The Culdesac

The interview was already happening

Fri, 05 Jun 2026 00:00:00 +0000

Last night at our Founder Friends event, a guy walked up to me with the kind of opener you don’t forget.

“This might be a little weird — but I’m interviewing for an internship right now, and the hiring manager told me to come find you and ask what I should say to get the job.”

I laughed. Then I asked him the obvious question: “Okay — what’s your current plan to sell yourself?”

Pick Your Table

Fri, 24 Apr 2026 00:00:00 +0000

We talk about drive like it’s a character trait. I believe it’s mostly a downstream effect of your environment. You don’t decide to feel urgency. You catch it — from the person shipping something on a Saturday, from the friend who just raised, from overhearing a conversation at the next table that assumes a bigger game than the one you’re playing.

Can a VC with Claude Code find better keloid treatments?

Tue, 31 Mar 2026 00:00:00 +0000

I have keloids. If you don’t know what those are, consider yourself lucky. They’re raised, rubbery scars that grow way beyond the original wound. They itch. They’re painful. They come back after treatment. And if you’re unlucky enough to be prone to them (hi), every cut, piercing, or surgical incision is a roll of the dice.

The standard playbook is steroid injections, silicone sheets, maybe surgery — which ironically can trigger more keloids. There’s no gold-standard cure. The research is thin. And if I’m being honest, it’s one of those conditions that doesn’t get a ton of attention because it disproportionately affects people of color and it won’t kill you.

Consider Living Near Your Kids

Wed, 25 Mar 2026 00:00:00 +0000

There’s a poster by Tim Urban that shows your entire life in weeks. 4,000 little boxes. It’s sobering.

But for parents, there’s a more specific version of this exercise: How much time do you actually have left with your kids? Conventionally the math people scare you with assumes they leave at 18 and are never under your roof again. Reasonable assumption - but neglects the benefits of living close by, or even together during their adult lives. This is something that has really been made clear to me when I moved back to Singapore 7 years ago, and had the opportunity to live with my parents, and for them to live with their grandchildren. It’s a whole different dimension of parent/child/grandchild togetherness.

Zero-Based Budgeting for Your Engineering Team

Sat, 21 Mar 2026 00:00:00 +0000

A founder I back asked me last week if I knew anyone who could help them rethink their engineering org from scratch. Not a layoff consultant. Not a recruiter. Someone who could help them answer a harder question:

If I were building this team today, knowing what AI can do now, what would it look like?

I’ve been hearing versions of this question from almost every CEO in our portfolio. And I think it’s the right question at the right time.

Belief Is Contagious

Thu, 05 Mar 2026 00:00:00 +0000

There’s a negativity problem in Southeast Asia’s startup ecosystem right now. And look — there are reasons for it. Markdowns, down rounds, slower exits, tighter liquidity. I’m not going to pretend the data doesn’t say what it says.

But here’s the thing: negativity is self-fulfilling in innovation ecosystems.

Innovation requires the suspension of disbelief. Someone has to look at a two-person team with a half-built product and say “I think this could be something.” That’s the spark. Without it, the cycle doesn’t start.

Why My Starbucks Name Is 47

Thu, 05 Mar 2026 00:00:00 +0000

Starbucks asks for your name because someone in a boardroom decided it would “foster connection.” The barista says your name, you feel seen, you come back tomorrow. Beautiful theory.

In practice, they butcher it.

Unless your name is Mike. Mike collects his flat white with the quiet confidence of a man whose name has never been misspelled. The system was built for Mike.

My name is Shiyan. Two syllables. Not complicated — unless you’ve never seen it, which is everyone at every Starbucks everywhere. I’ve been Shyan. Shayn. Cyan. Shi-Anne. Once, memorably, Sean.

Forget the Deck. Watch the Founders.

Tue, 03 Mar 2026 00:00:00 +0000

Last year, I sat through a forty-five minute pitch where the CEO answered every single question — including deeply technical ones — while the CTO sat silently and nodded. Not one substantive contribution from the person who was supposed to be building the product. The deck was fine. The market was real. But that meeting told me everything I needed to know about how that company was being run.

The deck is the easy part. Market size, traction, team slide — every founder knows the beats. But the most useful information in a pitch meeting has nothing to do with what’s on the slides. It’s in what happens between the founders when things get uncomfortable.

Teach Them to Be Human. AI Will Handle the Rest.

Thu, 26 Feb 2026 00:00:00 +0000

Every parent I know is asking some version of the same question: what should we actually be teaching our kids now that AI can do… most things?

It’s not a theoretical question for me. I have three kids. The oldest is nine. By the time she enters the workforce, the landscape will be unrecognizable. So what do I optimize for?

Not coding. AI writes code better than most humans already. Not memorization. AI has perfect recall. Not even “STEM” as a blanket answer — because the rote parts of STEM are exactly what gets automated first.

Writing Code Is Dead. Long Live the Meta Engineer.

Thu, 26 Feb 2026 00:00:00 +0000

Everyone keeps saying writing code is dead. They’re not wrong — but not quite right either.

What’s dead is the value of typing code. AI writes functions faster than I can describe what I want. It has more patterns in memory than any engineer could accumulate in a career.

What’s alive — more than ever — is knowing what to build and why.

The Meta Engineer

There’s a new archetype emerging. I’ve been calling it the meta engineer.

The Art of the Group Chat

Mon, 23 Feb 2026 00:00:00 +0000

You know a group chat has gone off the rails when someone asks for credentials. “Well, what’s your background in this?” Or worse — “that came across as pretty condescending.”

The moment that happens, something’s already broken. A good group chat runs on collegiality — people sharing what they’ve learned, building on each other’s thinking, assuming good intent. Nobody’s pulling rank because nobody needs to. The ideas speak for themselves.

Three Books Every Startup Founder Should Read (That Aren't About Startups)

Sat, 21 Feb 2026 00:00:00 +0000

The best books about building startups aren’t really about startups. They’re about people — how they work together, why they fall apart, and what it takes to lead through the mess.

Here are three that I keep coming back to and recommending to founders. They’re all short reads. They’ll all change how you think about your job.

1. Leadership Without Easy Answers — Ronald Heifetz

This is the book that rewired how I think about leadership. I took Heifetz’s class at the Kennedy School, and his core idea has stuck with me ever since: the hardest leadership problems aren’t technical — they’re adaptive.

Humans Hate Change. Your Job Is to Help Them Through It Anyway.

Fri, 20 Feb 2026 00:00:00 +0000

Most startup advice is about strategy, metrics, hiring. Very little about how people feel — and yet feelings are usually what determines whether a team ships or stalls.

I’ve been thinking about this a lot lately, partly because I keep seeing the same pattern play out across startups I’ve worked with. And partly because of something I learned years ago in Ronald Heifetz’s class at the Kennedy School that I keep coming back to — his framework on adaptive leadership crystallized something I’d been struggling to articulate.

Press the Buttons, People!

Thu, 19 Feb 2026 00:00:00 +0000

My computer science grad cousin and his data scientist wife are peering at my laptop screen, looking at a little app I built — the bane of every Singaporean parent’s existence: a Chinese dictation practice tool for my nine-year-old.

I’m walking them through the prompts I used to build it in Claude Code. “How long did this take?” they ask. Less than 30 minutes.

To prove the point, I do a live demo on the spot. We build a simple app to help people learn the ingredients and auspicious phrases for Chinese New Year yusheng — you know, the “huat ah!” stuff. Five minutes later, it’s running on my laptop.

Forest City: A Ghost Town Finds Its Residents with the Network School

Tue, 09 Dec 2025 00:00:00 +0000

There is a certain irony in finding one of the most vibrant communities I’ve encountered in what was designed to be a ghost city.

I recently visited Network School, Balaji Srinivasan’s experiment in intentional community and co-living, now housed in the shells of Forest City.

Forest City sits just across the Causeway from Singapore, a massive development built by Country Garden, one of China’s largest property developers. The original vision was audacious: 30,000 residential units on four man-made islands, a gleaming city for the future. Country Garden pre-sold apartments, collected deposits, and then ran headlong into the twin headwinds of China’s property crisis and Malaysia’s political sensitivities around foreign ownership. What emerged was a monument to overreach—pristine towers, empty streets, and the eerie quiet of a place built for hundreds of thousands but inhabited by almost no one.

Chef's knife? Or Kiwi peeler?

Tue, 29 Apr 2025 00:00:00 +0000

A chef’s knife can do almost anything in the kitchen — chop, slice, dice, even peel if you’re determined enough. A kiwi peeler? It does exactly one thing, and only if you happen to have a ripe kiwi handy.

Lately, I’ve been thinking about this knife vs. peeler analogy as a way to make sense of the explosion of AI applications, startup ideas, and even how we teach kids math. There’s a big difference between building general-purpose tools and building hyper-specific ones. And in a world where flexibility and adaptability matter more than ever, this distinction is becoming critical.

How much reality should you give a child?

Tue, 01 Oct 2024 00:00:00 +0000

If you’re a parent, or involved with small children through blood or friendship, chances are you’ve been forced/privileged to observe a performance or two. Perhaps it was a song, something approximating a sporting event, or the performance of a musical instrument. Unless your child is a prodigy, most of these early performances are adorable but not particularly outstanding.

Recently, my daughter was upset because she felt that at an impromptu post-meal performance in front of family and friends, adults were more interested in their phones than listening to her sing. So - what is one to do? On the one hand, we all wish adults were less glued to their devices, on the other, to really break through and capture someone’s attention you need to think about your audience and what is compelling for them. Singing a few songs doesn’t cut it in this day and age!

Welcome 2024!

Mon, 01 Jan 2024 12:00:00 +0000

A new year is always a great opportunity to reflect and set some goals - inspired by Der Shing’s blog, thought it useful to jot down priorities and give myself a chance to check back in a year to see how well I did against my stated intentions.

Priorities

Health
- Improve sleep quality
- Improve VO2max
Relationships - Quality time focus
- Kids
- K
- Parents
Work
- Time blocking more aggressively — Using Flow Club
- Building more process/automation/async comms — Using Async & Loom
Community Building

A year of podcasting

Mon, 01 Jan 2024 00:00:00 +0000

Late last year, Jeremy Au invited me to do a weekly podcast with him, riffing on the latest news in the Southeast Asia Tech scene. Now I love listening to podcasts (Acquired, Odd Lots, Stratechery), but I had some trepidation about being so out there with my thoughts in public. I figured it would be a good way to challenge myself. (good tweet from Kevin Lee on getting over this fear)

Early entrepreneurial efforts

Mon, 27 Mar 2023 00:00:00 +0000

One of my favourite childhood memories was picking fruit from my best friend’s yard, loading up her red radio flyer wagon, and wandering around her neighbourhood selling oranges to her neighbours. We had no guidance on pricing, and no real goals other than wanting to be able to buy snacks at the pool snack bar we often frequented. Other revenue generating activities in my youth included raking leaves ($0.25 per giant trash bag) which seemed way more fun than waiting for my grandma to reward me for good grades. I’ve often wished I’d been encouraged to pursue some of these earlier entrepreneurial endeavours more, vs. being directed to study harder!

First Day of School

Tue, 03 Jan 2023 00:00:00 +0000

I’ve always loved first days - of school, work, trips - it is a moment bursting with possibility and anticipation. (and of course the school canteen, the best part of Singaporean schools)

Today was my daughter’s first day of primary school - first grade for my American readers. It was utterly adorable with all of the children lined up for assembly in the school hall with the parents seated behind the kids. This was a day reserved for the P1 students - a nice touch I thought to make the whole experience less overwhelming for the kids. They took the time to explain their two week orientation, and how they were focused on 3 specific outcomes: 1) making friends, 2) understanding teachers’ expectations, & 3) getting comfortable with the new environment.

Understanding Silicon Valley: A Discovery Operating System

Tue, 04 Jan 2022 00:00:00 +0000

This article was published as part of the book “America: A Singapore Perspective” edited by Tommy Koh and Daljit Singh. The full book can be purchased here.

Koh Shiyan and Karen Tay

Chances are, you can access this article from a smartphone right now: a device that was unimaginable for most just twenty years ago. In milliseconds, it serves up real-time directions, messages, music, entertainment and distraction for six billion people around the globe.

On building communities

Tue, 08 Dec 2020 00:00:00 +0000

I’ve been building communities all my life. In the beginning, it was accidental - I noticed that most groups were willing to do things if someone (anyone!), provided a small amount of direction, “Hey guys, let’s go to the beach and do X, Y, Z,” vs let’s all stand around discussing things we could do for 30 minutes, with everyone politely deferring to everyone else and no decision being made.

Metrics - what matters and why (to a pre-seed investor)

Sun, 16 Aug 2020 00:00:00 +0000

The idea of metrics for a pre-seed startups can feel rather oxymoronic; what does it even mean to have metrics when the business is so early? To add to the confusion, investors say conflicting things about the types of metrics they are looking for.

Forget the investors for a second - as a founder, what do YOU want to know about your business? You are smart and talented and could be doing a million other things. What things should you be looking at to validate your own ideas?

Pandemic baking and remembering how to learn

Mon, 01 Jun 2020 00:00:00 +0000

I’d taken up baking like everyone else during the COVID-19 pandemic, precipitated by a friend’s kind gift of a 3 year old sourdough starter. My first attempt was pretty sad. It didn’t rise, was weirdly dense without the holes you want inside, and the outside was pretty uneven. It’s also the first skill I’ve taught myself this year since we’ve mostly been in survival mode between work, COVID and kids.

Race, power and what we can do about it

Mon, 01 Jun 2020 00:00:00 +0000

If you’re watching the news, and face it, who isn’t, it’s disheartening to watch what’s happening in the US right now.

Yesterday, we sent a note out to our portfolio founders:

Sitting here in Southeast Asia, which has it’s own troubled history with race, colonialization and conflict, it’s been so hard to watch what’s been happening in the US.

Not only are we still dealing with the surge of cases of the coronavirus, which we know is affecting so many of your businesses, but in addition, you may have seen in the news a lot of racially charged incidents that also happened this week. This spans from a police officer murdering weaponless George Floyd to a woman threatening to call the police on a Black man who was birdwatching and rightfully trying to tell her to put a leash on her dog. These are not one-off cases, but just the latest in a series of incidents where Black Americans are the subjects of casual police brutality. For those of you who are not based in the United States, a lot of this may sound completely senseless. I, too, couldn’t explain any of this to my kindergartener. It just doesn’t make any sense.

Strategy, and why product-market fit alone isn't good enough

Tue, 26 May 2020 00:00:00 +0000

Every week I write a note to our portfolio, and in each one, I share one thought that I think is relevant for our founders to noodle on. This week’s note got some good feedback, so thought I’d share it here.

I was listening to my favorite podcast, “Invest Like the Best” where Hamilton Helmer was being interviewed about his book and subsequently spent my Saturday reading the book. Typically, I find most business books sufficiently covered in the 20 min TED talk version, but thought this book had a lot to offer startup founders. Helmer discusses what strategy is, and how all successful strategies can be boiled down to one of the 7 Powers, and in what stage of a company’s lifecycle one could be acquiring power.

Scaling - The Agony and Ecstasy of scaling a high-growth business

Sat, 02 May 2020 00:00:00 +0000

I’ve given various versions of this talk, and thought it might be worth sharing out the slides here for folks. Will add a transcript of the comments on each slide when I free up a little. Playing around with Loom so this is my maiden attempt =)!

Watch the Loom video

So you want to start a company...here's a reading list

Wed, 31 Jul 2019 00:00:00 +0000

I recently met with an incoming MBA student, who is leaving his cushy PE job for business school so that he can start something of his own. He asked if I had any recommendations on a) how to optimize his business school experience to best prepare himself for entrepreneurship, and b) if I had any books to recommend. It’s something that’s been on my mind as I’ve just finished teaching a 12 week product management class at Singapore Management University and one of the major challenges has been for me to impart the context and experiences of 20 years spent in Silicon Valley.

How to write a great investor update

Wed, 22 May 2019 00:00:00 +0000

One of my portfolio CEOs recently asked me for some examples of a great investor update newsletter and I thought that was a good opportunity to articulate the key components of a great investor update.

I mean we’re busy operating our business getting s*** done, selling to customers, building product; do I really need to spend time communicating with people who may or may not even be paying attention? YES! The answer is yes absolutely. An investor newsletter is one of the most scaled ways to communicate with your stakeholders. It is also an opportunity for you to reflect on the month that has passed, ask for help and provide signposts for what folks should expect in the coming months and quarters. A lot of investing is about connecting the dots on an entrepreneur, industry and business. Having a regular newsletter provides more intermediate data points for investors to anchor their thoughts about you, your team and your business around rather than only seeing you when you’re in the middle of a fundraising process. In our own business we write a monthly note to our Limited Partners (LPs) and we also include those who have indicated an interest in investing as part of that distribution. This has enabled us to build relationships with potential investors who were not part of Fund 1, but who are now committed to Fund 2.

Building a Product Management Community in Southeast Asia

Thu, 14 Feb 2019 00:00:00 +0000

Picture: From L to R, Shiyan Koh (Hustle Fund), Radhika Dutt (Radical Product), Anna Gong (Perx), Reshmi Roy (Skyscanner)

Last night, I had the privilege of moderating a panel hosted by Women in Product, where we explored what product management was to our panelists, as well as perspectives on growth, metrics, localisation and careers. It was a broad-ranging conversation, appropriate given the wide range of experiences of our panelists. We probably could have spent 30 minutes on each topic alone!

Why I decided to join Hustle Fund

Tue, 11 Sep 2018 00:00:00 +0000

After almost 6 years at NerdWallet, and having had the chance of a lifetime to build a business from scratch with my friends, I was looking for something that would engage me in a similar way. In Drive, Daniel Pink writes about Autonomy, Mastery and Purpose as the key elements of intrinsic motivation, and I realised the NerdWallet experience was special because it hit all these intrinsic motivation buttons:

the feeling that we were solving a big problem, bit by bit (Mastery)
we were helping real consumers (Purpose), and
we were charting our own path every day (Autonomy)

In joining Hustle Fund, I have the opportunity to build an asset management business with two great friends that I trust and respect; invest in a region that I’m extremely bullish on, and work with smart, motivated people every day who are trying to build big, sustainable businesses. Eric, Elizabeth and I believe that we are at the beginning of a multi-decade journey to build an investment firm that is firmly focused on enabling all entrepreneurs, regardless of resources or location, a shot at receiving funding and coaching. We are obviously just at the beginning of this journey, but it feels amazing to have vision alignment with partners.

What I've been doing since leaving NerdWallet

Wed, 05 Sep 2018 00:00:00 +0000

After nearly 6 years building NerdWallet, I left at the end of March to move back to my home country, Singapore. It’s been nearly 18 years since I first arrived in the US to start university at Stanford. I never imagined I would be here so long, and now it’s time to begin navigating my return.

My motivation: I have an almost-two year old daughter - I want her to experience growing up in a safe place, surrounded by family in a geography that is poised to experience a ton of secular growth. I want her to know what real char kway teow tastes like =). I don’t want to worry that she’s going to be shot in school by some crazy person. =(

Communities and the Cul-de-sac

Wed, 24 Jan 2018 00:00:00 +0000

“Wouldn’t it be great if we could all be neighbors with our best friends? We could come home from work, trade stories over a glass of wine while watching our kids play together?”

This is the vision I tried to sell my college friends after we graduated, because once we scattered to the far-flung corners of the world, or let’s face it, once some people moved to the East Bay, it became increasingly difficult to get together on a consistent basis. With every additional child, the logistical coordination burden becomes even more overhead. Which means you see each other a few times a year even though you may live geographically not that far from one another.

About

Mon, 01 Jan 0001 00:00:00 +0000

Shiyan Koh

Singapore-based early stage VC @ Hustle Fund.

On the board of Stanford Club of Singapore, Stanford Rugby, and Q Chamber.

Previously @NerdWallet, @BridgewaterAssociates, @IVP, @JPMorgan.

Mother, Wife, Enthusiastic reader and thrower of dinner parties.

Twitter @shiyankoh · Threads @shiyankoh