m gonna produce it on my own and put it on my YouTube channel.”

He followed up. “The downsides are very little…I think I’ve gained writing skills from it. I mean, I’m having meetings with Disney and they’re giving me advice. It’s very fucking crazy, right? Even if it doesn’t work out, I don’t see it as a loss.”

Seeing him huddled up here late into the night, with Views having become his shining beacon, a guiding light, I think I believe him.

Eventually, we say our good-byes, and the next day, I’m on a plane back home to Chicago.

The following Wednesday, Isaiah posts the video we got to see up close, dubbed “I Opened Up a FREE Gas Station!” Between the title and thumbnail, it’d be easy for a casual viewer scrolling through the app to mistake the video for clickbait. But from the jump, you can tell that this isn’t your classic YouTube fare, trading a more typical low-lift vlog for a pseudo-scripted documentary style reminiscent of cult classic comedy show Nathan For You.

That’s the beautiful thing about what creators like Isaiah are able to accomplish. Through sheer creative force, practicing his craft for years and picking up new skills through YouTube tutorials, he can write, direct, edit, and distribute an 18-minute video in just a week, a video viewed by millions.

With just his team of four, a willing sponsor in Audible, and a limited merch drop tied in to boot.

When visiting Los Angeles, I came with a certain perception about the types of people found in Hollywood. In some respects, these biases were proven correct. Between the Tesla-wielding Uber driver, the Armenian actress, and the SoundCloud rapper, everyone I met seemed to be living two lives, putting on a show in their own respective way.

This duality of what’s real and what’s not, the image we want to put forward into the world versus what the world wants to see from us, is a dynamic certainly not unique to the entertainment industry. As stakeholders everywhere rethink the way they make decisions, interested not only in what someone’s done but what that person has to say, the ability to build convincing characters and tell good stories has arguably never been more vital.

That’s why Isaiah flips back-and-forth on his comments about quitting YouTube one day. There’s a burning fire to leave Steezy behind on the path to a more traditional career in filmmaking, yet the prankster’s power in harnessing community — and the tangential business opportunities that have followed — is undeniable.

“Everybody in their early 20s goes through an existential crisis,” Isaiah says. “I don’t see it as a negative thing. It sucks. But it’s also fun in a way…it’s fun to be human and, like, experience that it’s completely normal. It’s growth.”

A still from “I Opened Up a FREE Gas Station!” (Photo via Steezy Kane)

Nonetheless, what’s fascinating about his growth — and many other contemporary creators — is that it’s all happened in front of us. We’ve grown up with Steezy; for a certain subset of our generation, the Pier Jump is a more relevant part of the cultural consciousness than any celebrated studio or sidewalk star could ever possibly hope to be.

Josh, the freelance videographer I had caught a ride with after the Burbank shoot, told me a story from when he first started working with Isaiah. At one point, he had a friend who was going through a “really bad situation. He was in debt over $30k, and his girl left him with the kid.”

Josh follows up. “My friend would watch every one of Steezy’s videos and say, ‘This is my only happiness right now.’ Laughing at his videos…a lot of times, people really do build a relationship with YouTubers through the screen. And it kinda helps them forget about their problems for a little bit.”

One day, Josh was browsing Craigslist for gigs when he stumbled upon a post from Isaiah, as the creator was looking for an extra cameraman. “When I mentioned that I’d gotten booked with Steezy, my friend was tripping out, saying, like, ‘No fucking way,’” the videographer recalled. “And I got to tell Steezy what he did for my friend.”

During my interview with Isaiah, I recounted Josh’s story to see if the creator still remembered it. Turns out, he did.

“It’s crazy…I can’t really fully grasp onto that idea,” Isaiah told me, reflecting on the unfathomable amount of lives he touches on a daily basis. “How do you react to that?”

He took a long pause. “But I do think that’s one of the biggest reasons why I make videos…I want to make people laugh or inspire them to create something else entirely, like how Casey made me feel. I want to recreate that feeling.”

Isaiah does worry that he’ll forever be known as the guy who jumped off the pier. The fans that originally came for Steezy — a sophomoric kid known for having fun and messing around — certainly won’t all hang around as the creator opens this next chapter of his life, pursuing a new slate of goals. But there’s something inherently beautiful about that.

As he grows up, his community is doing the same, redefining their relationship with him and this persona he’s shared so openly with them for the better part of a decade. The ones who do stay, though, will be stickier than the casual TV audiences of yesteryear, as the raw connection his fans have forged through years of trials and tribulations is incredibly palpable. That connection is how the creator believes he will break out of the box, transcending his beginnings to attain that next level of artistry.

In a city of dreams and a culture running on passion, Steezy isn’t alone in trying to reach new heights. But I think Isaiah — the quieter, introspective auteur with plenty to say about the intricacies of influence and fame — will get there.

All that’s left is something he knows better than most, repeating the thing that led him down this path when he was merely a teenager trying to make a couple bucks off of YouTube.

A leap of faith.

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Steezy Kane's Leap of Faith

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