Pivoting from Founder to Investor with Sylvester Wee

In this Q&A, we talk with Investment Partner, Sylvester Wee, about his journey launching his own fintech company to becoming a venture investor, and how his experience as a top-ranked tennis player directly informs his ethos as an entrepreneur.

"Two roads diverged in a wood, and I – I took the one less traveled by, And that has made all the difference."

– Robert Frost

When did your journey as a founder begin?

My entrepreneurial journey began as an undergraduate student at Wharton, where I saw close friends start businesses to solve real-world problems. I joined them in some of their work, and a part of me always wanted to build something from scratch myself.

After school, I returned to GIC, Singapore’s sovereign wealth fund, to fulfill my scholarship commitment. There, I became increasingly focused on technology investing. In 2019, I realized I didn’t want to wait another two decades to become an entrepreneur. I was fortunate to be accepted into Harvard Business School, where I started experimenting with ideas that resonated with me. After several iterations, my startup evolved into a fintech company focused on financial inclusion in the United States.

What was it about financial inclusion that motivated you?  And why focus on the US?

It stemmed from my personal experience navigating the US financial system as a newcomer. Despite having a solid credit history in Singapore, it held no weight in the US, forcing me to rebuild from scratch. With limited financial options available, I felt invisible and realized that many others faced similar challenges.

Because of this, I learned the intricacies of the US financial system, the challenges of the current credit landscape, and the promise of frontier technologies like blockchain to make things better, faster, and cheaper.

So that was your introduction to open, distributed networks? 

Yes, in many ways.  By working with banks, processors, and payment networks, I saw the complexities of building consumer-facing fintech products, the outdated systems and high customer acquisition costs. It seemed more effective to use open banking technologies to bring my products to market quickly.

Can you be more specific about “open banking” technologies?

Sure.  I experimented with privacy-preserving credit underwriting methodologies.  I explored shared data analytics and collaboration tools to improve my internal processes and external interactions. Because of my own experience with financial exclusion, I worked to develop innovative technological solutions to expand financial access for underserved communities, foster interoperability across business systems, optimize costs, and improve the overall economic viability of serving these customers.  And that’s what open tech does.

Is that what next motivated you to build Sentinel Global?

It’s a big part of it.  Open technological systems offer increased collaboration, speed to market, and innovation. I have seen how open banking, privacy-preserving systems, and blockchain technology can make financial transactions more secure, efficient, and affordable, despite regulatory and implementation impediments. However, the infrastructure supporting these technologies is still in its early stages. 

I decided to help build Sentinel Global to have a broader impact on some of these emerging technologies. By investing in innovations surrounding data security, digital assets, and interoperability of systems, we aim to facilitate the institutional adoption and commercialization of these frontier technologies. Our goal is to contribute to a financial system that’s more inclusive and fair for everyone.

And what would you say you bring to the Sentinel Global team?

As an investor and founder/operator, I directly understand the operational complexities and financial considerations in building a company. With this dual perspective, I’m here to assist founders in scaling their teams, preparing for milestones, and building companies with empathy and understanding.

Also, my experience working with banks, payment networks, and processors gives me some valuable insights into what these institutions look for in emerging tech companies. These relationships also help me stay in the loop on the latest trends and advancements and how institutions are using tech to enhance their existing systems.

You have an amazing fun fact: you were once Singapore’s #1-ranked tennis player and represented the nation in the Davis Cup and qualified for the Australian Open.  How did that experience prepare you in your current journey as an investor and entrepreneur?

Tennis taught me to appreciate the ups and downs, delayed gratification, and the power of a strong support system. I learned these lessons firsthand as I faced numerous setbacks and challenges while trying to break into the international tennis circuit back in the day. My sporting journey has shown me that with the right mindset and attitude, I can overcome any obstacle that comes my way. I am confident that these learnings will continue to guide me as I build Sentinel Global and support the development of innovative tech businesses in the decades ahead.

If you want to talk to us more about distributed technology, open banking, or challenge Sylvester to a tennis match, send us a note at hello@sentineglobal.xyz.