From playing “Magic: The Gathering” with Post Malone on his YouTube podcast to acting in the live-action remake of “Mulan,” Lakeside alumnus Jimmy Wong ’05 has accomplished a lot in his career. This made it extra special when this accomplished content creator warmly agreed to meet with me to discuss how his time at Lakeside prepared him for the complex roles and responsibilities he has in his career as one of the original influencers of our generation. 

It quickly became clear that there were several experiences that helped shape who he is today. One of these prominent experiences is a now-common (even Lakeside-defining) practice: school computers. “My class was the first ever, maybe even in the history of the world, to get laptops in seventh grade,” Wong recalls. The ability to access laptops, in the prehistoric times when laptops weren’t widely available to students, was a massive learning opportunity for him and his peers. It allowed them to get started learning the language of these “novel” machines earlier than most, a training Wong describes as “important to all the things I’ve done since.” The ability to understand the workings of a computer set in motion the process of turning Wong from the average kid to the media master he is today. 

Wong remembers the small class size at Lakeside fondly. These classes allowed him to be gently shoved out of his comfort zone and learn how to be creative and solidify himself as who he was. He mentions how smaller class sizes allowed for “less obscurity.” Everyone had to pay attention and contribute — there was no fading into obsolescence in the back of English class. These small classes were an outlet that forced him to learn “how to talk” — a skill essential to his career. Wong clarifies that this lesson was more than avoiding those dreaded “likes” and “ums” — it was learning how to express himself with his words. 

The close-knit classes at Lakeside had subsequent downsides for Wong as well. As a result of the minuscule class sizes, he found, one was known for who they were, not who they became: “Everyone just has such a solid image, from when they first met you, of who you are. You’re that. And I always wanted to escape that.” 

This is the space from which Wong’s desire to start content creating and acting came. It was this idea that he could talk and express who he was: in the most intimate way possible, the creator and their camera. It created a space for him to tell the world who he was and who he became; he didn’t have to always be defined by the kid he was in fifth grade. 

Considering Wong’s original notoriety came from his viral response to a video posted by a UCLA student mocking Asian people, it felt important to ask him about his Lakeside experience in regards to DEI.  I was curious to learn if DEI was even a main focus of the school at the time; according to Wong, it wasn’t. During his stint at the high school from 2001 to 2005, Lakeside was still developing its relationship with the ideas of diversity, equity, and inclusion. Wong notes that there was a mix of people on campus, but the idea of equity, that someone should be where they deserve to be no matter their financial situation, was still something being developed. 

Instead, it was the world of content creation that offered him an equal playing field. Wong describes his gratitude and appreciation for the goal of mediums like Youtube: “It’s trying to give opportunities to people that maybe didn’t have them before.” He mentions how, in the early YouTube days, there was an explosion of Asian YouTubers such as Ryan Higa and Wong Fu Productions. “We didn’t have an outlet to express ourselves,” Wong says; that’s what YouTube allowed them to do. In his view, YouTube was the original proponents of DEI, which is what led the platform to become the powerhouse of social media we know it as today. It was the tantalizing promise of freedom that had Wong and millions of others hooked.

However, this opportunity, this medium for free expression, is something that Wong does not take lightly. At the end of the day, as he notes, “YouTube boils down to what the person wants to say to the world.” While this seems like something to celebrate, Wong highlights the intense responsibility he feels as part of this simplification. His idea that content should always be trying to help others learn and grow, even in the simplest Minecraft video, is essential to how he creates his content. Wong cites what he thinks content creation would be in its most “optimal” form: “I think if content creation is at its best, peak, awesomest, most responsible, it’s always going to try to dole out advice and set a good example, help pave the way.” 

The question then arose of why Wong felt compelled to make content in the first place. When I ask him about the advice he would give others who wanted to start creating content, Wong says it’s essential to focus on “why” one wants to be an influencer. If it’s to gain “validity” or to garner views, one will lose sight of the purpose of YouTube and their responsibility as a creator. This becomes apparent as we start discussing the many downfalls of YouTube and some creators — how some will do anything for views. 

Moreover, this idea of asking “why” doesn’t only protect others from someone else’s disregard, but it protects the person asking it; as Wong adds, it helps one manage their expectations. He specifies his time working on the set of the live-action remake of “Mulan”: on set, he had to remember why he was there to act and what his role was. If he, a smaller actor, went into the movie, demanding to make his part bigger, he would’ve “absolutely failed,” he says. “My character’s name wasn’t Mulan.” He was there to play the part of the side character, Ling, but that didn’t mean he couldn’t have taken advantage of the experience. He mentions that one’s attitude changes what they take away from the situation; if he went into that film set with the attitude of “I’m going to study every aspect of how this works,” he would’ve gotten a “master class” in Hollywood. It’s all about why and how one will present themselves. 

Our conversation returns to Wong’s time at Lakeside and how it helped him ask “why.” He reduces it to “just having a lot of really smart people around me all the time.” The school taught him the value of “never being the smartest person in the room.” To be the smartest person in the room is to be too arrogant to realize that everyone is human — there will always be someone better at math, writing, sports, chess or any other material skill in this world, and that’s what intrigued Wong. He was infatuated with what made someone more skilled at something than he was; that was the key that led him to ask “why?” It was Lakeside, he notes, that enabled him to chase this infatuation because he was constantly surrounded by people that were better than him in some aspect of life. It was this ability to surround himself with the right people that led Wong to who he is today, and that was his final advice to us Lakesiders. We need to take advantage of the opportunities we have at this school to surround ourselves with those who are better than us so we can constantly improve, or we’ll get complacent — Wong’s greatest fear. But that’s a story for a different time.