Breaking New Ground in a Foreign Land

For Chester Yow, the decision to leave Singapore, his hometown, wasn’t an excursion but rather a mission. After two years in the military, Chester aimed to challenge his own comfort zone, venturing far away from the familiar into the unknown of a new country on the other side of the world. “I wanted to prove that I can be successful in another country, in another city,” he shares. While it is common that many Asians would like to take the stable route to be near their community, Chester wanted to flip the script and rewrite his story.

Drawn to the fast pace and competitive spirit of New York City (NYC), Chester quickly realized that real estate was made for him—because for a person who doesn’t enjoy 9-to-5 office jobs like Chester, real estate allows the flexibility while maintaining the discipline needed to survive in NY. It is this combination of freedom and responsibility that has become the driving force for him to start building a network from scratch in this city that never sleeps.

Shattering Stereotypes in the Heart of New York

“If you can make it there, you’ll make it anywhere.” It’s a common, inspirational pipeline when speaking of New York. It’s inspiring enough to imply that challenges will always remain—not to bring you down, but to toughen you up. Chester’s no exception. With a heart filled with unrelenting passion and determination, it was still not enough—especially when dealing with racial discrimination and prejudice.

As a fresh-off-the-boat Asian in the U.S., he soon faced the harsh realities here—that discrimination can be both subtle and publicized at the same time. “You do get looked down on as a ‘minority’ at times, and people tend to judge or doubt you faster. I sometimes get, ‘Wow, your English is so good’ (English is the spoken language of Singapore), or ‘Why aren’t you a doctor, lawyer, or accountant?’” he recalls.

But instead of surrendering to the stereotypes, Chester leveraged them as inspiration. “I work harder than the next person, I study harder, I make sure I’m more prepared, I do everything necessary in my power so that there’s no doubt in anyone’s mind to question my capabilities.”

And his effort paid off. By exceeding expectations and proving himself with actual results, Chester is, step by step, changing common misconceptions—not only for himself but also for an Asian working in real estate in New York. Then, even those who doubted him reached out to him for work.

What grounds me is knowing why I work so hard and who I’m working for—my family, my loved ones, my future self 30 years down the road, and my own future family. I’m working hard for them. Having that quiet confidence to keep my head down and keep going is crucial, too.

The Life-Changing $450 Million Development Project

“Tough times don’t last, tough men do”—a quote from my military days that has stuck with me. Ryan Serhant also says, “You are allowed to quit—just make sure it’s on your best day.” You control your own destiny, and building mental toughness is essential to success. Mentorship is crucial for any entrepreneur, and one of Chester’s mentors can be traced back to his military days.

That advice led to a breakthrough in his career. One of the biggest turning points came in 2017, when Chester helped launch a $450 million luxury real estate project in Manhattan. As part of the SERHANT. team, he had the opportunity to bring the project to Ryan Serhant—one of the industry’s most prominent figures—and collaborate directly with his top-tier team.

“That project didn’t just help me close more deals (and earn more), it grew my network with consumers and other top agents, to learn the ropes of new development, and to work and learn closely with Ryan, thus growing my career exponentially,” Chester shared. It was an experience that catapulted his career and opened doors that might’ve otherwise taken years to access.

Staying Rooted on Unfamiliar Ground

As someone who grew up in Asia, Chester was raised with a mindset rooted in caution and logic. “We’re often taught to think of the worst-case scenario, to lead with reason, and to stay guarded and conservative. But that can sometimes come off as negative or dismissive,” he said. Living and working in the U.S. challenged those values and pushed him to adopt a more balanced approach. “I’ve learned not just to be prepared for the worst, but also to lead with optimism, follow my heart, and be vulnerable. Embracing failure and change has been key to my growth.”

That flexibility in mindset has helped Chester adapt and thrive in a fast-paced environment like New York. Even after many years away from Singapore, he’s maintained a strong connection to its culture and community. He regularly attends events and is active in organizations that support Asians in NYC. “There are so many ways to stay connected to being Singaporean and Asian here,” he shared. “I have a great group of friends and partners—we collaborate, support each other’s businesses, and stay rooted in our culture. In fact, 70% of my clients are Asian, and working with them helps me stay connected as well.”

Connect With Chester Yow

“Work hard, work smart, stay persistent, and block out the noise around you. Find a purpose that gets you out of bed every day and use it as your daily motivation. Hold on to the people who believe in you—and forget the ones who don’t.”

Website: Chester Yow

Instagram: @chester.yow

From the Boardroom to the Comedy Club

Julie Kim didn’t begin her career in comedy—she initially followed the stereotypically ‘Asian’ path of stable jobs in academia and office work. Born and raised in Toronto to a Korean immigrant family, her upbringing took place in a tight-knit, two-bedroom apartment above her family’s grocery store. “At one point, there were seven people in the apartment,” she recalls. “And for a solid six or seven years, I slept on the pull-out sofa bed in the living room.”

With multiple degrees under her belt—including a Master’s and two attempts at a PhD—she straddled the worlds of business, education, and motherhood. Amidst the hustle and bustle, there remained a silent passion in her for a creative life. “At first, I wanted to speak well to stand out among a sea of old white men in boardrooms,” she says. “I also wanted to do a difficult, admirable thing. It was a checkbox.”

A Dramatic Shift to Comedy

Julie didn’t quit everything overnight to pursue comedy. She experimented with it while holding multiple stable jobs, contract roles, while also pursuing her PhD, oscillating between full and part-time focus on her studies. But passion has a way of growing, and eventually, she did what she had to—crossing what she describes as ‘a bridge between conventional pursuits and creative pursuits.’ She stepped away from academia, turned down secure opportunities, and entered a world full of uncertainty and creative risk.

However, Julie was no stranger to the industry’s harsh stereotypes. She faced mistreatment and discrimination, navigating everything from blatant racism to sexism disguised as condescension.  “One booker tried to push me out of the scene because I winced when someone tried to make me kiss him against my will,” she shares.  “A few local comics hated or resented me from the start because I didn’t ‘need’ to do comedy—as if they deserved it more because I had other options. It was a different kind of discrimination I hadn’t encountered before, but for sure it taught me to stay far, far away from the bitter ones in this industry.”

Despite this, Julie pressed forward like the boss that she’s always been. “I had to learn how to produce and promote my own shows. And that built tenacity,” she says. “Now, I’m centered in my identity. My cultural identity and my confidence in it are central to much of the  success I’ve had in the past few years.”

Today, she’s one of Canada’s most sought-after comedians, performing alongside stars like Ronny Chieng, Atsuko, JR de Guzman, and more as she headlines major comedy clubs across North America. “This is the best time of my life,” she says. 

“I’m having the time of my life. But also, I’m still working on a little scarcity mentality and the feeling of constant survival mode,” she shares. “Part of me really enjoys that and part of me needs a new car and a real vacation.”

Being a Mom on the Mic

Being a mother in comedy isn’t easy—especially when constantly on the road. Julie has faced criticism from all sides: family members, fellow parents, and the weight of societal expectations. ‘I deal with it by blocking people out of my life or turning them into jokes—or both,’ she says with a laugh.

Her journey as a mother isn’t separate from her comedy—it is integral to it. “To do my work well, I need to be grounded, happy, and creative. So I try more and more to take care of myself to be those things,” she reflects. “I think it’s an accomplishment to still be writing and performing after more than a decade of true hustling. It’s taken a lot of grit, perseverance, some audacity, and foolishness.”

Julie Kim’s list of accolades is stacked: writing and producing Simu Liu’s iconic I Am Canadian monologue at the JUNO Awards, winning a 2023 Canadian Screen Award, and headlining four sold-out Just for Laughs shows in Toronto.  She’s also written for Kim’s Convenience and Run the Burbs, two shows centred around Asian Canadian families that have reached global audiences. 

As she continues to tour across North America, Julie is also working on upcoming television and film projects and producing her new podcast, Bothered. Next, she will prepare for a new 2026 tour of her solo storytelling show called ‘No One Special’ and writing her first book. 

Connect With Julie Kim

Website: https://www.juliekimcomedy.com/shows 

Podcast: https://www.juliekimcomedy.com/podcast 

Instagram: @juliekimcomedy

YouTube: @JulieKimComedy 

Facebook: Julie Kim

TikTok: @juliekimcomedy