Hsu Ken Ooi is the Co-founder and Managing Partner of Iterative, a 12-week YC-style startup accelerator for SEA. Before Iterative, he was the Co-founder of Decide, a price-forecasting startup acquired by eBay.

🎙  How would you explain your job to someone outside tech?

My job is to raise $ from one group of people and invest it in another group of people building things people want.

When I was a founder, as sort of a joke, I would tell my parents that "I build the internets." Now, most people know what an investor is. For people who are into Korean dramas, I tell them I'm like the investor in Startup.

🤨  What's something about you or your job that would surprise us?

Sometimes hard to tell what is surprising to people, so here are a few:

1. There's no even semi-rigorous formula to early-stage investing. It's not like a checklist where if a startup has X, does Y, etc., then you invest. It's highly contextual.

2. I used to be a semi-professional Counterstrike player in college.

3. I almost failed the 8th grade, ran away from home and was generally a nightmare of a teenager.

🏅 What has been the biggest highlight of your career so far, and why?

Tough question. Most people assume it's selling one of our companies, but I honestly can't even remember what happened on those days. I can't think of the biggest highlight, but everything that comes to mind shares the same ingredients. It's (1) the beginning or middle, never the end, (2) it always involves being with others and (3) after some kind of adversity.

🤓  What's a startup trend or space you're watching this year?

I mean, everyone is watching Web3. I often think about investments in terms of a statistical idea called Expected Value. You calculate expected value by multiplying the probability of success by the magnitude of the success. I've never seen something come along with the potential magnitude of success as Web3. Chances of it being everything people say, I don't know, probably low. But if it's even half right, wow.

🎓  What advice would you give someone starting out in your industry?

Get in the game. If you want to start a company, build something that someone (anyone!) might want to use. Don't worry about market sizing, business model, etc. Just build something people want. Nothing happens if you're not in the game.

🗣  What's one thing you can keep talking about for hours?

This is going to be hugely nerdy, but I could talk about the implications of Godel's Incompleteness Theorem for hours. Problem is, no one wants to talk with me about it for that long.

🎬  What's your favorite movie/TV show?

Futurama but more recently Rick and Morty.

🍨  What's your go-to ice cream flavor?

Salted, Malted, Chocolate Chip Cookie Dough!