Hsu Ken Ooi: from Rebellious Child to Chief Product Officer and Accelerating​ Southeast Asia's Startups - E8

· Founder,Singapore,Popular,VC and Angels,Podcast Episodes English

Notable Quotes

“I always make the joke with friends that the two things that have taught me most about myself are relationships and startups”

“If you want to go fast, go alone. If you want to go far, go with others”

“One of the things that I try to do with that leadership part is that: appreciate that they are making a choice to follow me on this. I'm not forcing them to do that. They are making that conscious choice themselves.”

“For startups, specifically, there's just a lot of doubt, self-doubt. I don't know how much founders talk about this. This is something that I want to address at Iterative, is that we need to build safe spaces for founders to be able to talk about the self-doubt.”

“Honestly, a part of my thesis for why we're doing this in Southeast Asia is that I find no difference in terms of raw material or intelligence or work ethic or any of that between founders in Singapore and founders in San Francisco.”

“To get started you just need to find a problem that some people have and honestly, in the beginning, don't even worry about how big of a problem it is. Just find some group of people who has some problem that they feel acutely and solve it for them. And I want to make a note of my formulation of what I just said. At no point did I say product, and at no point did I say software.”

“My mother is the dreamer. I don't think I would be doing startups without my mother's attitude towards stuff. She was the one that was like, “You can do anything that's possible," which is very cliché, but also a great thing for your mother to tell you. My dad was the one that was like, "Okay, if you're going to do that thing, here are all the things you need to do. Here's all the hard work it's going to take.”Bio

Hsu Ken Ooi is the Co-Founder and Managing Partner at Iterative. Iterative is a Y Combinator-style accelerator focused exclusively on Southeast Asia. In their latest batch, they chose the top 9 companies out of over 300 startup applicants. The domains range across proptech, fintech, direct to consumer and logistics.

In 2009, he co-founded Decide.com with Hsu Han Ooi, Brian Ma and Ian Ma. Decide.com was an early machine learning company that predicted the future price of consumer goods. It raised over $16M total funding and was acquired by eBay in 2013. Since then, his other tech executive roles include being the Chief Product Officer at Workmate, an on-demand blue collar staffing platform in Southeast Asia that has raised over $10M total funding. He was formerly VP of Product at Weave. Weave was a platform that delivered a personalized professional introduction every week and was part of the YC summer batch of 2014.

Hsu Ken has a Bachelors of Science in Mathematics and Statistics from the University of Washington. His hobbies are books, cooking, and football. You can find him on Twitter at @hsukenooi.


(01:47) How Hsu defines his leadership style

(09:40) Getting started in building a company

(16:02) Most common challenges in starting up

(19:13) Common Myths about startup success

(25:04) Hsu’s role models

(31:28) Why focus on Southeast Asia?

(33:37) Key resources before you startup


How Hsu defines his leadership style

  • Don’t dismiss leadership 🙂: Hsu initially felt like leadership and management were a “waste of time” in a team of smart folks. However, as his first company grew, he realized smart and ambitious people needed direction and a sense of where they fit into the bigger picture. This wasn’t easy and he learned on the go, making a lot of mistakes on the way. There is a meta-game to managing, which means being adaptable and open to feedback.
  • Teams make the dreams work: Putting smart people in a room does not make magic happen automatically. Admit that you're not good at everything and that you need help from others. Remember that everyone on the team has a version of leadership, even if they're not the CEO.
  • As a startup founder, your primary role is to recruit people around your vision and to inspire them. Rally everyone around this vision so that they contribute their full energy and talent.
  • Propose, rather than dictate, plans: When creating a roadmap or plan, propose it to your team members and invite their feedback. This shows your appreciation for their perspectives and allows everyone to agree on the direction of moving forward.

Getting started in building a company

  • Build things out of passion: Hsu Ken started his career as a consultant but felt unfulfilled, so he began working on nights and weekends to build various projects, simply to get the practice and understand every aspect of creating a website, which mean setting up Linux, Apache on his home PC.
  • Find the right partners: It's not easy to find folks sincerely interested in working on a startup, and many of his friends didn't show up when invited to work together. Hsu's brother interestingly connected him with Brian Ma (because of Guitarhero) who then shared similar morals and interests, and being open made them come together and startup!
  • Get comfy with setbacks: Hsu and Brian built many products that didn't go anywhere for ~2 years, with some not even managing to get a single sign-up. Despite encountering such challenges and working from a basement, Hsu's startup managed to raise a couple of million dollars. The early days of "grinding it out" became valuable.

Challenges / Hurdles Faced by Hsu

  • Self-doubt in starting up: Universal among founders and needs to be more talked about. Hsu Ken felt small when he saw his friends progressing in their corporate careers while he was struggling as an entrepreneur. His realization that his actually having fun building the startup despite the worries gave him his true north compared to his peers.
  • How to cope with self-doubt: He never completely extinguished his self-doubt, he has learned how to build environments and frameworks to efficiently operate with it.
  • He does meditation as a means of achieving distance from self-doubt
  • Catches himself recognizing it as a temporary feeling and not a defining characteristic of himself.

Common Myths

  • Overnight success is a myth: eg Notion, which has been around for seven years. Success usually comes from consistent hard work rather than sudden breakthroughs.
  • Silicon Valley founders are not inherently more gifted: There may be a perception that founders from Silicon Valley or San Francisco are "wonder kids," but in reality, there is no significant difference in intelligence or work ethic between them and founders from other regions. The main difference is the level of ecosystem development and support available in each location.
  • Rebellion is ok: Hsu Ken’s past rebellion against authority and expectations in school eventually led to his personal development and success in startups.
  • Get deep with personal desires and goals: When Hsu Ken’s parents expressed that they no longer cared about his decisions, it allowed him to take control of his life and make more deliberate choices.

Role models in life

  • Hsu is not a celebrity person, so he won't say the Elon Musks or Bill Gates's of the world :)
  • For him, it was his parents. Coming from humble backgrounds, worked hard to provide a good life for their children. He admires their courage in taking risks and stepping into unknown territories, such as moving to a new country.
  • When Hsu shared his Wall Street Journal feature with his mother, she told him she was proud of him long before his successes
  • Hsu's father worked his way up over 20 years to eventually run all of Intel's worldwide manufacturing. This same drive and ambition seem to have been passed down to him and his cousins, who have all pursued entrepreneurial ventures in various industries like anime and technology.

Why Southeast Asia

  • The region's startup ecosystem has grown significantly and offers numerous opportunities for entrepreneurs to build successful companies. This is reminiscent of China's explosive growth 10-15 years ago.
  • However, founders in the region do not have the same level of support as in Silicon Valley, making entrepreneurship here a courageous endeavor. Engaging with and helping local entrepreneurs could have a substantial impact on their success.
  • Hsu Ken Ooi's Y Combinator style Accelerator Iterative provides the SEA context and assistance to local entrepreneurs.

What support is available to others

  • Read Marc Andreessen’s blog on pmarchive.com
  • Explore Paul Graham’s essays, particularly “Do Things That Don't Scale” which emphasizes the importance of not focusing solely on scalability in the early stages of a startup.
  • Get out there and solve problems: Startups are primarily about solving problems, so focusing on that aspect will help entrepreneurs learn and grow in their journey. Notice that he does not say product or scaleability or software or fundraising. or anything else but solving a problem.


(01:46) Jeremy Au:

Hey, Hsu Ken, so good to see you.


(01:49) Hsu Ken Ooi:

Good to see you too.


(01:50) Jeremy Au:

It's really interesting to see you really focus on building up this accelerator for Southeast Asia. We've heard such good things about it.


(01:58) Hsu Ken Ooi:

Yeah. The response has been amazing and I’m really excited to get to meet more entrepreneurs and work with entrepreneurs in Southeast Asia.


(02:05) Jeremy Au:

So, for those who don't know you, how about sharing your leadership journey?


(02:10) Hsu Ken Ooi:

I thought leadership was a waste of time, to be honest. I thought about it as almost corporate brain washing. I thought that if you get a couple of smart people in a room together, there doesn't need to be any leadership. And there definitely, doesn't need to be management. Management to me was a dirty word. It just seemed to be a way to control people. So, there was no leadership journey to start, at least consciously. But I think as you start companies and those companies start growing, you are naturally drawn into those roles and you have to kind of fit into those roles. Honestly, at the first company, I did what I thought was the thing that I was going to do, which is we hired a bunch of people, I got them all in a room, and I was like, "Great, make magic happen." And nothing happened. Right? And it wasn't so much how they did stuff.

They actively came to me and were like, "Okay. Well, what are we going to do? How are we going to do it? How should I do this?" These were very smart, very ambitious people. they were looking for help on how all of this was going to fit together. That totally just threw my perception of what management meant. The thing that I viewed as management, it was just very bad management, which was very much just like, "Do this, don't ask questions. You don't need to know why it's that case. Just do what I tell you. I don't need to explain anything. the thing that has become kind of clear was that, when you work with very talented, very smart people, they care a lot about why they are doing the things that they're doing. They care about where they fit into kind of the bigger picture.

And I think the progression for me was that first company, I threw a bunch of people in a room, nothing happened. And then I had to throw that view of the world away and then get to work of like, "Okay, so I guess we should make teams and we should have reporting structures. Okay, how does that work?" But at the time we started that company, I was 22. We worked on it for six years and it grew to about 40 or 50 people. And I think those couple of years where it was growing really fast was just, honestly, me trying to keep up with the speed. I felt I was getting to some level of management, kind of know-how for the stage that we were at, the company would accelerate. I was totally out of my depth, right? A 10 person company is very different from 25 person company and then at 50 it's kind of this whole another thing. So, I was constantly just got comfortable, then having to accelerate and learn again and kind of making lots of mistakes along the way.

At the second company I sat down before we started that company and was like, "Okay, here are all the list of things that I did wrong as a leader and a manager in the first company. I want to do them differently in the second company." The thing that I learned at that second company was I didn't make the same mistakes at the second company, some are the same, but you just end up making newer different mistakes because every company is so different. The people that you work with are very different, everything is different.

So I think after the second company, it was very clear to me that you can't treat leadership like some sort of whack-a-mole game. That's like, "Oh, there's only 20 mistakes that you make. And as long as you don't make these 20 mistakes it works." It doesn't work at all. And the thing that came out of the third company was you want to get good at the meta game of managing, which is like, "How do you get good at being good and improving at being a manager?" That is when it really kicks in, right? So, you're going to make mistakes as a manager. How do you get yourself in a place where you recognize that you need to make a change? How do you go about making that change quickly and kind of in a considered fashion? And then how you communicate that.

So there's that whole process around how to do that. And getting good at the process is a much more valuable skill than knowing what things not to do and not making those mistakes. It's a much better approach to that. So, that's kind of where I am now, is getting good at that part.


(05:49) Jeremy Au:

Wow. That's quite a journey. How do you find leadership important for yourself and your peers?


(05:57) Hsu Ken Ooi:

I came from this place where I didn't think very much of it, I didn't think that highly of it. I think the saying that encapsulates how I feel about it now is that, "If you want to go fast, go alone. And if you want to go far, go with others." And honestly, my personality, I think as an introvert is like, "I just kind of want to do everything alone. I'm much more comfortable that way." The thing that I've learned is that you just can't do anything that ambitious by yourself, if I'm being honest. You need help from other people. And you need help, not just because there's not enough hours in a day, you need help because you're not going to be good at everything.

I'm not necessarily good enough at everything I need to be good enough in order to accomplish the things that I want to accomplish. And so, you have to lean on other people to kind of do that. So, anytime that you are bringing other people into the fold, there is some version of leadership. And leadership is not only just being the CEO. Right? I think everybody has some form of this. Where it becomes important, especially with entrepreneurship and startups, is your primary role is recruiting people around this vision that you have. And you're doing that constantly, right? In the beginning it's like, "Okay, I have this idea. How do I get people excited about this?" Which is an inspirational part, which is really important to get in the beginning.

Once you have the people it's like, "Okay, how are we going to all work together to make sure that we are putting all of our force and effort into one direction." Sometimes when I think about teams, and sometimes they're my teams, are not going well it's like, "We're all pushing in the relative right direction, but we have 30% loss because some of the force is going tangential to that." So, it's not all going up the hill. We're kind of going sideways. To me, especially in startups, it can be summarized as, you need to be able to recruit and inspire people and rally people around this vision that you have. Then you need to be able to get people into the right spots, in the right roles so that they can effectively spend their energy in doing that.

The last part that I personally take a lot of responsibility for is that, when people come join me or a company or somebody on my team, they are lending me their time and their talent and energy. I take that responsibility seriously because they don't have to do that, right? There's lots of places that they can do that. They have spent a lot of time cultivating those things over the course of, literally, their life. One of the things that I try to do with that leadership part is that: appreciate that they are making a choice to follow me on this. I'm not forcing them to do that. They are making that conscious choice themselves.

Sometimes I have to make some roadmap, like a product roadmap or something, let's say very tactically, right? I actually call a meeting, a proposal meeting. What I'm going to do in the meeting is I've put together a roadmap and I'm going to propose it to everybody else on the team. Proposal is a really important word because I'm not saying, "Hey, I'm going to decree from the mountaintop this is what you all are going to work on." I'm proposing it and I'm making my case that this is something that we should all spend our energy in doing. I want to hear feedback on that. Now, I'm not a consensus-driven person. I don't think consensus, all the time, will get you the best results.

But I do think that people appreciate that kind of respect where you're kind of going to them and being, "I don't take what you guys are doing for granted. I'm going to propose what I think we should do. I have good reasons for it. We should have a conversation around those reasons. After that, we can agree and move forward." But that's something that I've carried with. We started doing that at the second company in response to a problem that we had at the first company. And I've carried that into every company. And that process of, "Hey, this is a proposal. I'm coming to you. You guys are my investors. You guys invest with your time and energy. And I want to make this case to you." But honestly, startup founder is mainly just this, right? You're recruiting and you're getting people aligned around things. So, there's probably nothing more important than the leadership aspect of it.


(09:40) Jeremy Au:

It sounds like you've really done a lot and learned a lot. Take us back all the way to the beginning. How did you personally get started in the journey?


(09:49) Hsu Ken Ooi:

So, I've been doing startups for almost, I don't know, 13 years now. I can remember those first two years so vividly. Most of the stuff in the middle just kind of go by really fast. For whatever reason, the first few years I could pick out everything about it. So, I graduated from school and I wanted to always build stuff. I was just trying to figure out, what do people who want to eventually start a thing do? I ended up being a consultant. I was basically making a lot of PowerPoint presentations and it wasn't what I was looking for.

I wasn't building stuff. When you're a consultant, you may work on a project, you may make a recommendation, the client may or may not take that recommendation. Even if they take the recommendation, you kind of roll off that product. So, you never see it through. It was not the experience that I wanted. Since I wasn't getting that from my actual job, I was spending all my nights and weekends building stuff on the side. I remember building all kinds of really dumb ideas. To be honest, I just wanted to get the practice of building, I didn't actually care what the ideas were.

So I remember one time, one project I was working on, I wanted to know what it was like and what it took to make a website on the internet from start to finish, all the way through, nobody helps with anything. But back in the days, this was 2008, I had to set up a server. There was no AWS. I literally set up a server, installed Ubuntu onto it and configured Apache. I wanted to know every step of it because it just was this thing that I cared about it So one of the nights I was working on it really late, it was five or six in the morning by the time I realized it. I just remember an overwhelming feeling of annoyance in having to go to work. I recognize that's a ridiculous kind of feeling to have. Everybody has to go to work. Everybody goes to work every day, I just felt so annoyed that I had to go to this job that I frankly didn't care about. I was just annoyed by it. "If this is the rest of my life," I was 22 or 23 at the time. "If I've got 25 years of this, I don't know if I'm going to make it right? I don't know what's going to happen, but I don't know if this is going to work." And so, I remember getting changed and I was a consultant, so I got to wear some button up shirt and I got to put on some nice pants. I got to do all this stuff and I'm riding the bus to work.

And I remember the entire time being, "Is there a way to not have to go to work? At the time I was like, "Oh, startups seem to be a way to make a livelihood and do the thing that I really like to do." like, "Okay, I guess I want to do a startup." Honestly, I had no idea what a startup was. This is 2008.

I was living in Seattle at the time. I didn't know anybody that worked at a startup. I think somebody sent me a TechCrunch link once. So, I started trying to find friends to work on this startup with me. And the thing that I found was, I would talk to my friends about, "Hey, we should work on a startup." A lot of friends were like, "Yeah, we should totally work on a startup." And I was like, "Great, Sunday afternoon. Let's meet at this coffee shop and let's work on a startup for five hours." I would show up Sunday afternoon in a coffee shop. No one else would show up. I just remember being very frustrated and surprised, "Why weren't people taking this as seriously as I was?" And just being disappointed over and over.

This was a thing that I really cared about and nobody else seemed to kind of care about it. Fortunately, I have a brother who is the best engineer that I know, still is the best engineer I know. He was working at a startup called Zillow. Zillow is one of the first property sites in the US. But when he started there, they were pre-launch and about 40 people. When he was working there, he kept telling me about this guy named Brian Ma. At first the stories of Brian Ma were, "Hey, there's this guy that I play Guitar Hero with. He's really good at Guitar Hero and I'm really good at Guitar Hero, and it's really fun." And I was like, "Great, fantastic. I'm glad that you have a friend at work to play Guitar Hero with."

So then one day he was like, "Hey, remember that Brian Ma guy I've been telling you about?" I was like, "Yeah." He's like, "Oh, he's going to quit." I was like, "Oh, okay. Well, what is he going to do?" He's like, "Oh, he's going to start his own company." I was like, "Oh, that's interesting. What does he think he's going to do?" He's like, "Oh, I don't know. He's got this idea or whatever. He wants me to do it with him." And I was like, "Oh, are you going to do it? He's like, " I don't know. I'm going to tell him if he gets funding, I'll quit. But I don't know. He wants to come over and pitch me." I was like, "Oh, well you should listen." He's like, "Okay." And then a couple of days later, he calls me, and he was like, "Hey, so Brian's going to come over. I told him that you are interested in startup stuff. And he said, you should come over." And I was like, "Okay."

So, I go over to my brother's house, Brian Ma is sitting there. We're sitting in his couch and his TV and Brian walks us through this 60 slide deck of his idea, and we don't ask any questions because frankly, none of us know anything enough to ask questions. We just had no idea. We were like this is the first time I've ever had anybody pitch me anything. At the end of it, Brian's like, "Hey, you guys should work with us." And I was like, " Okay. Well, maybe we can do this Sunday thing." Because that had been my test at the moment, was like, "Will you show up on a Sunday, basically to work? And if you're going to show up on Sunday."

So I was like, "Okay. Well, next weekend let's show up on the Sunday and we can work on it." He was like, Great." So, he's like, "Okay, let's meet up at your brother's house Sunday. And we're going to meet at one o'clock." I said, "Great." So, I show up at one o'clock on Sunday and Brian and his brother are there. they've been there for a while. And I walk over he’s like, "They've been here since 10:30." And I was like, "What?" "They've been here since 10:30. They just said they got excited. So, they came over and started working." I was like, " Oh." Honestly, at that point I was in. I have finally found people who are as excited about this as I am. I don't know them very well, frankly and I don't know if I would give other people advice on finding co-founders this way. But I was just in, there was a thing that I wanted to do. Now there were people who took it seriously like I did. So honestly, that was it. We just started working together from then. we all quit our jobs. We all worked on it full-time. We worked out of my brother's basement. We spent two years building all kinds of products, probably two dozen that honestly didn't go anywhere.

I remember, distinctly, one of our products didn't get a single signup. We couldn't get our friends to sign up. Nobody signed up. You reach a new level of low when you build a thing and you can't get a single sign up, not one. And that was us.

I can say the rest is history or whatever, but we got lucky and we raised a couple of million bucks, and we went into the next stage. But those were the early days, humble beginnings kind of grinding it out for two years. And that was really valuable to us.


(16:01) Jeremy Au:

Amazing. What hurdles did you personally face? And how did you overcome them?



(16:05) Hsu Ken Ooi: Gosh, there are so many hurdles. I always make the joke with friends that the two things that have taught me most about myself are relationships and startups. For startups, specifically, there's just a lot of doubt, self-doubt. I don't know how much founders talk about this. This is something that I want to address at Iterative, is that we need to build safe spaces for founders to be able to talk about the self-doubt. I felt it very acutely the first time around. We spent two years building stuff, right? And we built a product that no one signed up for.

When we spent those two years, I didn't make any money and I didn't have any insurance. We didn't turn on the heat in my brother's house because we were trying to save money. I literally sat in a folding chair at a folding table and we brought in sleeping bags. So, we sat in a sleeping bag while we worked, because we were so cold because we couldn't turn on the heat.

I watched all of my friends progress. They were PMs at Google, and they were becoming senior PMs. They were moving up this corporate ladder and driving nicer cars. I was going to work in the freezing cold in my brother's basement. I had gone through life and gone through school, it's structured and people pat you on the back and you go to work and there's a manager who's giving you feedback all the time and telling you on the right path. You start a startup, none of that is true, there's no structure and no one's patting you on the back.

I started wondering whether I was the right person to do startups and be an entrepreneur. I didn't know any other entrepreneurs at the time, and I didn't know any other founders. There were a lot of days where we would build a thing and I would pour everything into it. It would take us months and we would launch it, and no one would sign up. I would go home and be like, "What am I doing with my life? Are we ever going to get there? Am I the person who is on a desert Island trying to come up with a theory of relativity, but just hasn't realized that I'm not capable of doing that, but everybody else has realized that?"

I think the thing that kept us going was, we just seemed to be having more fun than them, if I were being honest. They never wanted to really talk about their work as much and we just couldn't stop talking about it. Even though I didn't drive as nice of a car, it just seemed I was having a lot of fun hanging out with my friends and doing this thing. And so that kept us going.

You have to figure out a way to cope with that on some level and continue. I'd love to tell you that, that has gone away, but it honestly hasn't. Three startups in. Sometimes I'm sitting in things I'm like, “I don't know what I'm doing. I don't know." The thing that I've realized around that personal journey, around the doubt thing is that, you're just never going to extinguish it.

So the name of the game is, how do you build environments and frameworks so that you are able to operate efficiently with that doubt? I've been a big meditation person for a long time. I used to not want to admit to myself that there was doubt because if I admitted that there was doubt, that meant it was real, which made the doubt worse. And so, the thing that I've taken from meditation is that, it's better to admit that there is doubt, but recognize that you are not your doubt.

Doubt is the thing that you are feeling. It is temporary. That is the thing that you're feeling at that moment. You are not the doubt, right? That's given me some kind of distance between, this is a feeling that I have, just like anger or sadness, these are all feelings that you have, but they're not me. That was the biggest thing to overcome for me personally. It's still something that I work with now.


(19:13) Jeremy Au:

What are the common myths that you've encountered so far in startups?


(19:18) Hsu Ken Ooi:

Gosh, I feel there are so many startup myths these days because the press has gotten a hold of startup culture and loves to push myths on stuff. I will give you the very general myths and then I'll work on the, not as typical myths. So, the general myths around overnight successes and stuff is just not true. Having been in Silicon Valley for a while, they just don't happen.

You may hear a story about a founder who had made a thing and then in three months It's like, "Oh, Clubhouse, they've only been alive for three months. They haven't even launched publicly, and their industry is at a hundred million dollar valuation." The facts of that are true, but those founders have been working in that space for a very long time. They've been building those networks over a very, very long time.

Notion's actually been around for seven years. They're having their moment right now, but they've been around for seven years. That guy has been grinding it out as a solo founder for seven years. So, this whole idea of overnight success is totally not true. And I think people have talked about it, but in my experience also kind of not true. I think maybe the less common myth, maybe this one is personal to me, is, I think sometimes, and it's been interesting to come back around to me, is that I'm originally from Southeast Asia.

So I was born in Penang. My whole family's from Penang. My parents still live in Penang. I moved to the US when I was five. That's how I got a very strong American accent. So, when I tell people I'm from Penang, nobody believes me. I speak Hokkien, which is very funny to people because it's Hokkien, but with an American accent. So, I went to the US when I was five, but I used to spend every summer in Penang. So, it was nine months in the US when it's school and then three months in Penang living with my grandmother. And so, it's been interesting kind of having that experience living in the US. Then living in somewhere like Silicon Valley and then moving to Singapore and getting involved in startups here. One of the things that sometimes I get a sense of from founders in Singapore is that San Francisco people or founders are some kind of a wonder kids. They're God's gift to everybody.

It’s just not true. There's lots of very smart people there. They're very ambitious and all of that. Honestly, a part of my thesis for why we're doing this in Southeast Asia is that I find no difference in terms of raw material or intelligence or work ethic or any of that between founders in Singapore and founders in San Francisco. The only difference to me is just that the ecosystem here is less developed. So, it doesn't support that raw material as much. I think my story is probably a case in that too. I didn't do really well in school. I was very rebellious. I don't know what it is in Singapore, but in the US it's eighth grade, which is right before you go to high school. On the last day of junior high, I very vividly remember I went to my eighth grade teacher and I was like, "Did I fail the eighth grade? Do I have to do this again?"

She just laughed, and she goes, "No, they would have told you that a long time ago, but you are close." I was like, "Oh, okay." I was just very rebellious. I know Singapore, there's some very big tests in Singapore student life here, and this is probably blasphemy, but I would literally skip school on test days. Only test days. It was me proving to everybody that I was the one in control and I was rebelling to my parents. Just complete hatred. Again, some contexts, my dad skipped three grades in school and I'm his eldest son. I'm sure it's like this in other Asian families, but Chinese families, that's a sin. For his eldest son who he sacrificed everything for and move to another country that has, “more opportunity”, to just not show up for school. So that caused a lot of friction. My parents had grounded me, and they kicked me out. I'd been caught sneaking out and all of this.

I remember that summer. I was halfway through high school and they sat me down and they said, "Look Hsu Ken, we have tried everything. We have gotten you tutors. We have grounded you. We have done everything. From this point on, this is your choice. We feel we have done everything and more that you could ask of parents. You don't want to go to college, don't. That's on you." The funny thing that happened was, they took away the thing for me to rebel against.

Basically what happened, those next few years I had a 4.0 GPA in high school. The reason why is because after they had that conversation with me, I didn't have anything to rebel against. Then I had to sit down and be like, "What do I want?" So, it's no longer what do my parents want? It is no longer what does society want of me? They've all basically said, "We don't care." When I got to the point where I was like, "What do I want?" I was like, "Oh, actually going to college is probably a good idea." so, I kind of got to work in doing that. Even in college, I did pretty well. I went to a pretty good school. I didn't go to Harvard. I went to the University of Washington.

That bit of rebellion helped me a lot in life in the sense that, from that age I started now thinking about the world and what do I want to do? What do I want to get out of it? Not what my parents want me to do, not what society wants me to do. I think having that agency for yourself kind of from an early age is helpful. The other part too is that, when you fail a lot early in life, you don't need to be perfect anymore the rest of your life, because you've just failed a lot. I'm not actually naturally that good at many things. When I do hard stuff now and I suck, and I always suck, I'm always just like, " Okay, cool. This is the process, you suck. Okay, how do I not suck? How do I get better at this thing?"

This is something that I tell, especially new college graduates that work on my team, they always ask questions about, "Oh, how do I get to a pay raise?" These are very tactical questions. I would say, "Stop. It doesn't matter that much whether you know all these technical things. The thing that you want to get good at, is you want to get good at being good at things." That's the game. That's especially true if you want to be an entrepreneur. You are always going to be doing things that you suck at and you don't know how to do. So, the best skill that you can learn is, how do I get over the fact that I suck at this thing, and how do I get to work on getting good at that thing? I feel my experience in Silicon Valley is, there's a very direct correlation between the very good founders and their ability to be good at that. That is a really important thing that I learned from a young age, just because I just wasn't naturally good at stuff.

So, I'm not surprised when I suck. I have some friends who are very talented, and they're surprised when they suck. And they don't know what to do because they're so used to being good. When it happens to me, I'm like, "Okay, that's fine."


(25:04) Jeremy Au:

Yeah. So, who are your role models in real life?


(25:08) Hsu Ken Ooi:

Role models in real life. I'm going to give a really cheesy answer, but I'm going to make it very specific and personal. Honestly, I'm not much of a celebrity person. So I won't say the Elon Musks of the world and the Bill Gates's, although I feel they're all kind of great. Honestly, it's my parents. Let me talk a little about why that is, especially for me. My parents didn't grow up with very much. My mom was one of ten. I think my dad was one of seven. My dad grew up sharing a room with six of his brothers and sisters. They did not have much. So much so that neither of them went to college. Frankly, because they couldn't afford to. My dad was the second eldest brother. Jeremy, you might know a bit of this too, but especially that generation, the older kids tend to not have as much money.

So they didn't go to school, they would go to work first. The older siblings paid for the younger siblings' education. So, my dad was the second, so he didn't. My life has an insane amount of advantages compared to their life. They were just two kids from Penang who didn't grow up with very much. To cut a long story short, they ended up in America. My dad started working at Intel in the late 1970s and he was originally an accountant. Then he ran one of the lines in the manufacturing factory. Then he ran a room in that factory. Then he ran the factory and then he ran Malaysia's factory. By the time he retired, in I think 2000, he ran all of Intel's worldwide manufacturing.

So all semiconductors and all chips built by Intel during the nineties, came from a factory that he ran. he used to tell me really great stories about his direct manager. I think from the topic of this podcast, probably a lot of people have read “High Output Management” by Andy Grove. A management tome now, right? Everybody reads it. My dad's direct manager was Andy Grove for 10 years. Gordon Moore from Moore's law, he used to have to go to a biweekly meeting with Andy Grove and Gordon Moore and explain why Intel couldn't produce more chips. I remember as a kid, he would just tell me, "Oh, Gordon Moore and Andy Grove." I was a kid and I just was, "This is my dad's work friends." I didn't care. When I got to college and I was reading computer science books I'll be like, "Oh, Gordon Moore."

I remember calling my dad and be like, "Hey, so I'm reading about this guy named Gordon Moore and Moore's law. That can't be the same guy that you're talking about." He's like, "It's the same guy." I was like, "Why didn't you tell me he was important?" He's like, "I tried to tell you all the time. You were seven and you don't care." So, I think that their story of where they come from and my father playing a part in this whole computer revolution and my mother having to take care of us and play a lot of the familial roles while my father's doing this stuff.

They had never left Malaysia before. And then they moved to Jamaica for three years, or Barbados for three years. I was almost born in Barbados, I would have been Barbadian. The joke I like to say is that Rihanna and I would have been friends. The joke that comes after that is, I'm 10 years older than Rihanna. We definitely would not have been friends. My mom used to tell stories of the late seventies in Jamaica, the number of Asian people in Jamaica at the time was a handful. She went to the market on one of the days, it was the first time that they moved there, and there literally was a crowd of people around her touching her hair and lifting her up in the air and being like, "Look at how small she is." The amount of just unknown and risks that they took, to me, that's just amazing. None of the risks that I've taken, starting companies, blah, blah, blah, can match that. That's so amazing and I'm very thankful to be able to have my part in that. I'll share another story about my family with this.

I'm not the only entrepreneur in my family. My brother started the first company, but actually there's two or three other founders within my extended family, my cousins. If you're into anime or Korean dramas, and if you ever watched Crunchyroll, my cousin is actually the founder of Crunchyroll from way back when. They sold it a while ago. He's also the director of engineering at Hot or Not way back in the day, which is just hilarious to me. I have a Hot or Not t-shirt from back then, which is awesome. And we all got together one day, and my parents always give us a really hard time about, " Why can't you guys get normal stable jobs? We worked so hard to bring you to America so you would work normal, stable jobs. And all you guys can do is quit your jobs," and "start companies but basically not make money for years." We were talking about it once.

I think it was really interesting, we all had the same answer and we just had never talked about it before, which was, we felt they did the hard work of getting us into this position to have the opportunity to do these things. I don't have to get a stable job. That is a complete privilege that I completely owe to my parents. Maybe this is partly a cultural thing, but I think of family in generational terms of like, "What can you do for the family?" And we all had the same feeling, which was like, "Look, you guys got us into this position. It is now our responsibility to take risk and to try to get the family into the next part." We all felt that way. Look, we could just go get jobs. Maybe this is a story I should tell at some point, but before starting what ended up being Decide, I basically turned down being the second PM at Gmail.

They flew me down there and went through the whole list of interviews. I turned that down. This is 2008. I think the Google shares would have been very valuable if I had joined that at the time, it would have been a really good experience. But I just felt my parents had done this thing and it's really important for us to kind of carry on with that. And so, it's our generation's turn to make good on these opportunities that they've given us. So, I think that the Elon Musks and Jeff Bezos's of the world are great. I learned a lot from them, but my primary role models are my parents. I like to think of myself as a blend of my parents. My mother is the dreamer. I don't think I would be doing startups without my mother's attitude towards stuff. She was the one that was like, “You can do anything that's possible," which is very cliché, but also a great thing for your mother to tell you. My dad was the one that was like, "Okay, if you're going to do that thing, here all the things you need to do. Here's all the hard work it's going to take.” He was the one that did that.

One last story I'll share about my mom, which is probably the most meaningful part of everything that's come out of startups and stuff. It doesn't even really have to do with startups. We were working on Decide and we were written up in The Wall Street Journal. I was 25, The Wall Street Journal was a big deal to me. It wasn't like TechCrunch. We were printed in the print ad. I remember it was Thanksgiving, I bought the newspaper and I went to my mom and I said, "Hey mom, look at us. We're in The Wall Street Journal." And my mom took the paper and she smiled at me. She said to me, "I was proud of you guys a long time ago." I think to this day, that still makes me teary because that to me is everything that needs to be said about my parents. So, they're always going to be role models.


(31:28) Jeremy Au:

Why are you so excited about Southeast Asia?


(31:30) Hsu Ken Ooi:

Personally, I still like to think of myself as from Southeast Asia. So, I want to be a part of the ecosystem here, and I want to contribute in a way that I think is helpful. I think some of my experience from the Valley can be helpful. We could have started another company, but I think it is more meaningful for me to help other founders here. Primarily because I think founders don't get as much support as founders in the Valley. And I think they are doing a very courageous thing with very little support at the moment. I just want to be in there helping them with that. The other part too, is that I think Southeast Asia is really at turning point. We can have a debate on how controversial that is or is not, but I don't think it's actually that controversial anymore.

The thing that really surprised me when I was traveling through Southeast Asia recently was just how much the region has grown in its startup ecosystems. So, I think that there is a lot of opportunity in a lot of different spaces for people to build companies here. I don't think that it's just a matter of porting over whatever works in other countries or whatever country is going to come over. I think we're at the tail end of that. And I think it's not so easy to just, I don't know, be an American and just show up in Southeast Asia. I guess I can say that because I'm a lot American now, and just be like, "Okay, cool. I know how to do this. I come from Silicon Valley here's how you kind of do stuff." It's a very different place.

I think it requires a different set of skills to be successful here. So, I think Iterative is a really good place for me because it checks the personal fulfillment bucket of working here and working with founders here. And then very selfishly, I just think this place is really going to go. I often talk to people that I feel this is China, 10, 15 years ago. Again, I don't know, this is probably not controversial anymore, but I think China's leapfrogged Silicon Valley a little bit.

Shameless plug, I'm starting a Y Combinator Accelerator in Southeast Asia. So, if you are interested in starting companies, we'd love to hear from you. We're also going to start producing a lot of content and blogs and give talks. So, we're going to try to be an active participant in the community to try to help entrepreneurship in Southeast Asia. And I think that this place is really going to go and I'd very much like to be a part of it.


(33:37) Jeremy Au:

What support is available for others, considering a journey similar to yours?


Hsu Ken Ooi:

Fanboying a little bit. When we were starting out, we all looked up to different entrepreneurs and mine was Marc Andreessen. Marc Andreessen has a really good blog that he wrote, I think, way back in the day, like 2006, 2007. He actually took it all down, but somebody happened to archive it. And so, if you go to a pmarchive.com, it's all of Marc Andreessen's blog. So, Marc Andreessen is still to this day, the person who I just really admire how he thinks about stuff and how he goes about doing stuff.

Paul Graham is an obvious one. If you're getting started in startups and you haven't read Paul Graham's essays, you need to spend a fair amount of time and just go through those. I feel CS Program is basically just an extension of Paul Graham's essays. But those are a few ones that are really good. One is, “Do Things That Don't Scale”. I think that's a really good one for people who are just starting out. A lot of times when we talk to entrepreneurs, they think they need to have a very scalable solution from the beginning. That's actually not how any of these things start. So, he outlines that really well. And then I think the final thing too, which I guess is not really a resource, but I want to make it a point to people.

You need to get out there. You want to read what you can. Andreessen's blog is great. Polygrams is great. You want to read all that you can, but you can only learn so much from reading. I think startups is something that you only can learn by going out there and doing. And doing is not something very big. It's not like you have to go fundraise. It's not like you have to go recruit. It's not actually any of those things. To get started you just need to find a problem that some people have and honestly, in the beginning, don't even worry about how big of a problem it is. Just find some group of people who has some problem that they feel acutely and solve it for them. And I want to make a note of my formulation of what I just said. At no point did I say product, and at no point did I say software.

You solve problems for people. That is a startup. That is what entrepreneurship is about, is that you are solving problems for people. I think that's the primary thing that you want to get out there and do is, just find a problem, something that will help people and do that for people. And you can worry about the fundraising and co-founder shares and revenue models and TAM calculator, it all comes later. Don't worry about any of that stuff, right? That's only necessary if you want to raise money or something like that in the beginning. Find a problem, solve a problem for some group of people, that's it. I think that's probably the best way I've learned.


(35:52) Jeremy Au:

Awesome. Thank you so much.


(35:54) Hsu Ken Ooi:

Thank you for having me.

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