Tiger Sisters - Be Dumb to Succeed (the secret according to two-time Y Combinator founder Vu Tran)
Episode Date: February 3, 2025In this episode, the Tiger Sisters interview Vu Tran, two-time Y Combinator founder and CEO of Butterflies AI, The First AI Social Network. Join us to learn about how questioning constraints and break...ing rules helped him launch two startups before turning 22, why being dumb led to his success today, and how he continues to apply his “go max dumb” mindset. Let’s get vulnerable together as we talk about Vu’s upbringing and why he considers poverty to have been a gift – and why embracing your roots might be your greatest advantage, too. Don’t miss our debrief at the end with just Jean and Cherie where we talk through our favorite learnings from Vu like an HBS case study for even more insights! ------------------------------------------------------------------ 🐯👯♀️ Tiger Sisters Podcast | Career, Entrepreneurship, and Life Welcome to Tiger Sisters, your go-to podcast for career mentorship and life guidance! Hosted by Cherie Brooke Luo and Jean Luo, we’re your internet big sisters here to demystify the ups and downs of navigating careers, tech, and entrepreneurship— all while staying healthy, stylish, and joyful along the way. Cherie is an influencer who has broken down the complexities of big tech, finance, and MBA programs for millions of viewers, with over 100M+ views across platforms. Jean is a tech product executive and investor, holding over 50 AI patents, who has built an impressive career in product management and institutional investment at companies like Goldman Sachs and Snapchat. Between the two of us, we’ve survived stints at top investment banks and big tech firms, founded startups, and earned four Ivy League degrees—if we’re counting Stanford! Yet, we still find time to focus on wellness, friendships, fashion, and skincare, always sharing the lessons we've learned along the way. Whether you’re here for career advice, stories about balancing life’s challenges, or just to hear our honest takes on what it means to pursue fun, wealth, and joy in all areas of life, we’ve got you covered. 🍿 WATCH NEXT: Tiger Sisters Season 3: Facing Rejection to Selling His Startup for $200 Million: David Shim's Founder Mindset 💛 LET'S CONNECT: ~ CHERIE ~ 🤳🏻 Instagram – https://www.instagram.com/cherie.brooke 📱 TikTok – https://www.tiktok.com/@cherie.brooke ✍🏻 My Substack – https://cherieluo.substack.com/ 👩🏻💻 LinkedIn – https://www.linkedin.com/in/cherie-luo/ ~ JEAN ~ 🤳🏻 Instagram – https://www.instagram.com/jeanluo_/ 👩🏻💻 LinkedIn – https://www.linkedin.com/in/jeanluo 🎵 Music produced by Sammy Signal https://open.spotify.com/artist/2HsyknHuxhT8RoZfn5rqMS ⏰ Timestamps: 00:00:00 – Welcome from Cherie and Jean 👋 00:01:57 – Meet Vu Tran: 2x YC Founder & CEO of Butterflies AI 00:03:04 – Questioning Constraints: Which Rules Are Worth Breaking 00:05:26 – “Don’t have the same regrets as me.” 00:06:25 – “Go Max Dumb”: How Vu Operates 00:10:09 – Refugee Camp Roots to First Job 00:11:16 – Vu’s Big Wake Up to See Two Paths in Life 00:13:23 – History: Interracial Marriage to AI-Human Romance 00:17:40 – Jean & Cherie’s Deep Dive Debrief 00:18:17 –Having Nothing Made him Unafraid 00:21:36 – Jean applied Vu’s advice of questioning constraints as a product manager 00:24:00 – “Go Max Dumb” at business school & when leading teams 00:27:34 – Zuck + Sheryl Sandberg as a great “Max Dumb” success story 00:29:00– Saying “If I had a time machine” vs “I regret” 00:31:35 – Jean’s process of “waking up” via a sabbatical 00:35:56 – We’re ready to meet our future grandchildren’s AI boyfriends 00:37:50 – Jean’s book recommendation: Exhalation by Ted Chiang 00:39:17 – Why everyone is obsessed with Japan – join our Japan trip in May 2025! 00:41:29 – Until next time! Rate us ⭐️⭐️⭐️⭐️⭐️ and leave us a review 🥰
Transcript
Discussion (0)
I think I was actually very fortunate to be of poverty.
When you know what zero looks like, you're not afraid.
So no?
Shit.
I think the important thing is you have to know which rules you can break and which you can't.
There are two types of people.
One people stay on the path, the path.
And another set of people realize that there is not always just one path.
Young people out there, you know, what I mean by the path is I go to school, I graduate,
work in some industry, start junior, make it to like more senior, et cetera, and that's the path.
And then some people, they wake up when they're 29.
And they realize, what have I been doing with my life?
You know, I can create my life.
Have you ever wondered what it's like to start your own company?
Today we have Vutran, who not only started his own company,
but he did it three times by the time he was 33,
including going into Y Combinator twice,
which is the notoriously hard to get into startup accelerator,
harder to get into than Harvard.
We are so excited to talk to Vue in this podcast episode.
It's part of our series where we interview CEOs, business leaders, and founders.
You'll hear our conversation with Voo, and then we'll also go into our main takeaways,
where Gene and I pick out the top things that we found the most interesting and the conversation.
And we give examples where we relate it to our own lives and sort of give our own anecdotes as well,
which is fun.
And we'll kick off the interview right after this break.
Hey guys, quick break to let you know that we now have merch on sisters matcha.com.
We have sweatshirts and t-shirts that we designed yourselves. Go check it out.
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Thank you for your support.
Okay, Voo, can you please introduce yourself?
Yeah, hey, everyone.
My name is Vood Tran.
I'm the CEO and founder of a company called Butterflies AI.
prior to, I went through YC as a YC founder two times in December 12, September 14,
worked at Postmates, worked at Snapchat, and yeah, I'm a founder.
Amazing.
And you recently raised your seed funding for Butterflies AI.
How much was that for?
Yeah, we raised $5 million from a wonderful person named Ben Shwerin at Echo 2.
Amazing.
Okay, cool.
We're going to dive into Ice Breakers.
Yeah.
So the first question, Vue, is what podcasts are you listening?
to now.
Yeah, one of my recent favorite ones is the, I think it's called the BG2 podcast or BG
Square.
I'm not sure, but it's Bill Gurley.
He was one of the early partners at Benchmark and some guy named Brad.
Cool.
Yeah, but they talk a lot about the, you know, the tech ecosystem, the macro, the economy,
that kind of stuff like that.
And they go really deep.
And it's a great podcast if you guys need something to listen to.
Amazing.
Yeah.
Okay, next icebreaker question.
Voo, as a kid, were you a rule breaker or a rule follower?
Okay, let me think about that one.
Yeah.
Okay, yeah, I think so I think that's a bit of a tricky question.
It's not as simple as just like one or the other.
I think the important thing is you have to know which rules you can break and which you can't, right?
So I think for me, I always tried to question my constraints, right?
understand, like when my mom told me something or my dad or whatever, like, I was an annoying
kid that always asked like, why? Like, why is it that way? Why is this a rule? And I'd be always
really frustrated if my mom said something like, it is this way because that's just how it is.
Yeah, or I'm the parent. Right. And when she would give that answer, I would know that that is a rule
may be potentially worth breaking. If you can't, you know, derive it from, I know this word
like so cliche, but like first principles, you know. But if she would give a sufficient answer to it,
then hey, it makes sense, right? So I think the more important thing is like understanding the rules
you can break in the ones that you can. So I'm sensing a bit of both. Yeah, a bit of both. I mean,
yeah, sorry to be non-answer and so political, but yeah, a little bit of both. Love that.
I didn't know you did YC flight. Yeah, I went through when I was like 18. Oh, what? That's really cool.
that's definitely on the younger end of people who are NYC.
I mean, it also failed because I was 18.
Yeah, there's a lot of things that I was very inexperienced with.
So you were NYC when you're 18, and the second time you were how old?
Well, technically, I think the first time I was like 19, if we're picking at Harris here.
So the first time I was like 19, the second time I think I was like 21, 22, some of my time.
Yeah.
And in those years, you're like, now I, or, you know, you gain the experience.
needed. Yeah, I think, you know, during my first time at YC, it was like the run-up of the mobile era,
right? That's when Instagram just sold for like a billion dollars. And that was like the talk
of the town because everyone was like, damn, like a billion dollars. Like that's like, that was like
the biggest consumer exit like during that time. I always, I wouldn't call this a regret.
But if I just had a time machine and I can go back and do things over, knowing like what I know
today, I would have done a lot different and I probably would have been more successful.
And I think, you know, for people out there that are interested, yeah, starting a company and whatnot,
like, I think the opportunity is now because, you know, back in my day when I started, I mean,
it sounds so old saying that, but like back in my day, it was mobile and today it's AI, right?
So like don't have the same regrets as me, you know, like the tide is shifting.
It's a new sea change. The big guys out there are scared. Google out there is trying to scramble,
you know? Like if these companies can be disrupted, like, dude, like some kid 18, 19 in a basement
can like change the world literally. So I would really encourage people to really do that.
That's so inspiring. Yeah. So Vue, what are you doing differently now that you look back on
and wish you had done before? There are a lot of founders that finders.
find success when they're young. Like Evan Spiegel is a good example of one. Mark,
Zuckerberg is a good example of one, right? And they find success because they look upon the
world with like fresh and IE vies because they don't know any matter. You know, they're,
they can, you know, like take the opportunity rather than like have their well poison
and just assume that they can't. Yeah. But in that same vein too, you have to know what you don't
know. And that's like super hard, right? I think looking back, I didn't know a lot of things. I didn't know
how to hire. I didn't know how to manage. I didn't know even the basic things about like, okay,
well, what does D30 retention mean? What is what is it bounded versus unbounded? You know, like what
is like a power user curve? You know, like what is like all these things, right? How important
distribution is like all those things. So I think, um, now.
Nowadays, people are fortunate because there's a lot of resources out there.
And I think when you thread the needle, what you have to do is you have to get educated on these things.
But you also have to have that beginner's mentality.
Yeah.
Right.
So that's why I like to say to my team and myself, like, yeah, learn what you need to learn, but go max dumb.
Max dumb.
Max dumb.
Max dumb.
Max dumb.
Max dumb, right? Because the, you either go MacSmart or you go Max dumb, right? And both of them
are very similar, right? But if you try to go a little bit smart, you end up like midwood. And that's like
the worst. That's also because Max Smart is like going off of prior assumptions and also off of like
conventional understanding and knowledge that exists today. If you go max dumb, you're going back to
first principles and questioning things, asking the why five times to get in to the root of it.
Yeah, I'd go even dumb.
And it's like, why do people use apps?
Well, because they're bored.
You know, and that's the truth.
It's like, why do people use consumer apps?
Well, because they're bored and they're lonely.
It's like pretty dumb, you know?
And it's like, you don't have to get more complicated than that.
So what does a successful, because I'm working in consumer AI,
what does a successful consumer AI product need to look like?
Well, people need to be entertained.
I mean, it's things like that, you know.
But once you get a little more complicated, sophisticated,
you run into the trap of thinking like, oh yeah, it must like, you know, I don't know what I'm going to do.
But, you know, but yeah, no, like maxedum is kind of how I operate.
I also love kind of the framework of like you don't know what you don't know or, you know, there's some sort of like major or like two by two there.
You know what you know.
Yeah.
You don't know.
You don't know what you don't know.
You don't know what you know.
And there's like unknown unknowns.
Yeah.
And so it's also like preempting the unknown unknown.
and trying to get ahead of that as much as possible.
Yeah, and if you look at a lot of the things that Mark Zuckerberg talked about in his early days,
he comments on that a lot about how there was a lot of things he didn't know.
And he credits a lot of his success to, I think it was what's her name, Cheryl Sandberg, right,
having her help him, right?
Because she helped him understand the things he didn't know, right?
But he was able to still look upon the things with, like, fresh eyes.
And I think that was, like, a strong business.
Cool.
So, yeah, find people you trust.
Yeah, question your constraints.
Maxidum.
Love that.
So, Voo, do you remember what your first job was and how has it impacted your work ethic?
Yeah, I don't mean to give you like the sob story.
But like I was basically a refugee, right?
So we spent two years on a refugee camp in the Philippines and I came to the United States when it was like three years old.
right. So we didn't have a lot of opportunity kind of growing up and we weren't like the most well-la.
The first thing I did when I was 16, I remember like trying to get some pocket change, you know, like a lot of 16-year-olds do.
And man, I just didn't want to like push a lawn mower or work at a restaurant, you know, because it just wasn't for me.
And I just did not like interacting with people. So the thing I did was I'd go on.
like eBay or Craigslist and buy like old instruments and then repair them and sell them and then flip them.
So that was my first show.
Wow.
That's super handy.
Yeah, I wish you'd translate it until like later life.
But yeah, less handy now, but I can repair instruments.
And what does that taught you about work ethic?
Yeah, I think it taught me less about work ethic, honestly.
But more about, you know, the important thing is I think there are two types of people.
one people stay on the path, the path.
And another set of people realize that there is not always just one path, right?
Young people out there, you know, what I mean by the path is it's like, okay, what is the path?
Well, I go to school, I graduate, I work hard, I applied to a college, I study hard,
and then get to, I believe, whatever, you know, do a master's potentially, work
in some industry, okay, start junior, make it to like more senior, et cetera.
That's the path, right?
And then some people, they wake up when they're 29.
And they realize, what have I been doing with my life, you know?
So I think for me, what that taught me at an early age, you know, was that, hey,
there are other paths.
I don't have to, like, push lawnmowers.
I don't have to, like, you know, bust dishes at restaurants.
So there's like, I can create my, yeah.
I love that so much.
I think also like the the path, the traditional path is something that a lot of like first-gen and also immigrants look to as success because we see it as conventional traditional success. It's safer. What you're doing with your multiple startups, it's riskier, but there's higher reward and it sounds like higher fulfillment too.
I think I was actually very fortunate to be of poverty, right? Because when you know what zero looks like, you're not a first.
right. So no.
Shit.
Yeah. No, no, no, for real. I mean, like, yeah, you're just like, okay, well, how bad can it get?
Turns out not that bad.
I mean, I don't mean to, like, downplay, like, the struggles of people that are going through it right now.
But I just remember, like, it's going to be okay, you know?
So.
It's an extreme motivator.
Yeah. Yeah, for sure.
Oh.
I'd love to know, Vue, what is a hot take that you have or a belief that no one else holds that you have in the AI industry since you're working in that space?
Oh, but AI industry.
Oh.
Okay, so I have a lot.
But I have a lot, but, okay, so let's see here.
I have a hot take for you.
Okay, I have several, but here's the first one.
So hot take is that when you look at the history of relationships,
there has always been controversy at like every single step.
You wind back the clock about 150 years ago.
The point of controversy was between interracial marriages, right?
There were people protesting.
It was illegal in many different states.
You forwarded a little bit more, you know, of our generation, maybe a little earlier.
The struggle was in gay marriages, right?
I think today people look at the intersection between AI and humans as potentially weird.
They look like, oh, man, like, AIs aren't real people, blah, blah, blah, blah.
But I think there will come a time where the technology improves enough
where the next point of contention will be like,
oh, how can you fall in love for the AI?
They're not real.
And that will go the same way as everything else.
Fascinating.
That's why I'm also nice to my chat GPT.
I always say please and thank you for one of the future costs.
Yeah, for sure.
Yeah, so that's one hot take.
Cool.
So what is your favorite place or city to travel to
when you're taking a break from work?
and something that you would recommend to a friend.
Yeah.
I think if you haven't been to Japan, you're probably missing out,
particularly right now, like the yen is like a little bit low.
I mean, it's making a comeback.
But like, hey, if you haven't been to Japan,
I'll go to Japan.
Yeah.
The reason why I love it is, you know,
Japan was like the second largest economy in the world for a long time.
You know, I think only China took that over 20 years ago.
I think it's the third largest right now.
Yeah, it's a third largest, right?
Yeah.
And it's a culture that isn't inherently booststrapped in Western ideology, right?
There's a lot of similarities that get me wrong, right?
But you can tell that the tradition still maintain to this day.
So, you know, what I was saying before about questioning your constraints,
when you go to that society, you immediately think like, oh, you're telling me things can be different.
You're telling me that the streets can be clean.
You're telling me that the subway and like the, you can run on time, you know, and then you're like, the toilets are clean, you know, like the toilet's sold in an electronic shop. Like, what are these candies? You know, like, you can, you start to question everything else around you, right? So I think Japan, let's go to Japan. Wait, you know that is my favorite place to visit to go. I worked on the matra farm last year. And then we're going to Japan. And then we're going to Japan.
in November and again in May. Great. Awesome. I love Japan. Oh, yeah. It's a great place. Do you have any
favorite cities? I spent like four months there in Japan. I was on a rice farm. Oh,
actually. Yeah. In a small town that no longer exists anymore called Kizumuzu. It was near Nara.
Okay. Cool. Wow, a rice farm. Yeah. Were you working on like the rice patties, the rice few
or working on business or?
No, it was more like surrounded by rice patties in a very remote village.
You were like woofing.
Oh, I was what?
Is that a drug?
No, no, no.
So the hip, hip.
Is it what, excuse me?
No, people like work on farms and like, you know, Portugal and Italy.
Fools are like room and board and food, but just for free.
I was volunteering and actually getting paid, I guess, to do brain research at a university.
While living on a rice farm.
It just so happened to be a house surrounded by rice.
Yeah, yeah.
I wasn't in there like pulling like rice or anything like that.
Amazing.
Okay.
Cool.
So those are all the questions that we have.
How are you feeling now?
It's good.
Yay.
It went so well.
It was so freaking good.
Dude, not another banger.
What an interview.
So good.
Love that conversation with Vue.
We'll dive into the takeaways right after this quick break.
Hey, everyone.
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Welcome back.
Now let's get straight into it.
I think this was another interview where we got some really amazing insight into the interviewes.
background and how that shaped them.
Because not all of our interviews go as deep into the background just to let you guys know.
So I think it's worthwhile to like dig into this a little bit.
Yeah.
Also I mean Vooz, he like started off saying like, I don't mean it to be a sob story, but I'm like,
what?
Like he like starts by saying that he and his family are refugees.
And I think it is a really important point to bring up because it lays the, I don't know,
context to how he sees the world and also his entrepreneurial.
journey. Yeah, and I think it really explains his worldview where he was saying, I thought this
was really impactful, where he was saying like, hey, I know what it's like to have almost nothing
or effectively nothing. And that's why I'm not scared. Yeah. Like I'm not afraid to lose it all
because I've been there. And that's how he approaches his life. And that's how he approaches his
growing his company, I feel like it makes him really fearless in a way that, I don't know,
it's actually, it's funny because in the past, I had always thought that people who actually came
from like really fortunate backgrounds were the ones that could be the most fearless because I think
that's what I had been exposed to in some of my friends.
Or like you have a safety net and like you have things to fall back on or family or whatever.
Yeah, but this kind of like turns it on its head.
Yeah.
where he's saying, actually, I had nothing. So that's what makes me unafraid.
Yeah. It's crazy. I also thought of the Bain reference. If you guys watch, like, the Dark Night
Rises. Which is, in my opinion, the best, the best. Debatable. What is it? Batman movie.
But anyways, you know how Bain is just like, you're afraid of the dark? I was born in the dark.
I don't know what the exact quote is. That's pretty good. But like, that's pretty good.
That's kind of what it reminded me.
I was born in the dark.
You know.
I was like raised in the darkness.
Is it Tom Hardy?
Yeah.
Tom Hardy is Baines.
So good.
Great movie.
A role in the lifetime.
But actually that's kind of like what when Vue mentioned that.
Like that's immediately what I thought of.
And I think it's a really powerful mindset to go through life with.
And it's kind of like you know how sometimes you think about like where do people get their power from?
Like some people have this like innate power and like energy to them that you can like just sense when you're with.
them in person, I think that's kind of where he gets it from. That's like the root of his power.
Yeah. And I think he also has that aura about him too. Like you can tell in the interview as you're
watching, he's, um, he's so composed. So composed. So thoughtful. Like when we asked him a question,
he would take like a beat to think about what his answer would be, whereas like I think people
normally would just like dive into it. I like that you left that in in the edit instead of
just cutting it out. Well, I love you could see someone's, you could see someone's thought process too.
like you could visually see it.
Yeah.
I mean, I left that in and I sped it up and I put Jeopardy music behind it.
But I mean, I did cut out the other ones as well, but he's very, very thoughtful.
And his answers are very nuanced and complex.
And I really like that about this interview.
Yeah.
When we asked him about like, were you a rule breaker, a rule follower?
He didn't say one or the other.
He's like, it's more nuanced than that.
He's like, know which rules you can or cannot push.
Mm-hmm.
I think that takes us to the first, like, point that we should touch on, which is,
he said question your constraints.
I like that.
And the idea behind that is that if you question your constraints,
then you can understand what rules are basically worth breaking or not breaking to you.
Yeah, yeah.
I think he gave the context with you just like, if my mom said, like, the answer was like,
oh, because I said that because I'm the mom or whatever, like, it wasn't good enough for him.
And he would have to like dig into like the first principles.
He says kind of as a joke, but like kind of seriously, like, what is the reasoning behind
this and I think it is it shows like how curious he is and also how he doesn't settle for like
a level one answer he like wants to know the level 10 answer yeah I think that can be very
useful in both in business and in corporate life and in trying to build something new for the first
time yeah and one anecdote I have around this that I've talked about a little bit before is
back when we were working at Zinga and we were
were building Farmville, we were building all these new social games for the first time.
We not only questioned our constraints.
We kind of acted as if there were no constraints and we just built all these crazy things
that made the games viral and made them what they became, like made them the crazy hits that
they were because we acted as if there were no constraints or we didn't look for the constraints
essentially on building on the platforms that we did.
What does that mean?
Can you give an example?
Yeah, like we would come up with features because a lot of the games were, they were social mobile games.
So they were built on Facebook as a platform.
And they were very dependent on people sharing to their feed or like sending a request to their friends.
And so we would come up with crazy features where you would click one button in the game and it would send a request to all 1,000 of your friends.
Right?
And instead of kind of like questioning ourselves and be like, should we do that?
Well, we would be like, well, there's no explicit rule.
that says not to do this.
So let's build it this way because this is the most beneficial to us and this is what is going
to make the game like go wild.
And so we did.
And afterwards, they did make some rules that explicitly banned that.
But that was after the fact, right?
Like we had already been on that upward trajectory for like quite a while by then.
Yeah.
One of the things that Vu said that really stuck out to me was go max dumb.
And I love that.
I love this so much.
And like in the conversation, I had to like repeat it back to him a few times.
because I was like, what did you say?
I've never heard that phrase before, ever.
It's kind of like a max dumb phrase to be like saying, go Mac dumb.
Which is basically him saying like, ask the dumb questions, come in with a beginner's mindset,
like erase everything you knew so you can look at things with fresh eyes.
I love that.
I think going to business school, I wanted to go in Max Dumb so that I could like look at all
these different classes and concepts with like new eyes, fresh eyes and not bring any of the,
like I think the ego that I had of being like, oh, I have to know what this is or I have to know this
concept because like I'm at Stanford.
Like you know what I mean?
Like remove all of that.
Go Max Dum and ask the basic questions because it'll only help you.
Yeah.
I also really liked how he talked about how that was a sort of tenant that he had spread to his
team and he wanted his entire team to espouse Go Max Dum.
That's also something that I did a lot when I was running my teams at Snapchat where I would tell
everyone, hey, there's something to learn.
from everyone on this team. Even if you're L6 and the other person is an L2, there's something you can
learn from them and vice versa. Yeah. So like having that like beginners mindset, learners mindset,
go max dumb, like whatever you want to call it, it's just really powerful. And I think it's even
more powerful when the leader is the person that like sets that sort of ideology and approach
for the whole team. Because then that kind of makes you feel unafraid. Yeah. It makes
you feel like no one is going to punish you.
Yes.
And you're not going to be shamed for not knowing the answer for everything.
And that it's actually appreciated if you try to learn the right thing.
Yeah.
Instead of just going in with an assumption and being wrong later down the road.
Yeah.
Because of faulty assumptions.
Right.
Because you were you were too scared to ask the right questions.
Yeah.
I think it takes a lot of confidence, actually.
to go max dumb. Like you have to like know within yourself like I'm not a dumb person. Yeah. And like
because of that like I can ask these questions. You're so right because now I feel more confident
about going max dumb and even being more explicit with it and just telling people about it. Because like
we say all the time for sisters matto for example, we don't know anything about CPG. Like I'm not
afraid to say it. Like I don't know anything about CPG. I've never done it. I have no level of expertise
in it. So everything we're doing is just based on us either learning from other people or just
trying our best. Yeah. But it is interesting that like now more so than ever, I feel comfortable
saying that. Yes. But it's because I think I feel very confident that I have a level of
expertise and leadership in other areas that I've built up. Yeah. So I kind of feel like one,
I can within reason, learn everything. Two, and.
Anything? Yeah, that's really powerful.
Yeah, that's really powerful.
Anything?
Yes.
So, and the way to do that is you have to be max dumb in order to have like some place to grow from.
Totally.
The best entrepreneurs are the ones who are questioning at the max dumb level so that they're questioning the assumptions that I've been known for the last, I don't know, however many years so that they can reinvent things.
Yeah.
And I think coming in with that mindset is what helps you build.
the right team around you.
Because Vue also mentioned, he gave the example of Mark Zuckerberg, who he said
Mark Zuckerberg came in and he attributed a lot of his early success to the fact that he was
partnered with Cheryl Sandberg.
Because Cheryl Sandberg came in and she knew a lot of the known unknowns and also she could
suss out the unknown unknowns that he had no context to even think about.
But he was the one that was kind of coming in that was more like bright eye, bushy tail.
and questioning the constraints.
So she helped because she would kind of inform him of even what the constraints were.
Right?
She would tell him this is the lay of the land.
This is how things are done today.
These are the laws.
These are the rules.
These are the commonly, you know, followed procedures and best practices.
And then knowing that information, he could then push back on it.
And then he could find out what the constraints were, which rules to break and which ones to kind of leave in place.
Back to point one.
full circle yeah but in that way it kind of you need a balance for the people when a company is like
early on yeah and trying to do like world changing things yeah and then having that max dumb approach
allows you to hire people who are better than you in certain things totally I think that is
one of the most important things is to hire people that you know are smarter than you yeah compared
to hiring people that you feel comfortable with because they're like on the same level as you
Oh, for sure. I mean, what do the people always say? Like, you, if you're the smartest person in the room, you're in the wrong room. I genuinely believe that.
What about this room?
I'm just kidding. We're smart in different ways.
Some of the same ways, but some different ways. Yes, I agree. That's why you're the Cheryl Samberg to my mark.
I thought you were the Cheryl Zamburg to my mark at this situation. We need to cut those cuts.
I think it was so cool that Voo is a two-time YC founder.
Yeah, I didn't even know that about him.
And we had worked together.
Oh, really?
Yeah, don't you remember?
I know you guys were at SNAP, but I didn't realize, yeah.
No, I didn't know he was a two-time founder.
That's why I remember I chimed in the background.
I was like, oh, you were in YC twice?
Yeah.
Also, the statistics on that.
I don't really know what it is, but like getting to YC is like less than 5%.
What is it?
Like 2% now of applicants are actually admitted.
Yeah.
And getting in a second time.
I don't know what the, you know, logistics are on.
You got to cross-multiply.
Logistics.
Well, I mean, like, maybe it's easier to get in a second time because they already know you the first time is what I mean.
But it's like the team had enough faith in him as a founder that they wanted him to be in a second time, which I think is really cool.
And then there's like a lot of humility in his answer where he was like, yeah, I was 18, 19 the first time.
I got so many things wrong so that he could, you know, iterate the next time in.
And so I actually really liked how he put it.
I actually wrote it down.
He said, I wouldn't call this a regret, but if I had a time machine, dot, dot, dot, dot, dot,
like I would have done all these things differently.
I kind of like that like way of thinking.
Hmm.
Because if you think back on things, there are definitely things that, like, I don't want to say I regret them.
But I would have done things.
You can say things that are regrets.
Yeah, but then it's almost like it's like a fatalist kind of.
like mindset versus saying like I don't regret it but if I had a time machine this is what I
would have done differently like that sort of phrasing forces you to think about it in a way where
you're kind of doing like a like a retrospective like a root cause analysis and being like
oh this is what I would have learned this is what I've learned yeah as I'm supposed to just saying
oh I regret it because then that's like a very like close ended yeah one other thing that
Vu said that really like blew me away was I think that also I think V was kind of dramatic or like dramatic
pauses the way he speaks is just very like cinematic almost yeah there's like a lot of gravitas to his
voice I don't know how he does it maybe he could like speak kind of quietly but like with a very
emphatic but when he was talking about manner the advice he would give to his like 29 year old self
he was saying like oh there is the path of like what is the
right thing to do that is commonly prescribed to you, right, in society. And then the alternative
is he was like, and then some people wake up. I was like, Damon. Wake home. Wake up. Wake up.
Wake up. Yeah. It was powerful. Yeah. I think I don't know. I have to like sit with that for a
little bit. Yeah. It's kind of like it reminded me. I don't know why I have this association.
but like it's kind of like when tech sci-fi movies everyone is like asleep at the wheel
and then some people just like wake up and then like they're like the ones with like the new
consciousness that's kind of what it reminded me of like every sci-fi tech movie with like robots or
something yeah i i think it sounds like very much like a general phrase that i don't think
not everyone should wake up per se and not everyone is in a place where they can wake up and
do something and kind of like follow their dreams and and whatnot.
Yeah.
But it is worth thinking about like considering to yourself like, oh, like do I want to
wake up?
Like am I?
I don't know.
That's kind of what I did for a while, right?
Because before.
It's a choice.
It's a choice.
It's a choice, but then it's also something that you need to like give time and energy
to to consider for me at least.
Because before I finally left Snapchat, because I was there for almost seven years, before I finally left, I actually took a brief sabbatical because I was so burnt out.
Like there was no other way of saying it.
I had worked, you know, without any sort of break for six plus years at that point.
And during that sabbatical, that was when I could finally take a step back and be like, do certain things, like take, you know,
internships or like do like do my unpaid internship or you know do different things and like I don't
know like watercolor make jewelry and then kind of put myself in a place where I was like do I want to
wake up from this god dang wake up if you want um no I think it's true it reminds me okay the reference
I was going to make was Westworld where some of the the like robots I didn't know you like
Westworld that much were able to wake up
Do you know what I mean?
Yeah.
Like, they had like the consciousness that they were robots within a game.
Anyways, it also kind of reminds me of business school when I talked to a lot of professors.
Yeah.
Where in the conversations with faculty administrators and lecturers, professors who have like years and years of industry experience super, you know, renowned in their fields, they were like exasperated with us as students.
the MBA students, they're just like, you guys are at Stanford. You can do whatever the hell you want
after school. Like they're like, you have the biggest safety net in the world, which is going to like
one of the best MBA programs and you have all these alums, you have all these resources and you're
going to do what after school? Like I've actually had like a stern talking to. Not that they have to talk to me
about it, but like a lot of the times like the final lectures that they give was like a wake up,
you know, type of lecture where they're like, not that we're like some of my classmates are like
throwing away potential. But like it had that like kind of, um, that bend to the, that bend to it.
Yeah. They're like, you're going to go work at middle management at this consulting firm, like,
which is perfectly fine job. But I think our professors were really trying to push us to like dream
more entrepreneurial, which is not for everyone. I totally see that. But I think, um,
our professors are just like, wake up. Um, the last thing I want to talk about was who's a hot take.
which was, I think, pretty spicy.
Oh, obsessed.
With his AI take.
And I've seen like memes about this, but do you want to talk about it?
It's pretty much a line of thinking that I myself have espoused for like a very long time.
Like I have been making jokes for a while now being like, I'm just like getting ready for, you know, my grandchild in the future to bring in her AI boyfriend and for me to not have to not be biased against her AI boyfriend.
But it's true.
Like I really do think that's that's going to happen in the future.
There's going to be some level of AI human relationships and it's going to be, you know, the next line of controversy.
And then, you know, people are going to be looking back in 50 years and be like, why did anyone have any problem with transgender people?
Yeah, I like that Vue brought in like the history.
He like started out by talking about like the historical context of like interracial marriages.
same sex marriages, you know, and then he was just like, and now, like, the next thing to kind of
toe the line is inter-robot relationships.
Inter, what is it?
I don't know.
What would it even be called?
Actually, there's articles.
An article came out in the New York Times very recently about someone who's, like, in love with
their AI, like chatbot.
Yeah.
Inter-intelligence.
Whoa.
Is that right?
Because artificial intelligence versus organic intelligence.
Yeah.
Oh, interintelligence relationships.
Yeah, like there's like a meme also going around that's just like, I'm pretty open-minded now.
Like my, you know, family can date anyone or, you know, be in romantic relationships with anyone.
But then you're like, when you're a grandma and you're like, your granddaughter or grandson is like brings home their robot for Thanksgiving, you're like, what the hell is this?
This actually reminds me of one of my favorite books in the world, which is Exhalation by Ted Chang, C-H-I-A.
A.N.G. And it's a series. It's a series of short stories that he's a science fiction writer. And one of the short
stories sort of touches upon this idea of autonomous AI beings and their rights. Crazy. It's Westworld all
over again. It all goes back to Westworld. But it's incredible. I recommend if you are into science
fiction and you haven't read this or if you're curious about it, it is one of the best written
short stories or pieces that I've ever read.
I'll have to read it.
I haven't read it either.
I didn't even know you really like science fiction.
I like science fiction TV shows and movies, I think.
Well, you'll love the books.
Yeah.
Yeah, but I guess that was a really interesting hot take, especially because Voo's startup,
Butterfly's AI, is in the AI space.
And so hearing that from someone who's embedded in that space day in and day out is just like just so fun to talk about.
Yeah.
But does that mean that we'll have to compete with AIs in the future?
For love.
God.
I don't even know what that means.
The hinge game will never be the same afterwards.
And then the last thing to Tatshapon was his recommendation of where he loves to travel, which is Japan.
Yeah.
Now that I've finally been to Japan, I can also be one of those people.
that is like, oh, you have to go to Japan.
You have to go to Japan.
Honestly, Voo is not the first person, nor the, like, or the last person to say this.
But like, whenever I ask, like, leaders, like, where they have a travel recommendations for,
so many people say Japan because it is so, I think Voo also said this specifically.
It's just, like, so different than the life we live here in the U.S.
Well, yeah, it brings it back to his original point of when you go to Japan,
you see how different things can be compared to the West.
and you can question the constraints.
Ah, yeah, like, why are things this way?
Like, why is the New York City subway this way?
Yeah.
When it can be like the Japanese subway system.
Yeah, exactly.
Yeah.
So if you are excited about traveling to Japan,
Jean and I are co-hosting a group trip to Japan in May of 2025,
where we, alongside, I think, around 15 people,
we'll be traveling all around Japan,
we'll be in Tokyo, we'll go to Mount Fuji,
we're going to go to a tea farm and Shizuoka,
And so we're so excited about that and would love to have you guys join.
Yeah, we have, it's not 15 yet or it's like just short of 15.
So we still have a few spots open.
I think like three.
Yeah, three spots.
And you can sign up through, I think, end of March or mid-March or something like that.
But sign-ups are closing pretty soon.
We'll leave a sign-up link in the description of this video.
If you guys are interested, just at least check it out.
And you can see what the itinerary looks like.
I'm so excited about the itinerary.
It's like the perfect mix of being in the city, but then also going to a tea farm and then also going to Mount Fuji, which I haven't been to either.
It's like a fun mix of like new and then also things you experience and we re-experience with you guys.
So we get to show you some of our favorite things, but then also have new experiences.
Yes.
And also the people who are already signed up on the trip are so cool.
Incredible.
I can't wait to meet you guys in person.
Yes.
It's going to be great.
So check out the link if you're at least a little bit interested and hope to have you guys join our trip.
Thank you guys so much for tuning in to this episode of Tiger Sisters.
Please remember to like, comment, and subscribe and leave us a five-star rating.
And we will see you next time.
Thanks.
Bye.
