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