David Yin: Random Walk to Career (Journalist to VC Partner), Finding Yourself at Stanford & Harvard, & Drinking From Firehoses Startups - E269

David Yin, a partner at GSR Ventures, is not your typical venture capitalist. He started his career as a tech reporter at Forbes, gaining a deep understanding of the tech industry. After that, he became a consultant at McKinsey and the head of strategy at a fintech unicorn, gaining a broader perspective on business strategy. He eventually found his way to venture capital by chasing optionality in his life and testing different hypotheses, including trying out public equity and gaining a Stanford MBA & Harvard MPA. He viewed grad school as a reversible decision with limited downsides and potentially significant upsides.

David found that VC allowed him to combine his interests in investing and working with people in early-stage tech. Yin emphasizes the importance of being interested in what you do rather than just chasing money. Through his journey, Yin has learned the importance of focusing on one or two things at some point, as pursuing too many degrees or options can lead to diminishing returns.

He believes that Southeast Asia is an area of opportunity due to the geopolitical issues between the US and China. However, he also acknowledges the challenges of integrating into a new market for non-local founders, requiring both humility and local knowledge. Yin also discusses the importance of working together to build the regional startup ecosystem with a community of brave founders and supportive VCs.

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Jeremy Au: (01:43)

Hey David, really excited to have you on the show. It is been a great time knowing you for the past few years, and I wanted to have you on, so please introduce yourself.

David Yin: (01:54)

Yeah. Jeremy, thanks for having me on. I'm a big fan of your show. Always listen to get, the best insights from Southeast Asia around tech. So glad to be finally, on the show with myself. So to do a bit of intro myself, my name is David Yin, I'm originally from Singapore. I'm currently a partner at GSR Ventures.

So GSR Ventures is a $4 billion AUM early stage venture fund investing across the US, China, and Southeast Asia. So my role at GSR mostly focused on investing across Southeast Asia. But also looking at global FinTech and web deals. And before this, maybe this is something, that resonates with me basically, I've tried a few different things and taken a random walk of life to get to where we are here today.

So I started off my career actually as a tech reporter at Forbes. So I was writing about big tech companies such as Tanza and Kakao, writing about some of the smaller fast growth tech companies as well. Then spent a couple of years consulting at Mckinsey. Where I also focus, almost exclusively on FinTech projects, you know, such as building digital banks, helping, Crypto Companies figure out cross border payments and so on.

And then after that transition full-time into tech, was head of the strategy at a FinTech company, that became a unicorn. So it's quite good to see, to ride the rocket ship and see what it's like. And finally, I think over the years, similar to you as well, Jeremy just got very plucked into the ecosystem and started doing some intro investing advisory.

And, realized being a VC is a pretty fun job to get, to meet, interesting founders and folks like yourself. So that's what I'm doing now.

Jeremy Au: (03:28)

I love the phrase random walk to Korea. What does that mean to you?

David Yin: (03:33)

Yeah, I think part of it, you know, like growing up in Singapore we have this Singapore dream, right? It feels like that's a perfectly linear path to success, mean the holy grill of you go to a nice JC, you take a government scholarship go to Oxbridge or go to some nice Ivy League school, and then you come back, and surf, by your BTO, by your cars and all that.

I think that's kind of what a lot of, at least for myself, right, I was conditioned growing up to think that was the way of life. But I think yeah, the more random walk of life is just trying out a lot of different things. You know, between journalism, consulting, startups, venture capital and in between, I also spend some time doing, for example, tech investment banking, public equity investing and so on.

But I think in taking a more liberal artsy approach to things, I feel like a lot of these are more connected than we think. So even though they look very random but as I think Steve Jobs says, looking back, you really connect the dots in a certain face.

Jeremy Au: (04:29)

What are some dots that you've seen connect backwards, and seem to make sense looking forward?

David Yin: (04:35)

Yeah, so I think, just talk about, say, journalism and what I do as a VC now. I think journalism is very much about two things. One is you're trying to find some of these, under-reported stories. And the other part is you're trying to talk to folks. You interview folks to find a story. And in any sense, I feel like writing a story similar to writing an investment memo, right, and finding a good story, you figure out what's, maybe not being reported. You try to dig for information where there's no information. You talk to people in the ecosystem, you talk to CEOs and founders, and then we ultimately put everything together. I think it all goes back into a storyline. I think at the end of the day when people say that investing is both an art and a science.

I think the science part is very clear, right? You gotta make sure the usual acronyms, super IRS, and so on makes sense. But I think the art side of it, I think it's very similar to what I used to do in journalism.

Jeremy Au: (05:33)

I love what you said about the art of journalism, right? And I gotta ask, why did you start doing that? What's your motivation for starting out as a journalist?

David Yin: (05:42)

Yeah, it's a that's a great question, Jeremy. So I would say one of the heads of the reasons why I did it was because I started my own media platform when I was back in college at Yale. So this media platform at that time was focusing on US-China relations. And it did pretty well. It went over to, I think 150 different schools.

It was funded by companies such as Blackstone and all that. But at that time I didn't have any journalism background. So I first started off as part of starting this media platform, wanting to go work at a large media company. And Forbes is one of those that I've respected a lot. Obviously, if I had the benefit of hindsight, and if it's today, right, I'll work with Jeremy on your podcast.

But, back then was looking for an established media outlet to lend the ropes of how to create a great media outlet. So, thought of going to Forbes and when I was there, I think the exposure was great. I got so much freedom to just almost write about any story that I want and I get to talk to interesting folks. So it was a great first job.

Jeremy Au: (06:40)

What was your favourite part actually about that? Because, you know, you spent so many years writing folks you know, for example, Asia folk. A lot of folks are very happy to put that on LinkedIn, myself included. What were some favourite parts about it?

David Yin: (06:55)

Yeah, to be very honest, I think the first part is just the access. I remember even when I was, in my first month on the job, I remember interviewing like the, I remember at the time the chairman of EDB and the chairman of the Hong Kong Trade Development Council. I remember going to like events with, the head of state.

I went to an event with Joe Biden and all that. And so I think, first of all, it's just the access as a relatively junior person. I think number two is also the flexibility and the freedom cause most drops when you first start, you are basically at the bottom of the food chain. Obviously, in journalism, you still have a boss and an editor who tells you what to do, but by and large, you have it's as creative as it gets.

You get to just go read a lot of news. I remember one of the stories I wrote about was about the largest bo chain in America, and it really just came about because I was walking in Manhattan. And I saw this Bani store opening and they claimed that they are the largest Bani store in America. And I was like, oh my God, this is pretty interesting.

And obviously, it smelled very good. So I just went in and talked to them, and figured out that it was a good story and I wrote about it or another story that I think could be quite interesting. I wrote a fair bit about Israel and, the tech ecosystem there. And, it really started off because I had some friends from Israel.

Who all were interesting startups back then, this was me from, Singapore never heard too much about startups and I was just wondering like Israel and Singapore are very similar in size, and faced a lot of similar geopolitical issues. You know, why are there so many startup founders there?

So that took me to Israel where I just explore stories about its tech ecosystem. So I think having that flexibility to just find interesting stories and ultimately present them to a wider audience, I found that to be very,

Jeremy Au: (08:43)

And what's interesting is that from there you decided to become a management consultant. So what drove that transition from your perspective?

David Yin: (08:50)

Yeah. Obviously inspired by you, Jeremy, right? But in seriousness, I think, what I like about journalism is definitely digging into stories and learning about different industries, and so on. But I do miss the problem-solving part of things. Right? Whenever I find a good story. I guess the example I give is if you see a fire, I don't just want to tell people that, Hey, there's a fire there, right?

I want to go put out the fire. I wanna make sure that even if the fire happened, let's find a way to rebuild a place. So I think that was a part that was lacking, in journalism. So I thought that consulting will allow me to keep learning about many new things, but at the same time, also have that angle where I can solve problems and hopefully make an impact.

Jeremy Au: (09:33)

And from there you actually decided to go to grad school. So could you share a little bit about your decision to go to grad school, and I mean, not just grad school right, but to do, MBA and MPA? So could you share a little bit more?

David Yin: (09:46)

Yeah, so going to grad school, I think there's a few parts there. One is, I definitely, I think a lot of people that I really respect, I think they've gone to business school and they've really recommended the experience to me. And part of me also felt like I was at this stage in my career where I could either just really double down on what I was doing or I could really go to school to expand the way I think, to meet new people, get new ideas, and I think to have a better sense of who I am and what I want to.

I know it, it sounds a little, less practical than you should. Right. I wasn't there to really find a new job or to, do a career pivot. It was more to like, I know it's a bit of a luxury, but to really go find myself and figure out what I really wanted to do and, because I was interested in tech.

So Stanford was definitely a place I wanted to spend more time at was very fortunate to get in and I really loved my experience there.

Jeremy Au: (10:42)

Going to grad school to find yourself. So what did you find about yourself during that space and time?

David Yin: (10:48)

Yeah. So, one interesting thing about Stanford was before I went there, the application prompt for the essay was what matters to you, then once I got there, I think one of the questions that I just floated around in Silicon Valley a lot was, what's your superpower? So the way I think about those and maybe I'm overthinking, is that the first question is a bit about your why. Like, what matters to you? What are you passionate about? What do you care about? What's something you wanna solve? And I think the second part of the question after you get in is a bit about the how, which is, everyone is different. Everyone has some people who are good at building stuff. Some people are good at, spotting trends. Some people are good at, people management. I think ultimately it's more about finding a superpower that allows you to make the most impact, but also probably be the most successful. So I think going to Stanford, a lot of it was just figuring out this sort of what matters to me and also I think, what are some things that I enjoy doing and I'm relatively good at.

Jeremy Au: (11:49)

Why do you think you had to find yourself, at grad school versus somewhere else? Right? Some people, you know, go for long walks at work. You know, some people go hiking over the weekend. Other people, obviously take a sabbatical, right? Half a year or a year. Some Ayahuasca ceremonies in South America.So many ways to, you know, like find yourself. So I'm just kind of curious because, I think that's actually a question that a lot many people ask, right? Which is like, I've.

So I'm gonna grad school and there's a little bit of like a few logic steps in between, right? Which is like you wanna find yourself too is that's a good place to find yourself or, and entry, you know, there's a cost involved with that, right?

Then four, there's an opportunity cost involved with that as well. So I'm just kind of curious about how you talk through those dimensions.

David Yin: (12:29)

Yeah, yeah. First of all, you're absolutely right. It's definitely a big cost in terms of opportunity, cost, in terms of just the time and the money. I had a few particular frameworks that guided me in the final decision. I think the first framework was, Going to, I was very fortunate, obviously to go to a very good school and I thought of it almost like a lottery in terms of if nothing worked out over the next two years, at the very least I make some good friends.

I learn something about business, and I explore something new and learn something about myself. But at the same time, there could be a lot of opportunities I didn't know about you know, maybe I joined the next Grab joined the next Go-Jek. Yeah. If I had gone to a place like HBS in the same year as Naim or Anthony.

So I think there was this asymmetric risk reward that first of all formed my decision. I think number two was around regret minimization. So what I thought was, Hey, this is something I thought about for a long time. I think I owe it to myself to just give it a try. Whereas I feel like if I didn't give it a shot, at least, you know, maybe 50 years I'll be retired and I'll be thinking, all right, you know, what if I missed out?

And then the last part is, I tend to opt-in whenever a decision is reversible. So the way I thought about grad school was almost, you know, Hey, let me check out the school for a few weeks or a few months if I absolutely hate the experience first of all, I can drop out in the first few weeks I think, and I don't have to pay a single 10 of tuition or, if I really decide to drop out after a while and I don't think. Think the experience is worthwhile, but I can always, drop out as well.

So I felt that it was a very reversible decision, again, with I think a lot of potential upsides, but very limited downsides. So ultimately that's what I did, ended up not dropping out and having a good time.

Jeremy Au: (14:11)

I mean, I think that's interesting, right? Up into reversible decisions. Right? So obviously some version of like, disagree and commit reversible decisions in Japanese is like, okay, you know, those are easier to get into. But I think that works at a career slash sorry, company level.

But I think that's interesting on a personal level. So I'm just curious, what have been the other reversible decisions that you've opted into over the course of your career?

David Yin: (14:39)

Yeah. So I think most of the career moves that I've mentioned to you, in some ways you can also say that they give you a lot of optionalities, right? Not only do they close more doors, they at least leave many doors open, if not open more doors. So I think whether it's, for example, going to consulting.

It was, definitely quite a low-risk move that was pretty reversible. And even leaving consulting was to me, actually the perfect reversible move. Like some folks asked me, Hey, McKinsey you were doing very well. It's a nice cushy job. You have a lot of freedom. Like, when I was there, I was helping to start the startup practice, which was kind of a startup within a big company to work with startups.

So, I overall really enjoyed myself, but I felt that leaving McKinsey was such a reversible move. At the end of the day, if you are left in good standing, you sort of always have a job waiting for you. And whatever experiences you get outside of it, you can always position or frame it as something that's useful to clients if you ever come back. So when I decided to leave, it was almost a no-brainer.

Jeremy Au: (15:39)

When you say that optionality, right? There's always a big debate, right? Which is the curse of optionality, right? The joke is that all the grad school students, and all the consultants are all there for optionality and then they never opt into anything as a result, right? I'm curious about why you think about that. You know, is that ever too much optionality or is that too little?

David Yin: (16:00)

Yeah. So I definitely suffer a bit from that in the sense that I've frankly also chased a lot of optionality in my life. and I agree with you. I think at some point you just gotta. At least for me, I think you want to hunker down, you just want to focus on one or two things and you just want to keep doing those things.

So I think at some point, I guess one example is like, for example, going to more schools, right? I think going to, a place like GSB or HBS I think it opens a lot of doors, gives you credibility and so on. But imagine, after one of these schools, you go to law school again and go to medical school at some point, the marginal utility becomes maybe zero or negative but you incur a lot of costs. So I think I'm at a stage where I feel like pursuing more optionality I think doesn't help that much. But, earlier I definitely was opting to just get as much optionality as quickly as possible, and as early in life as possible.

Jeremy Au: (16:54)

And what's interesting is that you took that optionality search slash reversible decision dynamic and you decided to join venture capital. And I remember being actually personally surprised actually in some way. I mean, obviously, I wasn't surprised in terms of your skillset, but I was actually surprised by the decision in terms of choosing that. So I'm still curious about why venture capital ended up being that dynamic that you wanted to explore after grad school at Harvard and Stanford.

David Yin: (17:20)

Yeah. So one thing I did was I ran a series of sprints in my life where for every three months I tested a hypothesis. So initially my first hypothesis was that I wanted to maybe start my own education tech company. So because of that, I, for example, just talked to so many, Did a couple of projects at Tech Startups, talked to a lot of at Tech VCs, explored a couple of projects, talked to a lot of friends who work in education, and then I tried many different things as well.

I would say that one of the formative experiences was that I actually tried out public equity for a while. So when I tried out public equity, what I found was that I really like the investing angle of the public. Like, I think there's so much rigour to it. I think it's such an intellectual job. It's almost like playing a game and you want to be rewarded, and you get the kickoff being right in a way.

But at the same time, I think what I was missing out from doing public equity was, number one, I'm just very passionate about tech. I remember I was covering public equity stocks and I'll still be reading Tech Tech in Asia, listening to your podcast and all that. So I feel like that's what I do in my free time anyway.

So it's a bit weird that I'm not doing something in early-stage tech. And I think the other part that I realized was that I liked the aspect of a job where I got to work with people and grow with people. And I think that's something that I didn't really find in public equity. So as I thought about what I wanted to do, what I'm relatively excited by, I thought that venture capital was a good combination or it allowed me to do investing in early-stage companies. But also allow me to work with many interesting folks. So it's honestly a lifestyle that I enjoy.

Jeremy Au: (18:58)

And that was a good test and experiment, obviously to join venture capital. What have you noticed are the differences, I guess, from what you expect the venture capital to be versus what it turns out to be from your perspective?

David Yin: (19:12)

Yeah, it's a good question. I think one thing is just, I think I was very surprised at how ambiguous the job is at the end of the day. I like to say that there's, everyone has a different way of alpha. Everyone has a different investing style, right? Some people like, the sheer hustlers.

Some people like those with very deep technical backgrounds. Some people like companies, they're growing very quickly. Some people like sort of the undervalued companies, right? They're under the radar, under dark founders. So I think there's, it is very ambiguous, what's really sort of the, the right way to do it.

And I think at the same time it's also very hard to tell if you are really good at the, Right. You could invest in the company. It could go like crazy in the first one, two years and raise a lot of money. And you think that you have a jam in your hands and then you realize, okay, maybe the business model doesn't work or the company does, or the company may be outgrowing the founder.

Or alternatively, I think you've seen cases where the startups grow kind of, in very meet yore pace and then all of a sudden they, they found a killer product and they end up becoming, a very successful company. So I think that's the part where it's a bit ambiguous.

It's very non linear. I think that's what's fun as well. I think it would be super boring if you woke up every day knowing exactly what's gonna happen. I think number two, what I did not expect, about the job is also how surprisingly, where deals come from. Like when I first started the job, I went to watch HBO’s Silicon Valley, you know, which I think it's very funny, but, doesn't tell you the whole job.

But in reality, I think the job is a lot of serendipity. The founders of the startups that you find, of them, might just be something you read about in the news and you're like, wait, this is quite cool. Let me reach out to that or it could be you have a chat with, someone who works in a TikTok shop or Shopee and they tell you, oh my God, this brand is growing like crazy.

Or it could be one of your classmates, or your classmates' friend who's working on something and needs some advice. And as you talk to them you realize, wait, this is, uh, quite a good idea. So I think it's really, serendipitous and sometimes unpredictable where the best founders and startups come from.

Jeremy Au: (21:25)

I think the agreement I have is obviously about the speed of the learning curve, right? And I, myself was surprised by that. Right. could you share a bit more about what that means, and what that means for you?

David Yin: (21:36)

Yeah. So it definitely, felt like I was drinking from a fire hose when I first started the job. And I'm sure similar to you, we've drunk, you know, from a lot of different kinds of fire hoses before. But I think what makes this job, quite hard at the start was just, first of all, the lack of data.

Second, avoid kind of a lack of structure. And third of all, I think you need to have a very high velocity. So you just, for example, I think at the early stage you just have to meet a lot of companies and talk. A lot of them to even get a sense of what's a good company, who's a good founder, what's a good valuation and all that.

So I think that at the initial stage was just trying to benchmark, and have an anchor for all these things, and not having those to start with, I think makes it hard. I think what also makes it hard is not really having a true role model. I feel like, for example, in consulting, it was relatively easy to be like, all right, I want to be like this partner, so let me just try to, know, work with them as much as possible.

Follow what they're doing. And then you sort of just follow the path. Whereas in VC, I think it's a lot harder to be like, all right, I really like this vc, and I want to be just like him or her and end up investing like them. I think you just gotta find your own, kung fu in a way.

Jeremy Au: (22:48)

What do you think are some misconceptions about venture capital as a job?

David Yin: (22:56)

So I read this article that I thought was quite interesting and it had a two by two matrix. So one axis was, basically the concentration of jobs that MBAs from top MBAs tend to go to. The other axis is the concentration of people on the Forbes 400 list. So basically the outro wealthy and the rest of us.

And what was interesting was that there were certain jobs that were very well represented, and certain jobs are very underrepresented. So by the underrepresented, it means that the folks a lot of folks, for example, coming out of MBAs, want to go into VC, but you realize that the people who really make F.U. Money from VC, it's not that money.

Right. It's ultimately not a job that I think makes you happy money and makes you crazy rich, right? Even the best VCs in the world started their own firms and they're the best in the business. If you look at the Forbes list, they are worth three or 4 billion. Again, that's an insane amount of money, but, you could make a lot more money doing other stuff as well.

So I think first it's just about, some people think that us in VC we're just, rolling in cash every day I think it's a lot more, I think, of the day-to-day, you know, really trying to, in some ways similar to consulting or even journalism versus, maybe what people expect. I think the second misconception is maybe the pace of VC.

Definitely, during the bull market, things happen very quickly, but the reality is that it takes time for companies to really build, for companies to grow and for companies to grow across different stages and to eventually, So I think that was something that I personally found very surprised by. It wasn't like in the media, every one and a half years it feels like things are completely different.

Sometimes you're tracking a company from day one and maybe 10 years later they end up exiting. So it's a long journey.

Jeremy Au: (24:44)

Yeah, you know what the joke is like, you know, if you're a VC, you definitely have a nice house, but if the founder makes it you get to go on the yuck. So the problem, of course, the odds are only like one in 40, right? So I think that's the awkward dynamic here. And I think what's interesting here is, you kind of mentioned a little bit about, F.U. Money versus non F.U. Money.

I mean, How did you decide for yourself? Right? Let's, not venture capital. So you're basically saying, I'm not into the F.U. I'm into the non F.U. Money camp, I guess. What do you think about that?

David Yin: (25:19)

Yeah, I think one is still back to interest at the end of the day. Like, I could have stuck around in public equity and made pretty good money. I'm not sure if it's F U money, but I feel like if I'm not that excited about what I'm doing, it's really not worth it. Right? We're all at the stage in our lives where we wanna hopefully be successful at doing something that we're, we like versus just trying to chase this.

This thing. And I think I really felt this way when I was working at a public equity firm. It was a great job, a great firm, and great people, and I think that the other people doing it was just so much more passionate about it than me. And I think that's when I realized, all right, this is not gonna cut it for me.

Right? There's always gonna be someone who's, who really loves the job on top of the money. I think number two, to be fair, venture capital still offers a lot of optionality in terms of, you see a lot of good ideas. We see cases where VCs sometimes, join their portfolio companies at an early stage or they go start their own company.

So I think those options are still open. So hopefully, it doesn't mean that joining VC close the door to FU money.

Jeremy Au: (26:22)

And what's interesting is that obviously you meet all these decisions and you also made a decision to work across various borders, various countries. And I know a big passion of yours actually has been really like, for example, the US-China. Geopolitical dynamic.

Obviously, you're at, GSR, which is obviously very famous. China-based venture capital fund is globally oriented as well. So, I'm just kind of curious about what your thoughts are about, the whole dynamic in Southeast Asia.

David Yin: (26:50)

Yeah, So I think one slightly different perspective I bring as a VC is the more macro lens I have. And also some of the public equity exposure I have. So sometimes I almost start thinking from a very high level and it influences some of the micro-decisions I make. So to put things into maybe, more tangible terms.

One thing for sure is that I think Southeast Asia should benefit a lot from geopolitical issues between US and China. Cause at the end of the day when the US and China are not having the best of relationships, they look to Southeast Asia. They want to have more influence there this is why in the past few years we've had more top officials from both countries within the region.

We've had a lot of funds, investment funds and all that pouring money into the region. So I think in a way, the region really benefits from US-China relations start doing so well in fact, part of the joke is that, first of all, some people say that certain officials in China are almost like the CMOs of Singapore, right?

Whenever they make a policy that's not. For capital or for entrepreneurs, these entrepreneurs in capital end up flocking to Singapore and then going to different parts of Southeast Asia. So in some ways, I think the macro view actually makes, it on Southeast Asia.

Jeremy Au: (28:03)

And what's interesting of course, is that you see this wave, obviously of, Chinese entrepreneurs, like you said, expanding Southeast Asia, relocating and I think that's maybe very clearly appreciated by folks in some countries. I think, especially Singapore, I think is much more obvious. I think it's less obvious I think across Western Southeast Asia if I'm seeing a lot of them actually.

And then I think, that it's very even more underappreciated, I think outside Southeast Asia. Right. And so I'm just kind of curious about how long you think this China continue, and what the implications of that would be.

David Yin: (28:36)

Yeah, I think it's going to continue for a while just because I think there are a lot of structural issues why, Chinese capital money going abroad, right? First of all, the domestic market is relatively developed. The crazy growth years I think are over and extremely competitive there.

And I think number two, a lot of them have been encouraged by some of their overseas adventures. For example, I think, Pintu went into the US as TMU I think they're very encouraged by the traction that they saw with, both TikTok and also with her, right? Both companies are having most of the teams in China.

And, they managed to crack what's probably the most competitive tech market in the world. So similar to I think the rest of the world, including Southeast Asia. I think a lot of this Chinese capital and money are just gonna go abroad to look for more growth at the same time I agree with you.

I think it's not always a good thing or it's not always something that happens without friction. I think part of it, maybe sometimes comes from different cultures and different working styles. I think sometimes it also comes from Chinese founders, both assuming that whatever has worked in China works elsewhere and sometimes not having the humility to recognize that each market you have to localize and whatever you knew from China, I think it's a good reference, but it doesn't guarantee you a win in the playbook.

Jeremy Au: (29:53)

Yeah, I think the humility part is true and for almost every expatriate, and founder, right? I think when you are more of an immigrant founder, I think, you're kind of like, there's a little bit of an I wouldn't say hierarchy, but a little bit of dynamic where you're like trying to localize into the space. Right?

So I think there's much more of that mindset of like, I'm trying to integrate and we understand, but I think when you're an expatriate founder where you're feeling like you're coming, sliding down the scale because it's a less mature technical system, is maybe a more greenfield vertical in space, then. I think that confidence lets, you obviously make good decisions. As you said, PFA brings capital, I met, two Chinese founders and the strategy for building up in Indonesia was, to bring everybody that he used to work with from China to Indonesia. That was literally that talent strategy and I was very confident. And, but then like I said the guys all switched ahead a little bit, which was like, well, don't you also need Indonesian local talent and beyond as you know, sales, and marketing? So, what's that plan to integrate, right? And so there's a very kind of like that, I dunno, you can say double edge sword but I think that's, that humility is really key, right? And, I think things can blow up pretty fast if you're not humble about your approach as well.

David Yin: (31:09)

Yeah, probably I agree with you, Jeremy and I think other ex-pat groups sometimes have learned it a hard way. If you look at the Americans or the Japanese in their good old years of theirs. They're multinationals expanding overseas. I think some of them have also tried just bringing entire teams from Tokyo or New York overseas.

And I think they've also found that it doesn't work in your local teams for so many different reasons. So I think the idea is if you can bring the best from both sides hopefully you can create a better result.

Jeremy Au: (31:41)

Yeah, I think that reminds me, I think the rocket internet did not localize very well, but their talent that has, stayed on after five and 10 years has pretty much all localized much more, right? So I think remember right? The Rocket team was very much like this, really, you know, a lot of engineering was done in Europe, not no local engineering in Southeast Asia. So local product teams are screaming for features that didn't really get implemented versus, Today I think we see. Honestly, there's so many Germans and I was joking recently, my friend was like, wow, the number of Germans I met who are now building with a local co-founder.

And they've localized, right, in the sense of like they're very sensitive about what they know, sensitive about what they don't know, sensitive about what they're good at versus sensitive about what they're being bad at. you know, they often say some stuff like, oh well I learned from Rocket, or I need to understand, and you know, like the humility side kind really came out and it's not as if it was a script, right? It's like they just learned it a hard way. Right. So there's an interesting dynamic there. I think from your perspective obviously, as you think about, geopolitics and everything, I think one thing that I remember debating and discussing was like, she said something really smart venture capital and she said, I think folks are kind of like too optimistic about Southeast Asia next 10 years. And too pessimistic of Southeast Asia over the next 50 years And she's basically, you know, talking about the dynamic of obviously like long-term growth. Pace growth opportunities versus, the timeframe needed for venture capital investments. Right. And for founders who want venture capital cash right, to approve it within 10 years, I'm wondering what you think about that.

David Yin: (33:16)

I think there's a lot of truth to that. And I, myself, I'm very long term bullish on the region, and I want the region to succeed. At the same time, I think there are still a lot of short term challenges, for example, with infrastructure, and infrastructure is both in terms of the hard infrastructure, like digital payments, internet connectivity, nice roads, EV charging stations and all that.

And also on the soft side of things as well I think outside of Singapore education-level literacy is still relatively low. So I think a lot of these issues still need to be resolved and I think since we, we're both interested in tech and startups, I think a lot of founders in the local ecosystem I think are relatively new to the game and this market with some crazy highs and crazy lows would be good training for them in terms of how to build a better company the second time around if they do become a serial entrepreneur.

And I know I, I've been a media guy. I think it's always easy to buy into these nice fairy tales of some Harvard dropout who ends up starting a multi-billion dollar company, and it happens. I think the reality is that most founders tend to be somewhat experienced, whether it's having a few years of experience, doing their own startups before they start something that truly takes off or they've worked elsewhere where they develop more e.

So I think even for the local founders, I think a lot of them will really grow from this experience and properly build better and more resilient companies. But for now, it's definitely everyone in the ecosystem who is quite new. And therefore we also see some of the challenges that come with a fledging, but growing e.

Jeremy Au: (35:04)

And as you think about this, fledging ecosystem, could you share about a time that you personally have been brave?

David Yin: (35:11)

Yeah, so maybe outside of work. One thing I did after I graduated was I did backpacking around the world. I was around the world for three months, with just a few dollars and my passport and one particular thing I did, and in hindsight was a little dumb. I tried to do a land crossing between Jordan and Israel.

I just thought, Hey, it's a cool idea. I didn't realize there were so many, both logistical, but also geopolitical situations. And the funny thing was when I bought a bus from Israel to Jordan a bunch of, refugees ended up bordering the bus as well, and I was asking them where they're from and they're telling me that they were from Syria and they're running away from isis.

This was before ISIS was covered very much in, the media so in hindsight, it was quite a bossy and brave thing for me to do. But back then I just thought I was young. I wanted to explore the world. I didn't have too much money, so why not try the fun and risky thing? But all in all, it was good fun. I'm here and I'm still alive.

Jeremy Au: (36:12)

And I think you obviously, have been profiling many profiles of bravery, right? You did at Forbes. You obviously see that in venture capital for the various founders that you're working with. What are some, themes that you've seen personally that resonate with you for this landscape of brave folks?

David Yin: (36:31)

I, first of all, I think most of the brave folks, I think they just have a deep conviction in whatever they're doing, and very often they're contrarian as well. Before people thought that different business models could work out. Everyone thought they were probably crazy or dumb, or a combination of both. But I think they just have a very deep conviction that they're right and they end up persisting even though they're quite a contrarian.

So I think it takes a certain level of being able to be different from others. I think number two is that I think feathers of the same feather flock together. And I think a lot of times you also have brave people coming together. I think that's also what's important. Like even for venture capital and startup ecosystem, if you just have one, if you have five startups and one VC, I think it's hard for you to take off.

But if you have a lot of people in the ecosystem supporting each other, helping each other to make brave decisions make bold choices. And be different from the rest. I think that's how you allow the system to flourish. And I also really enjoy what you're doing with these podcasts cuz I get to hear from a lot of other brave minds and feel like I'm not so crazy after all.

Jeremy Au: (37:40)

Feeling not so crazy after all. I think that's a very interesting phrase. What do you think makes you feel crazy, I guess, in the context of bravery?

Well, I would say that growing up in Singapore, again, not living that very traditional, very linear path to success, I feel contrary almost every day. Right. I've seen my classmates, they're already having kids. They're already buying their second or third house, and I'm like, wait, I'm still on the, not on the same path.

David Yin: (38:10)

Right. Not like their life is charted out for the next 20 years. So in those days, I do feel like I'm, I'm a little weird, but I think just like I've bounced around between journalism, to consulting, to startups, to venture capital, and I can connect the dots looking backwards I have a certain conviction that whatever I'm doing now will lead me to a place that's fulfilling and impact for.

Jeremy Au: (38:32)

Wow. I think that's a really true point. I think you're right that there's often moments of feeling kind of crazy, right? versus everybody else in the world. If you had a time machine right? And, you went back 10 years, right? All the way back to 2013 and you, sorry, your 10 year old younger self.

Right. Not a VC, not a grad school student. Right. very much from, the start of your journalism career back then, even at McKinsey yet as well. Right. So what advice would you give yourself?

David Yin: (39:06)

So o obviously buying Bitcoin, investing in all that. If I could, I would. But I think I would have been braver actually. I think, again, looking backwards, most of these decisions ended up being pretty trivial. Ended up being quite addictive, but at that time it, I know it sounds weird to quit one job for another job, but at that time it wasn't an easy choice.

But I think if I could tell myself 10 years ago I'll just tell myself to be braver, to take more risks and at the end of the day, very few things are really life or death, and very few things are really IRRs. And at the end of the day, people also don't care enough they think about your failures.

People just see the times when you succeed and so on. So if you really end up failing, just cut your losses, fail quickly and try something else. So I'll definitely ask myself to be braver and to just take more risks and have more faith that everything is going to take me to the right place.

Jeremy Au: (40:04)

Looking here 10 years in the future. Seems very far away, but also sounds like it'll probably be over before we know it. Right? what's one hope for yourself, at that point?

David Yin: (40:16)

I think one hope is I do want to be at the stage where I've, I'm able to make an impact with my, whatever I'm doing. But I also really hope that I'm able to help other people in some way. So beyond just investing in good companies, hopefully, I can help other people in the ecosystem become better investors, become better founders be able to take brave decisions with their lives, be able to be more entrepreneurs with their lives be able to believe in themselves even if they didn't come from the most privileged background.

So I think being able to also do something beyond myself and help other people succeed, I think that's something that I hope to achieve in the next 10 years.

Jeremy Au: (41:00)

On that note thank you so much for sharing. I would love to summarize the three big themes I got from this conversation. The first of course was, I really love the phrase, you have a random walk to Korea from journalism to McKinsey, to grad school, to VC partner. And obviously, I think some of it is conventional and some of it is actually non-conventional.

Especially I think you mentioned some of the similarities between journalism to VC. For example, the app for crafting a story, learning about different industries, interviewing business leaders, and network access. As well as the differences, right? Looking at I R R return, working in growing founders. And I love the different anecdotes like finding out and writing a great story about the largest prya chain in the US by walking to the restaurant from the banner. The second I think we like was finding yourself a staff in Harvard. And obviously, there's a joke about finding yourself a startup and Harvard, it's a joke that I think a lot step and Harvard people kind of resonate with, but also I think there's a lot of truth, right? Because you mentioned about there's time there's space, there's a brand, there's optionality, and there's space, right?

To discover we shared right about what to why, what's the superpower of opting into reversible decisions versus optionality chased and your career testing sprints. Those are all very interesting. I think I don't know what break prompts are, but I think for folks who are looking to experiment and figure out what you're trying to do next and find themselves. Lastly, thanks for sharing about drinking from fire hoses. Definitely, I felt that too in this conversation. I think we got a lot of it, and we talk about all kinds of random things from, well, I would say random, but actually very deeply connected on a thematic level. We talk, for example, about how Southeast Asia benefits from the US and China's attention.

We talk about how you, yourself are surprised about drinking from a fire hose and how you cope with it. And we'll just talk about how, like the ambiguous choices, right? In venture capital, right? As a job. We talk about how there are so many different investing styles. For example, share hustlers versus deep technical founders are undervalued under dub founders versus fast-growth companies.

And we talk a little bit about the speed of the learning curve and how you're trying to accelerate it, as well as your surprise and openness to surrender fatigue as part of Korea. And of course, lastly, you're sharing about how bravery has been something that you enjoy and also something that you wish you had done more in your earlier public career and also how it always ends up feeling a little bit crazy to be brave.

So thank you so much, David for sharing.

David Yin: (43:26)

Yeah. Thanks so much, Jeremy. It's a pleasure as always talking to you and look forward to more of your episodes.