The winds of innovation: How sailing inspired a new way of leading tech

In this series, we explore the experiences of Singaporean business leaders who have ventured abroad and the ways in which they have navigated cultural differences to achieve success.

We hear from prominent homegrown C-suite executives and entrepreneurs who have expanded their businesses across Asia, Europe, and the Americas. Get insights on how they have adapted their leadership styles and business strategies to fit local cultural norms and how they have leveraged their Singaporean heritage to build relationships and foster trust with international partners.

When I co-founded Potluck Tech in 2023, I envisioned a company where “everyone brings something to the table”. This ethos is central to our work: helping startups navigate the turbulent waters of growth by bridging leadership gaps in product strategy and software development.

Unlike many consulting firms, we don’t just swoop in, solve a problem, and leave. Instead, we focus on fostering sustainable growth. We coach high-potential employees, assemble the right teams, and instil iterative processes that help businesses thrive long after we’ve stepped away. It’s a dynamic, evolving process that mirrors the startups we work with, and I wouldn’t have it any other way.

My journey to Potluck Tech was shaped by a career spanning decades in the tech industry. I’ve tackled some of tech’s most exciting challenges, from launching Google Translate and cofounding Google’s Beijing office to building an engineering team at TeachersPayTeachers in New York City. Along the way, I discovered the joy of solving challenging problems and nurturing talent.

But the most transformative lessons didn’t come from a tech boardroom. They came from an unlikely place — sailing across the Mediterranean Sea.

From Silicon Valley to the open sea

The decision to sail was sparked by a literal dream — one in which I saw myself hopping between islands, unburdened and free. That whimsical vision lingered, and soon, my husband and I were plotting a sabbatical to make it a reality.

Neither of us knew how to sail, but that didn’t stop us. We started small, taking lessons on laser dinghies, then moved on to larger boats and earned skipper certifications. Before long, we had bought a sailboat (the S/V Kaya, named after the beloved kaya) and were charting a course across the Mediterranean with our dog, Twiggy, in tow.

Living on a sailboat quickly redefined my understanding of control. Out on the water, even the most meticulous plans can be overturned by a storm or a sudden shift in the wind. Sailing forced me to embrace adaptability — an invaluable lesson I now carry into my work with startups.

l’ll tell you this — the Mediterranean was a classroom like no other. Some moments were breathtaking: anchoring beside an erupting volcano in Stromboli, navigating the Venetian lagoon to dock opposite Piazza San Marco, and spotting turtles and whales during a tranquil crossing from Sardinia to Menorca.

Other times, it was complete chaos. We once escorted a sailboat with a fire-stricken battery through the night. On more than one occasion, we found ourselves in the middle of unforecasted storms — violent “Medi-canes” that tested our resilience. Even on calm days, something was always broken, from rigging to appliances or a tuna that got away just as we were about to reel it in.

These experiences taught me more than resilience; they revealed the importance of community. Sailors in random ports became collaborators, offering advice or sharing meals. They reminded me that no one succeeds alone — a value I’ve carried into Potluck Tech.

Lessons in adaptability

Startups, like sailing, are unpredictable by nature. Both require a delicate balance of preparation, flexibility, and the ability to adapt when things don’t go as planned.

At Potluck Tech, we help startups navigate these uncertainties. Our approach isn’t about imposing one-size-fits-all solutions. Instead, we equip teams with the tools to tackle challenges head-on — such as bridging leadership gaps or learning to iterate effectively.

As a sailor, I’ve learned to go where the wind blows. That mindset informs my leadership coaching today. Founders often underestimate the creative, evolving nature of software development. It’s not about racing to the finish line but learning, improving, and growing along the way.

Still, while Potluck Tech is my main focus, my love for creating hasn’t faded. In 2022, I built Word-leh!, a Singlish-inspired word game, in just one day. Initially intended for friends, the game unexpectedly went viral, with 50,000 people playing daily at its peak. Word-leh! became an unexpected cultural phenomenon, sparking debates over Singlish words’ “correct” spelling. Is it “sibei” or “sibeh”? (Spoiler: Both are acceptable.) I even had to remove common misspellings like “skali” (actually “sekali” in Malay).

The joy of seeing people connect through something I created reminded me of what drives me most: building communities. It’s the same joy I find at Potluck Tech, where fostering collaboration is at the heart of everything we do.

Now, at 45, I’ve learned that success isn’t about rigid plans or ticking boxes; it’s about growth, connection, and enjoying the journey. Whether guiding a startup through turbulent waters or reminiscing about Mediterranean sunsets, I find fulfilment in the process, not just the outcome.

Potluck Tech is a culmination of these lessons. It’s about bringing people together, creating something greater than the sum of its parts, and tackling challenges with resilience and curiosity. Sailing taught me to trust the wind and lean into uncertainty. In work, as in life, I’m excited to see where it takes me next.