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  • Transforming the Future of Work: An Insightful Conversation with JJ on Entrepreneurship, Innovation, and Personal Growth

Awaken* newsletter

July 4, 2024

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In this candid conversation, JJ reflects on his remarkable journey, from gaining admission to Stanford GSB to founding Onloop. He discusses his proudest achievements, the challenges of building a pioneering company, and the invaluable lessons learned along the way. JJ also shares his vision for Onloop in the evolving landscape of remote work and generative AI, his approach to angel investing, and offers insightful advice for aspiring entrepreneurs. Join us as we delve into the experiences and insights of a trailblazing entrepreneur committed to transforming the future of work.

HanYue: You have accomplished a lot in your career. What’s your proudest achievement so far?

JJ: My proudest achievement remains getting into the Stanford GSB MBA program. Before Stanford, I had spent my entire life in Asia. Moving to Stanford marked a significant shift in both my career and personal development. Immersing myself in the challenging yet enriching environment of the Bay Area was transformative, and I just returned there for my 10-year reunion.

HanYue: Can you tell us about the origins of Onloop?

JJ: Onloop originated from personal frustrations I encountered while managing teams at Uber for 3.5 years, especially with inefficient HR processes. This led to extreme frustration with the outdated systems. After leaving Uber in September 2019, I started OnLoop to solve some of these frustrations. We developed our first product around changing how performance reviews get done using GPT3 in early 2021. We’ve come a long way building out our platform and focused on helping every manager become a great manager using habit-forming technology and applied AI It’s been an exhilarating journey, shaping a company that contributes to the evolving future of work landscape especially given all the transformative impact of distributed & hybrid work as well as the maturity of large language models (LLMs).

HanYue: What have you learned from building Onloop?

JJ: Building Onloop has taught me that a founder’s longevity hinges on their conviction in their mission and the people they surround themselves with. Pioneering in any field is incredibly challenging—far more so than creating a copycat startup. Jensen Huang famously said he’d say ‘hell no’ if asked to do it all over again. The world resists change, and you must consistently challenge the status quo. 

Growing up in an Asian household where academic success was prioritized and entrepreneurship was uncommon, taking a non-salary path wasn’t easy. This background often amplifies the voices of doubt during challenging times, yet confidence and eloquence are the most significant drivers of success in the early days. 

Life in your late 30s and 40s has many more responsibilities with respect to family so it’s not always easy to take the plunge, but the learning experience from entrepreneurship is absolutely invaluable. I’m better off for it, even if things don’t pan out as expected. Starting a company is like becoming a parent—it’s a transformative experience that teaches you new ways to live.

HanYue: What’s your vision for Onloop?

JJ: Our vision at Onloop is to help knowledge workers fully realize their potential during this era of significant transformation. The rise of remote work and the advent of generative AI—akin to an industrial revolution for knowledge workers—presents new challenges and opportunities. We aim to help these professionals optimize their careers in a rapidly changing environment. The knowledge work sector is vast and often influenced by chance, especially in job placement – knowledge worker wages are a multi-trillion dollar asset class allocated by chance. My goal is to develop and disseminate optimal strategies for knowledge workers, enabling them to seize the best opportunities available.

HanYue: Tell me about your angel investing career and how it impacts your entrepreneurship journey.

JJ: I don’t subscribe to the notion of work-life balance but prefer to maintain a purpose portfolio, which currently includes my family, OnLoop, and enhancing Singapore’s status as a global hub, especially for highly innovative companies. My approach to angel investing focuses more on the people than the ideas themselves, reinforcing my belief that the right people drive success. And I apply this same principle in my work with other CEOs and founders.

While I believe any manager can become great with the right support, a CEO doesn’t have a direct manager, making coaching essential. I therefore coach a handful of founder CEOs and  this interaction offers mutual learning opportunities and enhances my own growth as a CEO/founder 

Talking about angel investing, it isn’t just for the rich and wealthy. I have made six investments so far in the range of US$1,000 through syndicates to US$15,000 in certain founders that I know personally. I have learned that while my bets on ideas have failed, my bets on people have not. This supports my hypothesis that early-stage investing is 80% about the founding team. 

Lastly, having become a Singaporean last year, I feel even more committed to the Singaporean ecosystem and proud to build in it.

HanYue: Advice for young entrepreneurs these days? 

JJ: When I was single and enjoyed partying, I never imagined I’d find myself here today. People seek pleasure when they lack purpose, as Victor Frankl famously spoke about. Today, living a life of purpose is crucial for happiness — it involves engaging in activities that you deeply enjoy and believe are your calling. This philosophy has guided both my personal and professional life and serves as my constant motivation. 

JJ’s journey exemplifies the blend of purpose and innovation needed to navigate the evolving landscape of modern work. His insights into entrepreneurship, the importance of mission-driven leadership, and the power of transformative technology offer invaluable guidance for the next generation of innovators.

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From Singapore to New York: How Chester Yow Turned Doubt Into Drive

Breaking New Ground in a Foreign Land

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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.

Chester Yow, a Licensed Associate Real Estate Broker and Founder of the Chester Yow Team at SERHANT, smiling confidently in professional attire.
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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.

Chester Yow, a Licensed Associate Real Estate Broker and Founder of the Chester Yow Team at SERHANT, who overcame early challenges in the U.S. such as racial discrimination and cultural differences, smiling confidently in professional attire.
Chester faced many challenges during his early days in the States, including racial discrimination and cultural differences. 

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.

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“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.

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“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.

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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.”

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“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

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