Episode Drop: Garry Tan

The man behind the mask - YC Partner, Initialized Capital, Forbes Midas List, and YouTuber

Garry Tan: Designer, Engineer, Investor, Human

Episode Notes:

Garry Tan is a very close friend of mine. The co-founder of Initialized Capital is a veteran entrepreneur, investor, and online content creator. We share a familiar story: a couple of young Asian guys from a family of immigrants in America, building a career in tech, and eventually partnering at Y-Combinator. He also runs a popular YouTube channel, which has inspired me to create my own online content.

This episode is particularly special to me because of how vulnerable Garry was willing to be, and how deeply connected I felt to him after our conversation. It was his trust in me that allowed us to discuss topics he hasn’t revealed anywhere else – growing up with an alcoholic father, going through therapy, learning to pull back the mask, and recognizing when expectations can be self-destructive. I am incredibly grateful for the amount of trust Garry has placed in me as a friend.

This episode is a reminder for me personally that everyone is fighting their own battles. Conversations like this one with Garry represent why I started this podcast: to bring these stories to you.

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Transcript:

Justin Kan: [00:00:00] What's up guys, it's Justin Kan. You're listening to my podcast, The Quest, where I talk about the ups and downs of trailblazers around me, their human stories and the shit that they've gone through before and after finding success. This is the second of our April series to celebrate Asian icons.

You've probably seen what's been happening in the news recently with an incredible amount of Asian hate crimes. This is not okay. And we all need to do our part to bring attention to what is going on. And this month, we're going to be highlighting Asian American community members and leaders on our podcast.

And if you want to help, you can donate by the link in the show notes together. We're all going to get through this. So today my guest is Garry Tan. Garry is one of my favorite people. He is a veteran entrepreneur investor and content creator. Garry. And I were both partners at Y Combinator and today he has his own YouTube channel about entrepreneurship and startups.

In fact, Garry inspired me to start my own YouTube channel, and I really look up to him as a content creator. Garry is a super close friend and we both show the story of coming from a family of Asian American immigrants, and really figuring out how to build a career in tech in America.

Garry Tan: [00:01:14] The coolest thing about YouTube is that, you know, tens of thousands of people look at you basically spend 15 minutes with me every single week about whatever I want to talk to them about. And that's really cool. And the comments are often like Garry you're. So Zen, like, I love your super calming voice. Like you must meditate a lot and I'm like, you don't even know. I was like, are you kidding? Oh my God, like deep down. It's like, it's a mess. Right. I am like the most self-critical person.

Justin Kan: [00:01:49] It was really special because how deeply connected Garry and I felt during the interview really trusted me. And we dived into a number of topics that he hasn't really talked about anywhere else, such as growing up with an alcoholic father, going through therapy and battling expectations, not just for himself, but also for his kids.

This episode is a reminder for me, personally, that everyone is fighting their own battles. I appreciate how vulnerable Garry is and hope you can learn something from our conversation.

Thank you, Garry. Thanks for coming on.

Garry Tan: [00:02:18] Thanks for having me brother.

Justin Kan: [00:02:19] We've known each other for a very long time. It's been, I want to say like since 2008, right? 2007 or 2008.

Garry Tan: [00:02:26] Yeah, definitely. I mean, you know, everyone knew you guys from, I think Justin TV had just started. What was the timeline? I mean, I started my startup 2008, like January through March or so. And then we got into YC then. And of course, once you even find out about YC, you want to get to know all the founders who did it.

Justin Kan: [00:02:49] Okay. So tell me about, let's go back to your like first step though. I mean, I want to go actually go all the way back to you growing up. Uh you're from the Bay area. Tell me what it was like to be young Garry Tan.

Garry Tan: [00:03:01] Totally. I mean, I was debated, well, I mean, Part of the thing coming on here, I am so inspired by just your quest and how you've been able to sort of show that you can talk about mental health and, you know, have clarity around it. And then that will actually make you a lot more successful. So, Maybe I'll start there.

Justin Kan: [00:03:23] Yeah.

Garry Tan: [00:03:23] Like the super raw stories I haven't really talked about, but okay. I mean, basically my dad was kind of a raging alcoholic his entire life. Um, you know, his, his entire adult life. I mean, I'm gonna go kind of deeper because. You grew up in Singapore, uh, you know, that side of the family, I think they were basically, it was kind of like In The Mood For Love, you know, the movie it's like the Chinese diaspora and it's like, it's, you know, business people, it's sort of like the merchant class of China had to flee China and something like the largest ethnic group.

That's, you know, um, not the sort of ethnicity of that area in Asia. You know, whether it's Burma or Singapore or, you know, pretty much everywhere in Southeast Asia, it's Chinese. Yeah. So in a way we're a little bit like the Jews of Asia actually. It's like, you just get spread out everywhere. Um, and so, you know, my, my grandfather on that side moved to Singapore and then

Yeah. And my grandmother, um, you know, was actually illiterate actually. And she, she actually only speaks like, sort of, uh, a very, like, not even one of the common dialects of Chinese. And it was sort of like In The Mood For Love, but then kind of with like an opium twist actually. So I found out that my great grandma was really addicted to opium and, you know, obviously addiction has really plagued people.

Having addiction is the worst, it's like, it just causes so much pain. And, um, the reason why I go back that far is like just kind of being shocked at how far back, like my pain in my life went back to like the pain, like inflicted from, you know, many generations back in my family history.

And so that addiction caused my grandmother to extort more and more money from my grandfather. And he left the family and then, and then he, he actually left and like, I don't, I don't know who my grandfather on that side is. And so I've been like using 23 and me and getting my, you know, getting my dad to use 23 and me, because that remains like one of the core things that I think.

You know how you watch Westworld and there's like, you know, your beginning story, like the thing that sort of defines you, you know, I think now I realize having a lot more empathy for my father, that was like the defining thing, like not knowing who his father was. And it's like, I mean, it's funny because like, you know, this is my father.

It's like, it's not a movie. You know, this isn't like a, you know, a piece of fiction that I watched an HBO it's like, my father's defining thing is that he never knew his father. And then he, you know, my grandmother remarried into another wealthy family in Singapore, but my father was a stepson. And so, and being the stepson of, you know, I mean, he grew up like, you know, being in limos and, you know, I think they were all, you know, all bankers in Singapore, you know, there was a lot of money over there and, um, you know, he went to the best school, the best private schools, but he was all in, I dunno, You know how Chinese families are sometimes like, you know, what I hear about that is like, his upbringing was always that of being sort of the second class citizen within his own family.

Right?  And he could have the thing is like, it's not like they treated him poorly. It's just that he, he always felt that like second class. And so that's why my dad left. So he tested in. He's really smart, like brilliant with electronics. He basically paved his own way and he left Singapore because it was too small a fish bowl.

And it's like all of his, like extended half, you know, half brothers and sisters and family, it was like too much expectation. And that was the chip on his shoulder. And then that came with the dark side, which is. Like, uh, for whatever reason, like he became really addicted to alcohol, basically all through, like, I think probably once he went to college, he would drink like a six pack of beer every single night, you know?

Or like, I mean, maybe it's sometimes if it was bad, if something bad was happening in his life, he'd drink like. Two six packs of beer, like to this day, I can't, I can't drink Budweiser. Like I hate that beer.  . You're the King of beers. Like I fucking hate that beer, honestly. And then the difficulty about all that stuff is like, I also think that he.

He was like deeply damaged by his upbringing and his childhood such that like, he couldn't keep a job. And so, you know, the hard part is we moved like eight or nine times. It's funny because it, it, it probably gave me a lot of skills, which was just being able to make friends very easily. And it's like, it's.

Yeah, I can, I'd like going into new places because it's just a different game. And that's the weird thing, like, and I'm sure a lot of your guests, and you have found this too, you know, these things that sort of almost break you also make you,

Justin Kan: [00:08:17] Yeah, there's so many parallels to my own story, whereas, you know, I feel like my mom was similar to Chinese diaspora they fled the cultural revolution and grew up in Malaysia, uh, for 10 years and had this deep scarcity mindset. From like not having a lot, you know, growing up very poor in a rural area. And when she immigrated to the United States, she like brought that along and then the way she raised us, it was with this scarcity mindset.

You know, and like  have the feeling of not having enough, which I don't have a lot of empathy for her. You know, it wasn't her fault and I don't have no blame, you know, it's, it's very healed now, but it was that, you know, I grew up, it created all these patterns as an adult where I'm like, you know, I'm making money, but it's never enough.

Or like, I need more, you know? And so the, the generational trauma, like maybe their parents raised them a certain way. They got, you know, trained a certain way. And then they pass that along because of their experiences. And, you know, I, I understand that Garry.

Garry Tan: [00:09:18] Yeah. And it's intense because you know, now what I realized is because he, like, I remember growing up and he was always really just really proud of his education, which was great because it meant that, you know, he was going to invest in my education and he pushed me really, really hard. But there's a shadow side to that. And, you know, I only actually even realized this, it sort of broke me open like last week in therapy. I mean, for those of you who have not ever done therapy, like the, you know, the reason why you do it, it's like once in a while you get this breakthrough. And like, I mean, I dunno why it's usually, like you realize something it's like an epiphany.

And you actually break down and cry and it breaks your heart open. Somehow. I don't know, like I just had this happen about this particular thing, which is, you know, because I am so grateful and thankful for everything that I have in my life now. And I never thought I would have any of that because like, you know, we didn't have money for food sometimes growing up, you know?

And that's because my dad couldn't keep his job. And in those moments when he didn't keep his job. Like he would drink himself basically every single day. And my mom got paid like her $14 an hour job as, um, a nurse assistant and she didn't speak English and she has a hearing impediment. So, you know, we would survive in like a one bedroom apartment and then most, a lot of the money would go to most of the money would basically go to rent and beer.

And I remember like eating basically like bread and milk. And that was like the best I could do. Right. And this is like, why I understand we are so lucky in tech. We are so lucky. It's ridiculous. It's outrageous. Right. We don't have to worry about this stuff, but like if you're working class and you don't have skills, like I was that kid, you know, and, uh, like we ate well, when my mom would every, so often at her nursing home, someone would drop off a bag of, uh, you know, expired bread. And it's like, Thomas' English muffins are like my favorite thing in the world. Like I, today I still, I still buy them, you know? And then I like go on Instacart and I'm like, yeah, Thomas', that's what we're eating.

And it's like, that was like a good haul. And, you know, I remember there was an entire time in junior high when it was like, I became like the Thomas' English muffins, like, like recipe champion, like I could make, I can make sandwiches. And, um, I think that's why I love food so much now because you know, we didn't have it, you know?

So it's like crazy, you know, and it's not like my parents didn't love me, but we had like problems growing up, you know?

Justin Kan: [00:12:06] What's your relationship with your parents? Like now?

Garry Tan: [00:12:09] I mean, you know, I send them money every, uh, you know, I, I try to support them as much as I can, you know, and honestly, like, thank God.

Like my dad stopped, you know, he stopped drinking. He stopped, he like fell off the wagon a couple of times, but, you know, sort of in the past five years in particular, I think he's really, he started going to therapy himself. He went to AA. I brought him to AA. AA is amazing, by the way, it's like, I, you know, yeah.

What's funny is like, after going to AA, I realized YC and AA have a lot in common. We have our mantras, we have a group therapy session. We don't feel alone. And then we have like, we even have sponsors. Yeah.

Justin Kan: [00:12:50] There's a sense of community of going through an experience that most people think is isolating. But then when you realize, like it's a shared experience, there's like that strength in that community.

Garry Tan: [00:13:01] Yeah, it's awesome. So I feel super blessed now. And, um, I guess the only other strange thing that I don't know if you ever feel, um, you know, earlier you were saying just this extreme expectation, it's like anyone who's Asian who has like high expectation parents.

I mean, I don't know, I haven't met that many people who are part of the Chinese diaspora in particular, who like, don't get that from her parents. Um, and I didn't realize that that was like a diaspora thing. Like, you know, the immigrants, the people who left, they were actually sort of like, The people who had some wealth and it was taken, he was going to be taken from them and their lives.

I mean, it was taken and if they didn't leave,  they had to leave with like often the clothes on their backs. Right. Or they had gold, like sewed into their pockets when they like, you know, had to like sneak out of the country to avoid being killed. Right. Yeah. And I didn't realize this, but that was like one of the defining characteristics.

It's like, that's where that comes from. It's like, Our families were always the strivers period. Right.

Justin Kan: [00:14:05] They were strivers we're successful. And then, you know, had to run and like really value that education and kind of like working hard to rebuild it, you know? And that was my grandpa, my grandparents and their family, my, my grandparents had 10 children.

 My mom was one of the younger ones and they fled China like secretly, you know, he had a. Uh, business there and they, they had to, they, they fled. And, um, my two uncles, my two oldest uncles were like, not allowed to leave. And I mean, like you said, going back to what you were saying about feeling, being blessed, it's like, you know, you and I never had to deal with anything like that.

Right? Like, we're like even just basic security right now. It's such a blessing. So yeah. How did. You know, this family situation and kind of growing up in this environment, how did that affect you as a young adult in high school and then in college? Like how did you, how did this manifest into getting into startups or programming?

Garry Tan: [00:15:03] Yeah i've been reflecting on this really lately and like, starting to sort of wonder if we have free will actually

Justin Kan: [00:15:10] We're all like Dolores from Westworld.

Garry Tan: [00:15:12] Basically. I mean, it's funny, you know, the, the fiction hits exactly at the right time, in some ways like it's, that, that show is so prescient and my technological optimism and utopianism, um, basically comes from Star Trek: The Next Generation, you know, If my parents could afford cable, it would have been something else.

I watched like Star Trek every single day for like basically my whole childhood. And then I started rewatching it a few years ago and I'm like, Oh, that's why I think that, you know, what a good leader looks like is actually Captain Picard. Right. That's like my platonic ideal of like what a good leader looks like. And I like fail and fail and fail and like desperately wanted to be Captain Picard. Right. And, um, But going back to like, I guess the Chinese parents  expectation part. And I think a lot of this is, you know, I blame the addiction, you know, I blame my great-grandma's addiction to opium, putting my father on this sort of broken home path.

And then also, you know, sort of basically causing addiction in my father's life. Um, You know, all of the standards that I hold myself to, I realized my father deep down has like, he knows what success looks like. And then the difficulty is the addiction robbed that of him. Like he is super, super smart. You know, he was, you know, making his own electronic clocks in like the seventies, just for fun.

You know, he was a hackers hacker, you know, we get to play with software. He was playing with hardware in like, you know, He was like a maker before, you know, 30 years before a maker movement was a thing. Like if he was in the right place at the right time, if he was in the Bay area during Homebrew computer club, he would have been one of those guys.

Right. And then I realized the addiction, you know, he understood all the things that we understand about the world. And this was like, you know, before I was even born before either of us were born, right. He knew that electronics and computers were going to change the world and he wanted to be a part of it.

But then the addiction robbed him of that. And then what happens then? After that, I realized that he basically projected all the things he wanted to do on me, but then there's also that layer of like Chinese paternalism plus alcoholism. And so, you know, the epiphany I had recently was that he would always tell me that I was set apart.

You know, I would come home with a B plus on something. And he'd be like not good enough. And I'm like, it's good enough for this person. And he'd be like, it's not good enough for you. You are set apart. I mean, he was careful enough not to say you're better than other people, which I was thankful for. Um, but.

Cause that, you know, I think I, it's funny because like, you, you run across a lot of like kids who are, you know, the kids of wealthy people now, and you can kind of see like, Oh, if you go a little bit too far, like, it really alters their personality in a way that like, you don't want, but you know, it's like unintended consequence.

It's like, you're better than other, other people is like, Oh, that's, that's probably too far. You can feel that way, you know, but the outcomes, we're not going to be happy with the outcomes if that's what people feel, you know? Exactly. So, and then the hard part is like that was accompanied with, if I came home with actually a, B like a B on a test, like you're set apart a B on the report card.

I got a punch in the face.

Justin Kan: [00:18:33] Oh my God.

Garry Tan: [00:18:36] Yeah. I grew up thinking that was normal and it's not normal, you know, like that's, you know, it took a therapist to tell me like, Garry, like you went through something that is not supposed to happen to children. And so I'm even now still like, sort of processing that. Um, and now what I realized is like the result.

Is that I have a very extreme, super ego. Yeah.

Justin Kan: [00:19:00] That kind of keeps you on the rails.

Garry Tan: [00:19:02] Yeah. Yeah. I mean, it's like, I'm on the edge, you know, I'm always on the edge. If I can't come off the edge, even if I like, you know, spend a week meditating, I probably still would like the second I like came out of it. I'd be on the edge again, you know, and it's not something I talk about and it's not, I think it's not clear to people because you know, the funniest thing, especially after doing a lot of YouTube and a lot of people spend the coolest thing about YouTube is that, you know, tens of thousands of people look at you basically spend 15 minutes with me every single week about whatever I want to talk to them about. And that's really cool. Yeah. And the comments are often like Garry you're so Zen, like, I love your super calming voice.

Like you must meditate a lot and like, you don't even know. Yeah. I was like, are you kidding? Oh my God, like deep down. It's like, it's a mess. Right. I am like the most self-critical person. And the thing that I haven't been able to reconcile, I'm curious, like, how you think about it is like, how do you as a creator, like, I have that cycle within me.

Like if my video only does a third, as well as I usually do, like the immediate self, like it's like self hate, you know, like I punch myself in the face now, like emotionally it's like, I feel bad. And then, you know, I always think about Steve Jobs and how, when mobile me came out. He dragged like the whole team into the auditoriums.

Like, I dunno, I hear 50 people, a hundred people who worked on that product and he was like, you have embarrassed us. You've embarrassed, Apple. You've embarrassed us in front of our friends,  Walt Mossberg. And then he dragged out the leader of that group and he fired them on the spot and like, get the fuck out of here, you know?

And so I've, I haven't been able to like break that apart cause it's like, that's the hard edge that's, you know, I can't tell if it's necessary.

Justin Kan: [00:20:54] Yeah. It's like, you know, that really resonates with me because I had that experience my whole life, which is if it first there's these formative experiences, when you're young from your parents or peers, you know, that really made me. They were where they were saying care about these things, right? Like care about good grades or being successful. And then eventually you internalize that. And then for me, I was, I was repeating that to myself all through my career. Right. For, for decades, like, Oh, I'm not good enough. I'm I was very comparative to other people like this other person is doing better than me.

I needed to do better. And I would like, that was a source of like my own self torture, you know? And I want to highlight one thing you said was like, Yeah, you don't see that beneath the surface. Right? Like everybody thinks everybody else is like, Obliviously, like succeeding like that, that I looked at guy it's from, I dunno, Dropbox or Airbnb or friends of mine who are like really successful.

I was like, Oh, those guys are just like, they're super happy. They're succeeding. Nothing's wrong. You know, if I could just be there, then everything would be fixed for me, you know? And it's, you could do it on YouTube. You could say, Oh, I have 60,000 subs with there's someone with 500,000. And if I just like, you know, did you have to 500,000, then I'd be like set, you know?

And that, that, that we'll never stops turning. Um, but it's, it's so interesting to me that you said that, you know, beneath this or people think you're one way, but beneath the surface, like it's completely different and you don't see that. And that's how I felt my whole life. And I'm sure, you know, I know actually I'm not, you know, I'm not just sure.

I'm a hundred percent positive. There are people out there who watch your videos. And they're like, if I could just be what Garry's at my life would be fucking set like that is the calmest guy. He's like the most confident person is the person who is like that. That's a person I want to be in the world.

Yeah, they don't -

Garry Tan: [00:22:40] That's my mask, man.

Justin Kan: [00:22:42] Exactly. That's the mask. Love that. Thank you for sharing that. That's so vulnerable. You know, dude, I, I, um, I totally get it.

Garry Tan: [00:22:50] Think deep down and what I realized is like, we're the same. So, you know, and like that goes for everyone watching this, like, you know, watching now live, but also now listening or watching after the fact, it's like, know that we're not different.

I mean, I deeply know and believe that now, like everyone's the hero of their own story and there is no, you know, we were created, I deeply believe we were all human beings like created equally. And once you think about that and that everyone is fighting some sort of battle or war that you don't know about, you know, that will change the way you go about, you know, the world and your business.

And you know, when someone cuts you off. You know, there's something going on, right. But something in that person's life, and then it's a choice, right? Like we can play it the way, you know, a child would play it. Now that we're both parents, I realized there's sort of the innate and then there's the divine and we can choose the instinct or we can choose, you know, the, the elevated, and it's a choice at all times.

And the more we reveal ourselves and the more we are, the best version of ourselves, then the more we can reflect. Goodness and have an impact that, I mean, frankly, but you know, that's all I want, you know, we're all going to be forgotten all of this stuff, like all the money in the world everything's going to go away, you know, and what's happening right now is this great emergence of an internet consciousness that is actually human consciousness.

And, um, we get to be a brain cell or a blood cell, or, you know, a nerve cell. And, uh, and that's the gift.

Justin Kan: [00:24:34] I appreciate that sentiment in that, you know, and what I hear is like, we have this opportunity to kind of stop the generational trauma, right? Like, and re stop repeating cycles that maybe we're unconscious and now pass along the gift that you have to pass along to your kids, which is really the only important thing in the world is to give them the best possible upbringing and opportunity, but also like you know, for myself, I spent all this time was thinking, what do I want for my kid? You know, I don't want my kid to be rich or famous. I mean, if they want, if they get that, if they want that, that's okay. But what I want is like, for him to be the source of his own approval, you know, for, for him to be a kind person and compassionate, Uh, for him to, to be empathetic and to have self love and love for other people.

And that's all I care about. Like, I don't care about like, you know, being a doctor or an entrepreneur or following my footsteps or, or anything like that. And, you know, it took so much self work to get there, you know, like the Justin  10 years ago would be like, Oh, I want my kid to be like Bill Gates or whatever, you know, but  that that's like, I think that's self work to, to produce.

Garry Tan: [00:25:38] How did you do that? , I have to admit I'm not there . You know, Stephanie, my wife is absolutely there. And she's like, Garry, you can't have these expectations. And then for me, it's like, what I want for them is like the ability to experience, uh, you know,  flow, you know, except me, I came up with this idea or like, he's you actually it's, uh, for those of you in the audience watching, it's like, you know, the movie, Soul,  that moment when the main character of can play the piano and he floats off to like someplace else, And I felt that like, mainly when I was like coding and designing.

Right. Um, but I feel it now when I'm like editing a video or even on clubhouse, I dunno. It's like, there's something really powerful about, you know, like the other day we had Jaeson Ma who was on your show on the tech afterparty on clubhouse. And he was talking about, um, exorcisms. I'm like, this is insane and awesome, but I'm like, there's so many ways to experience flow and all of those are like sort of flow States for me.

And I want that for my kids. Right. Like I want, and then the hard part about it is like, I can't separate the flow state from excellence. Yeah. And then it's like, as long as I am not prescriptive about like how it happens, that is still what I want for them. And then I don't know how to reconcile that because of the excellence part.

And then, I mean, I I'm like, I need like 10 more years of therapy.

Justin Kan: [00:27:00] I think first thing is like, you're aware of it. And so that's like the first step in anything, right. Is that you're, you're aware of,  wanting excellence for them or wanting  flow state, which I think the flow state itself is, you know, that's a beautiful kind of unique part of the human experience. And I also would want that from, for my son, but like, you know, does it have to be accompanied with like a drive to excellence? That's I don't know if those things are, are inexorably linked and so, yeah, that's right. Um, for myself, right. You know, the way I got to it was just, you know, I, well, I remember one thing I'll share is I remember. I was so proud when my brothers sold Cruise, you know, my brother started Cruise and sold it too soon. Cruise. I was like, Daniel's awesome. But I was really like proud for myself in a way too is like selfish. Cause I was like, Oh yeah. I'm like, we're like the kind of brothers who have like billion dollar companies.

Right. And it's like a very, there was like an ego-driven dark part of it. I remember when he, when he sold it, I mean, I was also proud of him as a brother and, you know, he did an amazing thing, but there was this like selfish aspect of it that I don't think I've ever admitted.

Garry Tan: [00:28:05] Yeah. Thanks for sharing that. I mean, I hear that man, like basically we see the reflection of others in ourselves and then where does our identity end, and like, you know, our community begin and what should you feel good about? Yeah, I don't know.

Justin Kan: [00:28:18] I brought it up because for me, it was interesting, cause it was like kind of wanting success for, for someone in my family in a selfish way.

And I think I would have felt that way about my kid had I had a kid then, you know, I'll want my kid to be successful because that reflects well on me. Right. And I think as I did the self work. You know, therapy, big part of it, Ayahuasca, I've talked about like meditation, all of these things to realize that like, I will never find satisfaction in the outside world, like lasting satisfaction.

It helped me release all of the things that, you know, I thought would give me that satisfaction, you know, whether it was, uh, you know, bigger company or making more money or having more Twitter followers or even having my son be successful, you know? And so. That I think, I think it was just doing that self work that really helped me release it.

And I think that you're clearly on that journey, you know?

Garry Tan: [00:29:12] Yeah, yeah, yeah. I have to admit, I mean, you hear hearing, you talk about, you know, wanting your brother to be successful, but like sort of as a, as a part of you like that, you know, that resonates with me, you know, and then the hard part is like people, you know, sometimes people don't want it.

Right. And so sure. It's like, my brother has different values than me and. You know, my kids are going to have different values than me, and it's not my job to like impose my way of life on really anyone actually. . And that's the hard part. That's the part that I haven't reconciled. It's like my, my father played an extremely active, more active role than I wish he did.

Right. But then also if he didn't do all of those things, if I didn't walk through frankly, that abuse, but also, you know, His expectations and then it's not like he didn't love me also. You know, it also was very clear how much he liked desperately loved me. Which is its own thing. You know, like it, it became very hard for me to learn how to love people the right way, because I had all of these other things attached to love.

Justin Kan: [00:30:16] So those things for you are tools, right? Like he gave you like that's I think that was a big part of my own journey was to say, Oh, like I had this part of me that really wants to be liked by other people. It's the part of me that wants my more Twitter followers. And it's like, it was very unattractive for me to admit to myself at first, like you're the kind of guy who just wants to be like, liked online, you know, like nobody really wants to say that out loud.

And then the first step was to admit it. And the second step was to say, Oh, like, I love that part of myself. Like I accept that part of myself. Like I am that guy and that helped me, like that was a tool like the desire to be liked by the people helped me become a successful entrepreneur and help me be driven to like, not give up when I wanted to.

And obviously there's been material rewards in that and security and, and, you know, feeling accepted and prestigious or whatever. And many of those things ultimately don't matter that much downstream, but it did help me a lot. And I think having admitting that to myself and kind of accepting that part of me was, is like a kind of like was a critical step in the process of saying, okay, now how do I want to be in the world?

Do I want to show up a different way? Right. You know, but I don't think I could have just gotten to the end state of saying, Oh, now I'm like Zen. And I can like accept the world as it is. And I don't need things to be different without having gone through that process of seeing how I was in the world and saying, okay, I accept that.

And I love that part of myself.

Garry Tan: [00:31:39] That's a huge step. I honestly, I, I would be. Way more successful in my business career. If I had figured all this stuff out when I was 22, but what I realized now is all the things I just told you in this podcast is going to like go out to a bunch of people. Uh, I hid because the world isn't ready for it.

Right. I can tell you all these things cause like I'm good. Right. You know, we're made, you know, Justin, we are fucking made and I am so thankful for that. Right. But. But like when you're 22, you got to blend in. Right.

Justin Kan: [00:32:12] Let me challenge that assumption, because I think that you and I both think right now that like, had we .

Garry Tan: [00:32:18] Or when I was there, I thought exactly, exactly what you were saying, which is different. Thank you for that correction.

Justin Kan: [00:32:23] Yeah. Because when we, you know, when we were there, when we were young, we thought, Oh, like, if I have revealed this stuff, Like people aren't going to invest in my company to, I want to join my team. They're going to think I'm like weak. I'm going to look different. And I think, you know, for myself, I, I really believe that had I had these skills when I was younger, I would have been more successful. You know, if I wasn't willing to be vulnerable, like there was that good time with boss last night. Right.

And he was saying, if you, you know, as he's an executive at Facebook, right. He was saying that he. Like, as you became more vulnerable in the world, in the workplace, like he was actually perceived as stronger. Right. And that's my own experience too, is like, as I've kind of shared more and more online, people are like, Oh wow.

I want to, I want to work with that guy. I want to invest in that guy. I want to be like that guy, uh, more than it, whatever was the case before for me.

Garry Tan: [00:33:18] Well, I haven't figured that part out yet. Right? Like I'm with you where I wish that I figured I wish I did therapy and inner work. You know, on my own at 18 and 22, because I was spending so much time, you know, cause I went to Stanford and I was like the poorest kid in the dorm and then even going to work, it's like you have, you have to have that mask or it felt like you had to have that mask.

And I can't run the experiment again to know like what that would look like. I'd like to think that we would like get to where we are today or beyond where we are today, much faster, but the fear was definitely there. I, you know, I realized I spent. Way too long, trying to blend in and fit in and like, act like I was normal like that.

I wasn't abused as a child that I didn't have, you know, food insecurity as a part of me. Like, you know, that I'm carrying around all the time. Right? Like I hit all these things. And then now I realize if I had accepted them earlier, I would be a better manager. I would have actually done better things with my life.

I would have attracted way smarter people to come work with me. Yeah.

Justin Kan: [00:34:22] And one thing I want to touch on is, I mean, you've told this story before, but I think it's important for, for the audience. And listeners is like, you know, you had opportunities. We went to Stanford, you had opportunities to join a startup, right?

Peter Thiel was trying to recruit you to join Palantir as employee number six, seven, something like that.

Garry Tan: [00:34:39] Number one , I could have been a co-founder apparently

Justin Kan: [00:34:42] Co-founder of Palantir  but at the time you didn't have the like. Sense of security, to like actually make the leap. Right. And so how did you get to the point where you were like, okay, I can, I can go pursue a startup and pursue my passion.

Garry Tan: [00:34:56] I mean, I always wanted to work on a startup and growing up, uh, you know, read all the biographies of Bill Gates and Steve Jobs and, you know, it's like, what if someday? Right. Um, and then the funniest thing about it, I was reminded of this recently, but, um, in the moment. Even when I met Peter Thiel, like I knew he was a really good. Um, founder and he had sold PayPal and he, you know, but he wasn't like the legend yet. You know, he was wasn't the myth, the man, the legend. And so now it's like extra crazy, but in the moment it's like, you know, this is, this sounds kind of crazy. I know this person is really smart. And then my friends are smart.

Why didn't I quit? And it was actually because our realities are basically constructed based on the media narrative that, you know, we allow ourselves to believe. And so, you know, the media narrative now is like, do whatever Peter Thiel says. Right. And I say it myself on like my YouTube channel. It's like, you know, Peter wants you to go work at a place price.

But if I think about it, it's like, what, what is the implication of that? And I actually use this frame all the time now as like, what would the global brain think or say, because I think this is fractal, like doing therapy and understanding where I came from makes me now realize. Like I have an inner monologue that is at war all the time.

It's actually kind of like Twitter, right? Like every single argument I can hear both sides and I can sort of feel what feels right on each of those sides. And I can see how the people who have those opinions, they have those opinions for a reason. And then after that, it's like, how do you skip ahead? How do you make a better decision?

And, you know, that's sort of playing out. That's why social media is so interesting right now. It's like, these conversations didn't happen before they couldn't happen this fast. Um, and so the synapse of the global brain, it's like just firing a lot faster right now. Um, and in the same way, like when you're trying to make a decision, if you are to be a better leader, you have to recognize the different parts and then make that decision.

Um, Much faster and be in a much more integrated way. Right. You need to have that conversation and it's like, and then disagree, but commit like inside. That's how an org works. That's how a nation has to work. And then that's how you have to work in your own brain. Yeah.

Justin Kan: [00:37:16] So now you're like going super deep in the last maybe year and a half, something like that into the creator world and,  making YouTubes, uh, for your audience and people love it. You know, the response from Silicon Valley, I read the comments on your YouTube and people are just like so thankful. Um, so tell me more about like your passion for that and where that comes from and why like, I think you're right. That there is a element of creating that is really good. If, you know, both of us are kind of putting out messages of, I call it like edutainment, right? Like we're both entertained trying to be entertained, but we're also like trying to teach people something that maybe we wish we knew 10 years ago or 15 years ago. 

Garry Tan: [00:37:53] If we can skip people ahead, you know, so I so much, it's so much to unpack there.

I guess, off the bat, I have to give it up for Paul Graham. Cause it like, think about the impact of his essays on creating Y Combinator and creating our career, like being a really key part of your career and my career. Sure. You know, I'd be like stuck at Microsoft, like some other, yeah. Some other company just being, you know, designer code monkey someplace, you know, it was his essay that was like, you weren't meant to have a job that put me on a totally different course.

And it was like testing. It's like. I think about these things in terms of church, church or cult, really, but realized, I realized now churches good for you, cults are bad for you. You know, cults are like, Oh, the leader, there, it goes. And like does a bunch of heinous heinous shit like takes advantage of her followers, churches, like, you know, not all of them, but many of them like the intention at least is to like leave people better off than they and give them a community right.

And help make them successful. In what, in many different pursuits. Right. And so, you know, I got to give it up to PG and that's, you know what I want YouTube to be, you know, it is like, let's entertain them, but then let's also give them . So that's, I think that's like the backdrop, I mean, going, even taking a step back, it's like, it's really powerful to have a  platform for this.

Cause it's basically like, you know, these breadcrumbs into how to build companies, right. So, so it is sort of you and I sort of becoming more like nerve cells, right? Like, you know, that's, that's what you get to do. It's like, how do we signal boost? People who are smart and interesting and who are beneficial?

And that's what the world needs, especially right now, especially as the institutions themselves become decrepit and, um, not trustworthy actually.

Justin Kan: [00:39:42] And so tell me, like, I guess we're in the process of creating a new set of institutions, right? Uh, you know, people, whether it's people's YouTube channels or, you know, people's blogs or Twitter, um, One thing I, you know, that runs through all of your work and both YouTube, but then also on just like how you interact, you know, we worked together.

So like how you've interacted with founders and I've watched you interact with founders for over a decade. It's like is really like a kindness and compassion and support in a really being there for people.

Garry Tan: [00:40:15] But then you gotta, then you gotta tell them the real, like the real dirty you can't.

Cause it's like, yeah. I mean, I think that that, that second part is. Well, I want to use the first part to, to be heard. And then the second part is what they need.

Justin Kan: [00:40:29] Right. So, so tell me more about that. Like where did that come from and why is that so important to you?

Garry Tan: [00:40:36] Well, I think in a lot of my journey and a lot of like, sort of my deeper work, um, I'm starting to realize I basically, you know, have you, have you heard of the book, The Egg by Andy Weir?

At some point maybe 10 years ago, I basically decided to live my life as if that were true. Well, I fail it at all the time because I forget myself, but I realized that was at some point, you know, you get to choose whatever cosmology you live in. And I choose that one because that is what I think will get me to our collective goals fastest and the best in the best way possible.

And that's where the impact matters. You know, it's like, And some of this is rooted in what I read about from like the sixties and seventies, you know? Um, you know, I think people really don't think about enough, like to what degree, Timothy Leary and, um, you know, The LSD movement and the, all of those things were part of the counterculture that spawned the personal computer revolution.

And then, and then on top of that was the internet. And on top of that was the web browser on top of that was the mobile revolution. Right. And then, you know, we are right. So I think that that's where I want to go with it, you know, like how do we continue to remake all of society? And, um, and then the best way to do that is.

To think about what is beneficial for each other right now.

Justin Kan: [00:42:05] That's a beautiful thought. Perfect. All right. So now we will open it up Henry.

Garry Tan: [00:42:11] Awesome. Welcome Henry.

Henry Wu: [00:42:12] Hey Garry, I wanted to ask you a question. This one is from Jen. A lot of the time, people in startups talk about risking it all, you know, there's the quit, your job drop out of college mentality.

Did you ever feel like, because you had to support your parents? Did you ever feel like you couldn't take as many risks and how did that impact your startup journey?

Garry Tan: [00:42:30] Yeah. Yeah, definitely. I mean, you know, I wish I was as magnanimous as like wanting to support my parents at that time, you know? Um, the reality is coming out of college, coming out of college.

I was like, yeah, Stanford grad, you know, got my $70,000 a year job. I thought I was a hot shot. I ran out and got like the nicest apartment in Seattle, like in lower queen Anne, like right next to my favorite martini bar. And I bought like a brand new, uh, you know, jet black Honda accord, V6. And I was like, yeah, I got the V6.

I'm made now. Now I'm like street racing. I'm like 22 years old. It's like, I feel super dumb about that because, you know, I still had credit card debt. I had like $50,000, $60,000 worth of like student loans. Um, I was like deeply in debt. And then I went to a job that I. You know, I hated actually I hated working at Microsoft.

Honestly, it really fucking sucked. It was, it's not a fun time. Um, and I didn't do well. And, uh, and then the worse it gets, the more you sort of fall into like the consumerist trap, which I think like capitalism does sort of enforce on people. And I would like to save people from that, you know, The more, you, you know, you, when you have a high paying job that you hate, you end up taking the money and using it as like a salve. Like you get like cut on your arm. Because like you had a bad meeting or you can't get things done and then you're frustrated and then you go home and you ha you know, you spend like $20 on drinks at the bar, and then you go online or you like go to, you know, for me, it was like going to banana Republic and like buying banana Republic clothes at 22 was like the thing, you know, I can never afford this stuff before, you know?

And so I'm like, Oh my God, there's like so many things about like how I treated money and status and like, You know, my face, my mask, like all of these things seemed very important to me. And then it's like, none of that shit was important and it's like all that, all that it was important at that moment was like being a good engineer, being a good product person, being a good designer and making things for people.

And that was the thing that like, I was that I could have done right away, but instead I was like running a hamster wheel race, trying to like impress people who I didn't give a shit about. And then like trying to, you know, cut up, like cover up all these, like mini cuts all over, like the inside of my soul with like material possessions, you know, while I was like massively in debt and it's like me in a nutshell at 22.

And so, you know, I did it to myself, I did it to myself. Right. And so, and then it, it wasn't until later when I saw like the magic of how powerful it is to get product market fit. And to create something for people and interest at state of flow. Like by doing that, that I was like, Oh, there's like a whole other game here.

And like, I need, you know, I that's, so I don't know if it's clear from like some of my YouTube videos. It's like every single time, I'm like, you need to see this, like check out this crazy shit. That's that's what I'm trying to do is like, this is for you, right? Like if you can build this is for you, like do it now.

Like stop everything, like stop all the bullshit, you know, it's time.

Justin Kan: [00:45:46] Awesome, Garry. Thanks. Thanks so much for joining. This is such an amazing conversation. This is one of my favorites.

Garry Tan: [00:45:53] Yeah. Thank you, Justin. Thanks for doing this. Keep fighting the good fight. It's always great to spend time with you.

Justin Kan: [00:45:59] And that's the end of the episode with Garry.

Here's a couple of key takeaways. Number one, start therapy work early, both Garry and I would have been much better off had we started therapy at 22, but it took us years and billions of dollars to realize that these simple narratives we tell ourselves aren't always true. The earlier you get to work on yourself, the better believe me book a therapy session and get started on that process therapy is also super useful for well people.

Number two, it's okay to let down your mask behind every mask, as a story. And knowing that story often helps us truly connect with each other. Jerry always had a mascot and he thought that letting it that would mean sacrificing his career. But our experiences have taught us that when you're up front about the battles, you're fighting, you win more respect and affinity.

As a leader, number three, expectations can be dangerous. One of the things, the Asian psyche is the desire to achieve and Excel. We often get this from a parents and that becomes internalized until we don't realize it anymore. Garry's has been really hard on himself. Everything from how it startups are doing to how his videos are doing.

And he saw how that played subconsciously into a way that he interacted with these kids. Knowing these expectations are dangerous, both for ourselves and other people can be really important on the quest to find happiness, shout out to Henry our quest fellow from the discord server that helped with this episode.

You can apply to be a first fellow and check out all things pressed@listen.Justin.quest. If you like this episode, bang that five star rating on Apple podcasts and comment, which you learn. All right, next week, we've got Kelly, the star and executive producer of the Netflix show bling empire. I'll see you guys next Tuesday.