32: Chris Sacca - Drifting Back to Real

42:26And so I took some time to come home and we were building a house for my mom and dad. Um, my mom had some health issues that required her to be, to live on one floor. And so we moved out of our childhood home and we were building a house. Um, but the way we were building it because so that we could afford it sounds crazy. But when you pay cash to contractors, um, under the table, they, uh, don't have to declare tax on it. So you get massive discounts. And also they're just used to people not paying them or messing around with them. So we went to the bank and took out basically all the money my parents ever had, had an actual pile of cash and would say to a guy that we knew in our town, like, Hey, we need a foundation.

43:06And he'd quote us like 40. And we're like, what do you say? 15 cash. And like, I'll be here Thursday. And so we were building this house for cash. We were also using people that my dad had done. My dad is obsessed with doing pro bono work. And I used to be like, wait, we're broke. And you're like, yeah, but I know this guy's dad and his family and they need help. And I'm like, I get it, but we have no money. You know, I helped install my dad's first credit card reader in his office when I was a teenager because I was just like, let them take the credit risk, not us. It's probably why I became such a capitalist.

43:39But anyway, there are just people who owed my dad favors because he'd helped him with a situation. So I was working with one of those guys once. This guy's name was Todd. I won't say his last name, but he had started going to a mega church in town. We had one of those big Christian evangelical churches that had come in and wiped out. We were a Catholic town until then, and they just wiped it out. And everyone was going to this church. This is like your prototypical Trump voter today, kind of like just a hardworking blue collar laborer who felt kind of excluded from the elitist system. But we're laying brick and making small talk.

44:13And I was like, hey, what do you what do you what do you learn in that church? Like what? You know, and he's like, oh, man, last night was amazing. He's like, you know, Preacher told this story about, he said down in the south, I forget where he's like, you go to this one town, maybe like Arkansas, and you'll find this huge statue of Thor, you know, like just this massive statue. And he's like, you know, and Preacher explained that at the base of that statue, in that soil at the base of that statue, are all the naturally occurring elements you would need to make a watch. he's like you know you know you've got like the iron you know that you could that you could make into the metal and he's like and and and you've got the the glass in the dirt that you could that you could melt into the to be the face of the watch you know and he's like and and preacher said look if you're if you're if you believe in evolution then you should be willing to stand at that statue wait for lightning to strike and a rolex to pop out of the ground right my brother was there and we looked at each other like holy shit how many hours days weeks would it take us to undo that metaphor we're like how much science how much evidence how much how the fuck are the dinosaurs here you know like right like how much would it possibly take to and and i got to the point where i'm like maybe you can't like and and i started to realize that like good metaphor and simile and analogy like the true weapons of mass destruction it was another lesson in the power of language later in my life i was an attorney briefly i was general counsel at a company where one of our founders was literally arrested um by accusation false accusations from our main competitor they were trying to put us out of business and they had literally concocted this story about how he had accessed what was called an anonymous ftp server which is the standard of file sharing there were millions of these servers in the world and they all had the same username and the same password the word anonymous and the word anonymous and so so it was the opposite of a of a private or secure server and yet this company akamai had gone to the justice department and said and the FBI and said this guy just hacked a server um and so we knew we knew that it was bullshit and it was my first time really helping out in court federal court in front of this judge we get there the judge it's old as dirt and the prosecutor stands up and says judge I know there's a lot of technical mumbo jumble in here and they submitted 100 pages of bullshit my eyes glazed over I'm sure yours did too he's like so I'm just gonna make this easy for you and he's like what the defendant did here was akin to and he reaches in his pocket and he pulls out like a combination lock you know the kind you put on your locker in school and he's like we all know what this is combination lock right so what the defendant did here was akin to just trying every combination on the lock until he got the one that popped it open then stealing everything inside so i'm just i just chew on that and i'm gonna sit down and we and i was like fuck like all i've got are the literal inventors of this standard the guys who created the anonymous ftp servers were in the room not even paid just on the basis of like this is some bullshit why is this guy in jail actually yeah and we were powering like two to three percent of the internet at the time and they seized our servers and so and so i'm like how do i undo that yeah that was one of the greatest it was a false metaphor but how do i undo that i undertook the study and you know this uh of uh really i i dove deep into um colloquialisms idioms uh cowboy language and so years ago i taught a master class at oxford called um business language of the american cowboy to a bunch of these like flim flam comes from no but but like i i mean i already just grew up in a place that had a different dialect, different than dialectic, but a different dialect and just parlance than anywhere else.

48:28You know, now I worry that TikTok is homogenized how we all talk. My kids in Montana who don't have phones, but they learn it all on the playground from the other TikTok kids, have the same exact slang as kids in Seattle and kids in St. Louis. It's all the same. As, by the way, young people on our team, you know, and so young people on our team, I don't know, whether it's mid or sus or whatever those are dated now what are they and it's definitely not skibbity anymore or something like that or it's giving whatever it's all the same oh six seven there's like a flat are you a six seven do you know you're just like you what really have you gotten that old you don't know i've been watching tiktok all right hey shout out i'm 50 so to anyone listening right now who knows six seven i'm down but but no like i i started to realize the power of those things and so i really dove into when we communicate how do we make things as accessible and how do we help people file those in a way that they get comfortable like i got my head around that idea yeah one of the coolest things to do with chat gpt among the hundred million amazing things about it and by the way i also use claude and gem and i'll just use chat as to stand as a as the you know the shorthand for it talk to it about a real idea talk to it about a serious scientific concept which we do all the time in the hard science business and then ask it to explain it to somebody with declining reading levels so start with high school go to middle school go to elementary school when you start hitting third and fourth grade the the metaphors it comes up with are like oh my fucking god they're genius they're genius and they're like this is how i would explain it to somebody at the bar wow it's like what do you do and i'm like i'll tell you what i do brother and so it's really cool and so it's powerful and so i thanks for calling out my writing you know those update letters you talk about it is it is wild i wish the world saw more of them they usually contain a bunch of confidential shit someday um and so the audience is like 200 people but we work on those for a couple months and you know even as you're reading that blog post i'm like i just use the word snow and twice and uh this is what i saw i was like i use the word snow twice in successive sentences i remember having we were editing those letters and it's like yeah get up the thesaurus well chrystal and i are if i'm you know we're both type a plus plus i mean inside of our wedding ring it says inviolate agreement uh and so if you've worked in our home you know how we go at each other because we fight over every pixel yeah because every every pixel every word has to be perfect who can who can captivate you in a way that really makes you shut up anybody well chrysal made a joke last night at dinner we had david kwang uh the nerdiest magician of all time he's a cruciverbalist for the new york times he's a magic historian he actually wrote this incredible book called how to fool your parents it's a magic book for kids uh and he's come and stayed at our house and our kids have signed the magician's oath so they work on tricks together but but he um i love bringing magicians to meet engineers because engineer everything to an engineer or computer scientist or a scientist everything has a clear linear causal explanation yes and then when their senses betray them like they just stop you know i used to i used to bring david blaine to twitter and stuff he's an old buddy and i would just watch the smartest people i know go crystal always jokes about how i've become an obsessive student of magic so i think last night i knew how eight of the 10 things were done but she watched me and was like oh he doesn't know this one he can't figure it out and she's like david kong might be one of the only people who can shut up chris wow i mean i love a good listener talk about a type of storytelling too man yeah but but i mean okay so what i would say is there are authors who make me steve martin pj o 'rourke who's passed away since um chuck klosterman uh there there are authors where i'm forgetting like a dozen i i read too much but where i am like that sentence man how do i how could i ever rid your powers no overstory man no oh oh the overstory yeah yeah sorry i didn't remember that yeah no i i there are people and there are people who write substacks and where i'm just like or poetry i like i'm i've probably reread billy collins billy collins poetry is incredible because it is so well it's weird to describe something quotidian by using the word quotidian but it's the opposite of what i'm trying to say it's such accessible normal everyday language communicating incredible ideas from a completely like familiar life to any human being and i constantly reread it and intimidated by it and so i i think that to me is i don't know if i see it in speech as much like i love good orders i love powerful speakers and your writing is like that i would add i watch a I watch a lot of evangelical speakers.

53:36I watch a lot of ultra-populous Republicans. I tell our people, if you're not diving into... The whole Charlie Kirk thing is a horrible tragedy. I don't think he had the best intentions. I think a lot of what he was arguing was insincere. but I listen to it constantly. Like he went on Gavin's podcast. I think Gavin is a great person with good intentions, but Charlie ate him alive, you know? And, and I'm like, this is just a rhetorical master. This is a person who knows where they want to get to in an argument and can take people there and make them feel empowered along the way. And so there's no denying the effect he had and the relationship, his viewers and listeners and the people who showed up with him had and that power of debate to make somebody feel like they're invested and they follow the chain of reasoning to that end point.

54:32More like a story. Yeah. We, we have to not run away from that. We have to understand why people crave it and why it makes them feel like a coauthor of the story. Think of, I talked to Ira Glass about this 10 years ago. You know, I was on primetime television and I used to do, I was, I was out there. I was exposed. but the people who come up to me and have the strongest reaction to me were people who heard me on a podcast yeah like that startup podcast with alex bloomberg you know season one episode one i still get stopped in new york i think that's how i found out it's 2025 and i still get stopped in new york because of that so i talked to ira who is the greatest story like audio storyteller of all time um and like wildly intimidating as a result when you talk about speakers i would put him there uh and and so is alex bloomberg alex bloomberg who co-created this american life with him it's just incredible but i think about out.

55:34I think about why people feel like they have such an intimate, deep relationship. Like I could walk down the street in New York with Edward Norton. One of the great, I mean, you've been there. One of the great all time performers and a genius in his own right. And just so sui generis across. I mean, he's a CEO and a founder and just all the things. But if we walk down the street in New York, people come up to him and they kind of stick their arm out and like, oh, Mr. Norton. Oh my, literally Mr. Oh, Mr. Norton, I loved you in. And it's wild to see like, was it Primal Fear or the Hulk or whatever, you know?

56:08And so. He's not really a person. no he's characters he's a series of characters and i have always played myself like i've tried acting twice and i'm miserable and by the way both times they had me play myself but they scripted the lines yeah yeah and i'm like this is not actually what i say or if i said it this sounds weird the second time i can't i'm a shitty actor but um but because i play myself and because i tweet about myself people are convinced they know me and they come up and they get right in my personal space and they talk to me like we're pals and so so when i am on a podcast and i try to be as real as possible and talk about things people don't expect me to talk about then they believe we know each other yep this came full circle for me when uh i met alex bloomberg for that episode to tape it i we weren't i was not convinced that podcasts were a business yet right remember that you were there uh you were working with us at the time but hell yeah i was going to take a meeting with alex boomberg like i he'd been in my ears like this american life was kind of like my church yeah you know i'm not a religious person but that was a spiritual thing for me come out on sundays and um and at first i used to listen to it on the radio and then when podcasts were a thing it was like my go-to is top of my list and so when alex boomberg wants to meet me i'm like yeah yeah and i'm gonna pretend like i'm not fanboying by the way he's doing the thing it's amazing i just listened to it back it's incredible he's so nervous and then by the way that you're like telling a story back to him and it's awesome so but but i show up i go to walk into our favorite sushi restaurant in la mori and i as i'm putting my hand on the door handle i'm like wait i don't know what alex boomberg actually looks like right i have spent so many days with him his voice is in my head yeah and i have a picture of what he looks like because i hear his voice and i've related something else by the way his voice sounds just like iris and so i don't know if they influenced each other that way uh but but i walk in and i start panning this restaurant panicked like which of these people is is alex boomer and i'm like is that the guy is that the guy and then by the time i look all the way right there's a guy with a big boom mic and earphones on and i'm like oh all right it's clearly my guy but but i had i had been building the story yeah i had been setting that stage and costuming it and and i do think that's one of the and the long form nature of it i think there is a lot of reward with an audience for being real and being yourself not everyone adheres to that or they they're playing a character or they're saying something they don't actually mean because it's opportunistic or it's advantageous or manipulative to do so but but the power of podcasting like i i have this theory right now that if the dems ever have a president again or we even have free elections again i i'm not sure if it's a current politician i think it has to be something that someone that comes out of podcasting or sports you know i i even a he's waiting in the wings years ago i told cory booker you know cory's an incredible person and a true public servant and just an inspiring guy but i was like if you want to shatter like the glass ceiling of irrelevancy to america i was like you played football at stanford go on college game day just sit at the desk i did this dude so what's that chalamet did yeah yeah yeah Yeah.

59:29Yeah. I was like, just go and do not talk about politics. Don't even have them introduce you as Senator Cory Booker. Just talk about football. You know it. And then like maybe two years ago, I talked to Gavin here in New York, actually this week, two years ago. And I was like, I know you and a lot of people know you, but most people think you're just a slick politician. I was like, and they don't know who you actually are and why you do this and all the other opportunities you'd have. And so I said, have a sports podcast. Like you care about sports. I know you know how to talk about sports you never do you're a good orator about politics he's got all the facts but i was like but america doesn't give a shit about facts anymore so he came back to me later i saw him at the super bowl when the niners were playing and he said hey dude i'm doing it i'm like what are you doing yeah he's like so look i got this thing it's it's me and marshawn lynch and i'm like fuck yeah you're going beast mode you're going you gotta take care of your mentals and your chickens um i'm like that is amazing and and he's like and and they put it on serious and i'm like that is the opposite of amazing like you might get to i never heard of this you might get to a few truck drivers but like and and um and then they talked about politics and so i love what he's doing now i mean i think gavin's only hope is to just shake it up and break every norm uh and so i love what he's doing with his content right now uh it's there's no downside to it like there's a there's just a limit on what he could be politically if he doesn't build that connection with an audience and motivate people.

1:00:59But, but I actually think the best shot, and by the way, like I think George Clooney could have been president some years ago. Um, but I don't think it's going to be a traditional star now. I think it's gotta be someone who feels like they have a recurring, connective, vulnerable, authentic relationship with an audience. And, and I think today that's podcasters and athletes. You gave up on having an audience and you don't write publicly anymore. Oh, I miss it. I miss it. It's a drug, though, and you can get addicted to it. For all that self-reinforcing stuff, for sure. People would scream about me on the internet, on podcasts, or I mean on message boards and Twitter and stuff like that.

1:01:41I didn't love that. Everyone's like, don't read the comments. You're like, you can only read the comments. Twitter is only the comments. Yes. We're just built, back to that cognitive biases thing, we're built to like there's 20 flattering things and then there's the find the one fuck you i mean dude i saw a comment where somebody apparently my eyes turned down in the corners and that's associated with some level of retardation or something like that and and like i'm like wait what and like i like thinking about it for four days and no i started googling it and i'm like let me understand this i mean how are you look away from that it's like those eyes are associated with john malania is this old joke where you like walk by the middle schoolers on the street and they like know exactly the one thing to say to you that makes you just like just devastate you yeah it's that um last night i was out late in new york with our team i was standing i was talking to one of our founders actually this really cool guy carl who works for zanskar he runs zanskar which is this incredible geothermal company and i said you know it's funny because and a guy walks by and goes it's not funny and then just keeps walking and i was like dude what i just turn around i'm like dude you just made me laugh that was actually funny like you say my thing wasn't funny was actually funny but i loved it the timing was wow i was like you know new york is amazing but uh i want to talk a little bit about investing and risk we're gonna have to we're gonna have to do a little bit with chris saka here um famous line it may be lucky it's not an accident classic I've repeated that to many, many people.

1:03:15You also are very thoughtful about stacking the deck, playing a game you can control. I'm curious, so super open-ended question, but you have a really strategic and successful relationship with risk. And my sense is that most people wildly under, overrate risk or are afraid of risk. And I'm curious, obviously it applies a lot in investing, but I'm curious how you've used risk broadly in your life and maybe why it's less scary than people think it is. Okay, there's a couple components to this answer, but I'm going to tie this back to what you were just asking about, which is something I haven't talked about as much.

1:03:54But I do miss having an audience, and I'm writing something right now for an audience, but I really worry that ChatGPT has diluted the power of words and has taken a lot of the soul out of writing because it's pretty fucking good yeah it's not great but it's pretty fucking good and in the same way that i regret that i think instagram cheapened photography and took a lot of the soul out of photography i um and ai is doing it like ai image editing is just is doing it all over again and maybe sora is doing it for video and stuff but i have something i'm really obsessed with right now which is i uh i talked about a little bit with tim he knew i was working on this idea and he kind of forced it out of me to talk about it it was really preliminarily baked and since then i have someone i'm working with it on and stuff but we all kind of tease this generation for various ways in which we and by i'm i'm decidedly gen x i'm 50 i use a good skin cream but i'm definitely 50 uh and i'm 50 from western new york right a banged up place russ belt um i'm still really close to my friends from high school some of whom have had hard paths you know and um and it's caused me a lot like guys by the way guys like chuck closer man who've written about our generation have uh and then gene twangy's book about generations have made me prouder of being gen x than i ever was i think we were taught to be ashamed of ourselves because we were slackers and i've become pretty cool i've become pretty proud of who we were but or our but i've started to take responsibility in the same way that we think boomers need to take responsibility for the ways in which they fucked up our planet and economy we need to take responsibility for the ways in which we fucked up kids and so i i really have trouble talking about this without feeling like i'm like characterizing an entire generation of people is broken.

1:05:56And so you're going to yell at me. I take it. By the way, I'm not on social media, so I'm not going to see you yelling about me anymore. So go ahead, say it. But I worry we see too many people, I won't say all the people, but too many people who have no agency, no resiliency, no adaptability, take no initiative. A friend of mine phrased it once. My friend Matt from Bozeman said, they ask for permission to solve a problem. And like Crystal and I lit up. Yes, permission to ask the question. In a 30 person Zoom, they let everyone know they're going to the bathroom. And I'm like, you're a professional, makes hundreds of thousands of dollars a year, leads tens to hundreds of millions of dollars of investment.

1:06:43Go piss. Like just turn off your camera. If you turn off your camera for any reason, I'm going to assume it's for a good reason. Like I've trusted you to run a part of the business. You really don't need to let us know like the status of your bladder. And you've now imposed that cost on 32 people. You know, you've interrupted the discussion to let all of us know that you need to take a leak, like just go. And so what I, what I really worry about is that we don't give kids a chance to fuck up anymore. We don't give kids a chance to take risk and to make bad decisions, whether it's helicopter parenting or snow pile parenting or robbing them of a play-based childhood as jonathan height likes to talk about and putting them in the phone-based childhood which is actually way less safe than uh we we overclock for physical safety and underclock for online safety as jonathan's written about extensively and i i really love his heterodox approach to this i think he is one of the most honest brokers of truth and what he's trying to find out about what's happening to kids and originally it was girls and now he's realizing men and boys are so deeply affected by this too but but i think it at the heart of it it lies at we just don't give kids a chance anymore to make decisions let alone bad decisions like good decision making comes from bad decision making and the consequences of like whoops that was stupid feeling it yeah and just um god there was a there was a fight at our kids middle school last week and i don't know any i don't know the two kids were involved but unlike the fights we had in where there's 10 different camera angles of this fight right uh and i watched him two slaps got landed there were sixth graders two slaps got landed and other than that you could see both kids were fucking terrified of each other and of being in a fight and their sixth grade adrenaline was firing and so they were like like pretending yeah they were like posing as punching but there was like at least five feet between them and they were and then eventually got broken up the school and this is in montana this is a public school the school suspended the core witnesses to the fight for a day and then suspended the the participants or protagonists of the fight for two months oh my gosh and i'm like first of all in hockey you get five minutes to reflect on that and then you're back out on the ice.

1:08:58But I was like, wait. Crystal and I have worked extensively to help people. Did you ever come with us to prison? We've worked on helping California used brain science to pass a law that allows anybody who was sentenced to die in prison for a crime they committed under the age of 25 to be eligible for resentencing. Not necessarily freed. Not everyone should be freed. But there are some people who did horrible things when they were 16, usually as a result of horrible circumstances they found themselves in, but did horrible, inexcusable things when they were 16. But we now know your frontal cortex is not formed, fully formed until you're like 25, 26.

1:09:48There's just clear science on that. And we do dumb shit. And sometimes that dumb shit has, you know, like mild consequences and sometimes it's life changing for yourself and others. But I'm like, do you know what suspending two kids from school for two months does to their trajectory, to their social development, to their academic progress? Like what the fuck? For two kids who just had that adrenaline, I was like, what was the basis for the fight? And it was, it wasn't hate or racial or anything like that. it was just two kids who maybe had beef that got out of control in the locker room or you know or the in in the hallway and people talked it up okay by comparison i had this buddy in school um we called him hawkeye uh he knows who he is but who would see a fight start to break out in the hallway i went to a huge public school fights all the time uh i lived in fear of the hallway i was a nerd you know i was an easy target i had to make in the back program yeah i had to make friends with protectors, but like going to jail, you know, you got to like find the big guy to be your ally.

1:10:51But, but he would see a fight start to break out and he would immediately go on and break it up and be like, let's settle this after school. He would find a yard, like a kid who lived near a school, say, let's do the fight in this yard. Okay. He would bring a video camera, charge admission to the backyard, give a cut to the kids who are fighting. I mean, he would make so much. I know he would make so much money doing this. I was like, I kind of admired his entrepreneurship. And it was, I mean, look in school, uh, I sold blow pops. Uh, so did Hawk actually. I think he pioneered it, but, um, you know, I, I didn't deal drugs.

1:11:31I dealt sugar, uh, and it was totally against the rules, but I had a secret pouch in my backpack. Um, they were a quarter, five for a dollar sour apples cost a dollar cause they were rarer. They had a different font on the label. Um, nobody understood that we would buy those bullet pops for seven and a half cents wholesale but you could buy a box of sour apple so there was way more supply of sour apple in the market than anyone thought they thought they were getting the one yeah uh i also ran a card room in school i ran a literal like we played a game called bourree uh that i'm pretty sure no one listening has ever heard of it's mostly played on um in nba locker rooms and on flights right now it's a game that originated i think in louisiana um any any i've like any pro ball player has played bouré it's a progressive pot game the stakes are really high um and we ran i ran a spades room too that endeared me at president obama uh he throws spades um and so but we but i had a teacher mr main since passed away but um he paid him a cut right i gave him a piece of the vague man piece of the rake uh and so i ran a tab i i loan sharked i you know like this was i did shit like this all the time um and i would get busted and there'd be some consequences but it'd be like enough to shut it down for a week or two whatever all of this is like table stakes i get it obviously like people aren't taking enough risk you're also the guy who wrote a 25 000 credit card check into photo bucket yeah and oh like and but you see the relatedness of this okay like but by the time i wrote a 25 000 check to photo bucket by the way, a few years before that I had lost millions of dollars by basically trading on a crazy margin online.

1:13:22You were down$4 million, you had to work yourself off for a job that came out of Google not that rich because you had worked yourself out of$4 million of debt and then somehow also had enough conviction. You are using risk as your ally. There's a broad-based fear of risk that culture has today, obviously. And then there is like I don't know how, how you have the balls to, and part of it again, I think is that you're taking less risk than maybe it looks like from the outside looking in. I mean, you talked a little bit about playing rig games. So look, I, I was fascinated as a kid with, look, I started going to university for math in sixth grade.

1:13:59I would sit with college students at night. And, um, and so I was a math kid. I could calculate pot odds in my head. I could do expected value calculations and I knew enough I I loved books on casino science I actually just had one show up on my um desk I haven't read it yet but like just just before I was leaving to come to New York I have a new one on casino designed for addiction oh addiction by design uh is that it yeah yeah yeah my friend Blake Robbins yeah okay okay okay thanks I haven't read it yet I'm stoked but but I knew like there's a reason Vegas exists there's just no winning bet in Vegas.

1:14:37So I was always smart enough to not gamble, but I was fascinated by gambling, fascinated by the narrative, fascinating by lotteries, how everyone can attach themselves to the outcome of the lottery and that narrative. And how would you spend that money? A dollar and a dream, you know, but knowing it's a, it's a losing. Um, and so, so I only play rigged games and venture to me, venture investing is rigged. I am a horrible public markets investor. like i get invited on cnbc i don't i haven't done it in years but i'm like i i first of all like i would talk about a stock and then i'd look and i was like it didn't move either direction at all volume didn't change price didn't change uh i'm like so this sucks um but also i'm not a good picker of public stocks and i can't affect the outcome in venture like i look people have accused me of being self-promotional i'm like if i don't promote myself who's going to so but i also like I hope I've earned the right to take credit for things I'm good at and acknowledge the things I'm not good at but I'm good at increasing the likelihood of success of a company that's why people bring us our companies that's why the 214x we put up on our first fund and the 17x on fund two and every other everything we you know the six plus billion dollars of return to investors on just secondaries alone like i i it is not maybe lucky but it's not an accident i know how i've caused that and people like you might be lucky and i was like it's weird how i keep getting lucky huh like and you know like maybe 13 or 15 times i've been lucky weird right like it would be odds in the quintillions but by the way you said you're not good at publics i think it's also worth noting crazy lowercase one fund obviously people know you as this legendary angel seed guy.

1:16:20You made a lot of your money, as far as I understand, by owning most of like more Twitter than anybody when it went public. You clearly are amazing at backing up the truck when a thing is already working too. And that maybe is the underrated part. But that's because the odds have shifted, right? So my first check into Twitter was 25K. Yep. Money I didn't have. I used to show up at the office because I needed that money back someday. Jack always hated me hates me to this day but just I would just somebody badge me in and I was a self-appointed business guy because I'm like this thing needs to make some money and you were working to make you were actually improving it's all I I kind of did the first 30 million dollars later on you weren't doing much to help Twitter and yet you still saw what nobody else saw which is like there's an up and by the way a lot I think a lot of early stage investors believe in their companies but they're like I'm an early stage investor I have my whatever multiple and you're like no I'm going to go rally up risvy and and own the majority of this thing yeah and i mean suhail risvy was an incredible partner on that it unlocked a lot of capital um for me but but yeah i look i knew at that point it was mispriced people were still asking how's twitter ever going to make money i'm like are you fucking serious and i ended up having this personal mantra like i'm no longer here to convince them i'm here to take their stock and so i just went and rolled it up from people who didn't believe and uh yeah by the time of the IPO I think we owned like 16 % of the company and so like 15.8 I think was the number um and so I I do the same now like I just explained how the the expected value calculation of fusion had changed from the way the market prices it so now we're into fusion for 10 figures and when you have conviction you are smashing the throttle that it maybe is the difference yeah and i also know i can make fusion more likely to happen yeah and so and so i but that's it that's that's across all of these things and so when you talk about like having the stones to take risk first of all i think i think sometimes risk is mispriced and a lot of that is maybe rooted in narrative rooted in fear rooted in imposter syndrome

1:18:30and underpricing the ability to actually impact the outcome. But I also believe, I think we were working together when somebody asked, so what do all your most successful founders have in common? And I was trying to find a thread. And it wasn't how they grew up. I mean, I could say there's no doubt that kids... immigrant kids just are just like the, the things they overcome to get here and build stuff, their hustle, their desire, their focus is insurmountable. People who grew up with single parents have that same fire, that same adaptability and resilience. They've taken on responsibility in such an early age.

1:19:15Like it's, you can't deny that they're disproportionate representation within successful entrepreneurial roles or at these companies. But I kept looking, I'm like, are they scientists? Are they computer scientists? You know, did they all sell blow pops when they were kids? You know, did they have a hustle? A lot of them did, but not all of them. But the single thing I found among every one of our most successful founders is not only did they not prepare for the downside case, it just wasn't one of the options in the math. It just wasn't, zero was never a consideration or a possibility. Success is inevitable.

1:19:56Yeah. And so, I mean, you know this one, when I first sat with Kevin and Mikey, you were building Instagram. I was like throwing out a product idea and they're like, that's a great feature for when we get to 10 million users. I'm like, okay, you guys, we're meeting right now in a coworking space. You're two of you. We are in the dark shadows off stage of like Calacanis was running some pitch event. And I think by the way, Travis pitched on that same stage, that same night I spent time with Mikey and Kevin, if I remember it right. But I'm like, what's with this 10 million users thing? But Kevin wasn't trying to sell me.

1:20:33He just knew it. He literally knew it. You can just tell. You can tell in body language. You can just tell. Yeah. You can just tell. I think actually a lot of people can't tell. What does that mean? Hopefully you get to a point in your career where you can tell if somebody's selling you. You can tell if somebody's hitting on you. You can tell if somebody's trying to steal from you. Hopefully you start to get that read. and if you can't emotional read yeah if you can't you should be spending way more time with people you can try to train this i mean i remember being on a train in college and reading mike carrow's book of poker tells i think that was the author and it was basically and then um who is the micro expression guy uh there was a guy who trained everyone fbi and ca and like the eye wrinkles and um how to read micro expression so you can train yourself a little bit but it really comes from just knowing people and spending time with all types of people and so Travis who we haven't talked in a long time and so we don't agree on a lot of things but he was my closest friend for a while and um we spent a lot of time together and you know we worked on uber for six months before us incorporated and he was there he was an advisor of the company early by the way little known fact about Travis there was a point where he was weighing whether to become CEO of Formspring or CEO of Uber.

1:21:53Same, literally, those were kind of equivalents. Formspring was a flyer. A lot of people listening probably don't even know what Formspring was, but this was like the, I mean, it was big. This was the anonymous like question asker deal. Oh my gosh. Yeah, so. I think the world worked. Yeah, the world lucked out on that one. I mean, TK is just a wildly talented person, but one of his things that maybe might have led to his imbalance, and I do think Travis was one of those people who was so wildly successful that there was nobody around him who could say no to him anymore. And that might have been one of the things that pushed him to some extreme places.

1:22:27But TK, I remember being in the meeting where maybe Ryan Graves had shown some analysis. Ryan was, you know, first employee at... Foursquare. Well, he was... I don't know if he was first employee at Foursquare, but he was first employee at Uber. Oh. And so... Wasn't he CEO briefly? Of Uber? Yeah. I mean, Ryan was CEO in a time when it was a relationship business. Ryan looks like the Marlboro man. He is just this incredibly handsome guy from a cigarette ad from the 50s, but he also has a very high EQ. and so ryan at a time when drivers were suspicious of us ryan could walk into a room full of very skeptical armenian limo drivers at risk of maybe being pummeled and dropped in the back alley and walk out arm in arm with these guys and so i mean that's still who he is he is just a guy you can build a relationship and count on and and i think he's got an even higher eq at the time but there was a point where we started to realize it was a math company it was the biggest yield equation in history more than the airline pricing you know like we had more units and more data and surge pricing it was just becoming a huge equation and ryan just didn't come from the world of cohort analysis and regressions and stuff travis that's his kink like that's like travis can do it in his head and travis could just try i just remember saying you know travis being like hey once you take 2.71 rides on uber you're a customer for life that's the actual number i remember from an early board meeting it stuck with me forever um but travis could just do that and we started to realize like this is a math company this is less about relationships you know in the end maybe we needed more ryan and more relationships and the company would have been in a different place but the reality was turning all the math dials is is what made it as big as it was right maybe not as friendly as it should have been or could have been or maybe not as accepted or embraced maybe it never could have been we're in this meeting once i remember being in the meeting where ryan graves tells us the data show that houston is the next city we should go to based on cabs and black market and or uh sorry black car market and cabs and um and travis is like no we're going to Paris and we're like what and he's like they hate us there like I'm gonna win Paris and he went to Paris and he stayed in a hostel um and won Paris now by the way a lot of the original ideation for Uber happened in Paris Travis and Garrett and Melody McCloskey was there in the early days and we were around it was at Le Web Louis Lemieux's old conference and it was hard to get a car there and there was a lot of late night jam sessions and so that's where those guys really polished the idea for what was going to become uber garrett had already had his own personal car that he let some of us use here in new york but um but he's like i'm going to paris and so normal people don't do that but he just knew we would get it to be clear they set ubers on fire they dropped rocks from overpasses through the windshields and yet like he did it i mean later think about travis going to china like i'm gonna go up against a state-sponsored ride sharing company and by the way everyone likes to characterize that as a loss he turned two billion dollars into 17 billion dollars i'll take that trade every time like i didn't know it was a genius move i mean he definitely got punched in the face over and over in the figurative face over and over again trying to do that he was stalked harassed like drivers there were i mean but can you imagine going into maybe the most authoritarian you know like market where they don't like when somebody out there is rebelling and i mean people get disappeared sometimes they're right yeah and and so but so when i take it to my own journey when i lost four million dollars in uh in 2000 and the market crash by the way i lost 16 million dollars i was 12 million to the up and four million in the hole.

1:26:39I'd never spent any of it. I had nothing to show for it, but I was just, I was trying to pile into my geometric gains, you know, for my first couple thousand dollar bets. It started with my student loans. I told the school that checks hadn't shown up. I went to a check cashing place because I didn't want the, I went to a check cashing place, paid a ridiculous vague to do that and then kited them into the market. But when I was$4 million in the hole, here's the, what I've now been told it was different was at no point did I consider that failure or I'm out or I have to move back home. I was just so fucking angry that this was going to slow things down.

1:27:20That's the difference, I think. And so that is an internal locus of control, maybe more than anything else, which is like you've talked about this a lot of like when you're up, it's all skill. When you're down, you're unlucky. But I think when people really get hit on risk too, like they probably internalize that is like or sorry that maybe i got super unlucky i got killed you there was never a point where you're like it was out of your control it was just like i'm gonna make it back yeah yeah that's and again because i could impact that i'm like all right i gotta just build a thing and work that much harder and like damn i hate that the score has been reset where did the confidence come from like are you do you have any imposter syndrome in any context absolutely it doesn't all the time um by the way if you don't do listen to neil bryden's podcast blocks that's one of my favorite neil neil is in like a really cool person um but neil kind of pivoted stand-up comedy into that realm of vulnerability he wasn't the only one but he's had maybe three very successful Netflix specials in which his comedy is rooted in, in just bearing his soul, talking about depression, talking about struggles.

1:28:34I mean, his most recent Netflix special was incredible because he's like, for those of you who know me from three mics and from blocks, um, you're going to be a little upset because I'm happy now. And, and so, but, but one of the things he talked about in this special blocks was all the things that have gotten all his own things that have gotten in the way that had become obstacles he's either had to overcome or still weigh him down and he actually took it there was so much emotional response to it not just among audiences but among peers that he made it into a podcast where he brings on performers and creatives and they talk about their blocks well this is a guy who is so deeply respected and the nature of those conversations are so raw.

1:29:19He got Jerry Seinfeld to admit to imposter syndrome. Still. Jerry's still struggling with the idea, I'm not a standup. Come on, who can do that? Neil is uniquely good at this. And it requires an incredible amount of courage to talk about the things that banged you up along the way. I think we had a culture that really shunned and stigmatized those things. maybe we're opening up more about it maybe like therapy and trauma culture has been a little overplayed among some people but he gets people to talk about the real real and um and so but i just say that as like yeah i have imposter syndrome look i until a couple years ago we didn't even have an office we launched an office because we realized our young people weren't learning from our more experienced people and that sucked because a lot of learning happens in collisions in the audience or in the office or overhearing a call or being pulled in to take some notes or something like that um or at lunch you know and it just doesn't happen over zoom like i'm a i work from the middle of nowhere and there are definitely advantages to that like being in nature being outside of the bubble talking to real people all the time i actually feel more in touch with real politics than almost anyone i work with because i just am among real people like um like our you know one of our daughter's best friend's dad drives a truck like an amazon truck you know um or they coach sports or they you know like like they just or bartend or it's just real you know work in the hospital like middle class folk and and so being out of the bubble is like psychologically refreshing and perspective and from a relationship standpoint raising kids standpoint it's a free range town that we live in there's 150 bikes out in front of the middle school with no locks on them and so the kids can just roam without without phones by the way they just go and fingers crossed they come back they usually do um i think they have 100 track record of making it back home at this point there's three of them so the odds you know like but for me um not having an office where where do you remember when shark tank tried to film the opening reel of me and they're like well we got to go somewhere it says lowercase on the wall we don't have that place we borrowed a portfolio company's office and put a logo up on a projector and then pretended to have a fake board meeting were you in that clip i wasn't in it but okay yeah um and they're like well we'll come by your mansion i'm like i have a 2 000 square foot house it's not gonna impress anybody and they're like okay what about your boat like for laurie they rented a boat to make her look rich they they just sailed around like newport harbor or something like that um but but i was like i don't and they're like how is america gonna know you're rich and it was just it was really important for them that we look rich yeah but yeah because i don't look the same as the other guys because we never had a big office because we never had a big team and because i was never i didn't go to school for finance wasn't versed in finance and i was never really concerned with our irr i still can't tell you what it is or what it was i don't know i know our multiples because that's like how you think about cards etc how much money i put in how much money i get back or sports gambling like how much um by the way when i get to new york i can always use draft kings again it's great i can i can lay action on my bills uh i can yeah i bet a little bit of hockey it's horrible sports betting shouldn't be a thing it's just it's a horrible but I love it.

1:32:48But like, I always felt like I wasn't a venture investor. Even making the Midas list, I'm like, what am I doing here? You just listed off a bunch of superficial stuff. I get it. But also like, clearly none of this imposter syndrome is getting in the way of like, smashing the throttle down. Well, because I'm not a venture investor. I am a builder and a helper. And you have confidence in that. Yeah. Yeah. I'll tell you, and I'll tell you one of the things that I think I struggled with for a long time and now I have enough data to show is the tyranny of lack of relevant experience. The most successful people I work with have no domain expertise in investing.

1:33:37And that's me. When one of my mentors, Hans Swildens, convinced me to launch a venture fund, I was like, I've never managed anyone's money. I'm not even good at managing my own money. like uh i've had a collection agency after me at one point just because i forgot to pay the bill you know and um i also have had him after me when i couldn't pay the bill but uh but i was like how would i manage anyone else's money and he's like no no that's the easy part we'll do that for you i i used industry ventures back office for the first couple years of lowercase um he's like the hard part is picking the companies and making them better actually i think he might have said picking the companies and i added and making them better you've always been you one of the things i I remember way back when one of the, like people asked me how to learn from you and there's two parts of it.

1:34:23One is obviously you don't want to bet on the things that need you. You want to bet on the things that are going to work with or without you, but you would always accompany that with like, yeah, where is the deck stacked? And I can have an impact. Well, the greatest look at, at heart, each of us wants to be helpful. Yeah. You know, one of our daughters, Cece, started volunteering recently in school, tutoring other kids. She's like an academic superstar. And our kids are actually homeschooled for academics and go to school for orchestra, phys ed, and lunch and to play on sports teams. And so it's the perfect balance.

1:35:01Montana's amazing that they can do that. Yeah. You know, I found that the, and they were the ones who requested to homeschool. They just, academics for them were just amazing. they weren't as compelling and they were losing their curiosity and their thirst for learning and so that's fed in the way they get taught with these zoom tutors who are incredible and really help pace them and push them and challenge them but they also are regular kids you know um ride their bikes wearing hoodies goofing off uh getting a little trouble mixing it up doing dumb shit like i hope they would um i mean by the way like have you looked at the data like kids don't drink they don't hook up and they don't want their fucking driver's licenses you know and that's translating to the workplace now for sure as we talked about so i've watched her light up as a consequence of being helpful it's a new thing she unlocked she's a helpful kid around the house helpful kid to friends but being formally helpful to another person and unlocking what she's doing by tutoring kids who are english language learners and um and helping them catch up academically in their mainstream classes.

1:36:08And frankly, when I first started in venture, the trap was people would come pitch me and I'm like, oh yeah, I can make this better, but it wasn't already great. And so I, my first four or five deals were shitty where they were like, there's a me shaped hole here. Yeah. And, and, and that comes from imposter syndrome. I left Google, I left a hundred million dollars on the table when I left Google, it was financially a dumb decision and there were definitely days where i'm like what was i thinking um and so it wasn't 100 at the time it grew to be 100 but i bet you it was 20 yeah um and so it was stupid uh and it took many years before that was the right trade but when i first started showing up when i first started showing up in like you know y combinator or meeting with founders i thought at first i was gonna have to like fake it till i made it but instead i was immediately helpful.

1:37:03That was a great feeling, but I also had to build a feature of like when you work for a boss at a company and they assign you something to do, you're working for Eric Schmidt and he's like, Hey, I need you to do this. You can't be like, no, thanks. What else you got? Whereas when you start playing poker, you realize that most hands get folded, you know, or maybe you just check. And then once it starts getting raised, it's just folded. If they actually showed the entire poker game on TV, it would take nine hours and it would be boring as fuck. Right. Right. So they only show the super compelling parts and that makes people go to Vegas and do dumb shit.

1:37:35Um, they're like, oh yeah, I'm going to play the two seven and see how this goes. And so, but, but I started doing all like each thing that was pitched to me because I'm like, yeah, I can make this better. I can make it better. And it was filling a hole of like, can I be an investor? Yeah, I can make all these things better. So I had to learn to build a filter of like what I do for a living is say, no, it's hard to be an optimist and say no all day. And then from that, I find things that are amazing and that hopefully I can make better. So what I'm confident about is my ability to make things better.

1:38:06And that's something we really work with our team on is you don't have to have gone to business school. Like we have some people who have, and we have maybe one of the most brilliant analysts I've ever encountered in any industry, Kaii, AB4. We call her Kaii GPT. She's special. um but but at the same time we i think really successful investors don't have that our co-founder clay his resume betrays nothing that he would be an investor ever i mean he worked he worked incredibly impressive person yeah let's be clear when i was reference checking him you know the pod save america guys got back to me within the hour like absolutely yes and then um a person close to the president said um i picked up him like hey man what's up and he's like hold for the president and uh president was like clay hire him you'll thank me later and they handed it back to the guy and i'm like well we're done with the reference check in clay um and so seriously worked in the way yes yeah he he was a chief of staff too we we overlapped for like one month two months very tail end of my oh at lowercase yeah got to pass him clay uh we didn't hire clay to be an investor.

1:39:13Yeah. It was all the stuff. Once you were gone, we had to write an update to our, to our investors, to our LPs. We had a hundred companies and some of them were companies I'd never met because you did the deals. I didn't know any of these guys. So I said to Clay, like, Hey, I got to write about this stuff. And some of these are like young people, things that I don't understand. And I've never met these guys. And like, so can you go check in with them so I can fulfill my duty to our investors. Like here's what the update is. And he had 25 hours in his day at time, no kids yet. He's got four now, four under six, I think.

1:39:50Um, so he, he fanned out and started talking to these entrepreneurs and two things happened. One is they started calling us like, Clay's amazing. Can he be on our board? I was like, that wasn't even his job. He was basically supposed to be taking notes, but, um, he was not hired as an investor. He was supposed to help us with like politics and philanthropy. But two was, I think one of the quickest ways to learn this business was to get thrown into a portfolio that already had some age and some dents on it. So yeah, it's cool to get exposed to Uber and Stripe, but it's, I think, even more helpful to get exposed to shit that's been going sideways.

1:40:24You know, or that, that is one of the wrong directions. Everything at the very beginning seemed, it's all possibilities. It's all dotted line. Oh, dude, it's so easy in the beginning. Like I see this in our team now, like you can't lose. Yes. Most of the people we hire right now have never lost. Like they. Right. In life. Yeah. They've they all ace their SATs. They all were front row kids in college. You know, by the way, I actually think we hire fewer of these people than we used to. But like if you're going to have a science heavy team, these are the best scientists and they've all gone to grad school and they all like just never failed.

1:40:59But our business is one of failure. If you're not failing, you're not trying hard enough and you're not taking enough risk. And so you have to digest that failure. And it's funny, they struggle with it or they do the safe thing. And we have to teach that out of our teams often. Right. And so I mean, I guess it's sort of like teaching risk. Like how do you actually teach that? You didn't have to do a lot of that in lowercase era. Yeah. Got a big team now. Okay. So here's one thing I do about risk. I make sure that no one is individually accountable for our losses. I remember one of our early employees who I, who I dearly love, and we wouldn't have been able to build this without him.

1:41:41Listen to a podcast about Bessemer where it's eat what you kill, where everyone's compensated on their specific deals. And he came to us and was like, I want to do this here. And I was like, I don't think you do. Like, I appreciate challenging the model because everything we do is like an evolution of something that we're reacting to that we've seen somewhere else but i was like let me tell you what it was like to work in a law firm i was at fenwick and west which is awesome it was it was recognized as the seventh best place to work in america a law firm what like i mean i don't know what kind of scam they were running but i was like i filled out that survey people but anyway it was the seventh best place to work in america i was a first-year associate i needed help on something and i went two doors down to a fourth-year associate who is smarter shit very successful and i said hey man can you uh i was like hey hey sayer can you help me on this thing?

1:42:29And he's like, can I bill on it? And I was like, no, I just need. And he's like, then get out of my office and close the door. I was like, wait, we work at the same business, right? But just the incentives, it's not, I didn't take it. I mean, I probably took it personally, but I don't blame him. The incentives were such that he had to rack up hours. Every hour he was spending on my thing was an hour. He wasn't with his SO. He wasn't with, I don't think he had kids yet, but like he wasn't working out or having fun. So why would he fucking do it yeah like it's not a charity it was a for-profit enterprise i hated that feeling google was constructed the other way when i first got there i shared an office with ors wholesale their very first engineer one of the most brilliant minds of all time and a wildly successful person and google wouldn't be google without ors by the way there was a time when i mean he owned a real part of the company and was worth a lot of money and somebody showed me a picture of one of the first um t you know tgif's like friday gatherings all the employees when there was like seven people there and it was wearing the same shoes that he was wearing post ipo um it was it was amazing but i but here's a fun thing there was an alias at google that i subscribed to i was one of the lawyers there initially and it was called contracts at google anyone in the company who had a contract would send it to that alias and then somebody on the legal team would be like all right i got this one and review the contract and send it back um and one of the ways i learned the business is by just watching every single contract come through there, every type of deal from the ads deals to the real estate deals.

1:43:53But one that went through was our company ski trip to then Squaw Valley up in Tahoe. And I looked at him like, it was like 800 bucks a person. And I just mentioned like, whoa, that's a lot of money. And yours is like, let me see that. I mean, he was sitting behind me, basically running the entire data center strategy because that was what I was working on, right? For him. And it's like, I mean, multi-billion dollar budget, like in charge of all this engineering. He's like, what the? He's like, what's the phone number on that? And I'm like, and he just picks up the phone and calls the hotel and is like, we're not going to be able to come unless this price comes down and like gets it down to like 400 bucks.

1:44:27And it's like, great. And I was just like, we were all, he was a Googler, right? One among many. And he's like, I can impact this. I'm going to do it right now. And so every single person who works at lower carbon has a piece of the upside and every single person shares in each deal. I really needed a culture of where everyone was incentivized to high five and where everyone, if you went to them for help, they had every reason to help you or to volunteer to help you. You know, one of the days I became, I'm using these air quotes, ironically, like powerful at Google was after my work partner at Google, you know, all notes in Google were available in public and you could subscribe to notes from a meeting.

1:45:10And my work partner wrote, Chris doesn't know what to do about this. you know and they got published to everyone and i read the notes later and we had a really big blowout fight because i was like you ruined me yeah like everyone's gonna know i don't know what to do about this and larry page subscribes to these notes and like all these other people i'm like i like the emperor has no clothes the next meeting larry page showed up a guy you couldn't get scheduled to show up showed up because he had an idea and so did maybe like nine other engineers all there to help me, even though they weren't formally assigned to me.

1:45:47You know, I mean, what's the scarcest resource? It's human capital and building that stuff. And suddenly I was like, whoa, like I got backed into accidentally, regrettably, angrily backed into more power and influence and the ability to get shit done. And so I wanted to recreate that environment. You can ask any single person for help and they want you to succeed. In parallel though, I wanted to make sure that every single investment decision we made like we have an investment committee it's it's clay crystal and i um and crystal and i are the largest lps in the fund so we really have hundreds of millions of dollars riding on everything we do and i'm a capitalist and i have no allergy to making money and i do think what we do is is not concessionary it's not philanthropy it is the biggest business opportunity it's the biggest transformation in the economy right now um people talk about ai and i'm like ai is our big customer so yeah i agree and ai accelerates every single one of our science companies it's it's circular like that but i i want to make sure that every person in the company has a voice in the decision making process that we we have a dialectic environment where we have robust argument i do think by the way because we have a diverse team i've never seen an ad ominum attack or anything really devolve into actual fights but we if it's not if the debate isn't fierce enough, I'll be angry and upset about it and let down.

1:47:12Because I think the role of your colleagues is to push them. But when we make a decision, even though there might be a lead on that deal or somebody who brought it to us or somebody who's responsible for that, we had a deal where we took a$27 million loss. And I know the person leading that deal took it personally. And I'm like, you can take it personally. I'm not going to tell you not to feel all the feelings about what that was, but that's not on your, like your tab. That's not on your account. We're not keeping score, right? You're, you're a helpful person across so many other things and you wouldn't be here if we didn't think that.

1:47:47And so it's a bummer. We took the L on that, but that person wasn't capable of making those decisions unilaterally. That was a, that was ultimately like we signed the check, but that was a group decision. Right. And I won't let anything get hung up in committee and it doesn't have to nobody there aren't a lot of votes like it's not a democracy and we don't have a system where like someone gets a budget to like override everything else bullshit like we we are the decision makers been doing this a long time and i feel good but they get burned too hard too they're probably not going to take any risks next time which is absolutely and so i i really deeply i mean look so much what we do another thing we do is i have a rule if you get on invited on podcast go do it get your reps in and you know google that's why me up um and you know like that blog you're talking about the excerpt you wrote got me emotional about a particular event in my life but at the same time i'm thinking about how you know elliot schrag just hated that i was a voice out there and he would assign megan quinn who is now a dear friend and incredible incredible executive and entrepreneur in her own right to like mind me and to tell me to stop talking to people and um and every now and then i would say something like a very pivotal moment in my career.

1:49:00I was in Oxford being interviewed. I was on a panel and there was a, uh, someone from the press. I don't even remember which newspaper in the audience. And they said, um, Hey, how come I can't download Google maps onto my phone? Like, and I said, well, that's because your carrier has inserted themselves in between you and the thing you want. I think that has dangerous implications for the future of the web and mobile. By the time I woke up the next morning, that was all over every newspaper. Google versus the carriers. And to be clear, I was not a senior executive, but when you say something like that, it's senior executive Chris Sackett.

1:49:43I'm like, I'm not one. I know who all the senior executives are. I am not one of them. And so when you say the right thing, it's a true, like anonymous Googler. but and so senior executive Chris Saka has declared war on the carriers I am summoned back to headquarters where my boss lets me know this guy David Drummond lets me know like yeah so you should probably look look for another role and I'm like like in the company like maybe I work for Jonathan Rosenberg and product or something and he's like oh no no not not at Google and so and so he was like marching me to uh to the executive management group meeting where all the honchos were right and uh one particular guy was responsible for mobile who i've since made up with so i'm not gonna call him out but uh he's become very successful in his own right but he's like i need a sacrificial lamb i need to throw meat to the carriers to say we killed this guy and this is not how we feel right and so they were basically it was a foregone conclusion i was dead and they were going to talk about how to message it in front of me right like what what do we say at his anti-eulogy yeah and larry page was on his blackberry he didn't even look up and make eye contact and he said but what did chris say that wasn't true and you know there were i I mean, it was already decided I was gone.

1:51:12And he's like, I'm serious. Tell me the thing that Chris said that wasn't true. And it was silence for a while. And he's like, they are inserting themselves between us and our users. We've never stood for that. Everything we do is to keep Internet Explorer from resetting your search default so we don't have a direct relationship with our users there. Like everything we do with Firefox, et cetera, so that users have a choice and can always come to us. and we try to win on the merits of our product. Like that's everything we do. He's like, so tell me what's wrong with what he said. Like it may have pissed people off because it's true.

1:51:48I left that meeting with a multi-billion dollar budget to go scare the shit out of the carriers. And so, by the way, that was a huge hand of poker. We went to the Spectrum auctions. A guy who worked for us, Rick Witt, came up with this idea. What if we attached? What if we convince the FCC to attach net neutrality rules to wireless spectrum? And so it was genius. This jujitsu movie did. And so we did that. And then the carriers announced, well, it's easy for Google to say because they're not going to bid on it. And so you've just impaired the value of it. So we decided, you know what we'll do?

1:52:27We will say, you guys valued it at like$4 billion. We promise we'll bid$4.6 billion for it. and look, we had the money, but that's not what Eric wanted to spend that money on. He actually knew we were heading, it was 2007, but he knew we were heading into a recession. He just knew already. And so he's like, I would prefer not to put$4.6 billion in this. We had a plan for what to do. And part of my job was to make sure Verizon knew we were serious enough. So I was out doing tower deals. And I mean, I and my team were doing tower deals, getting trucks ready to roll. we had android in parallel by the way android is pissed off at me because they had a clause like andy rubin is going to make like another 150 million dollars or whatever if he signed up two carriers and now the carriers are like why the fuck would we work with google yeah i hate you but we needed to build this net neutrality there's no other company in the world that would let somebody roll five billion dollar dice like that and we want verizon had to eat the spectrum they couldn't afford to let us buy this incredibly valuable 700 megahertz it penetrates concrete etc but but they bought it and so your phone is essentially net neutral like and that was not the case back then but what i learned and and do you remember marissa mayer yeah she she's we were usually work rivals um but uh but we've become friends since and i really like her but she just said oh yeah my loneliest days at google are when one line is taken what i out of context of what I said and used it in a hit piece.

1:53:58And then I walk around and it's like, it's a ghost walking through the halls. Like I am vilified, ignored, despite she was a senior executive and had earned that, right? She was a total badass. And so one of the things we've done when codified for our team is take any invitation you have to be on a stage, a podcast, practice your storytelling, tell the story. And if you sincerely believe the words that come out of your mouth, they're not hateful or not toxic, but if you sincerely believe the things you say, we will forever have your back. Like now you're friends with Ryan Orbach. That dude's got hot takes.

1:54:33I mean, just sizzling hot takes, but he can just go out in the world knowing we got him, right? And so he can act without fear. Pretty cool. And so we just constantly, everything we do is designed like this. Like the other thing Crystal and I encountered all the time was ageism. And so, you know, one of our, I talked about Kai, I think she's 29. Like, I don't know. I haven't looked in the HR files or whatever, but i like she's just an incredible outperformer she's accelerated her career by using an army of ais but also to simulate situations for herself to like build board experience etc like role playing role playing with like ais and stuff like that yeah she's like all right i haven't been in a lot of board meetings but i can just build virtual board meetings and get the reps in and so but like i i you know i i think my own bias is like all right we need to add some 40 somethings to this company with a little bit of deal experience it's probably like hr yeah it's probably hr illegal to say that but like we need some more experienced people here and then it turned out the call was coming from inside the you know the house like it was like kai had this particular skill set we needed that when i talked about the tyranny of relevant experience one of our best investors right now is lauren forbes o 'connor who is a formerly chief sustainability officer for Los Angeles.

1:55:45She'd been in government and policy a lot of her life and zero, zero indication that she could be an investor on a resume. But God damn, does she make companies more, more valuable as a result. And so she came on as like an operating partner and very quickly became a partner partner. Crystal, my wife was wildly successful in the advertising world. Like won all the awards for her creative work, working at the coolest agencies and with the best partners. but she was the one who didn't go to art school like we met at the school of foreign service basically like you know precursor to cia right like and so but she found her way into that's a nice parallel life path for chris yeah no it's um she just ended up being you know she would stay all night literally sleep at work she would overhear something that needed to be done pick it up taught herself photography taught herself all the suite of tools you need like already because she grew up all over the world and loved art already had an eye for composition and and storytelling and because she was a third culture kid knew how to relate ideas to everyone so it was great at tags and humor she's also the only person i've ever known who can just i'd be like hey do you want to go to dinner she's like i need to write ads for an hour i'm like you can just sit down and be funny like she could just decide like i need to be funny for an hour creative sketch something out and then she'd be like all right dinner time i'd be like what and then that thing by the way six months later would be in a global campaign a funny one most of us need to sit for eight hours oh or it's like takes a week until like i finally am in the zone put it on do not disturb i'm feeling it you know the caffeine's right uh or most of the people we work with now the zin pack you know the i got my zin going i'm like dial bro you're not under this i'm like dial bro no um i haven't actually tried one i know because i won't be able to put it down but like Like, I think that lack of relevant experience might be the superpower.

1:57:39So we look for those people more and more now. I want to pull on that. We only have a few minutes left, so we'll zag across a bunch of ideas quickly. But one big one, you have walked away many times in your life. I see you as a particularly authentic person. And I think that's part of this. But you left the Google job. Nobody's supposed to leave that. The New York Times wrote about you or whatever. yeah i think they wrote something along the lines of why would this guy leave the greatest job greatest job in the world and i sat i literally sat at my mom and dad's kitchen table and cried was like what have i done it really was the greatest job in the world um you have the journal from when you were 20 and you wrote about how you're going to retire at 40 you walk away from lowercase like why why does anyone walk away from that you you have this minnesota speech you gave the commencement speech and you one one line in that is you talk about control deleting and this being a rare opportunity when you're 22 to like actually reset you become a beginner again nobody does that um in many ways it's almost like different chapters um maybe you're on the perpetual chapter now maybe not but but how do you what is what has caused that it's irrational it doesn't make any sense and yet you keep doing it because it's what you need to do yeah um remember that book the fourth turning where they say like the whole like history is in like these 20 year blocks.

1:59:00I've seen Van's, Van Neistat's videos. Van Neistat's video is fucking cool. All his videos are cool. But this one was really cool. The book report he did. What are they called? Seculum or something? I forget. Anyway, these 20 year blocks. I did an exercise where I wrote my life out and it fits in seven year blocks. Seven? Seven. Not by design. It just always has. Oh, looking back. Yeah. Wow. Retrospectively, it's always been seven. Wow. I literally, I think there was one that went eight. How far are we into this walk? 7 and so like the thesis started in 2017 and the execution started in 2018 and so i um i don't i didn't mean for there to be a regular pattern to it uh but i think there's a few things at play one is emerging curiosities for other things when i think i've kind of gotten a subject matter dialed you know it's funny i i got a chance to hang out with quest love the other night and quest love is i shared with him a story that he didn't remember at first but a gazillion years ago i'm standing with evan williams and tony shea the zappos guy who's no longer with us but we were in la and the the roots were playing and i was like you guys you know questlove randomly follows me on twitter like i didn't have a big following yet i don't know how he followed me but um he just did maybe it was like a mutual friend or something maybe it was janina gavankar or someone put us together but um i dm'd him while he was playing he his phone buzzed he reached down while still playing drums with one hand saw the message and wrote me back no way just and then put it back into his pocket and we were the giddiest school children ever that i remember like twitter talk about imposter syndrome we're like why would anyone ever care about this i hope i hope you know and so we lost our minds so i got to talk to him the other night and remind him of that story he's like oh shit i do remember that that was funny and um but i'd never spent time with him i've read everything he's written i think he's one of the most talented and provocative people ever his playlists are sick he's a crate diver i like to crate dive but that guy goes all the way um you know he teaches music i mean he's obviously a performer it's just he produces he's a film director just incredible dude so i felt like I was fanboying a little bit but we were at a discussion with a bunch of fancy unbelievable people and it was about climate and he came up to me and said um damn you remind me of the treasure of not being the smartest person in the room because often you know in music I just kind of know the most about like he's a historian of music and it wasn't it wasn't coming from a place of conceit at all he's just like i know how unfulfilling it is and he's like and so sitting here and listening to you talk about what you're up to and and um and posing provocative questions other people in the room who are in the space and challenging them and reclaiming the moderate middle like i i'm a climate investor who drives an f-150 raptor and eats meat because steak is fucking delicious right i tried being a vegan there's a hole in my life as he said that my reaction was yeah this is why this discussion to me like tonight was fun but a little empty because i wasn't being challenged and so i missed that you know we we recently hired um i didn't ask for it to be a young person but we hired a very young person i what i said was i so i read three to four hours a day i i track my time at 15 minute increments to just see where it goes to know who's wasting it, really, or how I'm wasting it.

2:02:50But it's three to four hours a day I read, every day. I'm obsessed with AI. Like, beyond obsessed. I am worried about the existential threat. I was in a room recently, Chatham House Rules. I was applied, so I can't specifically mention. But I was in a room with... The powers that be. Yes, 40 of them. You would know the name of every single person there. like your audience would know the name of every single person there and um it's very cool it's an annual meeting and it's the only reason i it's the only time i go to san francisco anymore i go once a year for this thing i'm the least influential person in the room absolutely and maybe the poorest uh and so but and then from across the political spectrum sometimes i'm shocked by the new fascism that i think has arisen and the new um lack of concern for humans for fellow humans and stuff that i think is now um the overton window has shifted on like what our responsibility is to other people so that's painful for me i usually come home from this meeting a little depressed um a lot of depressed actually uh but this particular year the moderator said all right everyone stand up we're gonna do this thing where i'm gonna pose a question and over this side is strongly disagree and over this side is strongly agree and so um by the way i'll just i i should give credit this this is hosted by um uh 50 years fund uh i forget what they call the event but um uh seth bannon and and uh this is this event is is kind of spearheaded by um d scott phoenix who is just a fascinating mind who by the way i worked with when he had a company worth a couple million dollars and now is one of the godfathers of ai right he built vicarious and sold it and i've the reason it's such a high-powered event is everyone respects him so much he can get them all to show up you know um and it's the first time i've usually met a lot of these guys that i've been reading about and so it's wild for me anyway he asks okay do you believe there is a greater than 10 chance that within five years ai has killed more than 50 % of humanity.

2:05:03All I'm going to say is every single person who works on AI full-time stood in the strongly agree column. Like, this was beyond even the job losses, even the unavoidable disruption to the economy. To the, I mean, you talk about like, yeah, I'm great at calculating odds, but I have no fucking idea what education looks like for our kids anymore or what skills I need them to be. I watch them write a paper and struggle with their bibliography and all that. And I'm like, that's a rite of passage. I love it when they procrastinate and waited too long and they're up too late and they're feeling the stress.

2:05:39I'm like, sit in that shit. Like that is some middle school shit you need to grind through. And yet, is that, am I teaching them how to shoe a horse maybe? Like, is that an outmoded skill? I mean, I stood there and I typed in a chat GPT or a clot or something and showed crystal. And I was like, and then I was like, write it like an eighth grader. you know and it was just like boom and i'm like but on the other hand by the way maybe teaching kids how to shoe horses is actually the more relevant skill to get back to but but i've never been more uncertain about anything in my life so i have this hole in my learning because i read about these companies that have scaled and i'm like wait how have i not heard about this ai company as obsessive as i am so we hired this i was like i need an ai person to work here and i don't know i mean ai is the biggest customer for what we do but i was like i don't know if we'll ever do a deal in pure play ai but we have this person this incredible line is her name i think she's 21 i just found out i had no idea it wasn't specced for like i need a you know she's definitely gen z i have to translate some of her slack posts sometime it's amazing we've had huge debates about what certain emojis mean in slack like i i mean you don't understand how much time i'm like i don't i want to adapt but i am old so you're becoming a minority one thing one thing i would love your audience to react to is what the um thumbs up emoji means when used in slack so i'm i'm like informed enough to understand that thumbs up on an i message uh to another peer is like whatever bro it's kind of dismissive right do i have that right like yeah yeah i i'm i'm 31 so i still use it normally but i think if you're 25 it's what do you how do you use it does thumbs up mean kind of like dismissive right okay so i had to learn a tap back or just a thumbs up thumbs up emoji yeah that's dismissive yeah okay okay um so i had to learn that but we had a big debate about what does thumbs up mean in slack because i started seeing it and i'm like wait are these people like just kind of like banging on each other a little bit and no i i was i was it was clarified to me that thumbs up in slack means like yeah i agree heck okay but the one that's really wild is you know that to the big eyes that's just the eyes yes the look yeah looking yeah and they're kind of looking at one side i have used that to be like hey i read your post right and i acknowledge it and it's not really a post it's informative it's not really a post that i have to disagree with or celebrate you know like a high five or whatever like it's just i agree with it by the way i high five things other people sparkle them and shit i'm like i'm clearly all right just know that my high five means high five uh so my prayer hands mean thank you or whatever but you know i'll do some fire i'll do like the up the stock going up one right i have a very limited repertoire oh um but but i got this lecture in like i was like this is how i use it and there's a massive debate that erupted around like no no no to some people that means like whatever you just read is suspicious and bullshit other people i i was with one of our founders last night julia from um vaulted who's just fucking badass and she said no no when i use it and they use teams at their at their shop but she's like when i use it it means i know what i just said is a hot take but i stand by it okay and so i was like okay that's a whole thing um but but like having that energy of like a complete immersive ai expert who is among this the the people the earliest founders and fully and it also speaks this language of youth it's i know that makes me sound even older to say youth but like to just speak that language has been like the biggest fucking boost for me i've loved having that energy and that and and that's where my curiosity is so so look climate is the least creative thing i've ever done like you're with me for a much more creative phase because we're building stuff where we had to we had to like we had to look into the crystal ball about like what are these people um what will they care about will they use it why will they use it we were creating stuff that was first impression almost everything we do in climate is a substitute good for something that's already made so we're building clean steel we know who buys steel who wants steel why they buy it how they price it and we just need to make better steel that they'll buy out of greed not shame and guilt do that across the board like nuclear fusion's a little different i think no it's different but i like i can't be like you guys what if we had this crazy i had this idea for this crazy physics formula you know like there's none of that shit at least and it's not coming out of me those guys might be really creative long time horizons too yeah and so um it's way faster now but so they might be doing that but i'm not and so i i started to feel like a little empty in that and so um crystal and i actually last year um came over the idea for a comedy feature film went to a great friend of ours steve brill to write it he's a really accomplished um director and writer and filmmaker and um you've seen so much of his shit you didn't even know it um but but and he uh we loved being in that process so he was the writer but we were giving notes and like and and and chopping it up and coming up with jokes and hijinks and there's a household name who's he gave us notes on the third act then the female lead who's like i can't even believe that she wants to do it uh gave us third act notes and it took us a while i mean braille rewrote that and stuff with some of our reactions to it and stuff so we'll he's the writer we're the story by cool but that felt great and i hope it gets made just to like get it out there yeah I also do a lot of physical art at home.

2:11:21And then I consider raising kids like a creative outlet. But I will end up doing more of that. I want to write. I have been writing. I do feel like ChadGBT is pretty good at it. And every time I kind of ask it for reminders, I actually, ChadGBT was pretty good at script writing. There was a time where we got notes from this famous star and I had an idea. And in real time, I wanted to give them back. They were in the meeting and I wanted to give them back to the people in the meeting before we lost attention and we had to set another meeting for a while. And so I quickly typed into Claude. It did not have the script.

2:11:56I just said, scene concept, he walks in, she's on her cell phone. This guy comes around the corner, almost catches her. He makes a lot of loud noises to cover for her. These are the names. Just a bunch of context. Write it. And it came up with enough funny dialogue to just immediately go, here's what I have in mind for the scene. Do you know what the challenge was after that? how to write that out like how to how did not have any eye content in there because it was pretty fucking good not great it wasn't yeah it wasn't brill level good it's gonna get harder it wasn't brill level good if it were up to me to write it i would have had a really hard time writing out he wildly eclipsed it because this is what he does yeah and so i i'll tell you what's demotivating about writing this book is like i could phone it in and it'd be pretty fucking good like i it's literally really fucking good and when you're me the internet has read a lot of what i've said and written right you can say do this in chris's voice we trained an internal bot on everything i've written and it's really good at being me like i could kind of step away and i think most of our investors wouldn't know that i didn't write that thing it knows my cadence of like fact fact fact fact punchline you know fact fact fact sigh and you know like analogy metaphor it just knows it a cadence and a verse that i didn't realize i had until i watched a machine replicate it i'm like wow i'm kind of predictable um but so i worry about that but i but i do think i've been trying to give the organization even more the lower carbon even more room to see how it operates without me more autonomy to make decisions without me clay is a singularly capable and powerful force in this business and um we'll have to check back on this in a few years we will i mean i i can't i am the largest investor and there's no way i'm stepping away from this one but look all those other times you talked about stepping away i started to realize either i didn't have a competitive advantage like with lowercase i realized i wasn't going to be the best again if we'd raise another fund and i also didn't care about the shit we were investing in like bless you and your e-gaming past but i was never gonna go to staples center and watch guys play League of Legends.

2:14:07I just didn't care. It's not a judgment on anybody else when I'm like, I didn't give a shit. And like these dating apps, I'm like, I don't even, first of all, if I install one of these, I'm going to get in trouble, but I just didn't fucking care. Yeah. Right? And so, and if you're going to do this job, you have to give a shit. Like, I, somebody had to remind me. I have to argue at any job. At this point, if there's any antidote to the AI thing, if there's any optimism, it is, you better find a thing you care about more than somebody else. And when you're, when you're starting a venture fund, nine nine six would be a holiday and so there is no i mean just yesterday somebody had to remind me that today's friday i had no idea which day of the week it was um and when somebody calls i mean i was on the phone late the other night with an entrepreneur who we backed in 2009 who was having board issues you know and like you're married to these companies they're they're 15 at least 15 year commitments yeah and so each time we raise a new fund i have to do that analysis from scratch.

2:15:04Do I really want to make this commitment? Is it fulfilling? Can I win? I don't want to do this for a few percentage points of return. I have to do it because I know we can change everything. And, um, and so I'm just constantly reevaluating that. And so, you know, in the case of walking away from lowercase, it was weird. It was, we were our most bankable. We had the most money being thrown at us in the early days. Nobody wants to invest. Everybody just started to figure it out. By the way, one of your past guests, cyan banister i had barely ever met her i'd seen her on tech crunch before i think we had once shaken hands i got her email address and i sprayed and prayed to every rich person i'd ever met she wrote us a 300 000 check it was the largest individual check uh to lowercase that worked out she's maybe the most successful angel investor ever i think so and so i don't think anyone knows who she is um or like as that like how impactful she is i genuinely think yeah and so um but and she's weird too like and and her story is like she would be traditionally unqualified that's kind of weird and like unrelevant you know irrelevant for this and i think that's why she's been so successful but um but yeah like i i think about this journey and um and and there was a time where I was just like, okay, everyone's throwing money at me.

2:16:26But really, truly for everyone, no one realizes the only person who really knows their scorecard is them. I could sit here and give you the most well-intentioned career advice ever. Jackson, like you are family to us. Okay, wait, I have to go to an aside really quick. You had the best, worst first day of work that anyone in history has ever had. I won't go into the details, but it was the fucking worst day ever. I mean, it was just one failure after another cascaded, cascaded, cascaded, legendary. I know you've never forgotten it, but the thing that Crystal and I talk about every time and just so you know, we don't share the details of how bad it was.

2:17:10It was fucking amazing. I mean, there should be, it should be a script because it was, it was just the worst first day of all time. Like, dude, seriously. uh but but you wrote the most accountable follow-up email in history i would put it up against anyone else's email after a fuck up first of all you acknowledged fuck ups i hadn't even noticed i was like oh my god i didn't even know that one went down yeah yeah yeah but i reread it this morning so you prepped for this podcast by i reread one thing um and it was that note you headlined it outlined it you bolded the subject matter titles you the narrative was really good it was chronological then it had like uh what i could do differently how i'll improve this and then like and overall like i know the impacts it had on you and the risks that had like and so it's poetry man nobody does that shit anymore and i i totally forgotten to bring it up but i i think it's it's why you always have a standing job offer with us it's why we consider you family it's why i don't really hang out on podcasts much anymore but i would i was flattered by the invitation here i do think you are one of the most self-aware constantly working on yourself and accountable people I've ever met.

2:18:32And you, and to do that at such a young age originally was just really special. Uh, I don't know if you're raised right, or you worked in the right settings or you had the right mentors, but like that was really, really different and special. And so, but you're the only person right now who knows what you actually want to do with your life and what you care about and how you weight those variables. And as someone who cares about you, I could, I could throw out ideas and I can be like, you got to do this thing, et cetera. And so when we announced we were quitting lowercase all these great people like why i mean you're good at it you did you know there's so much money and this and that but we're the only people who just knew like it the meaning wasn't there for us anymore you know and the aspen institute crown fellowship i'm in likes to say about pivoting from success to impact it wasn't really what we were looking for but we just saw this hole in climate where it had a bad rap people said it's worth money and you know souls go to die and stuff like that but we just saw there was this it was it was price wrong and so we knew we could go in there and shake shit up and have a massive impact but but it wasn't really and this might be a surprise to a lot of people i'm not a climate zealot like um you know my personal carbon footprint is inexcusable on the other hand the term carbon footprint was coined by ogilvy and mather at the behest of british petroleum to take the spotlight off of the industrial carbon economy and put all the guilt and shame on individual users, individual people.

2:19:59Make like, hey, it's up to you to take a shorter shower. And it's up to you to not eat the shit you want. That's why some people don't like you. Yeah, no, no. Oh, dude. Look, we would not have the lifestyle we enjoy today if it weren't for oil and gas, right? I was in a meeting the other night where we got to stop the oil and gas fraud, the mafia, and I'm like, how the fuck did you get here? Like, look at the room. Look at what we're eating. look at the furniture we're sitting on like we're just gonna quit oil tomorrow like my job is to give them a better cheaper faster easier safer alternative it turns out oil and gas tend to blow up from time to time but but like that's my job is to give you a choice that you choose out of pure self-interest in the meantime stop fucking making people feel bad like i there's nothing i hate more than the activists and we call them the soup throwers people go and fucking throw soup on a painting.

2:20:47I'm like, really? So that's how we're going to save the planet at scale. That's how we're going to transform the largest industries, building agriculture, industrial chemicals, energy, transportation. That's how we're going to do it by gluing our plan. We're going to glue ourselves to the floor of the U S open. That's how we're going to raise awareness and get people on our side. Like it doesn't fucking work. Like I honor the people in the trenches and you know, where a lot of our best people come from oil and fucking gas. Like if you want the best engineers And if you want the best workers, if you want to drill like Zanskar is like the most productive geothermal wells at the lowest cost ever, like some just incredibly clean, ubiquitous 24-7 power.

2:21:26Like those guys are all riggers who come over from like the oil pan, who come over from the panhandle of Texas, the patches, and they come over and drill these wells. It's the same fucking pipes, the same tools, the same trucks, the same gun racks, the same beer at the end of the day. it looks like a goddamn Chevy ad. Like, that's what's happening. That's what the clean economy actually looks like. Yeah, you really feel. And if you make these people feel bad, which is how Democrats have rooted their politics for years, is making people feel bad about their choices, how they live, despite their intentions, like it's an exclusionary purity test thing, then we are not going to get anything fucking done right now.

2:22:02And no, I'm not running for anything. Fuck that. But I have one last thing. We are sadly out of time, as much as I'm sure I could let you go forever. And I'm going to change gears slightly, but it feels very aligned with what you were saying. And I found something in your blog that really, again, I used the word authenticity earlier. It just really felt like you. And I think despite maybe sometimes the rants or the strong opinions, you are a pretty soulful dude. And I wanted to read it to you. Oh, my God. I'm going to end up crying. It's not something you wrote. It's something somebody you enjoy wrote.

2:22:36And it's called Manifesto of the Mad Farmer Liberation Front by Wendell Berry. Oh, okay. This is on your blog in 2009. So you have to bear with me. It's a little long, but I'm going to read it anyway. Love the quick profit, the annual raise, vacation with pay. Want more of everything ready-made. Be afraid to know your neighbors and to die. And you will have a window in your head. Not even your future will be a mystery anymore. Your mind will be punched in a card and shut away in a little drawer. When they want you to buy something, they will call you. When they want you to die for profit, they will let you know.

2:23:07So friends, every day do something that won't compute. Love the Lord, love the world, work for nothing. Take all that you have and be poor. Love someone who does not deserve it. Denounce the government and embrace the flag. Hope to live in that free republic for which it stands. Give your approval to all you cannot understand. Praise ignorance for what man has not encountered, he has not destroyed. Ask the questions that have no answers. Invest in the millennium. Plant sequoias. Say that your main crop is the forest that you did not plant, that you will not live to harvest. Say that the leaves are harvested when they have rotted into the mold.

2:23:41Call that prophet. Prophesy such returns. Put your faith in the two inches of humus that will build under the trees every 10 ,000 years. Listen to the carrion. Put your ear close and hear the faint chattering of the songs that are to come. Expect the end of the world. Laugh. Laughter is immeasurable. Be joyful, though you have considered all the facts. So long as women do not go cheap for power, please women more than men. Ask yourself, will this satisfy a woman satisfied to bear child? will this disturb the sleep of a woman near giving near to giving birth and finally go with your love to the fields lie down in the shade rest your head in her lap swear allegiance to what is nighest your thoughts as soon as the generals and the politicos can predict the motions of your mind lose it leave it as a sign to mark the false trail the way you didn't go be like the fox who makes more tracks than necessary some in the wrong direction practice resurrection i feel like um i forgot i forgot i quoted that um again that's one of those writers where like how how could i consider myself uh an organizer of words but um my reaction is like i feel like you just found another one of those letters i wrote to myself that became prophecy do you listen to Matthew McConaughey's book Green Lights or you gotta listen to it you can't read it it's like six hours of chilling with one of the most interesting storytellers of all time but and he's got the perfect accent perfect stories just amazing but in the end one of the reveals is a this isn't a spoiler but it's a letter he wrote to himself with his life goals in it when he had no business writing that letter and he'd kind of forgotten about it and then he rediscovered it and realized it'd come true one of them was an oscar when basically all he'd said on film was all right all right all right and um and so but you know you know that when i was 41 i found a letter i'd written not even a letter it was it was honestly i was i was going to school in ireland and i was i only went to this one class to basically try to get closer to this one girl and we did this little thing in the back of the class where we would write five questions for each other and pass the booklet to the other person to answer those questions pretending to pay attention and then answer them and she said what do you want to be when you grow up and i wrote this response i think i've written down or shared somewhere, but it was basically like, I don't know what it's called.

2:26:20I just know it's going to have a lot of high stakes, high risk, high reward, a lot of talking on the phone, a lot of negotiating. I'm going to do it halftime from the mountains, halftime from the beach. Whatever it is, I'm going to do the best there was at it. And I'm going to quit when I'm 40 and do something else I really want to do. Whatever it was, I don't think I ever even ended up with that girl at all but I ended up with the notebook and it was in my garage and Crystal and I were cleaning up my garage our garage and um you know when I was 41 and we found it and I was flipping through it and I came across that reading it with her and she's like my god you're you're late every single bit of it we lived in Truckee and had a house on the beach in LA like every single word of that and by the way one of the things I had in mind when I wrote It was the scene in Rain Man where Tom Cruise is trying to import Ferraris in this warehouse and he's just got multiple phones going and it's sparse.

2:27:19There's like a desk, you know, a couple of desks, two chairs. He's trying to balance these phone calls and deals are falling apart. I literally wanted that. Not Ferraris, but I was like, that's that to me is the kind of business that a not rich kid with no network could just do with the power of of ideas and thought and speaking. That's what I that was kind of what I had in mind. And I didn't know what that job was. I knew I didn't want to like bill hours or anything like that but when I look back at what I made happen I'd forgotten I'd written it I knew I wrote it for me I don't think I was writing it to impress anybody it was just too I don't think it was particularly impressive but you know when you read that I get a little emotional because I think like I'd forgotten about that for sure I'd forgotten about that but I think a lot of my journey has been trying to get my biggest goal for myself is hoping that my drift is back to is closer to real is back to the real me the me that hopefully I've been or that was covered in layers of either pretense or inauthenticity or striving or I was in college I didn't have I didn't talk about my politics because I thought I would offend half of my future potential employers at each stage i have found the opportunity to speak my mind be be more real dress the way i want to dress live the way i want to live you know bill clinton invites me to this meeting every year here basically it's a room full of suits world leaders and fortunately and he throws it to me to say the things that nobody else wants to say swear while doing it drop a cowboy phrase in there but just like just stir it up yeah and we've developed a fun friendship over the years because i just stir it up and you know i was up to be an ambassador if hillary got elected i was going to be an ambassador and i remember president obama being like that's not a good job for you being ambassador is not about saying what you actually feel he's like that that i'm kind of glad that didn't work out google story yeah he's like i'm kind of glad that didn't work out for you but but i do try to drift and there's rapids along the way and i gotta get a paddle out and push and but i do try to drift back towards real and real for me was i did grow up laying down in the field i i did grow up with artists and performers and writers and actors in our family i did grow up with my mom and dad who constantly were introducing the arts as well as science to me who were teaching us about love and collaboration and openness and about our responsibility to other people and about the real privilege of raising kids i mean the the thought and the heart that i can see in retrospect that my mom and dad put into raising and nurturing us while also not being pushovers and like having real real values communicating values but also boundaries and edges and consequences and responsibility and and hard work and um and accountability and just how i try and reflect that and what i do now i tried not working for a bit and that lasted like 60 days i i've tried stepping back and i suck at it the only the you know i get a real pleasure from hopefully helping raise the people who can do it better than i can lower carbon's getting there like getting to the place where but but sometimes the thing i think it's missing is the freedom i found to be able to say exactly what i want to say you know i've had to teach people don't be so nice you know don't be so cooperative and so don't be submissive like the world needs a little more alpha and you know the most expensive employees in an organization like that aren't the ones you pay the most they're the ones who drag the most on everybody else maybe they come in like eeyore from winning the poo just sad every day or they're toxic or they just can you reread this email for me before i send it i'm like just fucking send the goddamn note like what are they gonna say you know and um and so i there's an inflection point coming for me at some point soon um but but it's fun that you read that because it reminds me i that's kind of a scorecard i'd like to measure myself against a little bit i think i've done some of that you know i don't know if i i remember like there's a lot in there about women and birthing when chris and i first got pregnant she asked me to sit down and watch a pregnancy movie i grew up in a catholic town where the day they teach girls about periods they let the boys play connect for and they told the girls don't show the boys that pamphlet on the bus ride home it was like a secret that was the level of stigma around like female reproduction like just didn't grow up in a place talking about cycles or any of that and so when Chris when we got pregnant and Chris was like watch this movie I'm like wait really are you sure like I can have a couple drinks first like I really expected to be grossed out and it was this cool movie by Ricky Lake of all people um the old talk show you know like sensationalist talk show host who kind of took this honor as a personal issue and it was about it was about how women are built to do this how right now hundreds of thousands of women around the world are giving birth in conditions much less safe than that's happening in the United States, but how essentially embrace that woman as someone built to do this, not a patient.

2:33:09The United States treats women giving birth as patients. Put you in a hospital, don't trust your body, drug you up, put you in stirrups, which is the least natural way to deliver a baby. It keeps your tailbone from flexing out. It's built to flex out. And so a lot of women break their tailbones in birth or there's nowhere for the baby to go and the whole industry is tilted towards cesareans because that's where more money is and the cesareans are all done at like um 4 30 p.m and at like 9 30 p.m so 4 30 so the doctor can get home for dinner and 9 30 so they can get home and sleep that night i mean they all it's it's a fucking scam but but i just i didn't have in in mind that that was a path for me i probably it was one of those things i had the strongest rejection of like fuck that i'll be the guy in the lobby with the cigars not in the room doing it but you know three babies in it became kind of part of my identity how much i felt like the fatherhood journey starts way before that baby comes out but definitely while that baby's coming out and all the way through and so i feel like maybe that i kind of like that it's reflected in that verse because i don't think that was part of my identity at all for a while you know and um and so anyway jackson i gotta say i really like i i love listening to you by the way i told my team last night i was coming here 50 of them listen to you and the one who knows you is jackson the other people raise their hand are like no no i just i listen i'm like how the fuck do you know about jackson doll it's amazing um but i love listening to you i i told you before we started rolling i asked chat to bt what you would ask me it was pretty fucking good man those are some b plus a minus questions and i i want to go back and answer those just for myself you should it's like form spring crystal was like that's form spring yeah um but i like i think the um depth and originality of your questions i think what you pull out of people but more than anything the guests you curate i i i felt a little bit imposter syndrome coming on here because i think you've got some incredibly dynamic creative challenging people doing stuff and i i looked this morning i scrolled through spotify and i knew the names of four of your guests before they got here um lux capital guy cyan i don't know there were like a couple i was like all right yeah even then it's still an interesting discussion i'm learning new things because of the way you talk but you know i bought nadia's book which was in our company color so it was even better but um And, you know, I learned about Stripe Press, which as close as I am to the Collison brothers and the Stripe, I didn't know about that culture there.

2:35:43And, and so I really, I'm just really grateful for the work you're doing. And this is, and I was just awesomely thankful to be here. So, and I hope I lived up to your expectations, man. Yeah. More, more than I could have asked for. Thank you, sir. This was really a pleasure. Right on, brother. Good to see you. Hopefully not another eight years. Yeah. We'll do a little quicker this time.