Transforming the Future of Work: An Insightful Conversation with JJ on Entrepreneurship, Innovation, and Personal Growth - AHN Media Group
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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 This led to extreme frustration with the outdated systems.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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Today, Anta controls around 23 percent of China’s sportswear market, surpassing both Nike and Adidas within the country. Its dominance at home has helped fuel its rise on the global stage, where it now ranks as the third-largest sportswear company. This growth reflects both strong local demand and strategic expansion beyond China.

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Why Bhutan is the Smartest Place for Founders and Entrepreneurs to Reset in 2026

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That is exactly where Bhutan comes in. Its slower pace and untouched stillness create the kind of environment that gives ambitious minds the room to pause, reflect, and return with sharper focus.

The Philosophy That Reframes Success

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The Travel Model That Guards Your Headspace

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The Environment That Resets How You Think

Bhutan’s landscapes make it easy to slow down without trying too hard. In places like the Phobjikha Valley, the wide open views and quiet surroundings create a sense of calm that is hard to find elsewhere. Even visiting Tiger’s Nest requires a steady climb, which naturally shifts your pace and focus.

There is no constant noise pulling your attention in different directions. Instead, the stillness gives your mind room to settle and process things more clearly. It is often in these quiet moments that new ideas begin to form.

Over time, you notice a change in how you think and respond to things. Decisions feel less rushed and more intentional, which is something many founders and entrepreneurs struggle to achieve in their usual environment. By the end of the trip, the reset feels real and something you can carry with you.

If you are looking for a reset that goes beyond rest and actually changes how you think, explore Bhutan with Druk Asia here:

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Kickboxing began as a way to cope during a season that felt completely overwhelming. It gave Alice a physical outlet when her thoughts wouldn’t quiet down and her emotions felt too heavy to carry.

A few months later, Alice’s coach asked if she would consider competing. The idea unsettled her because she had never fought before and had never faced someone trained to strike back. For two months, she wrestled with the decision. What frightened her most was not losing, but the possibility of doubting herself under pressure.

When she finally committed, her routine became disciplined and demanding. She trained three hours a day, carving out time in the early mornings and late evenings while continuing to care for her children and grow her work.

The night before her first fight in Iowa, a coach told her that the real fight was already over because it happened during the grueling months of preparation. Once she realized that, her nerves calmed and a quiet steadiness took over. Even as she approached the ring to step in and fight, she felt unusually calm. She didn’t win that match, but she stayed on her feet until the final bell, and for a woman rebuilding her life, that was more than enough.

What the Ring Taught Her About Pressure

Alice went on to fight three more times. Afterwards, Alice turned her sights to competing in triathlons and even placed first in her age group at the Alcatraz Duathlon. While the medals were nice, the real reward was the quiet discipline she built through the discomfort of training.

She came to understand that fear does not simply fade with time. It softens only when you decide to move toward it.

She also learned that preparation changes how you carry yourself in difficult moments. When you put in the work, you stand differently, breathe more steadily, and think more clearly under pressure.

Today, those lessons shape how she sits with couples navigating divorce and teams facing workplace conflict. When emotions rise and conversations begin to unravel, she remains steady, drawing on the same discipline that once kept her composed in the ring.

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Alice now runs Shikina Mediation and Arbitration full-time, helping divorcing couples, families, and organizations reach agreements they once thought were out of reach. Most clients come to her when communication has broken down and trust feels fragile.

Early in her career, she tried building her business by networking with attorneys, but quickly saw the bias against non-attorney mediators in a field long dominated by older white men. Instead of forcing herself into a system that did not fully welcome her, she shifted her focus to working directly with couples and workplace clients, growing her practice into a thriving full-time business over the past decade. In 2025, Alice was awarded the prestigious Raymond Shonholtz Visionary Peacemaker Award by San Francisco’s Community Boards.

Her work has expanded beyond the mediation room. She hosts the podcast, Negotiation with Alice, now over 100 episodes strong. She authored the book Negotiating with Your Kids, and continues to teach communication and conflict resolution to executives and C-Suite staff. As a second-generation Okinawan American whose parents survived the Battle of Okinawa as children, resilience runs deep in her story. 

Nothing in business, she says, will ever feel as intimidating as stepping into a ring to face an unknown opponent. In that ring, she rebuilt her confidence. At the mediation table, she now helps others rebuild their lives with clarity, courage, and peace.

Discover more from Alice Shikina here:

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Learn more about Shikina Mediation and Arbitration here:

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