Welcome to the Girl Dad Show. Thank you for tuning in to another episode of the Girl Dad Show. I am super excited to have Christine on the show today. Christine, thank you so much for taking time out of your busy schedule to be with me here today.
So excited to be here. This is like a fun reunion.
I know. I feel like I haven't talked to you in years. Quite literally years. And we haven't seen each other in maybe a decade long. Yeah. You know, it's crazy that I run into people and I feel like, oh, it's been, you know, it hasn't been, you know, been a couple years and they say it's been more than 10 years and so the time has just like flown by.
Yeah. But I have I have very fond memories of being in batch three at 500 Startups and I think of you very fondly and associate with that experience. For whatever it's worth, it's really good experience for me. But I don't I don't want to I don't want to cut your intro short. So, let's jump right into it. Why don't you tell the listeners what you do for a living and who you are?
All right. Well, as Young said, I'm Christine Sai. I am CEO and founding partner of 500 Global, which used to be called 500 Startups in the early days. 500 is a global venture capital firm. We primarily invest early. Usually is one of the first or the first kind of institutional investor into a company. We'd like to build the relationships with founders super early, whether they're in the US or around the world. Today we've grown into more than two billion in AUM. Portfolio is 3,000 companies and growing and they represent 80 countries around the world. So we really value and continue to have conviction in the thesis we had very early which was that great companies and iconic companies will come from all corners of the world and we really want to find them.
Yeah, that's awesome. And it's so fun to see how much you've taken this organization and grown it over the last apparently more than a decade. But I will I am curious what led you before to 500? How did you get into venture?
Well, it's a it I feel like I can start from kind of like when my professional career started or I can start from like when I was born or when I was born or even long before I was born because I feel like all of those things have influenced that. But I guess
Wait wait wait no do the born thing now. Now I'm curious what what about the born
I was born with a term sheet in my head. I well the reason I say that it goes back to even before I was born because I think a lot of my love for venture and why I still get up in the morning every day excited about it is the love of technology and I feel like a lot of that influence on being excited about tech and products it really comes probably from when I say before I was born I think of my parents and particular my mom who took up computer science before it was you know before it was really mainstream it was like code doing programming on punch cards if you people know what punch cards are. But since then, you know, we moved to the mainland. I was, you know, fortunately we moved to Silicon Valley like to the Bay Area and growing up in a household where there was computers around my my you know, my mom was worked in Silicon Valley as an engineer. So I think a lot of that early exposure, which is very unlike I think many of the founders that we backed, they didn't come from that kind of environment. And so I forget that oh it's it's really unique to be able to just be surrounded by technology. And I think that just led me to being really excited about the internet and products and building websites and kind of, you know, on and on. And so that's I think fundamentally for early stage venture, it's I I feel like if you don't really love technology and and products, then it doesn't seem like it's a great fit. But I I love, you know, I I love I love
Yeah, it's so cool. And I I will say that that's a huge component of of how we grow up, like nature, nurture. But I do think that how you grow up is so so powerful in what you do in life. And I think that it has a huge impact on my life as well too. And so that's really interesting to hear you say that cuz I think I've pivoted back into main street businesses because of my my childhood and how I grew up. So it's kind of funny. But
The punch card thing before Go ahead.
Oh, I mean I forgot. So you you know I grew up in Bay Area and I forgot where you grew up. I'm I'm sure you
I grew up in the I grew up in the Bay Area. I was born in Oakland, but my dad my dad had a very typical immigrant story where we owned a little liquor store in Oakland and so I grew up in a in a brick and mortar kind of very very very typical stereotypical Asian immigrant story. Yeah. So
A number of those in my my family. It's like and they were even more stereotypical. They were in LA.
Yeah. Exactly. So I think that's always been embedded in me as well too, watching my dad build these service businesses. And now that I'm older, I'm I'm kind of reverting back to it. But can you before I go into the other stuff, I just have to know cuz I do know what these punch cards are. I had a mentor that was a old school engineer. Can you just like walk me because it's it is what I think it is, right? It's one of those paper sheets where they have the the code is literally punched out in holes and then you run the paper through the thing, right? And then that prints out that's the code, right? Like that it
Yeah. Like there was no, you know, cursor or cloud code and no like or emacs or whatever you use to code. like it was I can only say this secondhand cuz not like I had direct experience with it but they were basically like paper cards and holes punched I don't actually know how what was used to punch the you know to get to that point but effectively that's what you would put into the computer and I remember my mom mentioning if one got out you know it's just you you drop them then it's just like game over like it's all ruined so so
We've come so far it's crazy to think about that, right? Can you imagine writing lines of codes and little hole punches? It's insane.
I wonder if the analogy is like I mean, let's say writing papers, you know, handwrite it or typewriter and then now maybe you don't even write it. You you have something generated for you and then you maybe edit there. So, there's human in the loop, but I'm sure plenty of analogies in in other areas.
Yeah, totally. I love it. I I definitely want to see one. I've heard about it and I've never actually seen it. I'm definitely curious, but I think they have one at the tech museum in Mountain View, so I'll have to go check that out. But
Yeah, the computer history museum. Yeah.
Oh, computer history museum. Sorry. Yeah. Yeah, I misnamed it. Yeah, that's right. Okay, so now back on the regular show. Sorry, I got I got curious about the punch card. But on the on the journey. So then you grew up in it. You grew up in tech. And that's really cool that your mom did that actually because isn't that kind of pioneering in a little ways? Like a female socio so like society likewise like a female engineer back then is also kind of unique too, isn't it?
I believe so. I I mean I I don't have like specific data points on this, but just from what I was aware of, even within my own family and my friends, it was not common to have your mom be maybe it wasn't so and maybe where I grew up, maybe it wasn't so uncommon that the the mom worked, but it was definitely uncommon that they were in in a technology like in in tech in in a tech company and
And as an engineer developer of of all things. And I certainly within my Korean family that was highly highly unusual. So, but you know, I didn't really think of it at the time. I mean, she was certainly like one of the few immigrants in her teens and let alone female. And so, I'm sure there was quite a bit of a cultural gap that she had to adapt to. Thankfully, both my parents spoke English very well even before they had me and my brother, before they met. So, so I'm sure that that helped. I lot know a lot of stories of kind of that typical story like the immigrant dream whether they're from Korea or you know Hong Kong, Taiwan they come to the US for you know a better life or they for their kids and they leave behind a more educated type of role to think you know go into like they open a store or something that they would not have done back home but because of the language barrier but they still do it you for their for their families and so very very classic immigrant story. Yeah, it's very cool. I love that. What? That's awesome. She sounds like a gangster. I love it.
Okay. Yeah, she sounds like she's like a badass. That's great.
And then what does your dad do?
My dad also I I actually think so the entrepreneurial side probably comes from him because when he he my parents met in in Guam. So they actually both went to Guam from Korea to Guam for different reasons. And it's sort of like Hawaii where there's you know a lot of Asians there. I mean at the time
It was a common landing point or launch pad from to get to the mainland US and obviously Guam is US territory.
But my dad was you know kind of got his start in like an architecture and construction and then when we moved to California he actually opened his own firm like his own kind of contractor form. So he always worked for himself. And it's funny now I think about it as we're talking about this. Yeah. I mean it's it's not a startup per se but just more the fact of running your own business an entrepreneur and all of the trials and tribulations of that but at the time I just knew oh dad you know APA has his own company mom works at Intel and it just seemed very normal to me
Yeah that is a startup that's awesome that's so cool so you had an engineer techn technologist mom and you had an entrepreneur dad
Yeah it's a a good combination I guess
Very good combination that's you are right it is pre-born you you were basically getting getting ready for this before you even were born. That's lovely. Yeah. Okay. So then now let's go to the next step. So then what what led what were you doing before you became the CEO of 500 Global?
Well, most of my career or actually all of my career was was in in Silicon Valley and in the Bay Area. So I went to Cal Go Bears. You know when I when I graduated it was a terrible time in the the valley and just you know was the do right the com boom and bust. That's right. you know I worked at a small software company a few months after after I graduated and that was a bit more of like I'll just take some you know get some job right so it was a small software company that was still a kind of family family-owned but it was a pretty big business it's just more that they never raised capital it was all you know all owned by the the the family it was you know I have a vague memory of what I did it was probably not very glamorous I didn't you know it's a 21 year old clueless. And then I about was there for a few months and then you know I moved over to one of the few tech companies I was hiring at the time which was Google. And I remember I just I loved Google. I used it in school and and I thought like oh my gosh if I want to work on the internet and tech this is the place to be. It wasn't Yahoo. It wasn't anything else. And so I went there and then you know I was there for most of my early career like seven years. And when I joined the company, it was 2003. So about a year a year before they went public. And the company I think was maybe still less than a thousand people. And then when I left in 2010 to start 500, it was it definitely exceeded five five figures. I I don't quite remember the exact number but you know during that time I think a lot of what influenced me to then leave and go into venture and start 500 was really the the ability to work on platforms that a lot of developers used or or you know publishers used and I think at some point I started to realize oh you know they're startups or you know maybe they were dotcoms startups and they the prospect of working with them to any of them could be building like the next Google or the next YouTube which also was at YouTube for a bit. So somehow I always found myself on that side of the business. I never worked on any Google consumer products. It was always developer facing or publisher facing. So I think that kind of started to get me interested more and then I realized about this thing called venture. Didn't quite get that you have to like return you know generate returns. I just thought venture you get to work with these early stage really really early developers and it seems that like that's what I was drawn to.
So funny. So when did you think when do you feel like you learned what venture meant like the actual mechanics of the business?
I think I started to pick up on it through you know so I I was really fascinated by it. I think a lot of it was at the time, this is like mid 2000s, VCs didn't, it was a very small industry for one thing, and it was not very transparent and the couple or one or two people that would actually blog about it and it's not like today where everybody's on X and and building their own brands and they use AI to generate content. It it was like blogger. Yeah. So Fred Wilson was one of the early OG bloggers and he would write all about like being, you know, he was on the board of Twitter and a lot of great companies, Zingga and and then he would talk about company building and I cold emailed him, you know, in 20, you know, 2007 or so and asked him to come speak at Google. And back then having a getting an email from someone at Google probably was more, you would get noticed more than today. he actually responded to a cold email and that was like an example of how I just started cold contacting people in venture just because I was very interested and just learning about it and I biggest takeaway for me I think was that everyone has different backgrounds I didn't get too much about like a lot of the mechanics on the fundraising and starting a fund and every everything else I so I think a lot of that I kind of learned after the fact
Yeah like a true like a true startup founder I love it
Yeah I remember hearing from some you know there's a lot of during that era of Google. There were so many amazing people that came out and started companies or started, you know, became great investors in that kind of early 2000s era. I I remember one of them mentioned you she went on to, you know, be an entrepreneur, CEO, and now is an investor, but she remember she would take customer calls and they would ask her for I forgot what term it was, but they would ask her for like an SO like a term sheet or like an LOI and then she didn't know what that was, so she was like, "Uhhuh. Uhhuh." And then she would be googling like what is this? Yeah.
Fake it till you make it. You're right. Yeah. Fake. Yep.
That's right. That's like that's like that's how early stage startups are sometimes. You know, you just got to keep moving forward and just butts through it and figure it out as you go. So now So now that you're in this position and obviously there's a lot of trials and tribulations through it. Have you ever asked like and like your kids like what they think you do for a living? Do they have any comprehension of the scale and scope and of like what you're building and and the purview of of your domain and your role?
They've definitely had a lot of exposure just from I mean I I would say like meetings they overhear me on and I think especially during the pandemic when everyone was at home they would you not a lot of space to hide but yeah I think they if I were to ask them I'm sure they would be able to say in a very high level like mom you know invests money or gives money to people and then the companies they grow and then maybe she'll get money back and then sometimes I've heard them spouting off like GP LP the company, but I don't know if they quite know to that level of detail. So, I But I It makes me think I I should when they when they get home, I'll I'll ask them. So, can you explain what mom does?
Yeah. Tell me what you think I do. Yeah, I'm I'm actually really curious, too. Yeah, that is that is funny. Yeah, please do. And have you talked to your parents about what you do and what do they think about where you're at?
Well, they I so I think they have a general idea as well, although there is always kind of like a so what happens when the company, you know, a company is XYZ, right? And so they I think they they might be potentially at the same understanding as my kids, although maybe a bit more, but so but I think that they I remember, you know, when initially when I was going to leave Google and go, you know, start this thing, they were very very nervous and very like because they don't know the world. They know if like they know what Google is. they know that's at least at that time seemed like kind of safe big company growing company and and then they're like you're going to go you know start this thing with some some person I don't know and but I think today they they get it they I think also especially as I took over as CEO like now seven no not seven years ago how long has it been my why is my math so terrible it's like nine years ago actually so I think even then I think there was parents always worry about their kids they especially worry about their youngest daughter, right? But now I feel like they I'm sure that they're they're proud because my dad will stalk me on LinkedIn and and he'll he'll Yeah. And he'll ask me, "Oh, I saw on LinkedIn and or I saw on this social media about XYZ and sometimes he knows before I do because the 500 team will post things on the 500 channel and I don't even see it and he he sees it right away."
Oh, he has it on he has the alert on. He's he's watching. Yeah, I love that.
He has an alert set up. Yeah, that's awesome. Oh, dads will still be dads. I love that. That's great.
Yeah. So, they like what you do and they they don't may not grasp the concept of what you do, but they definitely love it. That's good.
I think so. I feel like at this point, I think they have some, you know, some idea. I don't know if they know the inner workings, of course, but I think they they they will always they'll never stop worrying about their kids. So I probably much like we will never stop worrying about our kids. But I know but you know I think they they are they're proud which makes me happy.
That is good. Yeah I I agree with you. My mom is like so like that. Like I could literally win the Nobel Peace Prize and she would literally be like yeah okay that's great. Are you eating healthy and are you are you happy? You know what I mean? Like like that's that's what her response would be. You know like you know and I'd be like mom can you please like take a minute and focus on what I'm trying to tell you? She's like, "Okay, okay, honey." Yeah.
I think my parents like perpetually think that we are hungry. Like, we can, you know, we can cook. I mean, maybe not great, but we have kind of a rotation of meals. And then my but my mom like I think she's just like, "No, like I'll make you." And actually, just today she brought over a big jar of soup and for what is it? The tok like beef soup. She's like telling me how to, you know, heat it up. And like I I know, but I think it's you know, it's just sort of sort of like I'm sure she knows we can cook ourselves, but she just like, but I can't help it. I must make sure you you are fed, you know, real food.
We'll always be their babies. Yeah, for sure.
Yeah. Yeah. Much like our our little ones.
I know. Are you Are you Do you think you'll be like that as well?
I'm not a very prolific cook, so that part I don't know if I would be that useful, but there probably is. Yeah, you know, it's funny like growing up you think about you can either go both ways like you can either be like I'm not going to do what my parents did or you you maybe you think the other way. I I think by and large it's it's usually like oh my parents didn't understand me especially the immigrant if there's an immigrant golf and as like first generation kids and then you think I'm not going to do that but then you do it.
It's hard to it's hard to unwind. You can't get that out of you. But so we'll we'll see. I think one thing I do appreciate with with our kids is that given the ages that they're at, you know, you always think, oh, this is they're going to not this is when their view of their parents starts to decline because they have their own lives and getting older, but then I I do find it I I do find it fortunate that I think for both of them, you know, we still have a very close relationship and they certainly will tell us things that I I can't imagine I would have told my parents at that age as like a teenager, right? So, yeah. So, that's good.
That is good. And I I I see it more as like I totally know what you mean, by the way. Like how you want to like do the opposite pendulum of like how you're raised and then you end up replicating it. It's called trauma, Christine. It's called PTSD and trauma.
Yeah. you know, even like even with so with let's say you know my kids are a little bit little bit far off you know there's some years but the older one you know it will be getting actually maybe a lot of the kids are starting to think about like post post high school and college and then right thinking about you know don't want to pressure them one way or the other especially given like who knows like what what's going to happen with with colleges and
Yeah but it at the same time. I wonder how we'll be in terms of like like where what they choose to study or what they want to do. So, I don't know. We'll see.
Do you have a secret wish like of what you want them to do? Obviously, you're going to support them and their dreams and passions, but like inside of your heart, is there something you're like, "Oh, man. That would be awesome if they did that."
You know, I genuinely want them to pursue something that they are excited about. So, I would hate for them to be like, "Oh, I'm going to do this major because my mom or my parents wanted me to." And we we we really don't tell them like, "Oh, you should really consider engineering or being a doctor." Unlike probably everybody's immigrant parents, right? They'll be like, "Oh, you should be great if you're a doctor or" and my parents actually didn't push me on the doctor part. No, no, no. They never pushed me on the doctor path. I think they felt like, oh, you know, being a doctor is pretty hard. But, you know, I I so I on that
So uncorean of them. on my life.
But I think for my kid like I so you know I genuinely nothing really comes to mind of like oh I really want them to be in this major but I probably do think if they wanted to pursue something that I probably myself found very like maybe very either very technical or like not as easy as other subjects then I would be kind of like you know they they did that. But I I wouldn't necessarily go say you are going to be a math major or you are going to be some science or engineering major. So So we'll we'll you know we'll see what happens.
Yeah, that's awesome that you're taking that stance of just like letting them explore and find what they make what makes them happy. That's great.
Well, famous last words, but do you have a secret wish though? Like without without swaying them like if you have like like a thing cuz like for me I will tell you I'm not going to sway them. I'm going to I'm going to support
them in whatever they do. But deep down inside, I would love it if they were musicians. Like, I would love that.
