What's up, guys? It's Justin con. You were listening to my podcast the quest where I talked about the ups and downs of Trailblazers around me. They're human stories and the shit 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.
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 Gary tan Gary's one of my favorite people. He is a veteran entrepreneur investor and content creator Gary and I were both Partners at Y combinator and today he has his own YouTube channel about entrepreneurship and startups. In fact, Gary inspired me to start my own YouTube channel.
And I really look up to him as a content creator. Here's a super close friend and we both share the story of coming from a family of Asian American immigrants and really figure out how to build a career in Tech in America.
It's the coolest thing about YouTube is that you know, that 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 Gary you're so Zen like, I love your super calming voice.
Like you must meditate a lot. Yeah, I'm like you don't even know. Yeah, it's 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.
This episode was really special because how deeply connected Gary 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 Gary is and hope you can learn something from our conversation.
Thank you, Gary. Thanks for coming on. Thanks for having me brother. We've known each other for a very long time. It's been I want to say like since 2008 right of 2007 or
2008. 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 why see you
I want to get to know all the founders who did it.
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. You're from the Bay Area. Tell me what it was like to be young Gary Dan.
Yeah, totally I mean
I was debating. 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. Yeah, like the superraw stories. I haven't really talked about but okay, I mean basically my dad was kind of a raging alcoholic his entire life so, you know his
His entire adult life. Yeah, I mean I'm gonna go kind of deeper because he grew up in Singapore, 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 I would say it's like the Chinese diaspora and it's like it's you know business people is sort of like the merchant class of China had to flee China and something like the largest ethnic group that's you know, not the sort of ethnicity of that area in Asia.
You know whether it's Burma or Singapore or you know, pretty much everywhere. It's Chinese southeast. Asia is 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. And so, you know my my grandfather on that side moved to Singapore and then like
during cultural
revolution. Yeah, and my grandmother, you know was actually, you know illiterate actually and she actually only speaks like sort of 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 look 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 played people having addiction is the worst and it's like it just causes so much pain and the reason why I go that back that far as like just kind of being shocked at how far back like my pain and 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. Yeah, and then and then he'll 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 23andMe and getting that, you know getting my dad to use 23andMe because that remains like one of the core.
Are things that I think you know how you watch Westworld and there's like, you know, you're beginning story like the thing that you know, sort of defines, you know, yeah, 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 it's 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 watch an HBO. It's like my father's defining thing is that he never knew his father.
Father and then he you know, my grandmother remarried into another wealthy family in Singapore, but my father was the stepson and so and being the stepson of your I mean he grew up like, you know being in limos and you know, I think they were all you know, all bankers and Singapore has a lot of money over there and he went to the best school the best private schools, but he was always in I don't know. You know how Chinese families are sometimes like, you know what I hear about that.
Like his upbringing was always that of being sort of the second class citizen within his own family, right? Yeah, and he could have the thing is like it's not like they treated him poorly. It's just that he always felt that like second class. And so that's why my dad left. So he, you know 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. Yeah, 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 a dark side which is like a 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 drink like two six-packs of beer like to this.
I can't I can't drink Budweiser. Yeah, like I hate that beer. That was his beer. Yeah, 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 acted it probably gave me a lot of skills, which was
Just being able to make friends very easily. Yeah, 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 to you know, these things that sort of almost break. You also make you yeah, thanks.
There's so many parallels to my own story worth. You know, I feel like my mom was similar in Chinese diaspora. They fled the cultural revolution grew up in Malaysia for 10 years.
And had this deep scarcity mindset from like not having a lot of growing up very poor in a rural area. And when she emigrated to the United States like brought that along and then the way she raised us it was with this scarcity mindset, you know, and like not have the feeling of not having enough which I don't have a lot of empathy for our you know, it wasn't her fault and I don't know blame, you know, it's very healed now, but it was that, you know, I grew up it created all these patterns as an adult worm. Like, you know, I'm making money, but it's never enough or
Like I need more. Yeah. No. Yeah, exactly. And so the the generational trauma like maybe their parents raise them a certain way. They got, you know trained a certain way and then they passed that along because of their experiences and if so, I understand that Gary.
Yeah, I mean and it's intense because you know, now what I realize 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. Yeah. I mean for those of you who have not I've ever done therapy like the you know, the reason why you do it is like once in a while you get this breakthrough
Through and like I mean, I don't know 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, 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 a nurse assistant and she didn't speak English and she has a hearing impairment. 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 understand we are so lucky in Tech. We are so lucky. It's ridiculous. All right, and 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 that like I was that kid, you know and like we ate well when
My mom would every so often at her nursing home someone to drop off a bag of you know, expired bread. Yeah, 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 going into the car and I'm like, yeah Thomas is that's what we're eating and it's like that was like a good haul, you know, I remember there's an entire time in junior high when it was like I became like the Thomas English Muffins like like recipe Champion like,
I can make I can make sandwiches and I think that's why I love food so much now because you know, we didn't have it. Yeah, 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,
what's your relationship with your parents? Like now?
I mean, you know, I send the money every, you know, I try to support them as much as I can, you know, and honestly like thank God like my dad.
Dad stop, you know, he stopped drinking. He stopped he like fell off the wagon a couple times but you know sort of in the past five years in particular. I think he's really he started going to therapy himself. Yeah went to AA I brought him to a a a a is amazing. Jiahui. It's like, you know, what's funny is like after going to AA I realized why C and A A have a lot in common. Yeah. We have our mantras. We have a group therapy session. We don't feel alone. And then we have like a we even have
Earth you know, yeah, this is 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 and that Community.
Yeah, it's awesome. So I feel super blessed now and
I guess the only other strange thing that I don't know if you ever feel, you know earlier you 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 for who are part of the Chinese diaspora in particular who like don't get that from her our parents. Yeah, and I didn't realize that that was like a diaspora thing like, you know, the emigrants the people who left they were actually sort of like
People who had some wealth and it was taken it was going to be taken from them and their lives. I mean it was taken and if they didn't leave they had they had to leave with like often the clothes on their back 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 is like that's where that comes from. Right that's like our families were always the Strivers. Yeah he riod right the
worst worst drivers.
As were 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 in their family. My grandparents had 10 children one of my mom was one of the younger ones and they fly in China like secretly, you know, he had a business there and they had to they fled and my two uncles my two oldest uncles were like not allowed to leave and I mean like you said go
To what you were saying about feeling being blessed like you and I never have to deal with anything like that. Right? Like we're thinking even just basic. So hopefully, you know, 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 how did this manifest into getting into startups or programming or?
Yeah. I've been reflecting on this really late.
Li and like starting to sort of wonder if we have free will actually fall like Dolores from West World, basically, I mean, it's funny, you know the fiction hits exactly at the right time in some ways like this that that show is so prescient and my technological optimism utopianism basically comes from Star Trek the Next Generation, you know, if 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
Watching 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 want to be Captain Picard, right and but going back to like, I guess the Chinese parents will 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 like sort of broken home path and then also, you know sort of basically causing Addiction in my father's life.
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. Yeah, and then the difficulty is the addiction Rob that of him like he is super super smart, you know, he was you know, making his own electronic locks in like the 70s just for fun. You know, it was a hacker's hacker, you know, we get to play with software. He was playing with Hardware in like, you know in he was like a maker before, you know to 30 years for a maker movement.
It was a thing. Yeah, 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, you know, 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 that after
That I realized that he basically projected all the things he wanted to do on me but then there was also that layer of like Chinese paternalism plus alcoholism. Yeah. I'm 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+ on something and he'd be like not good enough and I'm like, it's good enough for this person and he like it's not good enough for you. You are set apart. I mean he was careful enough not
Say you're better than other people which I was like thankful for but because that you know, I think I it's funny because like you run across a lot of like kids who were you know, the kids have wealthy people now then you can kind of see like, oh if you go a little bit too far, right really Alters their personality in a way that like you don't want, you know, it's like unintended consequence. So it's like you're better than all those 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 a accompanied with if I came home with actually a be like a be on a test like your set apart a be on the report card. I got a punch in the face. Oh my God.
Yeah and
your I grew up like thinking that was normal and it's not normal. Yeah, that's yeah. I took a therapist to tell me like Gary like you.
Through something that is not supposed to happen to Children. Yeah, and so I'm even now still like sort of processing that and now what I realize is like the result is that I have a very extreme
super-ego. Yeah, I kind of keeps you on the rails.
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 you know, a week meditating. I probably would like still would like the second I like came out of it. I'd be on the edge of
Again, you know, yeah and it's not something I talk about and it's not I think it's not clear to people because the funniest thing especially after doing a lot of YouTube and you know, a lot of people spend is the coolest thing about YouTube is that you know, that 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 Gary you're so Zen like I love your super calming voice like you must meditate a lot. Yeah. I'm like you don't even know.
Yeah, it's 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 I third as well as I usually do like the immediate self like it's like self-hate. Yeah, you know, like I punched myself in the face now like emotionally, it's like I feel bad and then you I always think about Steve Jobs and how when mobileme came out he dragged like the whole team into the auditorium's like, I don't know. 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 Mall Walt Mossberg, and then he dragged out the leader of that group and he fired them on the spot like get the fuck out of here. Yeah, you know and so I haven't been able to like break that apart because it's like that's the hard Edge that's you know, I can't tell if it's necessary. Yeah. It's like,
you know that really resonates with me because
I had that express my whole life which is if it first there's the formative experiences when you're young from your parents or peers, you know, that really made me they were where they were seeing 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 decades like, oh, I'm not good enough. I'm I was very comparative to other people like this for the person's doing better than me. I need to do better and I would like
A source of like my own self torture, you know, and I want to highlight one thing you said was like you don't see that beneath the surface right? Like everybody thinks everybody else is like obliviously like succeeding be like
that like this like
I looked at like the guys from I don't know Dropbox or maybe your friends of mine were like really successful. I was like, oh those guys are just like they're super happy to 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 can say. Oh I
Sixty thousand Subs with their 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 wheel never stops turning but it's so interesting to me that you said that you know beneath the sir 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 one of Gary's that my life would be fucking set like that is the calmest guys like the most confident person. He's the person who like that's that's a person. I want to be in the world and they don't you that's my mask man
exactly. That's the mask.
Thanks for sharing that so far in the war. You know, dude. I totally get
it I think deep down what I realize 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're 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. No, you know, that will change the way you go about
You know the world and and your business and you know, when someone cuts you off, you know, there's something going on, right? There's something in that person's life and that is choice. Right? Like we can play it the way you know, I child would play it now that we're both parents. I realized they're sort of the innate and then there's the Divine and we can choose the instinct or we can choose, you know, the elevated and it's a choice at all times and the more we Revere 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 that 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 we get to be a brain cell or a blood cell or
You know a nerve cell and and that's the gift really respected
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 it stop repeating cycles that maybe were unconscious and now a passed a law that gift that you have to pass along 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 the time.
Thinking what do I want for my kids? 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 in the world, you know for yeah for him to be a kind person and compassionate for him 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 it like, you know, being a doctor or an entrepreneur following my footsteps or anything like that and you know, it took so much self worked.
There, you know like the just about 10 years ago would really like how I want my kid to be like Bill Gates or whatever, you know, but my that that's like I think that's self work
to produce. How did you do that? Yeah, I have to admit. I'm not there like oh my you know Stephanie, my wife is absolutely there and she's like Gary you can't have these expectations. Yeah, and then for me, it's like what I want for them is like the ability to experience. Yeah csikszentmihalyi as flow, you know to accept me I came.
Up with this idea or like he's actually is for those of you in the audience watching is like so, you know the movie Soul. Yeah that that moment when the main character of can play the piano and he floats off the like someplace else and I felt that like mainly when I was like coding and and designing right, but I feel it now when I'm like editing a video or even on clubhouse, I don't know. It's like there's something really powerful about you know, like the other day. We had Jason ma who was on your show on the tech after party on.
House and he was talking about exorcisms. Yeah, 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. Yeah. I mean, I don't know how to reconcile that because of the Excellence part and then I mean, I'm like I need like ten more years of therapy. I think
what your first thing is like you're aware of it. And so that's like the first step in anything right is that you're aware of of wanting Excellence for them for wanting a 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 you know 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 inexorably linked and so that's right for myself, right? You know the way I got to it was just
You know, I want to remember one thing. I'll share as I remember. I was so proud when my brothers will Cruise, you know, my brother started cruising me sold in cruise. I was like any was awesome. But I was really like proud for myself in a way to is like selfish because I was like, oh, yeah. I'm like, we're like the kind of Brothers who have like billion dollar companies, right? And that's like a very eager 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
Never
admitted. Yeah, thanks for sharing that. I mean I hear that man. Yeah, like basically we see the reflection of others in ourselves. And then yeah where does our identity and and like, you know our community began and what should you feel good about? Yeah. I don't
know I brought it up because for me it was interesting because it was like kind of wanting success 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 that you know, I won't waste kid is best because that reflects well on me, right?
And I think as I did this self work, you know therapy big part of it. I was'cause talked about like meditation all 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 or whether it was 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-worth that really let homie release it and I think that you're clearly on that Journey, you know? 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. Yeah, you know, and then the hard part is like people, you know, sometimes people don't want it right and so sure it's yeah, like my brother has different values than me and you know, my kids are going to have
From values than me and it's not my job to like impose my way of life on really anyone actually. Yeah, and that's the hard part. That's the part that I haven't reconciled. It's like 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 yeah, but also, you know his expectations and then it's not like he didn't love me also.
You know there also was very clear how much he liked desperately loved me which is its own thing. You know, like 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. So those things for you or tools right like he gave you think 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 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 yeah.
Kind of guy who just wants to be like liked online, you know like that. Nobody really wants to say that out loud what and that the first step is to admit it in the second step. We say, oh like I love that part of myself. Like I accept that part of myself. Like I am that guy in 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 and that and security and and, you know feeling accepted and
Prestige or whatever and many of those things ultimately don't matter that much Downstream, but he did help me a lot and I think having admitting that to myself and kind of accepting that part of me was a 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, 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. Yeah, that's a huge step. I honestly I would be way more successful in my business career. If I had figured all this stuff out when I was 22, but you know what I realize now is all the things I just told you in this podcast is going to like go out to a bunch of people I hid because the world isn't ready for it. Right? I can tell you all these things because like I'm good like, you know, we're made, you know, Justin,
We are fucking maid and I am so thankful for that. Right but but like when you're 22, you gotta blend
in like let me challenge that assumption because I think that you and I both think right now that like had we
I thought had we or when I was there. I thought
exactly exactly when you were there. You thought is different. Right right, because
when thank you for that correction. Yeah,
because when we you know, when we were there when we were young we thought oh, like if I reveal this stuff like
When I can invest in my company to I want to join my team. They're gonna think I'm like week done that I'm going to look different and I think you know for myself. I really believe that had I had these skills when I was younger. I would have been more successful, you know, if I was willing to be vulnerable like there was that good time with baz last night, right? And he was saying if he would, you know as he's an executive at Facebook, right? He was saying that he liked as he became more vulnerable in the world in the workplace.
Like he was actually perceived in his stronger, right? And and the thing that's my own experience to 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 yeah invested. Like I want to be like that guy. I'm more than it ever was the case before for
me. 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, because I won
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 Master 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.
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. All right, like I hit all these things and then now I realized 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,
and one thing I want to touch on is when you told the story before but I think it's important for the audience and listeners is like you had opportunities went to Stanford out.
To join a start-up right Peter teal was trying to recruit you to join palantir as employee number six seven something like that. And number one, I
guess whenever one sorry, I could have been a co-founder apparently outer palantir,
but at the time you didn't have the like sense of security 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 start-up and pursue my like passion.
I mean, I always wanted to work on a start-up and growing up a you know read.
All the biographies of Bill Gates and Steve Jobs and you know, it's like what if someday right? Yeah, and then the funniest thing about it, I was reminded of this recently but in the moment, even when I met Peter teal like I knew he was a really good founder and he had sold PayPal and he you know, but he wasn't like the legend yet. Yeah, you know, he wasn't the myth the man the legend, you know, 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 were basically constructed based on the media narrative that you know, we allow ourselves to believe still and so, you know, the media narrative now is like do whatever Peter Thiel says right and I say it myself unlike my YouTube channel. It's like Peter wants to go work at a place. You probably should do that. But if I
I think about it. It's like 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 now, 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 is like, how do you skip ahead how do you make a better decision? And you know that sort of playing. Yeah. 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. And so the synapse of the global brain is like just firing a lot faster right now 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.
Much faster and be in a much more integrated way, right you 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 that's how you have to work in your own brain. So
now you're like going super deep in the last maybe a year and a half something like that into the career world and totally making YouTube's for your audience and people love it, you know the response from Silicon Valley. I read the comments.
Your you choose and you are just like so thankful. 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.
And yeah if we can skip people ahead, you know,
so I so much so much to unpack there. Yeah, I guess off the bat. I have to give it up for Paul Graham because 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 in my career sure, you know, I'd be like stuck at Microsoft like some other, you know, some other companies just being you know, designer Code Monkey someplace. Yeah, it was his essay that was like you were meant to have a job that put me on a totally different course and it was like test and it's like I think about these
In things in terms of church church for cult. Really? Yeah, but realize I realize now church is good for you Cults are bad for you, you know culture like, oh the leader goes in like does a bunch of heinous heinous shit. Yeah, 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 the in 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
You know what? I want YouTube to be, you know, it is like let's entertain them. But then let's also give them, you know a big old piece of vegetables. So that's I think that's like the backdrop. I mean go even taking a step back. It's like
It's really powerful to have a platform for this because it's basically like, you know these bread crumbs into how to build companies, right, you know, 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. Yeah, especially as the institution's themselves,
Has become decrepit and not trustworthy actually.
It's so tell me like I guess we're in the process of creating a new set of Institutions right people whether it's people's YouTube channels or you know, people's blogs or Twitter one thing. I do know that I run through all of your work and both YouTube, but then also on just like how you interact, you know, we work together. So like how you've interacted with Founders and I've watched you know,
I could Founders for over a decade. It's like is really like a kindness and compassion and support in a really being there for people and I think that you have this
then you gotta eat then you got to tell them the real like the real dirty. You can't because it's like yeah, I mean, I think that that second part is well, I want to use the first part to be heard and then the second part is what they need,
right? So tell me I'm sorry about that like you where did that come from? And why is that so important to you?
Well, I think in a lot of my journey and a lot of like sort of my deeper work. I'm starting to realize I basically I have you heard of the book The Egg by Andy Weir. He's the guy who did yeah. So book 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 the fastest and the best in the best way possible. Yeah, 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 60s and 70s, you know. Yeah, I think people really understand think about enough like to what degree Timothy Leary and you know the LSD movement and the all of those things were part of the counterculture. That's
On 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 you know, here 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 and then the best way to do that is to think about what is beneficial for each other,
right?
No, that's a beautiful thought Perfect. All right, so now we will open it up and read awesome. Welcome Henry. Hey Gary. 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 can take as many risks? And how did that impact your startup Journey?
Yeah. Definitely I mean
Yeah, I wish I was as magnanimous as like wanting to support my parents at that time, you know, 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 Hotshot 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, you know, jet black Honda Accord V6 and I was like, yeah.
The V6 underneath now unlike 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. I was like deeply in debt and 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 not a fun time.
And I didn't do well and 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 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 you're 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 know you go.
Home and you have you know, you spend like 20 dollars 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 that that 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 I was like, none of that shit was important. It's like all
that all that 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
As like that was me in a nutshell at 22. And so, you know, I did it to myself. I did it with myself, right? And so and then 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 interests data flow like by doing that that was like, oh there's like a whole other game here and like I need you know, that's so I don't know if it's clear from like some of my YouTube videos like every single time. I'm like you need to see this like check out this crazy shit.
That 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. Awesome
Gary. Thanks. Thanks so much for joining. This is such an amazing conversation. This is one of my
favorite. Thank you Justin. Thanks for doing this. Keep fighting the good fight. It's always great to spend time with you.
That's the end of the episode with Gary. Here's a couple key takeaways.
He's number one start therapy work early both Gary and I would have been much better off had we started therapy at 22, but it took us years and millions 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 is a story and knowing that story often helps is truly connect with each other Jerry always.
Mascot, and he thought that letting it down would mean sacrificing his career. But our experiences have taught us that when you're upfront 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 baked into the Asian psyches that desire to achieve ends Excel we often get this from a parents and that becomes internalized until we don't realize it anymore Gary's been really hard on himself everything from how its startups are doing to how his videos are doing and he saw how that
played subconsciously into 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 quest fellow and check out all things Quest at listen dot Justin died Quest if you liked this episode bang that five star rating on Apple podcast in common, which you learn. All right next week. We've got Kelly the star and executive producer of the Netflix.
Bling Empire. I'll see you guys next Tuesday.
