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 This led to extreme frustration with the outdated systems.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.