Work.

After leaving Tech in Asia, I’m taking a break, recharging, and building stuff under Slothware Labs where Ian and I build for joy.

I also do coaching as comrades for founders.

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(If you're looking for the deep dive into my 16 years here, you can read the elaborated version here.)

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 infra 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

• 2011 — Seed from East Ventures
• 2013 — Simile Venture Partners (and East Ventures again)
• Aug 2013 — Series A from Fenox VC
• Jan 2015 — Accepted into Y Combinator’s Winter 2015 batch
• June 2015 — SoftBank, Walden International, Marvelstone, Eduardo Saverin, Andrew Solimine
• Nov 2017 — Investment from Hanwha
• Jan 2024 — Acquired by SPH Media

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:

• 49 active (39.2%)
• 32 inactive (30.6%)
• 35 acquired/exited (30.2%)
• 116 total (100%)

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 ~1,000 pieces a month. It took time and a few pivots. Monthly traffic rose 30%, and journalists got more time for stories they wanted to report.

Another big push I did was setting up Daily Toast, a social media-native publication. With a small team, we developed AI-assisted carousel social content. The process started with internal evals, graduating only when our AI workflow proved to be better than human writers in blind tests.

In the first six months, Daily Toast racked up close to 15 million views. From start to launch took just eight weeks. I'm incredibly grateful to the team for working day and night on this project.

We also had to change how we build software when domain experts and engineers write it together, and how fast the feedback loop can be. I got more confident because I had done the work. At TIA, AI is now part of almost everything we do, and we will keep using it.

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.

Transiting out

On 31 March 2026, I stepped down as CEO of Tech in Asia. I’m proud of what we built, and grateful to the team who built it with me. I’m taking time off to be with my family.

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.

It made money, but the model had a ceiling. We were stuck to one location and to the hours we could teach. I could run the day-to-day. I was not the right person to grow it past that. I wanted a business that could grow without adding more of my hours. After nearly five years, I stepped down. I took that lesson into Tech in Asia.

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.

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.