I realize that there’s a key perspective missing from this story in the weeks following my swing through South By.
What about today’s aspiring creators, the ones who arrived in Hollywood with little more than a vlogging camera and a bootlegged version of Final Cut Pro on their laptop? The generation after Rhett, Link, and Lilly, that grew up watching David Dobrik cruise around the streets of Los Angeles in 2018 and thought, Hey, I can do that too!
Luckily, I know someone who fits the archetype well: Isaiah Shepard, a twenty-four-year-old aspiring filmmaker better known online as his prank-happy alter ego, Steezy Kane. So, in late March, I call him up, and he agrees to lend his voice to this story.
I first met Isaiah in 2022, when he invited me to his apartment in Hollywood (the neighborhood) late one night. We immediately bonded over our mutual love of Donald Glover and Martin Scorsese, riffing on our own creative hopes and dreams into the early hours of the following morning.
Coincidentally, Dobrik lived in that same Hollywood apartment building when he first moved to L.A., and Isaiah often ran into members of the creator’s Vlog Squad. “It was like a strange village,” Isaiah recalls. “We’d always just bump into these characters we were watching on YouTube.”
Born in Austin, Isaiah describes himself as the type of kid who never spoke in class. He instead opted to express himself by uploading prank videos, modeled after the Danny Duncan types who were taking over YouTube in the late 2010s.
“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.”
One of those outrageous, crazy things: jumping off the Santa Monica Pier to get a girl’s number in 2018. That video racked up tens of millions of views across YouTube and Facebook. All of the sudden, Isaiah went from being a broke eighteen-year-old visiting Los Angeles—sleeping in his car, sneaking into the UCLA gyms just to shower—to cashing his first AdSense check, worth seventeen thousand dollars.
For the next several years, Isaiah continued to film videos back home in Texas. The more pranks he pulled off, the more fans tuned in, growing his channel to over three million subscribers in the process.
YouTube was never the end goal—Isaiah shared that sentiment publicly back in 2019, proclaiming his desire to quit the platform within five years to pursue a filmmaking career in L.A. At that stage, though, it was clear that YouTube would serve as the vehicle to get there. So eventually, with more cash (and a pair of friends, Alejandro and Fil, from Austin), Isaiah packed up his car and moved to Hollywood in 2021.
“I Jumped off the Pier for Her Number (ALMOST ARRESTED) re-uploaded,” Steezy Kane, (Oct 2024)
Not long after one of his first viral stunts, Isaiah cashed in his first AdSense check (which was over $17,000.
His first several months here were rocky. “I remember a panic attack,” he tells me. “Being in such a huge city, it was so intimidating.”
In between were moments of genuine awe for the city’s standing in the pop culture subconscious. “I was watching Mulholland Drive one time,” Isaiah says. “There was a scene where the actress is running on Sunset Boulevard, right outside [my] apartment.”
“I didn’t think I would get starstruck for pavement,” he jokes.
Compared to Austin, where Isaiah would get strange looks the minute he pulled out a camera to film, creative careers felt more normalized here. With momentum behind him, Isaiah got to work in his new city, uploading regular pranks and vlogs alongside Fil and Alejandro.
Through brand deals, merch drops, and AdSense, the trio’s goal was to get the channel to six figures in monthly revenue. “When we first moved, I was making, like, ten thousand dollars a month,” Isaiah tells me. “Which was not enough to pay rent, to pay [Fil and Alejandro] for their work, and to pay for video props and expenses.”
The channel peaked at fifty thousand dollars in one month. Getting there required several straight weeks of long days and long nights. The burnout that followed led to a month off from uploading anything.
In the pursuit of stability, they felt like they were right back where they started. Plus, it’s not like Isaiah had years of management experience to lean on. He was twenty years old.
“It’s not a good idea to live with the people you’re doing business with,” Isaiah says. “We didn’t know what we were doing, but we were trying to be friends and make money together and live the American dream in L.A. Doing YouTube, uploading weekly.”
“And we almost got there,” he follows up, with a hint of sadness in his voice.
Frustrations boiled over. Money dwindled. Fil and Alejandro moved back home to Austin. And Isaiah began to grow tired of playing the Steezy character all the time. Kids ran up to him on the street, excited to meet who they perceived to be this millionaire prankster — not a shy kid trying his best to avoid getting evicted from his apartment.
Famous and broke, every creative’s worst nightmare.
Isaiah doesn’t look back on his time in Los Angeles as worthless. “I got to network with a lot of creators out there,” he says. “Someone’s probably going to be a late-night host, or a documentarian.”
Though progress was hard to track on the day-to-day, there were periods where Isaiah felt like his ultimate goal — of breaking into the film industry — was within reach.
In 2022, he started developing a scripted television show based on his experiences navigating the creator scene in Los Angeles. Heavily inspired by Donald Glover’s FX series Atlanta, Isaiah was ecstatic when he landed a meeting with executives at Disney (FX’s parent company).
He never heard back from them. But there was a feeling of validation, that the creative talent he’d showcased on YouTube translated to the traditional industry. He’d at least gotten into the room Rhett and Link grew tired of sitting in.
The following year, one of his fans (a director by the name of Rick Darge) reached out with a proposal to co-write a comedy sketch for Vanity Fair. The project featured Abel Tesfaye — aka R&B singer The Weeknd.
Darge asked Isaiah if he wanted to come to the set at The Weeknd’s house. Isaiah says it was probably the quickest yes he’s ever said in his life.
Up until then, Isaiah had only ever produced videos with friends or freelance videographers he’d found through Craigslist. At the Vanity Fair shoot, “I get to learn their workflow, I get to see how they work in the traditional [setting],” he recalls. “That’s another way living in Los Angeles helped me a lot.”
Gaining confidence, Isaiah took an extended break from YouTube to pitch Atlas (a camera lens company) on funding his narrative short film, A Trip to Amsterdam. Atlas granted him thirty thousand dollars, a relatively modest budget for many directors’ standards. But Isaiah was used to making a lot with a little, so he built a crew and flew to The Netherlands to shoot.
Isaiah Shepard shaves his head in the Amsterdam canals for his documentary feature A Trip to Amsterdam. The film was originally supposed to be a narrative that Shepard says was inspired by an "ego death." / Steezy Kane
The trip, to put it bluntly, was a disaster. One videographer lied about their experience (none). Isaiah had to tell the rest of the crew to leave early. He salvaged what he could by exploring Amsterdam himself, cutting together a pseudo-documentary.
“It’s not entirely involved with the city of Los Angeles, but, you know, the reason why I moved there was to pursue film,” Isaiah tells me. “And then when the first film became a disaster, it kind of broke down my identity. It made me question, like, do I even want to do this?”
Freshly in debt and struggling with his mental health, Isaiah followed his former roommates’ footsteps and moved back home to Austin at the end of 2023.
I grabbed lunch with Isaiah in March when I was in town for South By. He seemed to be in high spirits then, happy with his decision to finally leave L.A. He’s seeing his family every week, and he’s reconnected with friends—Fil and Alejandro chief among them.
The desire to make movies is back, too. Isaiah credits the growing creative community in Austin for that.
The drive to make YouTube videos, however, is not. Isaiah is quick to point out that what’s “beautiful” about YouTube is the freedom to “make what you want” without “answering to anybody else.” He’s grateful for the community he’s built on the platform, too. While the views may have dwindled over the years, there’s still a core group of fans that continues to return, cheering on his grander pursuits.
Nevertheless, over our last several phone calls, Isaiah mentions that his bank account has pretty much hit rock bottom. Here he is, sitting on a channel with millions of subscribers (something Alejandro refers to as a “gold mine”), yet he’s struggling every time he so much as looks into a camera lens. He notes that it’s been five years since his prediction in 2019. Committing to YouTube now feels like stagnation.
A month after we talked, Isaiah returned to his popular “Singing in Public” format for the first time since 2021. His video went viral, dropping at the height of the Kendrick Lamar vs. Drake beef and peaking at No. 4 on YouTube's Trending charts. Interactions like this actual comment from X, however, showcase the discrepancy between where Isaiah wants to take his creative career—and what fans say they want to see from him. / Steezy Kane
“The YouTube channel isn’t any different from when I was making videos in my bedroom in high school,” Isaiah tells me. “I’m writing the videos, I’m editing the videos, I’m choosing the camera that I’m going to use…I’m running the show, and it’s still no different.”
But in his mind, there’s a missing step between what he’s accomplished so far and becoming a capital-S Showrunner: “Everything I’m doing is what I think I should be doing,” he says. “The final product looks fine, but I don’t have any of these traditional media skills because I’m still that kid in my bedroom.”
Isaiah feels like that’s the way the industry looks at him, too. In an effort to gain that experience (and a more regular paycheck), he’s applied for assistant writing jobs at FX, HBO, and Vanity Fair without much luck. He’s sent his work to agents, who always seem interested before ghosting him after a couple of meetings.
By now, I’ve talked to enough people in the entertainment industry to know that these struggles to get a foot in the door aren’t unique to Isaiah. And besides, at least he has something that most Hollywood transplants don’t. Why not continue to prove himself by producing more ambitious projects — and distributing them on YouTube?
“There’s no narrative series on YouTube because people can’t just take six months to develop a show and post it,” Isaiah says in response. “When you take that six-month break, the algorithm declines your channel because you haven’t been posting.”
“They tell you in YouTube Studio, like, ‘Taking a break actually helps your channel,’” he continues. “No it f**king doesn’t.”
