Editor's Note: Claire Li’s journey from corporate leadership to entrepreneurship is a testament to adaptability and resilience. From founding Terracotta Chinese to creating TrueVibe, her focus has always been on fostering authentic connections—whether in careers or relationships. This story highlights the power of embracing both corporate and entrepreneurial experiences to drive meaningful change. Dive in to discover how Claire’s pivots can inspire your own career journey.

From Corporate to Entrepreneurship—And Back Again: My Career Pivot Journey

For over a decade, my career has blended corporate leadership with entrepreneurial ventures. At companies like Google, Palo Alto Networks, and Tencent, I thrived in structured environments, leading global talent programs, employer branding efforts, and diversity strategies. Yet, despite these accomplishments, I felt a growing pull toward something more—something that corporate roles couldn’t fulfill. This drive led me to explore entrepreneurship twice, with each transition deepening my understanding of resilience, strategy, and purpose.

My First Entrepreneurial Attempt: Terracotta Chinese

My first entrepreneurial venture was with Terracotta Chinese, an e-learning platform designed to help working adults learn Chinese online. But beyond language learning, my deeper mission was to empower stay-at-home Chinese mothers to build their own teaching businesses, giving them a pathway to financial independence and career growth.

The experience was eye-opening. I dedicated my energy to developing the platform, strategizing business development, and pitching to investors. However, despite the passion behind the project, I encountered significant challenges that reshaped my understanding of entrepreneurship:

Strategic Direction is Crucial – A clear, well-defined vision and business strategy are essential for startup success. While the mission was strong, I learned that having a structured plan for scaling and sustaining the business was equally important.
Entrepreneurship is a Journey, Not an Overnight Success – Startups require immense patience and resilience. Results don’t come instantly, and setbacks are inevitable. This experience taught me to embrace the long game, pivot when needed, and stay determined despite challenges.

Although Terracotta Chinese didn’t evolve into a long-term venture, the lessons I gained were invaluable. They laid the foundation for my next entrepreneurial leap, giving me a stronger base to build upon.

Building TrueVibe: Redefining Modern Dating with Purpose

After returning to corporate roles and honing my expertise, the call to entrepreneurship came again. This time, I approached it with greater strategy, patience, and preparation.

TrueVibe isn’t just another dating platform — it’s a response to the transactional nature of modern romance. I’ve witnessed how swiping culture reduces people to profiles, valuing convenience over meaningful connection. With TrueVibe, I’m focused on something different: fostering genuine bonds built on trust, shared values, and emotional depth. My years in recruitment and community building—connecting talent to opportunities and growing networks like the JAPAC Women’s Network—taught me that real connection requires intention. TrueVibe brings that intentionality to dating.

We launched our first event in February 2025—Chiang Mai Date Night—where 24 like-minded individuals from across the globe connected face-to-face in a curated setting. The result? A 75% match rate. In a world flooded with endless digital options, there’s still something special about real, human interactions. This encouraging outcome inspired us to move forward, and we’re excited to bring TrueVibe Date Night to Tokyo in March, supported by a local co-working community.

Although it’s still early days, seeing people connect with and find value in my approach inspires me and strengthens my belief in TrueVibe. It’s not about quick fixes—it’s about fostering meaningful beginnings.

Challenges and Breakthroughs

Shifting from the corporate world back to entrepreneurship brought its own set of challenges. Unlike the structured corporate environment, entrepreneurship demanded adaptability. I found myself wearing multiple hats—strategist, marketer, product developer, and customer advocate—all at once. The focus shifted to funding, product development, and user acquisition. In contrast to the corporate setting, where resources were more readily available, every decision had to be made with careful consideration of sustainability and impact.

However, my background in program management and talent acquisition proved to be an invaluable asset. I leveraged my experience in user experience, community building, and employer branding to establish a solid foundation for TrueVibe. Drawing on strategic planning skills developed at successful global tech companies, I was able to navigate business challenges and pivot when needed.

Lessons Learned from Founding Two Companies: Navigating Entrepreneurship and Career Transitions

Founding two companies has provided me with valuable insights into navigating career pivots and building meaningful ventures. Some of the most valuable lessons I’ve learned include:

Clarity of Vision is Essential – Whether in the corporate world or entrepreneurship, a well-defined strategy is crucial for success. Without clear direction, even the most passionate ideas can struggle to take off.
Resilience and Patience are Non-Negotiable – Entrepreneurship is rarely an overnight success. The ability to persevere through setbacks, pivot when necessary, and remain committed to the long-term vision is what distinguishes enduring ventures from short-lived ones.
Bringing Corporate Learnings to Entrepreneurship – The strategic planning, stakeholder management, and leadership skills I honed in corporate environments proved invaluable when launching my own ventures.
The Power of Community and Connection – Whether empowering stay-at-home mothers through Terracotta Chinese or creating meaningful dating experiences with TrueVibe, building a strong, engaged community is foundational to any successful venture.

Balancing Corporate Roles and Entrepreneurship: Finding Purpose in Career Transitions

My entrepreneurial journey has certainly shaped me, but it’s my corporate career that provided the platform to influence at scale. A standout moment during my time at Palo Alto Networks was receiving the Women in ICT DEI Champion Award for Southeast Asia. This recognition affirmed my commitment to creating inclusive, community-driven spaces. Whether in talent acquisition or entrepreneurship, I’ve consistently been passionate about fostering meaningful connections, and this award was a reflection of that belief and passion.

*Claire receiving the Women in ICT DEI Champion Award for Southeast Asia, a recognition of her commitment to fostering diversity, equity, and inclusion within the tech industry.*

"Transitioning between corporate roles and entrepreneurship has provided me with a unique career perspective. It has shown me that corporate careers and startups are not opposing forces, but complementary paths that shape professional growth.

Returning to corporate roles after my first entrepreneurial venture wasn’t a step backward; it was a strategic move to refine my skills, expand my network, and gain fresh perspectives. During this period, I absorbed new knowledge and applied it to my next venture. The key takeaway? Entrepreneurship doesn’t have to be an “all-or-nothing” decision. There’s great value in leveraging both worlds to build a meaningful career.

As I continue this journey, I’m grateful for the corporate experiences that shaped me and the lessons learned from both entrepreneurial ventures. The transition has been challenging, but it has reaffirmed my belief that true success comes from following one’s passion, taking calculated risks, and staying committed to a vision that creates positive change.

How I Went from Global Recruitment to Building a Startup (Twice!)