Chia Jeng Yang: Reset Your Hunger, VC to Founder Transferable Skills & USA vs. SE Asia Startup Ecosystems - E420

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


“I'm good at resetting how hungry I am. I was at a high-paying VC job and I could do whatever I wanted. Understanding your hunger and what you truly are, and being able to commit helped me to navigate things, which means I was willing to swallow my pride and start from the bottom and hustle my way through, and I really want this to succeed. There wasn't a framework. It was about being able to be confident internally that I am definitely doing this and that I really want it from the depth of my heart.” - Chia Jeng Yang, Cofounder of WhyHow.AI

“It's part of the general work-life balance, whether or not that exists, or whether or not you submit to it. It goes back down to what you identify as and whether you are comfortable with what you identify as can be obsessive. That wasn’t necessarily the best way to think about it, but those were the quotes that really inspired me growing up, which is, ‘Don't talk about what you would live for, talk about what you would die for.’ I certainly have a little bit of an obsessive personality. And so that philosophy does fit. It’s also a privilege to be able to devote everything to a cause because it's not not something people can have.” - Chia Jeng Yang, Cofounder of WhyHow.AI

“The US ecosystem is so dynamic and competitive. The way you need to think about businesses, funding models, competition, and who the natural stakeholders are in the industry is extremely different. The common stereotypes about business models, markets, and understanding local culture aren't always going to be generally true. I appreciate the opportunity to be competitive in a very different way, and in a slightly bigger market and a very dynamic space. Obviously, Southeast Asia is dynamic in its own way, but given the tech-focused nature of venture capital markets in the US, it's really interesting. And not having slept much in the past three, four years has been a good way to ensure I'm up to trends and being competitive accordingly.” - Chia Jeng Yang, Cofounder of WhyHow.AI

Jeremy and Chia discussed his experience changing careers from Southeast Asia VC Principal to US AI founder. He outlined the non-transferable nature of many VC skills when becoming a founder. While VC offers a high-level understanding of market and investment dynamics, it lacks the hands-on operational skills needed to build a startup from zero. They also compared the competitive, fast-paced U.S. startup environment to Southeast Asia's, highlighting differences in market depth, competitive intensity, and entrepreneurial opportunities. Chia emphasized why you must "reset your hunger" for success, advising on the need to reassess personal and professional goals when switching roles or geographical bases. Such shifts require not only skill adaptation but also a profound change in personal drive and resilience.


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(01:39) Jeremy Au:

Hey, Chia! Good to see you again.

(01:41) Chia Jeng Yang:

Hey, good to be here.

(01:42) Jeremy Au:

You are now officially the most recurring person to come back on the BRAVE podcast. Lots of love.

(01:48) Chia Jeng Yang:

It's always good to be back. It's always good to have a chat with you.

(01:50) Jeremy Au:

Yeah. I wanted to chat with you because, since the last time, you were a well-known Southeast Asia VC writing thought leadership. And now you're an AI founder in the US, and a lot of folks are like, what's going on with Chia? Also, there's a lot of folks who look at you as a role model because you're like, Oh, you made the double jump, in terms of role, in terms of industry, as well as geography. So it's a triple jump. So from that perspective, want to kind of like dig a little bit deeper into it. So it's not necessarily like a classic interview thing, but more like a chit-chat session.

(02:18) Jeremy Au:

The big one is why you decided to become a founder instead of sticking on as a VC.

(02:23) Chia Jeng Yang:

Yeah, I went into tech and I went into venture with the explicit goal of trying to start something at some point. And so I like to describe it as I ended up spending a little bit too much time in venture. I obviously enjoyed my time there. we were able to accomplish a whole bunch of really great things with great people, great founders, great colleagues, et cetera, but I always had this urge to build something and make something happen and really be able to fill a gap that I saw in the world. And I was honored and privileged enough to have the opportunity to do so, fairly recently with a bunch of co-founders that I greatly respect. And so that's been, that's been a really interesting journey. And it's been interesting. It's certainly something that took a little bit of adjustment. And I've always been pretty good about understanding very fast moving industries and understanding where value lays, at least I hope so. And being able to take a leap of faith and trust in myself, trust in the problem that we think is really valuable. And that's been paying off quite handsomely recently. And so I've been really excited by everything.

(03:23) Jeremy Au:

Amazing. So we're definitely talking about what you're building and, what you had to learn along the way, but, on the career side, there's a lot of folks who enter VC with the idea that it gives them that ladder or that staircase to becoming a founder, eventually. Do you feel like that hypothesis panned out? Because right now, you sound like a Manchurian candidate, but as a VC founder, I've, I look like a VC, but I'm actually secretly a founder to be, so how do you feel about that?

(03:45) Chia Jeng Yang:

I don't think so. I don't think my years in venture really helped me too much. looking back I probably should have if I wanted a straighter path, I don't regret anything I did, but if I wanted a straighter path, I probably would have started something sooner. And I do think I should have started something sooner, but of course, I would have probably have done something completely different back then, just because of the nature of what the market was like and where it was, et cetera. So I don't regret anything on that side.

The only thing that venture really helps with is just trying to understand how people think about investment opportunities, how people think about what's interesting. that as an investor yourself and spent a lot of time kind of investing, you also understand the difficulty of being very comfortable as an investor. It's a very well-paid job where you get to basically say no to people 99% of the time and you don't risk anything fundamentally. And so, that's a great job. And it's honestly a privilege to be able to say, I don't want that. And I want to do something else. And I'm definitely privileged to be able to do that. And it's very easy to kind of fall into it. And it's very easy to have a very cynical mindset about, what should exist, and what shouldn't exist especially when feedback loops are so long and you may not necessarily be correct, especially given everything that's happened historically with zero interest rates in the venture scene. And so, building really gets you a lot closer to understanding what's truly fundamental as opposed to what could be broken about the business model.

(05:03) Jeremy Au:

That's something that I also found valuable because, I used to be a founder, right? Twice. And then after that, I joined the VC side and I felt like what I definitely got out of it was that I understood how VCs think in terms of their process, why they like information asymmetry, and why they delay and take their time on turnsheets.

So I really got a much better sense of the capital raising process, but definitely, I agree with you that to some extent, the skill sets of how to build were not very well-used in that sense. Let's double-click into that a little bit, I guess. So what are some myths or misconceptions about VC skill sets that don't really apply to being a founder now from your perspective?

(05:40) Chia Jeng Yang:

Yeah, for sure. that vCs are great at cataloging things. And as someone who voted a lot, I'm certainly guilty of that. I did an okay job at being a cataloger of information and that cataloging process is helpful. Paul Graham's YCS is a fantastic example of timeless advice that's going to be helpful even if you're starting a company, 50 years from now and things like that. that what I've come to understand is that there are, it's much harder to make assessments on non-obvious opportunities. And if things are moving super quickly, it's hard to catalog it. And so you have this time lag, , where unless you, as a file, you as an investor are very close to the ground and have a good understanding of how your portfolios are doing things on a very operational basis, it's very hard to keep up. It's something, when I was investing, I tried to do a little bit of. I wouldn't say I was very good at it because it's hard. You're spread super thinly and let alone trying to get into granular operational details is basically impossible across multiple companies. And so, I see that gap and that gap is where a lot of opportunity really arises fundamentally.

(06:45) Jeremy Au: Yeah, I really like what you said about cataloging because I really feel that as a VC, it's almost like you have to cover every geography, every vertical, and have that landscape view of who's the best team and not, but you don't focus on anything if that makes sense. And then your values also synthesizing and maybe promoting that knowledge as well in some way, either to an LP or to your teammate or to your partner, or to some founder who's learning for the first time. So a lot of information, traffic warden, traffic light, kind of dynamic there. So I guess, one thing I struggled with personally is that that as a VC, the inverse or converse of that traffic warden is that there's almost a requirement to be agreeable in the sense that there's a bit of consensus orientation in that sense, versus as a founder, you get to be disagreeable. You get to be more opinionated about something that you do know very well. I'm just wondering how you feel about that.

(07:34) Chia Jeng Yang:

That's a really interesting framing. I really liked how you've done that. that's right. being able to understand, it is such an interesting thing because I've personally written a lot about how momentum investing works in the venture space as a descriptive thesis of how it happens and things like that. And you can see kind of consensus being, obviously besides a very natural social phenomenon that people tend to adhere to also having a very positive kind of financial outcomes. And it's certainly something that has a good reason to exist. And you're right in the sense that actually kind of non-consensusness is helpful and valuable. Of course, you have the counter-thesis, which is, that non-consensus could mean that you're early, non-consensus could mean that you're wrong, non-consensus could mean that you're right, but no one likes you, and no one likes the fact that you're right. And so there's a kind of a whole spectrum of things there.

(08:24) Chia Jeng Yang:

And about for example, the stories of some of the alternative, like vaccine approaches, for example, that never really popularized until it became obvious that things like that were needed. So it's a very interesting dynamic, but at the end of the day, the job is to ultimately get results as fast as possible. And it's still the job to fulfill at the end of the day. And it's an interesting dynamic. it's a dynamic that needs to be watched out for, but at the end of the day, the results need to be hit. And that means identifying and figuring out the best way to drag as many people along that journey with you. That still needs to happen.

(08:59) Jeremy Au:

What are the skills that you had to learn now that you are a founder from your perspective? What are things that you wish you had learned earlier or gotten some like download earlier in terms of DLC?

(09:09) Chia Jeng Yang:

Yeah, for sure. you can't have too much experience in product. I love it. product is one of my favorite phrases "A great product is a function of strong opinions expressed," and a strong opinion can't be contradictory. A strong opinion must be forceful well-expressed well-communicated and coherent. And I love understanding how products and opinions match me. It's a conceptual exercise that needs to be obviously drilled down through its very tactical conclusions. So, product for sure. having as much experience with products really helps prepare you for building anything, really.

(09:47) Jeremy Au:

Yeah. And what's also interesting in terms of your shift as well, is that you also move geographies. So you move from Southeast Asia and Singapore to the US. Can you share a little bit more about that?

(09:57) Chia Jeng Yang:

Yeah, for sure. It was interesting. I mean, I'd spend a little bit of time investing in the US before this. I'd spend a little bit of time thinking about it in the US but not a significant amount of time. But, this is maybe where VC helps you a lot. VC is all about entering, and for entrepreneurship's obviously a magnitude of that, but VC is all about entering any room and just trying to know everyone and pretending that you're important. And being a founder is maybe that's the important bit, but, being in the room and being able to get great takeaways from various experiences, and that is one thing VC and entrepreneurship does have in common.

(10:29) Jeremy Au:

Yeah. And what's interesting is that to some extent we have inverse relationships, for a while in terms of journeys. So for myself, I was a US founder moving to Southeast VC. I'm back to building. And then for yourself, you were moving from Southeast Asia VC to US founder. So a little of a Benjamin Button here. What do you think is, and we've talked about this as well. You asked me for advice. I talked to you about it. We also swap notes on Southeast Asia VC. So you helped me out as well. What's some advice you give to people from your perspective?

(10:54) Chia Jeng Yang:

Yeah, that parallel is hilarious. And also that we're the first and second Singaporean in two plus two. So it's a bit crazy life parallel when you mean advice, do you mean people moving from Southeast Asia to the UD?

(11:05) Jeremy Au:

How would you compare the ecosystems at a high level?

(11:07) Chia Jeng Yang:

Yeah, the US ecosystem is super dynamic. It's extremely competitive and the way that you need to think about businesses and funding models and competition and who are the natural stakeholders in the industry is extremely different. And besides the common stereotypes about different business models and different markets and understanding local culture and things like that, which aren't always going to be generally true. I appreciate the opportunity to be competitive in a very different way, in a slightly bigger market, in a very dynamic space. Obviously, Southeast Asia is dynamic in ts own way, but given the tech-focused nature of venture capital markets in the US, it's really interesting. And not having slept much in the past three years, three, or four years has been a good way to make sure I'm up to trends and being competitive accordingly.

(11:57) Jeremy Au:

A lot of folks in Southeast Asia now are very optimistic and we were very confused by the optimism several years ago. And then now, people are very, very pessimistic about Southeast Asia as a tech ecosystem. And so I've met many founders and VCs who are very much, I didn't process moving to the US or thinking about doing so. What do you think about that?

(12:14) Chia Jeng Yang:

It's interesting. I mean, look, I'm still optimistic about Southeast Asia. It's home, first and foremost, for myself. And Southeast Asia suffered a little bit from a mismanagement of expectations as opposed to kind of economic reality. Southeast Asia is still one of the healthiest regions in the world, but we had a lot of expectations riding on it and it intersected very neatly with the specific zero interest rate period that we had and the general euphoria that took place over the last four years, which is a global phenomenon, not Southeast Asia one. And so, when some of these expectations may not necessarily perform, you start to think about some of the falls against it, right? And one of the big complaints is really monetization in Southeast Asia and the depth of the market and things like that. And so a natural reaction to maybe mismanagement expectations about that, and the timelines for monetization obviously means that you try to go and think about what a great lucrative deep markets like the US to tackle. And so, it's a very natural reaction to things. moving forward, sufficiently, we'll still be an interesting market, but obviously, the nature of the opportunities change the nature of expectations to change. The fundamentals are still there.

And so we'll see a rise. I've been on record saying many times that Southeast Asian markets parallel Indian markets that were very similar euphorias back in the day 10, 15 years ago in India, and no one is going to say that the Indian tech market is bad, even though some people will argue that the Indian tech market is suffering from a very similar euphoria right now. There will potentially be some correction that will happen then, and similar attitudes will rise and fall, but look, India now has a great booming tech market that is exporting software all across the world and is a great powerhouse. And so we'll see similar things at some point, it'll just be a matter of managing expectations of timelines.

(13:59) Jeremy Au:

Yeah, I really like what you said about timelines, right? Over a 50-year timeline, Southeast Asia's economic fundamentals keep growing. The strong dynamics and over the next 10 years, the ecosystem is structurally harder than the US ecosystem, especially for VC fund outcomes. Of course, within the next one year, there are still a lot of tech opportunities as an employee and as a contributor versus the euphoria a couple of years ago. I guess from your perspective, this debate is about how much structurally harder Southeast Asia is compared to the US. So you now starting to get a little bit of experience on both sides. Some people, including myself, would probably peg it at least maybe three times harder, I would say, as an ecosystem, I was just putting apples to oranges here. Southeast Asia is a very wide region as well, but, I guess when I say this, I'm also looking at Singapore, Indonesia, and Vietnam. some people are more bearish. they think maybe, it's 5 to 10 times harder. I'm just kind of curious. What do you think about that?

(14:50) Chia Jeng Yang:

Yeah, it's hard for me to put a number. I don't think I have enough experience to really understand that. you're probably the best place to actually understand, especially with the latest data because you're also building in a relative, it was still a relatively tough time and definitely not in the peak of the euphoria period. So you've really had to appreciate, that, it is harder in the sense that there are competition and the bars is way higher, right? The people you're competing with are insane in a whole bunch of different ways. And you really need to know what you're talking about. And there's no way to hide it, especially if you're like me. I'm basically an immigrant to this country and had fewer resources than I would have back home. that's my perspective fundamentally, but I do think you're right.

I do think that at the end of the day, the depth of the market really is reflective of everything. If you're in very deep markets, your ability to charge, your ability to make money from disposable income is just incrementally much harder. So is it 5 to 10x? I don't know enough to say, but it's certainly hard as a general rule. And timelines to success are just one thing that you could be as smart as you want. You can be as hustly as you want, and be as well connected as you want but if timelines are timelines and the market then, it's fundamentally a question of are you willing to wait 15, 20, 25 years to succeed in Southeast Asia? And that's a very tough question because it's very, very hard to say that. And many famous founders like Jensen talks about how if they knew this is going to be that hard, like this long, I wouldn't have done this because it's their life. It's literally your entire life for an anchor outcome and that's really hard to ask for people.

(16:16) Jeremy Au:

I really love what you said about outcomes and timelines here. That 15 to 20 years is probably the right way to think about it in Asia, especially. since it is a unique privilege to be in America and to be able to think in a 10-year timeline, which is, because of the capital and acceleration that it has. So it can be very much people are like, "Hey, I'm going to build a startup for 8 years or 10 years and be done with it and then move on to the next thing." But I agree with you. In Asia or other emerging markets, being comfortable with perseverance may mean that you're around for 15 to 20 years. it's a little bit of a higher bar for what kind of business or vertical you want to build in, honestly. When you think about all of this, and obviously this has been a lot of transition, are there any particular resources or mindset that you felt like, because you had to navigate these changes in terms of VC to founder, from Southeast Asia to the US and obviously from a generalist to more of an AI focus perspective, any general things that you had to turn to have a mindset around?

(17:08) Chia Jeng Yang:

I'd like to say that there was a set of resources or even like a framework. It really wasn't the biggest thing that was the most helpful for me, was I'm pretty good at resetting how hungry I am. And what that means is that it was easy, before I did this, I was at a pretty high-paying VC job and I could coast and do whatever I wanted. And again, that's just true for VC in general. And the main exercise I had to do was how much do I want this. Being a founder is less sexy. It's probably not sexy anymore. Am I doing this because I want to do a sexy thing? Am I doing this because I really want to solve a problem and own it and solve it end to end? And how hungry am I for that? And that's really it, which is understanding of what you want and then being able to understand how hungry you truly are for that and being able to commit. For me, that's how I've been able to navigate things, which is being able to, say, look, I'm willing to swallow my pride and start from the bottom and just hustle my way through because I really want this. And I really want this to succeed. And what I'm going to spend my time doing. And so, that's really it. There wasn't really a framework. There wasn't really anything. It was just like being able to be confident internally that I am definitely going to be doing this and I really want it from the depth of my heart and that's how I'm going to do things.

(18:23) Jeremy Au:

I really love what you said about resetting your hunger. And obviously, you shared earlier about how VC is very comfortable. You get to say no 98% at a time. You're being paid well. People come to you. It's a bit of an ego trip, I would say. So I guess when you think about resetting your hunger, was it unpleasant to reset your hunger or was it pleasant or what can we go deeper into that?

(18:42) Chia Jeng Yang:

I would say it's definitely not easy. I'm in a very privileged position. A lot of what I've done in my life does carry through. And so I don't get to reset from zero. I hear stories of people in America, the classic American story of how they were doctors in their home country, treated with respect, came here, became a cleaner, and worked their way up, right? that's the kind of attitude that I admire a lot. And I'm not that I came to America through Harvard, right? That's not starting from zero by far. And if people can do that historically in America, I can try to at least do my best to match that. And that was my attitude, and that's what drove me. And was it painful? Obviously. there's a lot to it but that's where it comes back down to, "Hey what kind of life do you want to lead? How hungry are you really?" Because yeah, both of us, we can pretty much do other things that are way more comfortable and way more lucrative. And so that's really it. So yeah, it was definitely painful for sure but that's something that you need to be, to calculate as part of that formula.

(19:40) Jeremy Au:

The interesting thing is that hunger is often seen as a negative thing. Like you shouldn't be hungry. I actually got that feedback, it was like, and I'm just like, yeah. you know,

(19:50) Chia Jeng Yang:

Maybe hunger and hustling. hustling is certainly viewed in a more negative tone in other geographies. And I've certainly been in a country in a country before, which is probably not the one that audiences will think it is, but I've been in the country where, when I complimented someone and say, you're a hustler, they initially took that as a potentially an insult. They're trying to ask me, why do you say this? And so that's interesting, right? And maybe I'm living life wrong, but I do want to be hungry. And I do want to be able to how much of an impact I can make. And I pay the costs for that. You do too. We pay a cost to our health. We pay our costs on certainly our social lives and other things like that, but that's what is who we are, and then we are okay with that, hopefully on some level. Hopefully at a very deep level. And as long as you have alignment there, then that's fine.

(20:34) Jeremy Au:

Yeah. What's interesting as well is that you're making a set of decisions to build on that hunger. And how do you manage that? Because you talk about trade-offs, right? Like in terms of, body and soul and so forth, but, obviously, there's a big push on work-life balance, which is not a right phrase, but like the integrated health system and all this other stuff, how do you think about that?

(20:53) Chia Jeng Yang:

It's a tough question. It's part of the general work-life balance and whether or not that exists, or whether or not you submit to it. It goes back down to what you identify as, and whether you’re comfortable with what you identify. What you identify as can be completely obsessive, there was not necessarily the best way to think about it, but those were the quote growing up that really inspired me, which was, "Don't talk about what you would live for, talk about what you would die for." And to me, I certainly have a little bit of an obsessive personality. And so therefore that philosophy does fit, but it was also a reflection that I'm glad to be somebody who can obsess. that's also a little bit of a privilege to be able to devote everything to a cause is not something people can sometimes have.

(21:32) Jeremy Au:

Yeah. Do you often use the word reset in a conversation and how do you reset personally?

(21:38) Chia Jeng Yang:

Good friends. I have the privilege of having good friends. I have the privilege of my fiance. I have the privilege of many mindless activities that I do. that's what I personally do but at the end of the day, I'm really appreciative of even the founder process, because it also helps you understand who your friends are and who will actually be there for you when things go to shit. When you can't really devote the time that your friends deserve and who stick around. And so I've been a lot more grateful and a lot more grateful for the relationships I have in my life. And it's not something that I may be if they can fully recognize before.

(22:09) Jeremy Au:

It's been about at least five years, no, longer since we first hung out. Where was that? In Orchard Road, Singapore. Was that 2016, maybe? 2017.

(22:19) Chia Jeng Yang:

No, we met in 2017 because I was working in Sri Lanka at the time.

(22:25) Jeremy Au:

Right. And you were telling me about your dream to be a founder one day.

(22:28) Chia Jeng Yang:

Oh, really? Yeah, I probably said that.

(22:30) Jeremy Au:

Yeah, you said that. You were like, Jeremy, I want to talk to you on this coffee chat because you're a founder right now. Is Harvard a good place to do entrepreneurship? Should I go to 2 Plus 2? Should I not go? People who don't go to high HBS tell me I shouldn't go to HBS and their MBA is worthless. And then I was like, why do people who don't go to something tell you not to go? It's like people who are not parents telling you to not be a parent, versus you should be at least be a parent to tell people whether you regret having kids or not.

Anyway. So any advice, if you had a time machine going back in time, back in 2017, right? So it was like, almost wow, seven years ago, effectively. If you had that time machine to go back, any advice you'd give to your younger self? If you were doing a coffee chat with your older version of yourself instead of me.

(23:09) Chia Jeng Yang:

Yeah, there are two kinds of lives, and the first kind of life is where you recognize that certain things require very deliberate planning to get to. Trivially, for example, if you want to be president, it's not necessarily a straight path, but there are things that you have to do to get that. And this means building three or being a partner, a consulting firm, or whatever, may not be a straight road, may not be an easy road, but there's a very straightforward road you need to dedicate yourself to. And then there's a road where you'd be a founder and you're basically in the business of managing chaos.

I was trying to optimize for both at the same time and it was because I was afraid to go all in on a very fundamental level. And I was attempting a manage risk in a way that couldn't be mentioned. So my advice moving back would probably be to take a lot more risk. If you're dedicated to the path of taking risks, which I was and I ended up straddling a little bit. I should have found it a lot easier earlier because I realized a lot of the things I thought I was preparing myself and giving my experience myself experience for fundamentally wasn't that useful at the end of the day.

Again, I don't regret it. It got me to the place I am today, but if the goal was really to, be in the business of managing risk being able to control risk, and figure out how to create opportunities through risk I should have gone on.

(24:21) Jeremy Au:

Awesome. On that note, thank you so much for sharing. And I'll catch you again next year.

(24:26) Chia Jeng Yang:

For sure. Thanks for having me, Jeremy.

(24:28) Jeremy Au:

Got to keep that top spot, buddy.

(24:29) Chia Jeng Yang:

Thanks for having me.

(24:30) Jeremy Au:

Okay. All right. See you, man.