Projects

🦗 Grasshopper Inc

My first shot at entrepreneurship started when I was 10 with a pretty random business: "grasshopper trading." My older brother and I would catch grasshoppers and sell them to classmates to fund our recess snacks. We even had a price list: red-legged ones went for $1, blue-legged for $0.50. Eventually, we expanded into praying mantises, lizards, and spiders. It was scrappy, weird, and a lot of fun. But looking back, that was probably where I caught the builder bug.

🎴 Trading Cards Inc

At 15, I got into buying and selling trading cards. It was easy money—most kids didn’t really know the market value of their cards. I just stuck to one simple rule: buy low, sell high. Things were going great until I trusted the wrong shopkeeper who promised to help me sell my cards at my asking price. (He didn’t. And I lost it all, ouch and lol.) Still, it was a great crash course in how middlemen make money and a reminder to always pick who you trust carefully.

📘 Friends! Learning Center

At 19, my co-founder and I started a small education business: matching students with home tutors. We eventually raised some money to open a tiny space and run group classes and holiday camps. It was a scrappy setup, and we broke even in eight months. While profitable, I realized the business model had a ceiling, as we were tied to our physical location and personal hours. More importantly, I had the difficult realization that while I could run the business day-to-day, I wasn't the right leader to help it evolve. My passion was shifting toward models with greater leverage and scalability. After nearly five years, I made the decision to step down. That chapter was a crucial lesson in product-founder fit and the importance of scale; groundwork that I took directly into building Tech in Asia.

📰 Tech in Asia

Before Tech in Asia became Tech in Asia, it was called Penn Olson—a name I came up with when I was 23. Back then, social media was exploding, and I figured blogging about what was happening in Silicon Valley was the best way to learn.

I’ve always learned best by writing things down. So the name "Penn Olson" came from two words: Pen, because I wanted to write and reflect, and Awesome, because that’s what learning felt like to me. Penn became this fictional teacher figure who guided me through the early days of tech and social media.

In the early Penn Olson days, we weren’t just blogging. We also ran digital marketing campaigns. One of our wildest projects was for Singapore Airshow 2010—where we organized the world’s first tweetup on a plane (though the plane never took off). The media loved it, but we didn’t love doing agency work. Too many layers, too much fluff.

So we hit a crossroads.

The blog was drifting. We had to decide what we really wanted to be. As I kept reading and writing about Silicon Valley, I found myself drawn to sites like TechCrunch and Mashable. They weren’t just blogs—they were essential infrastructure for the U.S. startup ecosystem. But Asia had nothing like that.

That was the gap.

I tweeted out to ask what our readers wanted to see more of. The answer was clear: coverage on Asia’s tech scene. So we pivoted. Our first Asia-focused story got great feedback. Readership picked up. Then came our first investor, East Ventures. From there, we started building Tech in Asia.

How we were funded

My most memorable moments

One of my all-time highlights was being part of the YC Winter 2015 batch. My group partners were Kevin Hale and Qasar Younis. I also had the chance to get help from Garry Tan and Justin Kan and I'm super thankful for that.

Sam Altman was YC's CEO back then. On W15 Day 1, he said something along these lines: "There will be at least 3 unicorns from this batch, and 30% of you will exit."

He wasn’t wrong. My unicorn batchmates included GitLab, Razorpay, EquipmentShare, and GrubMarket (probably more). As of Jan 2025, about 10 years later:

Another milestone was getting acquired by SPH Media in 2024. It gave us a bigger playing field. We applied our startup mindset and processes in a legacy organization, and that was a learning journey on its own. We also went deep into AI which was pretty disruptive for the media industry.

AI at Tech in Asia

One big push I led was News by AI, a workflow that now publishes ~1,300 pieces a month. It took time (and a few pivots), but the results were worth it:

other tools we built (or building):

We also had to rethink how we build software in the AI era, especially how fast feedback loops work when "domain experts" and engineers all co-create. All these experiences helped grow my knowledge and confidence as we explore the future of work. At TIA, AI is now part of almost everything we do—and we’ll keep using it to supercharge our processes and team’s capabilities.

Not every moment was easy

There were also difficult calls to make such as doing layoffs. It's never easy, and never will be. I learned that the best you can do is to be direct and gentle. To respect both those who leave and those who stay. I wrote a bit about that here.