32: Chris Sacca - Drifting Back to Real

[00:00] I think sometimes risk is mispriced. And a lot of that is maybe rooted in narrative, rooted in fear, rooted in imposter syndrome, and underpricing the ability to actually... [00:09] impact the outcome. Somebody asked, so what do all your most successful founders have in common? And I was trying to find a thread. It wasn't how they grew up. There's no doubt that immigrant kids, just the things they overcome to get here and build stuff, their hustle, their desire, their focus is [00:25] insurmountable. People who grew up with single parents have that same fire, that same adaptability and resilience. But I kept looking, I'm like, are they scientists? Are they computer scientists? Did they all sell blow pops when they were kids? You know, did they have a hustle? [00:38] A lot of them did, but not all of them. [00:40] 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. I first sat with Kevin and Mikey who 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. [01:00] I'm like, okay. [01:02] You guys. [01:02] We're meeting right now in a co-working space. You're two of you. We are in the... [01:07] Dark shadows off stage of like Calacanus was running some pitch event. But I'm like, what's with this 10 million users thing? [01:14] Bye. [01:14] Kevin wasn't trying to sell me. [01:16] He just knew it. He literally knew it. You can just tell. Welcome to Dialectic Episode 32 with Chris Saka. [01:23] This is a special one for me, in very full circle. I worked with Chris almost 10 years ago, [01:29] at lowercasecapital.

[01:30] when I was just out of college and I learned so much from him about risk and investing and storytelling. [01:36] And if you're not familiar, he is one of... [01:39] The Great [01:40] early stage investors of all time. Lowercase one, his first fund, [01:44] is probably the best by multiple of any venture fund ever. [01:48] I think something like a 214x. [01:51] He was one of the first investors in Uber, Twitter, Instagram, Docker, Optimizely, Blue Bottle, and so many more. [01:59] And then... [02:00] When he was effectively at the peak of his powers around 2017, Chris, to use his words, hung up his spurs and moved on to the next thing. [02:07] He focused on politics for a while shortly after the election. [02:10] And now he runs Lower Carbon Capital, a play on that original name where he invests in climate startups, removing carbon from the atmosphere. [02:19] Stuff like cloud seeding, nuclear fusion, and much more. [02:22] Chris was also a guest shark on Shark Tank, which I got to work with him a little bit on. [02:27] And before lowercase... [02:29] He, among other things, won the Founders Award at Google for his time there. [02:34] was a lawyer when he first entered Silicon Valley. [02:36] And he went to the Georgetown School of Foreign Service. [02:39] He is someone who I admire perhaps most, [02:42] for... [02:44] his consistent desire to, [02:47] and willingness to stay true to himself, even if that means... [02:52] dramatic life shifts, closing chapters that [02:55] Others might ride forever. [02:57] and finding the next thing. [02:59] that feels true to him.

[03:01] We talk about writing. Chris is one of the best writers I've ever met, despite most of it not being public anymore. [03:06] We talk about risk and investing, imposter syndrome, [03:10] having a taste for the good kind of weird... [03:13] and thinking about life in the various chapters that it might hold as well as what that means for Chris. [03:20] It's a long one. It's a good one. I hope you enjoy it. [03:23] As always, thank you for listening. And if you like the episodes, please share them with a friend. It means a lot. [03:31] With that, here is Chris Saka. [03:34] Chris Saka. [03:35] What's good, Jackson? It's been forever. I think it's been like eight years. [03:40] In a long time. [03:41] Right on, man. It's cool. [03:42] I'm going to start in an unlikely place, I think. Not... [03:45] truly for you, but I think maybe for people who've [03:49] known of you only more recently. [03:50] which is you are one of the best writers I've ever met in my life. And, um, [03:55] You don't write very much publicly anymore. You actually haven't really written publicly much in the last decade or so. [04:00] I think he once said, nothing can stop time and bring us together like words done right. [04:05] So I'm going to take you way back. Did I write that before AI? I can actually take credit for saying that. I think it was like the 2000s. All right, right on. We're going to go way, way, way back for a bit of writing. You don't have to bear with me, but I'm going to read it in full from a section of a blog called Coast to Coast. [04:22] The title of this one is called 3,286 Thank Yous, November 30th, 2009. [04:27] This is partway through the post. [04:29] as you are riding your bike across America.

[04:32] The peak of my experience came quite literally in my push to the crest of the newfound gap, the 5,048-foot pass... [04:40] through the great smoky mountains that marks the border between Tennessee and North Carolina. Though the day started with my hallmark morning lethargy, the raw energy of the National Park, its autumnal coat, [04:52] and its rushing waters flipped a switch in me, and I peddled with abandon. [04:56] If you know this road, then you are quite familiar with its singular direction, up. [05:01] The more I spun, the sooner I climbed into a bracing snowy canopy, [05:05] With each switchback and the road's unrelenting grade, the road was wet, then slushy, and I weaved through the hesitant cars driven by snow-stymied Floridians. [05:14] As the inches accumulated on the ground, I accelerated with each fishtail of my rear wheel. I laughed and hooted with a carefree exuberance. [05:22] Oh, to be alive in the snow with a racing heart and heaving lungs. [05:26] I made it to the summit a half hour before folks started falling and our guides collected everybody in a van and declaring the road unsafe. I felt so charged. [05:34] The looks of disbelief on the faces of the tourists in their cars provoked cackles from me. [05:38] Travelers would stop and ask about my ride and shake their heads when I explained the goal and admit to having pedaled to that summit in the storm. Ha! [05:46] I felt crazy that day and yet so authentically me. I rested my bike against our group support trailer while waiting for the others and looked out over one of Earth's [05:54] most beautiful valleys, the snow swallowed errant utterances, and wrapped me in its unmistakable hush. I reminded myself that somewhere past the horizon was a beach.

[06:04] And in that moment, legs still surging with adrenaline, I finally knew that I would be there soon. Nothing would keep me from it. [06:12] Uh, all right. I got to say something funny to distract from. That makes me emotional. Um, [06:17] I really hope people are listening to this at 2X. That was a long clip. [06:25] Well, Jackson, I always appreciate how you ask things that nobody else asks. That's why I listen to you. [06:34] You know, just last night, [06:36] one of the people on our team [06:38] was talking to me about the need. He, he's just a great young person and he was, [06:44] He's like, I feel like I need an adventure. [06:46] I feel like I want to take a little time and go on an adventure. And it was fun for me because even as an employer... [06:52] And no point did I think about it as like PTO. [06:55] I was just so excited for him. [06:57] to want to go do something. And he was talking about the Camino Santiago. And then I was like, Hey, Crystal, my wife and co-founder and best friend forever. [07:05] Um, [07:06] I was like, you know, she went and did Machu Picchu and El Sangate like multiple times, you know, at the height of her career, she left and went and did that. [07:15] And, [07:16] I was reminded of this bike trip. [07:19] You know, it was I started pretty fat and out of shape on the West Coast and was like shredded and strong by the East Coast. [07:27] It was essentially more than 100 miles a day, right? It was just nonstop. [07:31] But... [07:32] What I... [07:33] What I loved about it...

[07:36] was how few times in our life we have a very singular focus. [07:41] I got up in the morning and I knew my exact purpose. [07:44] And I knew the only thing I had to do was get to the other side. And I had a mantra, tonight I will be in my bed. [07:51] Um... [07:52] and [07:53] It's the same thing that got me through Iron Man's. But even Iron Man's, you're like, look, it's just one day of pain. And there's lots of people on the side cheering for you. And so... [08:01] But for... [08:02] for writing. [08:04] It was the last time where I only had one thing to care about, and the way that frees your head up, [08:09] to maybe let other thoughts come in or not. It is the most meditative thing I've ever done. [08:16] repetitively and I would call Crystal at the end of the day and be like all right love I'm going to bed and she's like it's five where you are I'm like yeah I'm definitely going to bed like I have probably I've never eaten more like because I had earned it I'm like I'll have two chocolate shakes and uh [08:30] But... [08:31] But I... [08:34] When I got to South Carolina and dipped my wheels in the ocean... [08:39] I cried a lot. [08:41] It was the hardest thing I'd ever done. By the end of that trip, I was wearing three pairs of bike shorts on top of each other just because my ass was worked. No, I was just like... [08:50] Even sitting in a fucking seat, you know, going 100 miles a day. [08:54] The other things that hurt were like my shoulders and my, and my Achilles. You don't even think about it. You think it's like your quads. It's not. Um, [09:00] But I did my bike tires. [09:02] I made it. [09:04] I got on the plane. [09:06] And then I was wildly depressed for the next month.

[09:10] I obviously miss the dopamine that I've had in my body every day. [09:16] And I've heard this, like, Dean Carnezi, who's a guy who... [09:19] I think that's the name, yeah, who... [09:21] Ran coast to coast, got to New York and almost committed suicide or attempted it or considered it or something. And so he decided he would just run back to San Francisco. [09:31] because he was really chemically addicted to it. And he had that same purpose. I felt something like that. [09:36] And I would, it was like a real loss. I went through a sense of grief. But in the meantime, I was just so fucking distracted by everything else. [09:44] So I'd wake up in the morning and my purpose wasn't, um, [09:48] By the way, if there's another human being in the room, I have to make eye contact with him too. [09:54] I know, here's funny, as someone who's done primetime television, you're never supposed to look in the lens, but Josh is sitting over here, and like, I just think, I was raised right, I'm incapable of ignoring another human's presence, so... [10:07] So this is going to be weird because I'm looking right into the lens. I'm breaking every rule of Hollywood, but I can't help it. [10:14] Um, maybe Josh, you should just pull up a chair. Uh, no, but you can also like the audience is over there. Okay, cool. All right. Um, but yeah. [10:21] But like, [10:22] After that, I got back to this mode where I was reactive. What's in my inbox... [10:28] Maybe we were texting. Yeah, we were texting by 2009. But, you know, I was just... [10:33] responsive to everything else. And it made so much less room in my head. [10:38] to actually think, think about things. And so, and I miss that. Even living, you know, you remember we moved,

[10:44] Out of San Francisco. [10:46] Up to Truckee. [10:47] near Lake Tahoe and this is something I've explained many times but I was doing like 14 hours of coffees and brain picking and [10:55] You're like, yeah, I'll meet and hear your pitch. And at the end of the day, I was wildly over-caffeinated. It hadn't worked out. [11:00] had lost my voice, had... [11:02] Been in these things I enjoyed because I was helpful to their company and their product and these founders. [11:08] But I hadn't done anything on my own to-do list. I hadn't written anything. [11:12] I hadn't reflected. I hadn't worked out. [11:14] Like I hadn't even thought about the weekend and what I might do or anything like that. And so I was... [11:19] Moving the truck, he helped. [11:21] But even a truckie trying to start a business, as much as I wasn't doing daily meetings, [11:25] I was still just... [11:27] building a business, reacting to it, yelling at people on the phone, getting yelled at. [11:30] Like, you know, I would [11:32] Crystal and I would look up and be like, it's 4.30 and we're still in the clothes we slept in. [11:37] and we haven't been outside and ostensibly live in the mountains to be in the mountains. And, um, [11:43] And so let's hurry up and get outside before it gets too dark. But, [11:47] But the... [11:48] Bike ride. [11:49] for me, was the most meditative thing I've ever done. Now, to be clear, by the way, my biggest fear in the world is a 10-day Vipassana retreat. [11:58] I was like something I'm not saying that to be funny. It is truly I've reflected on this like snakes, bats, whatever, you know, all that stuff. Surgery. [12:06] All good. [12:07] Um, [12:08] But a 10-day Vipassana retreat. [12:10] where you can't read, you can't write things down, you can't listen to music, you're not supposed to

[12:16] really exercise you walk and reflect and do chores and [12:20] and sit. [12:21] You're pretty good at facing your fear in most parts of your life. Yeah, sure. But then the next hour, you're over it, you know? Or like, you're like... [12:29] Yeah, anytime I have a really strong reaction to something, that is a clue that we should do something. Have you met Augustus Dorco yet? I know of him. Okay. [12:38] So, [12:39] Augustus has this company, Rainmaker. He's one of our [12:43] Most unusual founders. I think it was important for you to invest in someone with a mullet after all these days. Dude, a mullet. [12:49] jean jackets lined with like, you know, sheep, uh, [12:53] Well, he has a huge American flag behind his desk. [12:58] He will unironically quote the Bible sometimes in the work he's doing. [13:04] But I remember we were having a team dinner. [13:07] in LA had the whole team gathered and two of our teammates had just come from a meeting with him [13:13] And they were like rolling their eyes. They're like, this guy. Oh, he is... [13:18] Just a little too big for his britches. The shit that was coming out of his mouth was absolutely crazy. [13:24] I don't know, man. Seems like a lot. You know, like the ambition might be way out over his skis. [13:30] And they were almost like, ah, seems like. And Crystal and I both had the same reaction. [13:36] No dessert for you. Stand up right now and immediately go back to that meeting. [13:41] And they're like, wait, really? And we were like... [13:43] If we invest in normal people, all this money is going to go away. Like,

[13:47] The alpha is in the fucking weirdos. Like, immediately go back there, and they're like, seriously? [13:53] But what he's doing is crazy. I'm like, yeah. Literally trying to make it rain. Yes. That's exactly why we need to go talk to him. And there might be political fallout and we might be the target of conspiracy theorists. We knew that then. I was like, [14:05] But that dude just sounds so unlike any other dude I've ever heard about. Go back there. And it... [14:11] And I was like, all the things you're talking about were not toxic. They were just fucking weird, right? Right. I don't want to invest in like sociopaths. [14:19] And so sometimes you end up with them and you're like, oh, fuck, I misread these signals. But Augustus is the opposite of that. And he's still he was we had dinner last night. [14:27] He's fucking weird, right? But that is at the heart of his success. And by the way, I was told recently that [14:34] One of our teammates was speaking at [14:37] a fancy school or something like that, like kind of like one of those recruiting talks. [14:41] And most of the questions he got were about Augustus. [14:44] Not about our climate work, but literally about this guy. [14:48] And so, anyway, that was an amazing lesson in... [14:52] We got to this point in our life where we realized anytime we have [14:56] really strong, like a disproportionately strong reaction to, [15:01] to something. [15:02] you have to train yourself to, that's probably a reason to lean in. Now, sometimes you might find like, I have a disproportionately strong reaction to Trump and it turns out I was right. What a piece of shit, right? And I'm sure that'll get me killed. [15:13] But... [15:14] Or at least jailed. Or indicted. You said that a few thousand times. Yeah, I'm on the record. If I were writing for the AIs, it's already there. But at the same time...

[15:23] I... [15:24] There are other times where you're like, this seems like bullshit, makes no sense to me. [15:29] And then you say that and you're like, wait, I probably need to go talk to some people. You start to learn. [15:33] You know, like we're huge investors in fusion. [15:36] We have the only dedicated fusion fund in the world. [15:40] We had a couple of small projects in Fusion basically to learn. It was family office money, and we're like, [15:46] And everyone had always said fusion is 30 years away and always will be 30 years away. It was like the refrain for that space. [15:53] And for at least 30 years, that was very true. [15:56] But... [15:56] What had happened was the actual productivity, like the net energy gains from these had started going... [16:02] exponential, in fact, double exponential. [16:05] where the exponent is also an exponent. [16:07] And so, [16:09] But as we started talking to other people outside of the fusion industry about it, they're like, dude, that's where dreams go to die. All your money will just get on fire. And we're like, [16:17] Okay, except those of you who are saying that just haven't visited a lab recently. [16:21] Like if you actually go and talk to the, [16:24] folks working on this and visit the companies first of all it's cool it's just the biggest magnets in the world and they're [16:29] Achieving temperatures of, you know, 150 million degrees Celsius, hotter than the sun. Pretty badass. [16:35] It's always fun to wear hard hats and vests too, by the way. But [16:39] But it's... but... [16:41] The strong opinion of the market and our initial skepticism ended up being this incredible clue to... [16:47] Lean in. [16:48] the signal of like, wait, just go find out. Don't accept anyone else. Like, [16:52] do your own research is now a stigmatized phrase for all the right reasons. And, you know, please take your Tylenol.

[17:01] But it was going to these, going to... [17:05] The actual lab talking, the actual scientists looking at the actual data revealed to us this anomaly in the market. That partially started with like a taste in weird. [17:12] Yeah, absolutely. Oh, oh, they're not normal people. Yeah. [17:15] Because these are people who have gone into a thankless industry. [17:18] That was underfunded and ignored and dismissed. Your guy leading fusion was at Los Alamos for like 20 years. Yeah. Do you know who you, uh, so Dr. Scott Sue, he's great. He joined us this year, um, to just accelerate our fusion strategy. [17:31] Um, [17:32] It was Clay's original idea to do this. [17:34] our co-founder but with no technical background but he was the one who's like look we can get smart on this space [17:40] If [17:41] I had taught him when he first joined a lesson Arian Sergei had shared with me, which is, [17:46] With the tools available to us today, and this was in 2003, [17:49] was there is nothing keeping you from being one of the 50 most knowledgeable people in the world on a subject. [17:55] within a year. [17:57] It sounds like ridiculous, particularly for those of us who didn't go to school for that thing. Right. [18:02] But if you're willing to exchange, [18:04] all your hours, read all the things nowadays, listen to all the things, uh, [18:10] And then go visit all the people who wrote those things. Literally. Can I come see you at your place? By the way, no one's asking to visit those people. Yeah. I, Oh, [18:18] Ryan Orbach, who's a buddy of yours and works for us, once told me that his cherubic youthful face is... [18:24] meant that people would literally accept them [18:28] accept him into their lab, even though he was essentially gathering as much information as possible.

[18:33] He's just like, people found me really harmless looking. And so I could go there and ask them any question. It was like, oh, look at this cute. Yeah, it's sort of like a student. This cute student who like wants to know about my work and. [18:43] He's just one of the best ever, but in one of the most [18:46] I think I've mentioned it before. I think he has like a certain reflexive Tourette's for the word why. He just can't help but interrupt you with what? But why? But why? But what's that? What was that word? [18:57] It's an it's it's awesome. No filter on that guy. [18:59] But I think... [19:01] You know, Clay really started, he read every book on Fusion and started meeting all the authors and all the skeptics and all the proponents. [19:07] And then when we started meeting the founder, something really wild happened. [19:10] Bob Mungard, the founder of Commonwealth Fusion Systems, which is kind of the... [19:16] most respected company in the space, the most known up in Boston. [19:20] Alan Eustis, the head engineer at Google, was the first one to tell me, you should go meet these guys. That's a pretty strong signal, right? [19:28] One of the greatest engineers of all time. Also the guy who... [19:32] just [19:33] built his own platform to jump out of space from without telling anyone. Do you remember that? So remember Felix Baumgartner did it for Red Bull, right? Cameras everywhere, lots of promotion. [19:44] And then Alan came along and did it from higher on a project he built and funded himself. A Google engineer. Yeah. The head Google engineer. [19:51] The top Google engineer just did it. [19:54] I mean, they filmed it and people found out about it later, but dude just did it. [19:58] All time. All time. But... [20:01] But so Bob Mungard, after we went and saw what was being achieved there,

[20:06] And the results that were happening... [20:08] And what a lot of people would say is finally, but... [20:11] He said, hey, [20:12] I want to introduce you to another guy who's, [20:14] doing [20:15] Who's trying to tackle the same problem, but with a totally different approach. [20:19] And, um, [20:20] ostensibly a competitor, [20:22] Right. And just let's be clear. Elon is not introducing you to Rivian. No, you know, [20:27] There's a lot of things Elon's not introducing you to today, but, um, but, [20:31] But so he sent us to this other team. [20:34] we saw a completely different approach [20:37] in terms of technology, but to the same problem. [20:41] And, [20:42] So before you know it, we'd written two checks in the space. [20:45] Um, and, and then as we spent more time that unlocked, like, Hey, these are, [20:50] people who actually care about fusion. We built more technical expertise [20:54] within the firm to make sure we weren't just faking it. Yeah. [20:58] And then we started to see like the facts on the ground had changed and we built a dedicated fusion fund. [21:03] Gave all our LPs an option to either opt into it or not, rather than forcing them into it or overloading. [21:09] our existing fund with too much concentration in this one thing. [21:12] But... [21:13] Now we're in eight fusion companies. [21:15] probably four [21:17] different approaches. [21:18] to the same problem. And then, [21:20] are also investing in kind of the vertical stack. [21:23] So some of these people just make magnets. Some just make superconducting tape. [21:27] Um, [21:28] The hockey stick is... [21:30] genuinely, like we, in our last investor update, [21:33] We posted the first hockey stick we had shown people.

[21:37] next to the current one. And the peak of the first one is the blade of the second one, right? By the way, humans suck at exponential curves, right? Your nose is right up against it. Tim Urban wrote the canonical blog post on this, but [21:50] Your nose is right up against it and you're estimating progress by what's behind you. It's just a cognitive bias. [21:55] And so, [21:56] But we just started to see truly exponential stuff. So we're out with our second fusion fund now. [22:01] And it's funny, we don't hold it against anyone who said no the first time. We kind of get it. [22:06] But these companies went from [22:07] Not if... [22:09] But when and now when is much sooner and even better, they have billions of dollars of commercial agreements. They're citing their plants. [22:17] By the time this comes out, we have just broken, um, it's actually tomorrow, but we're breaking ground on a, uh, [22:23] on a facility in New Mexico. [22:25] Uh, I was with the governor of New Mexico here in New York two nights ago. And she's like, I'm flying home for it. I was like, really? [22:32] And she's like, this is my obsession. Wow. So anyway... [22:36] Making sure to look at things with completely fresh eyes, but using the I have strong opinions. [22:42] as you know and by the way i think our culture has been drifting more in this direction [22:46] of trying to be [22:49] more heterodox about ideas. Not everybody, but I think a world that we kind of swim in is like, wait, wait, wait. That's been something that's been doctrine for a while. Maybe I should... [23:00] dive in and question. [23:02] And, [23:03] you know, we've, we, um, I'm close to the Collison brothers. Uh, [23:06] I helped them get in the country when they were literal teenagers. I think...

[23:10] I think... [23:11] Patrick visited Google when he was like 15. [23:14] And Paul Graham brought him by. And I gathered a bunch of awesome people. That guy is everyone. Literally, he finds them all. Yeah. No, no. He truly. Well, they were hacking on Lisp, which was Paul Graham's obsession. Okay, okay, okay. And so they were known to him. They took their first community money and bought a computer. [23:31] and used it to... [23:33] So anyway... [23:35] He brought Patrick to Google. I gathered a bunch of people who could independently assess. Patrick was one of the [23:41] smartest people walking the planet and then i just remember being like so what do we do do we hire you [23:47] do we appoint a guardian? Like, do we like, do you live in a dorm or do you live here on campus? Like what? I don't get it. Like, what are we supposed to do? Yeah. I'm like, I clearly you should be here, but what do we do about that? I don't even know. Um, [24:01] But Patrick and John, you know, over the last few years, [24:05] I think they've emerged from [24:06] People I used to think of as like younger brothers to people I just deeply admire. [24:10] I think they're doing it better than anybody else. As... [24:13] And maybe it's because they keep each other honest. They're really good at this weird taste thing, too. [24:18] Yeah, but I will... [24:20] Yes, I just want to finish this one point where... [24:23] I've spent the last few years like throwing hot takes out there. Like this is some bullshit. Reacting to some... [24:29] And they're like, but is it? [24:31] I'm like, you're right. Maybe I was programmed to think that was bullshit. Well, yeah, this is really interesting. So you brought up Elon and Tim Irvin, um, [24:39] Whatever you want to think about Elon, one of the most interesting things Tim ever wrote about or spoke about, I think, is he was talking about – somebody asked him, what's so special about Elon? And he said, what Elon is so amazing at is that he can –

[24:50] Look at the world as it actually is while the rest of us are looking at the world through the lens of five years ago. So you can't re-land a rocket. It's physically impossible until it isn't. It's the exact same thing you were saying about nuclear. [25:00] And I find that [25:01] somebody like Patrick, some of these guys, they have this ability. It's what you were describing around the weird thing. It's like this ability to sort of like, [25:09] filter out the total BS and sort of like let something enter the filtration system. [25:14] And like let it while the rest of us are just like, yeah, it's not worth our time. [25:19] That used to be Elon. [25:21] Hmm. [25:22] I've known him for 20 years. That used to be who he was. [25:26] What do you think, um... [25:27] The people are really good at someone like Patrick. People are really good at that. Like still what, [25:32] What causes that? I know exactly what causes it. It's... [25:36] The more successful you get, the more money you make. [25:38] the more like, [25:40] the more you built and achieved. [25:42] The fewer people around you call bullshit on you. Right. Sorry, I meant what sustains it. Yeah, so my point is Patrick and John have each other. [25:52] And whether you call it dialectic, which is a word I had to look up to remind myself why your podcast is called this and what it means. Actually, I'm not even going to say remind. I'm not sure I ever knew it. I'm not going to pretend. But that's why. But that's who those guys are. [26:06] right? Um, [26:07] Mm-hmm. [26:08] And so they keep each other incredibly honest in their thinking and who they are as people. [26:14] You know my wife, Crystal, really well. She's the silent co-founder of everything I've ever done. We've been best friends since we were 18 years old. She friend-zoned me for 14 years, so...

[26:23] but three kids later, et cetera. But, [26:26] But she is obviously the very first person on a daily basis to be like, you're so full of shit. [26:31] Or that is a tired idea. Yeah. Or I disagree. Or you're missing the point. [26:37] And or are you fucking serious with that right now? [26:40] Like, I've never seen anyone care less about celebrities. She's kind of exhausted by, like... [26:44] Are you actually friends with them? Or like, you know, and so like so nonplussed about like world leaders, just like, yeah, yeah, yeah. [26:51] Um, [26:53] And I mean... [26:54] I admire her for that as an individual, but it's also why... [26:59] I have been able to avoid the slope that would be so easy [27:04] to slide down [27:06] of like everything that comes out of my mouth is Bible. [27:10] Everything I do is infallible. [27:12] If you look at [27:15] some of the household name leaders who we now consider maybe off the rails. [27:21] completely imbalanced. Um, [27:24] maybe self-destructive or outwardly destructive. [27:27] you will find people who almost invariably have no one around them, [27:32] Who can say no? [27:33] And everyone around them is either sycophantic or opportunistic or has just made a living swimming in their wake. Yep. [27:40] And that becomes a self-reinforcing thing, right? I mean, look, I've... [27:44] I see this happen. Okay, my favorite Wikipedia page is the list of all the cognitive biases. [27:50] It's... [27:51] Just type in Cognitive ISE's wiki and you'll get there. And it is all the absolute flaws in our code.

[27:57] Like we are all the most hackable, the most self-confident, but hackable species. And you, by the way, most of us, you read through those and you're like, oh, I know somebody who's like that. I know somebody. Oh, that's funny. You project them out. Yeah, sure. [28:08] Yeah, I mean, I guess as you get older, things become less black and white and more gray, and you start admitting more of that vulnerability and fallibility and fragility. But... [28:20] I just see that... [28:23] Once you I mean, look, we we see this just just by virtue of making money. [28:29] Trump knew early on. [28:30] he had to establish himself as a rich person. And I mean, remember this is a guy who, if he had just taken the money, he was, [28:37] the inherited from his parents and put it in index funds, he'd be a 12 billionaire now. [28:41] Um, so he, he excelled at losing money. Uh, he was just horrible at deals. [28:47] And Wall Street wouldn't touch him. He was just a mess, right? [28:50] And yet you can read about how every year [28:53] he would fight with the Forbes folks to make sure he got on the list. He would submit. [28:57] documents that were likely false, et cetera, to just [29:00] Because he knew the validating nature of being rich in America. Yeah, it wasn't just vanity. Yeah. It was actually utility. That's a really great way of putting it. And so, by the way, Mark Cuban is actually rich. [29:11] And so I actually feel like he could be president because people take what comes out of his mouth as [29:16] Bible. I mean, I... [29:18] You predicted this 10 years ago. Are you still on the bandwagon? No, his family won't. They've agreed as a family that they won't do it. And I... [29:25] I can't disagree. Like the amount of danger and disruption and, and,

[29:29] uh i just can't disagree with that it's sad i wish we would get some of the most i think he's wildly qualified to do it um [29:35] But my job on Shark Tank was to keep him honest, right? Because what would happen is... [29:39] Heh. [29:40] He would just say something, and in the American impaneled jury of the audience, it's just like, well, the richest guy is the rightest guy. By the way, you should read the Reddit comments of when I used to fight with Mark. I found a few. I found a few. They are just like, who the fuck is this guy? Because he's only worth X, and Mark is worth a multiple of X, so this guy needs to shut his mouth. [30:02] There was no actual objective analysis of me being right. Sometimes, like, years later, you find out that startup that I was saying wouldn't work out didn't work out. [30:10] And I was right, but that didn't matter. Scoreboard. Dollar scoreboard. It was won by wealth. And so- [30:16] So I do think one of the biggest traps we all fall into is starting to leave our own bullshit. [30:20] And... [30:21] That is a, whether it's [30:23] Somebody writes the canonical blog post about a space. [30:26] Then they see... [30:29] I saw a guy write the canonical shared economy blog post, right? [30:33] Uber was shared economy, right? It wasn't... At no point did Garrett have this idea of like... [30:39] this grand thesis of shared economy. It started with a car that he had in New York that he wasn't fully utilizing. So he let a few of us use it when we were in town. [30:48] And then he started, you know, this idea came together of like, [30:51] One, he loved going to... [30:54] dance music at night and like edm stuff he's a really he makes his own music now but [30:58] Um,

[30:59] And he's like, I can't get a cab at night. [31:01] home from these places. I call, they don't show up, et cetera. And then he had this dedicated car and he's like, oh, I could let other buddies use this because I'm only using it for a fraction of the time that I'm employing this guy. [31:11] And so at no point was he like, [31:13] what if we could distribute the resource? You know, there was no thesis thesis. It was solving a problem. And he's brilliant. He's probably a lesson there. He's one of the all-time thinkers and way more reflective and philosophical than people ever give him credit for. [31:25] Uh, probably cause he doesn't self-remote or tell that story at all. He just lets his products speak for themselves. But, [31:31] But I saw another guy write the... [31:34] Shared economy. [31:35] blog posts that went wild, got shared, [31:39] And and then he would get all the shared economy deals. [31:42] And instead of... [31:45] evaluating each of them with fresh eyes, [31:48] inherently every single one of them confirmed that his blog post was right. Yeah. Yes. So we did a bunch of 85% okay deals. Yes. You can't invest in 85% good shit. [31:58] And his money went away. [32:00] On that note, [32:01] Obviously, there's downsides to it, but there's also incredible power in... [32:06] using language to sort of organize something for somebody or narrativize something for somebody. You've literally said, I write things that raise billions of dollars. [32:13] You are... [32:14] people probably don't know, especially these days, but like, [32:17] The lowercase, and I'm sure the lower carbon LP updates are... [32:21] Maybe someday in the biography or whatever, they'll be published. [32:25] But like, yeah, you are clearly an incredible investor. I want to talk about talent later. You're incredible at spotting talent. But like...

[32:31] You use language to do incredible things. You're obviously good at talking, too. [32:36] Um... [32:37] Why is language... By the way, like... [32:40] I had never really read a lot of it. Your blog from 2004 to 2009, you were blogging constantly. It was like vintage stuff. Oh, my God. You know what you're reminding me? [32:49] They might have just gone away. [32:52] I think I might have to pull it. Like, TypePad just went down on September 25th. I was supposed to, like, migrate it, and I totally forgot. You, I, I both have some archives. Did you access any of that this morning? [33:02] No. Okay. But you can... I think it might have gone away. If you go to the website, it doesn't show up, but you can find the archives on Google. Maybe you don't want the... All right. No, no, I want them. I... I... [33:10] I left it up there for a reason. I think I've been paying TypePad a couple dollars a month or something, but [33:14] Holy shit, you're totally reminding me that I've had this action item. Whatisleft.org, I think? Whatisleft.org, yeah. [33:20] When did you figure it out and what is so powerful about written language? [33:27] You have no need to... [33:29] Right. [33:29] I grew up in a storytelling family. [33:33] I mean, my mom... [33:35] was a teacher and professor and [33:38] Sometimes due to a lack of childcare, I would sit in the back of her classroom at university at night. She taught at night, you know, and we didn't grow up with any money. And so we didn't always have babysitters. So it was like I would have to go with her. [33:49] To, um... [33:50] to [33:51] Buff State and Buffalo. [33:53] And similarly, my dad was a small town lawyer. [33:57] Like literally small town handling just everything that people would need help with. They got into trouble or they needed to buy a house or divvy up their estate or something.

[34:07] And, [34:07] I would go with him to court. [34:09] And sometimes I would sit at the defendant's table. [34:13] I was once mistaken for the defendant. How old? I was doing my homework. I forget. I was just, I was doing my homework. So, [34:21] Or I would sit in the judge's chambers and before you know it, I am literally sitting side by side with a convict, you know, chained to the chair and I'm like, oh. [34:28] But, yeah. [34:30] But I also grew up in a family that... [34:32] told jokes and stories and we gathered, um, [34:36] You know, we were a skiing family. [34:38] And [34:40] The ski house didn't have a television. [34:42] And it was just we would sit around the table with friends and just tell stories. I learned early on. My dad is a masterful storyteller. [34:51] I learned early on just that joy of the hearty laugh from the whole table. [34:56] and [34:57] and the arc of the story, and how to set it up, and how to [35:01] Prime the punchline without giving it away yet. [35:04] And the beauty of a real joke. And my dad is just an inherently folksy person. We grew up. [35:10] in a small town in New York, um, [35:12] You know, I was... [35:14] When I was 14 or 15, I was deputized by the district attorney in our town to be [35:20] an investigator. [35:21] I was the only, I was their first white collar investigator. And it was mostly because I was the only kid around who could use a computer. [35:27] and they needed to do a white-collar investigation of like, they needed to do basically forensics, like white-collar forensics of some money flows. [35:35] And, [35:36] I was like the only person who could do it. Yeah. Yeah. I remember once, uh, the district attorney went down to the clerk and,

[35:43] to grab a couple files and the clerk is like, can't find them, whatever, come back next week. [35:49] He was really frustrated. I was like, well, let me go see. [35:51] And I went down and they gave him to me five minutes later. [35:54] And he's like, how'd that happen? And I was like, [35:58] I think because of my dad. [35:59] Like my dad learned to treat [36:01] Every human as a human. [36:03] It's something that I still... [36:05] I can't help but talk to every single person who touches the table, who opens the door, who you interact with at all. [36:11] But... [36:12] And what Crystal's dad would say is that every single person has a story. Give them a chance to tell it. [36:19] And you just start to realize that [36:21] We are all so... [36:24] Hungry. [36:26] for narrative, for stories, for tales. [36:29] For things to believe in that. [36:31] done right feel a little mystical can provoke emotion [36:36] Allure, they're pointing at something maybe. [36:38] And so... [36:39] My mom and dad both wrote and told stories for a living. [36:44] They're not published authors, but that's what they did. They organized... [36:48] Arguments. [36:49] And reasoning. And so it was... [36:54] I mean, I wrote my first... [36:56] I submitted my first story to a story contest when I was six years old and I won. [37:00] There was this cricket magazine, this literature magazine for kids. [37:03] And then as a result, I was like in the newspaper as a published author at age six. Yeah, yeah, yeah. The craziest thing about that was my mom... [37:12] um,

[37:14] My mom used that to help me meet with any author who came through the Buffalo area. [37:19] She'd pull me out of school. School for me was basically to be around other kids. I was six years ahead academically. [37:25] But I went there, they gave me a computer in the back of the room and I would just code and make stuff. [37:30] And then I'd go to gym class. [37:32] and so in lunch and hang out. They were just fine with that. [37:35] No, they... [37:36] Well, I tested out. I could have skipped. Look, I'm not unusual in your audience that I could have skipped way ahead. [37:42] But my mom and dad were very insistent that I didn't. [37:45] that I could... [37:47] go on dates and play sports with kids my age and just be normal. [37:51] in a normal town. Yeah. So I would sit in the back of the class and do my own thing. [37:56] you know, read college textbooks and stuff like that while, you know, [38:00] being normal kid. [38:01] And I feel really lucky for that. But along the way, any author would come to town, my mom would pull me out of school. [38:07] to go meet with that author. And if they, [38:09] were hesitant, she would literally send them the article like, no, no, this kid won a national story contest. And they were very cool about it. In the same way, Judd Apatow, who I love and look up to a lot, [38:20] And as a supporter of our work, like, I don't know if you've read Judd Apatow's book where starting at age 15, [38:25] he started interviewing the great comedians. I heard of this, yes. And he would say he worked for... [38:30] W whatever, whatever, you know, and it was really the [38:34] the high school radio station. [38:36] And then he'd show up and like Seinfeld would be like, oh, what? It's a fucking kid? But he'd still answer the questions. And so I... [38:44] I took advantage of that as a kid, and I would meet these authors, and I just started to really, like...

[38:49] And, [38:51] Words are free. [38:53] And that you didn't need art supplies, you didn't need canvases, [38:56] Uh, and, uh, [38:58] When I said I read college textbooks, there's a reason. My mom and dad had all their textbooks from [39:03] college and grad school. [39:05] And when I grew up, [39:07] We... [39:09] I had a bookshelf in my... [39:11] Room. [39:12] and they needed to fill it with something. And we didn't have a lot of kids' books yet. And any books we would ever get, we'd go to the library and read and return them. So the only permanent books... [39:22] For a while in my shelves were all their old college textbooks. And I just read them. [39:27] cover to cover seems like there was a mix of both sometimes deliberately and sometimes non-deliberately taking you really seriously as a kid. [39:34] Yeah, I... [39:36] Okay. That's a really good point. Um, [39:39] Because it's something we've learned to do with our kids. And... [39:42] Everyone thinks our kids are special, but I think our kids really are because we've given them the room to be. [39:48] to be [39:49] as big as they are and as much as they are we never baby talk to them i mean they're kids [39:54] And so we don't voice the problems of the world on them. We give them the room to be kids. [39:59] But at the same time, we entertain their deep... [40:02] I mean, we joke that our youngest is like always on mushrooms. She's 10 now. And... [40:07] We've now said this out loud in front of her and she's kind of run with it a little bit, but [40:11] her questions are like, oh, it would be so easy for me to dismiss that. But I'm like, yeah, why did that happen in the universe? Maybe I have to ask ChatGPT. But,

[40:21] But we've given them... That's TBT saving parents everywhere. Yeah, but we've just given them the room to be as... [40:26] as full as possible. And I think that is absolutely something my mom and dad did. They... [40:32] They really were... [40:34] insistent that I didn't feel trapped in this small town we grew up in. And then I felt like the world is my oyster without any real budget to do it. [40:42] I, [40:42] You know this. Starting age 12... [40:46] They did these things where they were insistent that we had really hard manual labor jobs at home. [40:51] character building to shitty jobs, literally. [40:54] When I say literally, one was in septic and sewer digging out septic lines. It was actual shit. Nice, nice, nice. [40:59] But just construction type stuff, equipment yard type stuff. [41:02] Um, [41:03] And then they also sent us [41:05] to stay with friends of the family who had white collar jobs, [41:10] in Washington, D.C., for example. [41:12] And I'd wear the same tie every day and just shadow them around at age 12. [41:17] and then try to write [41:19] Like I remember writing a lobbying leave behind book. [41:22] I was at the... [41:23] some lobbying firm for consulting engineers. [41:26] that a friend of the family worked at. [41:29] I, [41:30] read everything to try and get smart on what their platform was. And then I would tail along to [41:35] some senator's office. It was some high-quality swearing from some of those guys. Like, Howell Heflin, I think, from Alabama. That guy could spin a yarn. And then, [41:44] And then I would... [41:45] I would hand over this leave behind that summarized the points. [41:50] Part of it was because I knew how to actually use a word processor and could format bullet points and stuff. But...

[41:55] But I just remember like, oh, wow, the power of this one thing to get something passed. When you're 12 or 15, man. Whereas like I think most people when you're a kid or most people probably in their whole life writing, like writing some chore you do and then you turn 22 and then it's over. Yeah. And you never really learn the power. Yeah. And – [42:12] And, um... [42:14] I also learned really early on that, [42:17] Well, let me give you this example. I came home from college once. [42:20] I took some time [42:22] I was ostensibly going to college and ostensibly going to law school, but I was just showing up for the exams. [42:26] And so I took some time to come home and... [42:29] We were building a house for my mom and dad. Um, [42:33] My mom had some health issues that required her to be to live on one floor. [42:37] And so we moved out of our childhood home and we were building a house. But the way we were building it, [42:42] so that we could afford it. [42:44] Sounds crazy, but when you pay cash to contractors under the table, [42:49] They 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. [42:56] So we went to the bank and took out basically all the money my parents ever had. [43:00] had an actual pile of cash. [43:03] and would say to a guy that we knew in our town, like, hey, we need a foundation. And he'd quote us like, [43:07] 40 and we're like, [43:09] what do you say, 15 cash? And like, I'll be here Thursday. And so we are building this house for cash. We're also using cash. [43:16] people that my dad had done [43:19] My dad is obsessed with doing pro bono work and I used to be like, wait, we're broke. [43:23] 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.

[43:30] 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. That's probably why I became such a capitalist. But anyway, there were just people who owed my dad favors because he'd helped him with the situation. So I was working with one of those guys once. [43:46] This guy's name was Todd. I won't say his last name. [43:49] 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. [44:00] 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. [44:09] But we're laying brick. [44:10] and making small talk and [44:13] I was like, hey, what do you learn in that church? And he's like, oh man, last night was amazing. He's like, [44:20] You know, Preacher told this story about... [44:22] He said, "'Down in the South.'" [44:24] 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, [44:34] And Preacher explained that at the base... [44:37] of that statue and that soil at the base of that statue. [44:41] are all the naturally occurring elements you would need to make a watch. [44:45] 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. [44:50] And you've got the glass in the dirt that you could melt into the to be the face of the watch, you know. [44:57] And he's like, [44:58] And Preacher said, look,

[45:00] If you believe in evolution... [45:04] then you should be willing to stand at that statue, wait for lightning to strike and a Rolex to pop out of the ground. My brother was there and we looked at each other like, [45:15] Holy shit. [45:17] How many hours, days, weeks would it take us to undo that metaphor? [45:23] 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? [45:33] And I got to the point where I'm like, maybe you can't. [45:36] Like, [45:37] And, you know, [45:38] And I started to realize that like, [45:40] Good metaphor and simile and analogy, like the true weapons of mass destruction. It was another lesson in the power of language. [45:48] Later in my life, I... [45:50] was an attorney briefly. I was [45:52] general counsel at a company where [45:55] one of our founders, [45:57] was literally arrested by false accusations from our main competitor. They were trying to put us out of business. [46:04] And they had... [46:06] Literally concocted this story about how he had accessed what was called an anonymous FTP server, which is the standard of file sharing. [46:14] There were millions of these servers in the world. [46:16] and they all have the same username and the same password. [46:19] the word anonymous and the word anonymous. And so, so, [46:23] It was the opposite of a private or secure server. And yet this company, Akamai, had gone to the Justice Department and said,

[46:32] And the FBI said, this guy just hacked a server. [46:35] Um, [46:36] And so... [46:37] We knew that it was bullshit. [46:40] And it was my first time really helping out in court, federal court in front of this judge. We get there. The judge... [46:46] It's old as dirt. [46:47] and, [46:48] The prosecutor stands up and says, Judge, I know there's a lot of technical mumbo-jumbo in here, and they submitted 100 pages of... [46:54] a bullshit my eyes glazed over i'm sure yours did too he's like so i'm just gonna make this easy for you [46:59] And he's like... [47:01] What the defendant did here was akin to, and he reaches in his pocket, [47:04] And he pulls out. [47:06] like a combination lock. [47:08] you know, the kind you put on your locker in school. And he's like, [47:11] We all know what this is, combination lock, right? So what the defendant did here is akin to just [47:15] Trying every combination on the lock until he got the one that popped it open and then stealing everything inside. [47:20] So I'm just... [47:21] Two on that, and I'm going to sit down, and we... [47:24] And I was like, [47:25] Fuck. [47:27] Like all I've got are the literal inventors of this standard. [47:32] 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? And we were powering like 2% to 3% of the internet at the time, and they seized our servers. And so... [47:47] And so I'm like, how do I undo that? Yeah. That was one of the greatest things. [47:51] It was a false metaphor, but how do I undo that? [47:54] I undertook the study and you know this of [47:58] really [48:00] I dove deep into colloquialisms, idioms,

[48:04] cowboy language. [48:06] And so years ago, I taught a master class at Oxford called, um, [48:11] Business language of the American cowboy. To a bunch of these... Is this where Flim Flam comes from? No, but like I... [48:17] I mean, I already just grew up in a place that had a different... [48:20] dialect, [48:22] Right. Different than dialectic, but a different dialect and just... [48:26] parlance than anywhere else. You know, now I worry that TikTok is homogenized how we all talk. [48:31] My kids in Montana who don't have phones, but they learn it all on the playground from the other TikTok kids. [48:37] have the same exact slang as kids in Seattle and kids in St. Louis. [48:41] It's all the same. As, by the way, young people on our team, [48:44] 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 you know you're just what really have you gotten that old you don't know i've been watching tiktok all right hey shut up i'm 50 so to anyone listening right now who knows six seven i'm down so got it but [49:09] But no, like, I... [49:10] I started to realize the power of those things. And so I really dove into when we communicate, [49:17] How do we make things as accessible as, [49:20] And how do we help people file those in a way that they get comfortable? Like, I got my head around that idea. Yep. [49:26] One of the coolest things to do with ChatGPT. [49:29] Among the hundred million amazing things about it. And by the way, I also use Claude and Gemini. I'll just use chat as a test stand as a,

[49:36] as the, you know, [49:38] the shorthand for it. [49:40] 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. [49:47] and then ask it to explain it to somebody with, [49:50] declining reading levels. So start with high school, [49:53] go to middle school, go to elementary school. When you start hitting third and fourth grade, [49:58] The [49:59] 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 people. [50:07] Somebody at the bar. Wow. [50:09] He's like, what are you doing? 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, [50:15] Thanks for calling out. [50:16] My writing, you know, those update letters you talked about, it is it is wild. I wish the world saw more of them. They usually contain a bunch of confidential shit someday. And so the audience is like 200 people. [50:26] But... [50:27] We work on those for a couple of months. [50:28] And even as you're reading that blog post and like, [50:31] I just use the word snow twice. This is what I saw. I was like, I use the word snow twice in successive sentences. I remember having to, we were editing those letters. And it's like, yeah, get up the thesaurus. Well, Crystal and I are, if I'm, you know, we're both type A++. I mean, inside of our wedding ring, it says inviolent agreement. And so if you've worked in our home, you know how we go at each other. [50:52] Because we fight over every pixel. Yeah. Because every pixel, every word has to be perfect. Who can captivate you in a way that really makes you shut up? [51:01] Anybody? [51:02] Crystal made a joke last night at dinner. We had David Kwong, uh, [51:06] the nerdiest magician of all time.

[51:08] He's a cruciferbalist for the New York Times. He's a magic historian. [51:12] He actually wrote this incredible book called How to Fool Your Parents. It's a magic book for kids. [51:17] 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. [51:23] But... [51:24] But he... [51:27] I love bringing magicians to meet engineers. [51:31] Because engineer everything... [51:33] to an engineer or computer scientist or a scientist, [51:36] Everything has a clear, linear approach. [51:39] causal explanation yes [51:41] And then when their senses betray them, [51:44] Like, [51:45] They just stop. [51:46] You know, I used to bring David Blaine to Twitter and stuff. He's an old buddy. [51:51] And I would just watch the smartest people I know go... [51:53] 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. [52:01] But she watched me and was like, oh, he doesn't know this one. [52:04] He can't figure it out. And she's like, David Kwong 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 I mean... [52:13] Uh... [52:14] Okay, so what I would say is there are authors who make me... [52:19] Steve Martin. [52:21] PJ O'Rourke, who's passed away since... [52:23] Um... [52:24] Chuck Closerman, uh, [52:27] There are authors where [52:29] I'm forgetting like a dozen. I read too much. [52:32] but where I... [52:34] I'm like... [52:35] That sentence, man. How can I ever... You wrote Richard Powers? No. Oh, the Overstory? Yeah, sorry. I didn't remember that. No, there are people, and there are people who write

[52:46] sub stacks and so 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 [52:55] So... [52:57] 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. [53:02] It's such accessible, normal, normal. [53:05] everyday language, communicating incredible things. [53:09] ideas from a completely... [53:14] like familiar life to any human being. [53:18] And I constantly reread it and intimidated by it. [53:22] And so 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 lot of evangelical speakers. [53:33] Uh, I, I, [53:36] I watch a lot of [53:38] ultra-populous Republicans. [53:40] You know, I... [53:41] I tell our people, if you're not diving into... [53:46] The whole Charlie Kirk thing is a... [53:50] horrible tragedy. [53:52] I don't think he had the best intentions in... [53:55] I think a lot of what he was arguing was insincere. [53:59] But I listen to it constantly. [54:01] Like he went on Gavin's podcast. I think Gavin is a great person with good intentions. [54:06] But Charlie ate him alive, you know, and and I'm like, this is just a rhetorical master. [54:11] 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.

[54:18] And so there's no denying the effect he had and the relationship that [54:22] His viewers and listeners and the people who showed up with him had [54:25] And that power of debate [54:27] to make somebody feel like they're invested and they follow the chain of reasoning to that end point. [54:33] More like a story. Yeah, we have to not run away from that. We have to understand why people crave it. [54:39] and why it makes them feel like a co-author of the story. [54:42] Think of [54:43] I talked to Ira Glass about this. [54:45] 10 years ago. [54:47] You know, I... [54:48] I was on primetime television and I used to do, I was out there, I was exposed. [54:53] But... [54:54] The people who come up to me. [54:57] And have the strongest reaction to me were people who heard me on a podcast. Yep. [55:02] Like that, [55:03] startup podcast with Alex Bloomberg, you know, season one, episode one. [55:08] 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. [55:14] So I talked to Ira, who is the greatest audio storyteller of all time. [55:20] and like wildly intimidating as a result. When you talk about speakers, I would put him there. [55:25] Uh, and, and so is Alex Bloomberg, Alex Bloomberg, who co-created this American life with him. It's just incredible. [55:31] But, [55:32] I think about... [55:35] I think about why people feel like they have such an intimate relationship. [55:39] deep relationship. Like I could walk down the street in New York with Edward Norton. [55:43] One of the great, I mean, you've been there. [55:45] 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,

[55:52] Just all the things. [55:54] 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. [56:00] Oh my, literally missed her. [56:01] Oh, Mr. Norton. [56:03] I loved you in, and it's wild to see. Like, was it Primal Fear or the Hulk or whatever, you know? And so... He's not really a person. No, he's characters. He's a series of characters. [56:13] and, [56:14] 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. 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. [56:30] But, um... [56:31] 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. [56:39] And so... [56:40] So when I am on a podcast... [56:42] And I try to be as real as possible and talk about things people don't expect me to talk about. [56:47] Then they believe we know each other. Yep. [56:49] This came full circle for me when I met Alex Bloomberg for that episode to tape it. [56:56] I was not convinced that podcasts were a business yet. Remember that? You were there. You were working with us at the time. [57:03] but hell yeah, I was going to take a meeting with Alex Bloomberg. Like I, [57:07] He'd been in my ears. This American life was kind of like my church. I'm not a religious person, but that was a spiritual thing for me. Come out on Sundays. [57:16] And, um, [57:17] 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.

[57:22] And so when Alex Bloomberg wants to meet me, I'm like, yeah, yeah. And I'm going to 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, you're like telling a story back to him. And it's awesome. But I show up. I go to walk into our favorite sushi restaurant in L.A., Maury. [57:41] And as I'm putting my hand on the door handle, I'm like, wait, wait. [57:45] I don't know what... [57:46] Alex Bloomberg actually looks like. Right. [57:49] I have spent so many days with him. His voice is in my head. [57:53] 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. So I don't know if they influence each other that way. But... [58:04] But I walk in and I start panning this restaurant panicked, like which of these people is... [58:10] is Alex Bloomberg. 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, [58:18] All right. That's clearly my guy. But I had been building the story. I had been setting that stage and costuming it and [58:26] And I do think that's one of the... [58:29] And the long form nature of it, [58:32] I think there is a lot of reward with an audience for being real. [58:37] Being yourself, not everyone adheres to that or 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. [58:46] But... [58:47] But... [58:47] the power of podcasting. I have this theory right now that [58:51] if the Dems ever have a president again, or we even have free elections again,

[58:56] I... [58:57] I'm not sure if it's a current politician. [59:00] I think it has to be something that someone that comes out of podcasting or sports. [59:05] Stephen A. He's waiting in the wings. Years ago, I told Cory Booker, [59:09] Corey is an incredible person and a true public servant. [59:13] And just an inspiring guy. [59:15] But I was like, if you want to shatter like the glass ceiling of irrelevancy to America, it's like you played football at Stanford. [59:22] Go on. [59:23] College game day. [59:24] Just sit at the desk. Chalamet did this, dude. What's that? Chalamet did this. Yeah, yeah, yeah. Crushed. Yeah, yeah. I was like, just go. [59:31] And do not talk about politics. Don't even have them introduce you to Senator Cory Booker. [59:35] Just talk about football. You know it. [59:38] And then, like, maybe two years ago, I talked to Gavin... [59:42] Here in New York, actually, this week, two years ago. [59:44] I was like, [59:45] 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. [59:54] And so I said, [59:55] Have a sports podcast. [59:57] Like you care about sports. I know you know how to talk about sports. You never do. [1:00:01] 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. [1:00:13] I'm like, what are you doing? And he's like, [1:00:15] So look, I got this thing. It's me and Marshawn Lynch. And I'm like, fuck yeah. You're going beast mode? You're going... [1:00:22] You got to take care of your mentals and your chickens. I'm like, that is amazing. [1:00:26] And he's like, and they put it on Sirius. And I'm like, that is the opposite of amazing. Like you might get to a few truck drivers, but like,

[1:00:35] And then they talked about politics. [1:00:38] And so... [1:00:39] I love what he's doing now. I mean, I think Gavin's only hope is to just shake it up and, [1:00:45] Break every norm. [1:00:47] Uh, and so I love what he's doing with his content right now. Uh, it's, [1:00:51] There's no downside to it. There's just a limit on what he could be [1:00:55] Politically, if he doesn't build that connection with an audience and motivate people, but [1:00:59] But I actually think... [1:01:01] The best shot. And by the way, like I think George Clooney could have been president some years ago. [1:01:05] Um... [1:01:06] But I don't think it's going to be a traditional star now. I think it's got to be someone who feels like they have a recurring star. [1:01:13] connective, vulnerable, authentic person. [1:01:16] relationship with an audience. [1:01:18] And I think today that's podcasters and athletes. [1:01:22] You gave up on having an audience and you don't write publicly anymore. [1:01:26] Oh, I miss it. I miss it. [1:01:30] It's a drug though, and you can get addicted to it for all that self-reinforcing stuff for sure. Yeah. [1:01:35] I mean, people would scream about me on the internet, on podcasts, or I mean, on, on like message boards and Twitter and stuff like that. I didn't love that. You, you... [1:01:43] Everyone's like, don't read the comments. You're like, you can only read the comments. Twitter is only the comments. Yes. Right. [1:01:49] And we're just built back to that cognitive biases thing. We're built to like, [1:01:53] There's 20 flattering things and then there's the... Find the one. Fuck you. I mean, dude, I saw a comment... [1:01:59] Where somebody... [1:02:01] Apparently my eyes turned down on the corners and that's associated with some level of retardation or something like that. And,

[1:02:08] And like... [1:02:09] I'm like, wait, what? And like, I like 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 Malini 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. Yeah, that's that Internet. Last night I was out late in New York with our team. I was standing. I was talking to one of our founders, actually. [1:02:35] This really cool guy, Carl, who works for Zanskar, he runs Zanskar, which is this incredible geothermal company. [1:02:41] And I said... [1:02:42] You know, it's funny because [1:02:44] And a guy walks by. [1:02:47] And he goes, it's not funny. [1:02:49] And then just keeps watching. And I was like, dude, 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. It was actually funny, but I loved it. The timing was, I was like, you know, New York is amazing. But, uh, I want to talk a little bit about investing and risk. We're going to have to, we're going to have to do a little bit with Chris Saka here. Um, yeah. [1:03:10] Famous line, it may be lucky it's not an accident. [1:03:12] Classic. I've repeated that to many, many people. Um, [1:03:16] You also are... [1:03:17] very thoughtful about, like, stacking the deck, playing a game you can control. I'm curious, so super open-ended question, but, like, [1:03:23] You have a... [1:03:25] really, um... [1:03:28] strategic and successful relationship with risk. [1:03:32] And my sense is that most people wildly under overrate risk or are afraid of risk.

[1:03:38] And I'm curious, like, [1:03:39] 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. [1:03:45] Thank you. [1:03:46] Okay, there's a couple components to this answer. [1:03:48] But... [1:03:50] I'm going to tie this back to what you were just asking about, which is something I haven't talked about as much, but... [1:03:54] I... [1:03:57] I do miss having an audience and I'm writing something right now for an audience. [1:04:02] But I really worry that [1:04:04] ChatGPT has diluted the power of words and has taken a lot of the soul out of writing. [1:04:10] Because it's pretty fucking good. Yeah. [1:04:12] It's not great, but it's pretty fucking good. And in the same way that I regret that I think Instagram cheapened photography. [1:04:18] And took a lot of the soul out of photography. [1:04:20] I, um... [1:04:22] And AI is doing it like AI image editing is just is doing it all over again. [1:04:26] and maybe Sora's doing it for video and stuff, but [1:04:31] I have something I'm really obsessed with right now, which is I talked about a little bit with Tim. [1:04:36] he knew I was working on this idea and he kind of forced it out of me to talk about it. It's, it was really preliminarily baked. And since then I have someone I'm working with it on and stuff, but, [1:04:47] We all kind of tease this generation for various ways in which we... [1:04:51] and while I'm [1:04:53] decidedly Gen X. I'm 50... [1:04:56] I use good skin cream, but I'm definitely 50. [1:04:59] And I'm 50 from Western New York, right? A banged up place. [1:05:03] Rust Belt, um... [1:05:05] I'm still really close to my friends from high school. [1:05:07] some of whom have had hard paths, you know, and, um,

[1:05:12] And it's caused me a lot. Like guys, by the way, guys like Chuck Closterman who've written about our generation, um, [1:05:18] And then Gene Twenge's book about generations – [1:05:22] 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. [1:05:29] That's pretty cool, man. I've become pretty proud of who we were, or our... [1:05:35] But I've started to take responsibility... [1:05:38] In the same way that we think boomers need to take responsibility for the ways in which they fucked up our planet and economy. [1:05:44] We need to take responsibility for the ways in which we fucked up kids. [1:05:48] And so I really have trouble talking about this without feeling like I'm [1:05:52] Like, [1:05:53] characterizing an entire generation of people as broken. And 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. [1:06:03] So go ahead, say it. Um, [1:06:05] So, [1:06:06] But I... [1:06:07] I worry. We see... [1:06:09] Too many people, I won't say all the people, but too many people who have no... [1:06:13] Agency. [1:06:15] No... [1:06:16] Resiliency, no adaptability, take no initiative. [1:06:19] A friend of mine phrased it once. My friend Matt from Bozeman said, they ask for permission to solve a problem. [1:06:27] And like Crystal and I lit up. Yes, for permission. Ask the question. [1:06:31] In a 30 person Zoom, they let everyone know they're going to the bathroom. And I'm like, [1:06:36] You're a professional, makes hundreds of thousands of dollars a year, leads, [1:06:40] Tens to hundreds of millions of dollars of investment.

[1:06:43] go 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, [1:06:49] 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. [1:06:55] 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. [1:07:03] And so, [1:07:04] What I... [1:07:06] What I really worry about is that we don't give kids a chance to fuck up anymore. [1:07:11] We don't give kids a chance to take risk and to make bad decisions. [1:07:15] Whether it's helicopter parenting or snow pile parenting. [1:07:19] or robbing them of a play-based childhood as Jonathan Haidt likes to talk about. [1:07:24] 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. [1:07:34] And I really love his heterodox approach to this. I think he is... [1:07:37] one of the [1:07:38] most honest brokers of truth and what he's trying to find out about what's happening to kids and [1:07:44] Originally it was girls and now he's realizing men and boys are so deeply affected by this too. [1:07:48] But... [1:07:49] But I think at the heart of it, it lies that we just don't give – [1:07:54] Kids a chance. [1:07:56] anymore [1:07:57] to make decisions, let alone bad decisions. Like, [1:08:00] Good decision making comes from bad decision making and the consequences of like, whoops, that was stupid. Be on it. Yeah. And just, um, God, there was a, there was a fight at our kids' middle school last week. [1:08:11] And I don't know any, I don't know the two kids are involved.

[1:08:15] But unlike the fights we had in where there's 10 different camera angles of this fight. Right. And I watched him. Two slaps got landed. They 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. [1:08:42] This is a public school. The school suspended... [1:08:44] the core witnesses to the fight for a day. [1:08:48] and then suspended the participants or protagonists of the fight for two months. Oh, my gosh. [1:08:54] 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. But I was like, wait. [1:09:01] Crystal and I... [1:09:04] have worked [1:09:06] extensively to help people. Did you ever come with us to prison? [1:09:09] We have after. [1:09:10] we've worked on helping [1:09:13] California used brain science. [1:09:16] to pass a law. [1:09:17] that allows anybody who is sentenced to die in prison, [1:09:20] for a crime they committed [1:09:22] under the age of 25, to be eligible for resentencing. [1:09:26] Not necessarily freed. Not everyone should be freed. [1:09:29] But there are some people who did... [1:09:33] horrible things when they were 16. [1:09:35] usually as a result of horrible circumstances they found themselves in, but did horrible [1:09:40] inexcusable things when they're 16. [1:09:42] But we now know your frontal cortex is not formed, fully formed until you're like 25, 26.

[1:09:48] There's just clear science on that. [1:09:50] And we do dumb shit. [1:09:52] And sometimes that dumb shit has, you know, like, [1:09:55] mild consequences and sometimes it's life-changing for yourself and others but [1:10:00] I'm like, [1:10:01] 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... [1:10:16] It wasn't hate or racial or anything like that. It was just two kids who... [1:10:20] 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. [1:10:26] Okay, by comparison... [1:10:28] I had this buddy in school, um... [1:10:31] We called him Hawkeye. He knows who he is, but [1:10:34] who would see a fight start to break out in the hallway. [1:10:37] I went to a huge public school, fights all the time. [1:10:40] I lived in Fear of the Hallway. I was a nerd. I was an easy target. You're making the back programming. Yeah, I had to make friends with protectors, but going to jail. You got to find the big guy to be your ally. But [1:10:52] But he would see a fight start to break out and he would immediately go in and break it up and be like, let's settle this after school. [1:10:58] He would find a yard, like a kid who lived near a school. [1:11:01] say, let's do the fight in this yard. Okay. He would bring a video camera, charge admission to the backyard, and, [1:11:09] give a cut to the kids who are fighting. [1:11:11] I mean, he would make so much money doing this. I kind of admired his entrepreneurship.

[1:11:20] And, [1:11:21] I mean, look, in school... [1:11:24] I sold blow pops. So did Hawk, actually. I think he pioneered it. But, you know, I didn't deal drugs. I dealt sugar. [1:11:32] Uh, and it was totally against the rules, but I had a secret pouch in my backpack and [1:11:36] Um, [1:11:37] They were a quarter, five for a dollar. Sour Apples cost a dollar because they were rarer. They had a different font on the label. Nobody understood it. [1:11:45] We would buy those bullet pops for seven and a half cents wholesale, but you could buy a box of sour apple. [1:11:51] So there was way more supply of sour apple in the market than anyone thought. They thought they were getting the one. Yep. [1:11:55] I also ran a card room in school. [1:11:59] I ran a literal... [1:12:01] Like, [1:12:02] We played a game called Buree. [1:12:04] that [1:12:05] I'm pretty sure no one listening has ever heard of. It's mostly played on... [1:12:10] in nba locker rooms and on flights right now it's a game that originated i think in louisiana [1:12:15] any I've [1:12:17] Like any pro ball player has played Bure. It's a progressive pot game. The stakes are really high. [1:12:22] And I ran a spades room, too. That endeared me at President Obama. He'd throw spades. But I had a teacher, Mr. Maine, since passed away. You paid him a cut, right? I gave him a piece of the vague, man, a piece of the rake. And so I ran a tab. I loan sharked. I... [1:12:43] I did shit like this all the time. And I would get busted and there'd be some consequences, but I'd be like,

[1:12:51] 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 risks. You're also the guy who wrote a $25,000 credit card check into PhotoBucket. Yeah. And like, and maybe. But you see the relatedness of this? Yes. Okay. Like, but by the time I wrote a $25,000 check to PhotoBucket, by the way. [1:13:10] A few years before that, I had... [1:13:12] Lost. [1:13:13] millions of dollars by... [1:13:16] by, um... [1:13:18] By basically trading on crazy margin online. You were down $4 million. You had to work yourself off for a job. It came out of Google, not that rich, because you would work yourself out of $4 million of debt. And then somehow also had enough conviction. Like you are using risk as your ally. [1:13:33] there's a broad-based fear of risk that culture has today, obviously. And then there is like, [1:13:40] I don't know how you have the balls to... [1:13:43] And part of it, again, I think is that you're taking less risk than maybe it looks like from the outside looking in. [1:13:48] Thank you. [1:13:50] I mean, you talked a little bit about playing rig games. So look, I... [1:13:54] I was fascinated as a kid with, look, I started going to university for math in sixth grade. I would sit with college students at night and, [1:14:02] Um, [1:14:03] And so I was a math kid. [1:14:06] I could calculate pot odds in my head. [1:14:08] I could do expected value calculations and, [1:14:11] I knew enough. I loved books on casino science. I actually just had one show up on my desk. I haven't read it yet. But like just before I was leaving to come to New York. [1:14:21] I have a new one on casino designed for addiction.

[1:14:24] Oh, addiction by design. [1:14:26] Is that it? Yeah, yeah, yeah. My friend Blake Robbins. Yeah, okay, okay, thanks. I haven't read it yet. I'm stoked. [1:14:31] But... [1:14:32] But I knew there's a reason Vegas exists. There's just no winning bet in Vegas. So I was always smart enough to not gamble, but I was fascinated by gambling, fascinated by the narrative, fascinated by lotteries. [1:14:44] 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. [1:14:51] you know, but knowing it's a, it's a losing. Um, and so, so I only play rigged games. Um, [1:14:57] And, [1:14:58] Venture to me, venture investing is rigged. I am a horrible public markets investor. [1:15:02] 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, I can, [1:15:07] I would talk about a stock and I'd look and I was like, it didn't move either direction at all. Volume didn't change. Price didn't change. [1:15:14] I'm like, so this sucks. But also I'm not a good picker of public stocks and I can't affect the outcome. [1:15:21] Adventure. [1:15:22] Like, I, look, [1:15:24] People have accused me of being self-promotional. I'm like, if I don't promote myself, who's going to? But I also like... [1:15:29] I... [1:15:30] 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, [1:15:35] I'm good at increasing the likelihood of success of a company. [1:15:38] That's why people bring us our companies. [1:15:40] That's why... [1:15:41] the 214 X we put up on our first fund and the 17 X on fun too. And, [1:15:47] Everything we, you know, the six plus billion dollars of return to investors on just secondaries alone. Like I.

[1:15:54] I... [1:15:56] It is not maybe lucky, but it's not an accident. I know how I've caused that. And people are like, you might be lucky. And I was like, it's weird how I keep getting lucky, huh? [1:16:04] Like, [1:16:04] And, you know, like maybe 13 or 15 times I've been lucky. Weird, right? [1:16:09] Like it would be odds in the quintillions, but by the way, you said you're not good at Publix. I think it's also worth noting. [1:16:16] Crazy lowercase one fund, obviously. People know you as this legendary angel seed guy. [1:16:21] You made a lot of your money as far as I understand. [1:16:23] by owning 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. [1:16:36] 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 badged me in. [1:16:51] 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 it. You were actually improving its office. I... [1:16:58] Kind of did the first $30 million. But 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. [1:17:07] 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 RISD and own the majority of this thing. Yeah. And I mean, Seahel RISD was an incredible partner on that. It unlocked a lot of capital for me.

[1:17:24] But yeah, look... [1:17:26] I knew at that point it was mispriced. [1:17:28] 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, [1:17:34] I'm no longer here to convince them. I'm here to take their stock. [1:17:37] And so I just went and rolled it up from people who didn't believe. [1:17:40] And, yeah, by the time of the IPO, I think we owned like 16% of the company. [1:17:45] And so like 15.8, I think was the number. [1:17:47] Um, [1:17:49] And so I... [1:17:50] I do the same now. Like I just explained how the expected value calculation of fusion had changed from the way the market prices it. [1:17:58] So now we're into fusion for... [1:18:02] 10 figures. [1:18:03] And when you have conviction, you are smashing the throttle. That maybe is the difference. Yeah, and I also know I can make fusion more likely to happen. Yeah. And so... [1:18:10] And so I, but that's it. That's, that's across all of these things. And so, [1:18:15] When you talk about like having the stones to take risk, [1:18:18] First of all, I think [1:18:19] I think sometimes risk is mispriced. [1:18:22] And a lot of that is maybe rooted in narrative, rooted in fear, rooted in imposter syndrome. [1:18:27] Um, [1:18:28] And [1:18:29] And [1:18:30] under pricing the ability to actually [1:18:33] impact the outcome. [1:18:35] But... [1:18:36] But I also believe [1:18:38] I think we were working together when somebody asked... [1:18:42] So what are all your most successful experiences? [1:18:44] founders have in common. [1:18:47] And I was trying to find a thread... [1:18:50] And, [1:18:51] Like it wasn't how they grew up. I mean, I could say some like there's no doubt that.

[1:18:55] kids, immigrant kids, just [1:18:57] are just like the things they overcome to get here and build stuff. [1:19:02] Their hustle, their desire, their focus is insurmountable. [1:19:06] Thank you. [1:19:07] 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, like it's, you can't deny that [1:19:16] their disproportionate representation [1:19:18] within successful entrepreneurial roles or at these companies. [1:19:22] Um, [1:19:23] But I kept looking, I'm like, are they scientists? Are they computer scientists? [1:19:27] You know, did they did they all sell blow pops when they were kids? You know, did they have a hustle? [1:19:32] A lot of them did, but not all of them. [1:19:34] But the single thing I found among every one of our most successful founders was, [1:19:40] is... [1:19:41] Thank you. [1:19:42] Not only did they not prepare for the downside case, it just wasn't one of the options. [1:19:48] in the math. [1:19:49] It just wasn't [1:19:51] Zero was never a consideration. [1:19:54] Or a possibility. That's inevitable. [1:19:56] "'Yeah.' [1:19:57] And so, [1:19:58] I mean, you know this. When I first sat with Kevin and Mikey, who were building Instagram, [1:20:02] 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. [1:20:08] I'm like, okay. [1:20:09] You guys. [1:20:10] We're meeting right now in a co-working space. You're two of you. We are in the... [1:20:14] dark shadows off stage of like Calacanis was running some pitch event and, [1:20:19] I think, by the way, Travis pitched on that same stage, that same night I spent time with [1:20:24] Mike and Kevin, if I remember it right.

[1:20:26] But [1:20:27] But I'm like, what's with this 10 million users thing? [1:20:30] But... [1:20:31] Kevin wasn't trying to sell me. [1:20:33] He just knew it. Right. He literally knew it. Right. You can just tell. Like, you can tell in body language. You can just tell. Yeah. Yeah. [1:20:40] 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. [1:20:49] or, [1:20:49] you can tell if somebody's hitting on you. You can tell if somebody's trying to steal from you. Like 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. [1:21:00] You can try to train this. I mean, I remember being on a train in college and reading... [1:21:05] Mike Caro's book of poker tells. I think that was the author. And it was basically, and then, um, who is the micro expression guy? [1:21:13] There was a guy who trained everyone, FBI and CIA, and like the eye wrinkles and how to read micro expressions. So you can train yourself a little bit. [1:21:22] But it really comes from just knowing people and spending time with all types of people. And so [1:21:26] Travis? [1:21:29] We haven't talked in a long time, so we don't agree on a lot of things, but... [1:21:33] He was my closest friend for a while. And we spent a lot of time together and, [1:21:38] We worked on Uber for six months before it was incorporated. [1:21:41] And he was there. He was an advisor of the company early. [1:21:44] By the way, little known fact about Travis. [1:21:47] There was a point where he was weighing whether to become [1:21:49] CEO of Formspring or CEO of Uber? [1:21:53] Same. 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.

[1:22:05] I think the world worked. I mean, TK is just a wildly talented person, but [1:22:13] One of his things that maybe might have led to his imbalance, and I do think [1:22:17] Travis is 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. [1:22:23] to some extreme places. [1:22:26] uh, [1:22:27] But... [1:22:28] But TK... [1:22:29] I remember being in the meeting [1:22:31] where... [1:22:32] Maybe Ryan Graves had shown some analysis. Ryan was, you know, first employee at... [1:22:37] at, um, four square at, um, [1:22:39] Well, I don't know if he was first employee at Foursquare, but he was first employee at Uber. Oh. And so... [1:22:45] And, [1:22:46] Wasn't he CEO briefly? [1:22:48] Of Uber? Yeah. I mean, [1:22:51] Ryan was CEO in a time when it was a relationship business. Ryan looks like the Marlboro Man. [1:22:56] He is just this incredibly handsome guy from a cigarette ad from the 50s. [1:23:00] but he also has a very high EQ. And so Ryan, at a time when drivers were suspicious of us, [1:23:07] Ryan could walk into a room full of very skeptical Armenian people, [1:23:11] Limo drivers. [1:23:13] at risk of maybe being pummeled and dropped in the back alley and walk out arm in arm with these guys. [1:23:17] And so, [1:23:18] I mean, that's still who he is. He is just a guy you can build a relationship and count on. And I think he's gotten even... [1:23:24] Higher EQ at times. [1:23:26] But there was a point where we started to realize it was a math company. It was the biggest yield equation in history. [1:23:33] more than the airline pricing, you know, like we had,

[1:23:36] more units and more data and search pricing. It was just becoming a huge equation. [1:23:41] And Ryan just didn't come from the world of cohort analysis and regressions and stuff. [1:23:48] Travis, that's his kink. Like, that's, like, Travis can do it in his head. [1:23:53] And Travis could just try. I just remember saying, you know, Travis being like, hey, once you. [1:23:58] 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 [1:24:06] But, [1:24:07] Travis could just do that. [1:24:08] And we started to realize like this is a math company. This is less about relationships. [1:24:12] You know, in the end, [1:24:14] Maybe we needed... [1:24:15] more Ryan and more relationships and the company would have been in a different place. [1:24:20] But the reality was turning all the math dials 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. [1:24:29] Maybe it never could have been. [1:24:31] We're in this meeting once. [1:24:33] I remember being in the meeting where Ryan Graves... [1:24:35] tells us the data show that Houston is the next city we should go to. [1:24:39] based on cabs and black market and, or, uh, sorry, black car market and cabs and, [1:24:45] Um, [1:24:46] And, [1:24:47] Trav's like, no, we're going to Paris. [1:24:50] And we're like, what? And he's like, they hate us there. [1:24:54] Bye. [1:24:55] I'm going to win Paris. And he went to Paris and he stayed in a hostel. [1:25:00] and won Paris. Now, by the way, a lot of the original ideation for Uber happened in Paris.

[1:25:07] Travis and Garrett and Melody McCloskey. [1:25:10] was there in the early days and we were around, it was at LeWeb, 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, [1:25:18] 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. [1:25:26] Bye. [1:25:27] Um, [1:25:27] But he's like, I'm going to Paris. [1:25:29] And so, [1:25:30] Normal people don't do that. [1:25:32] But he just knew we would get it. To be clear... [1:25:35] They set Ubers on fire. They dropped rocks from overpasses through the windshields. [1:25:40] And yet, [1:25:41] Like, he did it. [1:25:42] I mean, later, think about Travis going to China. [1:25:46] Like I'm going to go up against a state-sponsored ride-sharing company. And by the way, everyone likes to characterize that as a loss. [1:25:55] He turned $2 billion into $17 billion. I'll take that trade every time. I didn't know that. It was a genius move. I mean, he definitely got punched in the face over and over again, in the figurative face, over and over again trying to do that. [1:26:08] 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? [1:26:18] And I mean, people get disappeared sometimes there, right? Yeah. And so... [1:26:23] But, [1:26:24] So when I take it to my own journey, [1:26:27] When I lost $4 million in... [1:26:29] Uh, [1:26:31] In 2000 and the market crash, by the way, I lost $16 million. I was 12 million to the up and 4 million in the hole.

[1:26:39] I'd never spent any of it. I had nothing to show for it, but I was just... [1:26:43] 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. [1:26:51] I went to a check cashing place. [1:26:54] Because I didn't want the... I went to a check cashing place, paid a ridiculous vague to do that. [1:27:00] and then kited them into the market. [1:27:02] But when I was $4 million in the hole, here's what I've now been told it was different. [1:27:07] was [1:27:09] 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. [1:27:18] Slow things down. [1:27:20] That's the difference, I think. And so... [1:27:22] That is an internal locus of control, maybe more than anything else. [1:27:27] 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. [1:27:33] But I think when people really get hit on risk too, like they probably internalize that as like, [1:27:38] or sorry, 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 going to make it back. Yeah. Yeah. That's. [1:27:48] And again, because I could impact that. I'm like, all right, I got to just build a thing and work that much harder. And like, damn, I hate. [1:27:55] 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. [1:28:02] It doesn't seem like it. All the time. [1:28:05] By the way, if you don't, do you listen to Neil Briden's podcast, Blocks? That's one of my favorites. Check it out. Neil...

[1:28:11] Neil is in [1:28:12] like a really cool person. Um, but, [1:28:15] Neil [1:28:17] kind of pivoted [1:28:18] stand-up comedy into that realm of vulnerability. He wasn't the only one, but he's had [1:28:23] maybe three very successful Netflix specials in which his comedy is rooted in [1:28:29] in just burying his soul talking about depression talking about struggles [1:28:34] I mean, his most recent Netflix special was incredible because he's like, [1:28:37] For those of you who know me from... [1:28:39] three mics and from blocks um [1:28:42] you're going to be a little upset because I'm happy now. And so, but one of the things he talked about in this special blocks was – [1:28:50] all the things that have gotten, all his own things that have gotten in the way. [1:28:55] that had become obstacles he's either had to overcome or still weigh him down. [1:28:59] And he actually took a... [1:29:00] There was so much emotional response to it, not just among audiences, but among peers. [1:29:06] that he made it into a podcast where he brings on [1:29:08] performers and creatives. [1:29:10] And they talk about their blocks. [1:29:12] This is a guy. [1:29:14] who is so deeply respected, and the nature of those conversations are so raw, [1:29:19] He got Jerry Seinfeld to admit to imposter syndrome. Still! [1:29:23] Like Jerry still struggling with the idea. Like I'm not a standup. Come on. Who can do that? Right. I mean, Neil, Neil is uniquely good at this. And it requires an incredible amount of courage to talk about. [1:29:37] the things that banged you up along the way. You know, I think we had a culture that really shunned and stigmatized those things. Maybe we're opening up more about it.

[1:29:45] Maybe like therapy and trauma culture has been a little overplayed among some people, but he gets people to talk about the real, real. [1:29:52] And, um, [1:29:53] And so, but I just say that as like, yeah, I have imposter syndrome. Look, I... [1:29:59] Until a couple of years ago, we didn't even have an office. [1:30:01] We launched an office because we realized our young people weren't learning from our more experienced people. [1:30:08] And that sucked because a lot of learning happens in collisions in the office or overhearing a call. [1:30:14] or being pulled in to take some notes or something like that. [1:30:17] Um, [1:30:18] or at lunch, you know, and... [1:30:20] It just doesn't happen over Zoom. Like, I work from the middle of nowhere. [1:30:25] And there are definitely advantages to that, like being in nature, being outside of the bubble, talking to real people all the time. [1:30:32] I actually feel more in touch with real politics than almost anyone I work with because I just am among... [1:30:38] Real people. [1:30:38] Like, um, like our... [1:30:41] you know, one of our daughter's best friend's dad drives a truck like an Amazon truck, you know? Um, [1:30:46] or they coach sports or they, you know, I, [1:30:49] like they just or bartender it's just real [1:30:52] You know, or work in the hospital, like middle class folk. And, [1:30:56] And so being out of the bubble is like psychologically refreshing and perspective. And from a relationship standpoint, raising kids standpoint, I mean, 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, [1:31:09] The kids can just roam. [1:31:10] Without phones, by the way. They just go. [1:31:13] And fingers crossed they come back. They usually do. 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...

[1:31:22] But for me... [1:31:24] not having an office, [1:31:26] Where... [1:31:28] 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 in the way. We don't have that place. We borrowed a portfolio company's office. [1:31:38] and put a logo up on a projector, [1:31:41] And then pretended to have a fake board meeting. Were you in that clip? I wasn't in it, but I remember that. Yeah. Um, [1:31:46] And they're like, well, come by your mansion. I'm like, I have a 2,000 square foot house. It's not going to impress anybody. [1:31:52] And they're like, okay, what about your boat? For Lori, they rented a boat to make her look rich. They just sailed around Newport Harbor or something like that. [1:32:00] But, [1:32:01] But I was like, I don't. And they're like, how is America going to know you're rich? [1:32:04] And it was just, it was really important for them that we look rich. Yeah. But yeah, because I don't look the same. [1:32:10] as the other guys because we never had a big office because we never had a big team [1:32:15] And because... [1:32:16] I was never I didn't go to school for finance, wasn't versed in finance. [1:32:21] And I was never really concerned with our IRR. [1:32:24] 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... [1:32:30] Think about cards, etc. How much money I put in and how much money I get back. Or sports gambling. Like how much... [1:32:35] By the way, when I get to New York, I can always use DraftKings again. It's great. I can lay action on my bills. I can bet a little bit of hockey. It's horrible. Sports betting shouldn't be a thing. It's horrible, but I love it. [1:32:48] But like, I... [1:32:51] I always felt like I wasn't a venture investor.

[1:32:54] Even making the Midas list, I'm like, what am I doing here? [1:32:58] 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, [1:33:07] Smashing the throttle down. Well, because I'm not a venture investor. I am a builder and a helper. [1:33:13] And you have confidence in that. [1:33:16] Yeah. [1:33:17] 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. [1:33:23] is [1:33:25] the tyranny of lack of relevant experience. [1:33:30] The most successful people I work with have no domain expertise in investing. [1:33:36] Thank you. [1:33:37] And that's me. [1:33:38] Like when one of my mentors, Hans Wildens, convinced me to launch a venture fund, [1:33:43] I was like, I've never managed anyone's money. I'm not even good at managing my own money. [1:33:47] Like, [1:33:48] Uh, I've had a collection agency after me at one point just because I forgot to pay the bill, you know, and, um, [1:33:54] I also have had him after me when I couldn't pay the bill, but, uh, [1:33:57] But I was like, how would I manage anyone else's money? And he's like, no, no, no, that's the easy part. We'll do that for you. I used Industry Ventures back office for the first couple years of lowercase. [1:34:05] Um, he's like the hard part. [1:34:07] is picking the company's [1:34:09] and making them better. [1:34:10] Actually, I think he might have said picking the companies and I added and making them better. You've always been... One of the things I remember way back when, people ask me how I learned from you and... [1:34:21] And there's two parts of it. One is obviously you don't want to bet on the things that need you.

[1:34:26] You want to bet on the things that, [1:34:28] are going to work with or without you. But you would always accompany that with like, [1:34:32] Yeah, where is the deck stacked? And I can have an impact. Well, the greatest... [1:34:37] I... I... [1:34:38] At heart, each of us wants to be helpful. Yeah. [1:34:41] You know, um... [1:34:42] One of our daughters, Cece, started volunteering recently in school, tutoring other kids. [1:34:48] She's like an academic superstar and... [1:34:51] Our kids are actually homeschooled for academics. [1:34:53] and go to school for orchestra, [1:34:56] phys ed and lunch and to play on sports teams like and so it's the perfect balance montana's amazing that they can do that yeah you know they i i found that the [1:35:05] And they were the ones who requested to homeschool. Academics for them were just... [1:35:10] they weren't as compelling and they were losing their curiosity and their thirst for learning. And so that's fed in the way. [1:35:16] They get taught with these Zoom tutors who are incredible and really [1:35:19] help pace that and push them and challenge them. [1:35:22] but they also are regular kids, you know, um, [1:35:25] Riding bikes, wearing hoodies, goofing off, getting in a little trouble, mixing it up. [1:35:29] doing dumb shit. Like I hope they would. Um, [1:35:32] I mean, by the way, like, have you looked at the data, like, [1:35:35] Kids, don't drink. [1:35:37] 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, [1:35:45] I've watched her light up. [1:35:48] Thank you. [1:35:48] as a consequence of being helpful. It's a new thing she unlocked. [1:35:52] She's a helpful kid around the house, helpful kid to friends, but being formally helpful to another person.

[1:35:58] and unlocking [1:36:00] what she's doing by tutoring kids who are English language learners. [1:36:03] and helping them catch up academically in their mainstream classes. [1:36:08] And frankly, when I first started in venture, [1:36:11] that [1:36:12] The trap was people would come pitch me and I'm like, oh, yeah, I can make this better. [1:36:16] But it wasn't already great. [1:36:18] And so I, my first four or five deals were shitty. Yes. Where they were like, they need, there's a me shaped hole here. Yeah. And, and, and that comes from imposter syndrome. I left Google, uh, [1:36:28] I left. [1:36:29] $100 million on the table when I left Google. It was... [1:36:32] financially a dumb decision and there were definitely days where i'm like what was i thinking [1:36:36] And so it wasn't 100 at the time It grew to be 100 but I bet you it was 20 And so it was stupid [1:36:43] And it took many years before that was the right trade. [1:36:46] But... [1:36:48] When I first started showing up in like... [1:36:52] you know, [1:36:53] Y Combinator or meeting with founders, [1:36:56] I... [1:36:57] Thought at first I was going to have to fake it until I made it. But instead, I was immediately helpful. [1:37:03] That was a great feeling. But I also had to build a feature of like when you work for a boss at a company, you [1:37:09] and they assign you something to do. You're working for Eric Schmidt. [1:37:12] And he's like, hey, I need to do this. You can't be like, no, thanks. What else you got? [1:37:16] Whereas when you start playing poker, you realize that most hands get folded, you know, or maybe you just check. [1:37:22] 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.

[1:37:35] they're like, oh yeah, I'm going to play the 2.7 and see how this goes. And so, [1:37:40] But... [1:37:41] But, [1:37:41] 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, [1:37:48] Can I be an investor? Yeah, I can make all these things better. [1:37:51] So I had to learn to build a filter of like, [1:37:53] what i do for a living is say no it's hard to be an optimist and say no all day [1:37:58] And then from that, I find things that are amazing and that hopefully I can make better. [1:38:02] So what I'm confident about is my ability to make things better. [1:38:06] And that's something we really work with our team on. [1:38:09] is [1:38:11] 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, Kai, maybe four. [1:38:21] We call her Kai EGPT. She's special. But... [1:38:25] But at the same time, we... [1:38:26] I think really successful investors don't have that. Our co-founder Clay is, [1:38:30] His resume betrays nothing that he would be an investor ever. I mean, he worked, he worked on an 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, [1:38:46] A person close to the president said, I pick up him like, hey, man, what's up? And he's like, hold for the president. [1:38:52] And the president was like, Clay, hire him. He'll thank me later. [1:38:55] And they handed it back to the guy. And I'm like, well, we're done with the reference check and clay. And so, [1:39:01] He also worked in the White House. Yeah, he was the chief of staff. We overlapped for like one month, two months, very tail end of my head. Oh, lowercase, yeah. Clay, we didn't hire Clay to be an investor.

[1:39:14] Yeah, it was all the puzzle stuff, right? Once you... [1:39:17] We're gone. [1:39:18] We had to write an update to our investors, to our LPs, [1:39:23] We had 100 companies and some more companies I'd never met because you did the deals. I didn't know any of these guys. [1:39:29] So I said to Clay, like, hey, I got to write about this stuff. And some of these are like. [1:39:33] 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? [1:39:39] So I can fulfill my duty to our investors. Like, here's what the update is. [1:39:44] And he had 25 hours in his day at the time. No kids yet. He's got four now, four under six, I think. Um, [1:39:50] So he... [1:39:52] He fanned out and started talking to these entrepreneurs. [1:39:54] And two things happened. One is they started calling us like Clay's amazing. Can he be on our board? [1:39:59] I was like, that wasn't even his job. He was basically supposed to be taking notes. [1:40:02] But he was not hired as an investor. He was supposed to help us with like politics and philanthropy. [1:40:07] But two was... [1:40:09] I think one of the quickest ways to learn this business is, [1:40:12] 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. [1:40:20] But it's, I think, even more helpful to get exposed to shit that's been going sideways. [1:40:25] you know, or that, that is everything in the very beginning. 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, [1:40:34] You can't lose. Yes. Most of the people we hire right now have never lost. [1:40:38] Like, [1:40:39] They... Right, in life. Yeah, they've... [1:40:42] I'll ace their SATs.

[1:40:44] 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 yeah, [1:40:51] If you're going to have a science-heavy team, [1:40:54] These are the best scientists. [1:40:56] And they've all gone to grad school and they all like just never failed. [1:40:59] But our business is one of failure. If you're not failing, you're not trying hard enough and you're not taking enough risk. [1:41:04] And so you have to digest that failure and, and, [1:41:07] It's funny, they struggle with it or they do the safe thing. [1:41:11] Um, and we have to teach that out of our teams often, right? [1:41:15] And so I, I, I mean, I guess it's sort of like teaching risk. Like how, how do you actually teach that? You, you didn't have to do a lot of that in lowercase era. [1:41:23] Yeah. Got a big team now. Okay. So here's one thing I do about risk. [1:41:26] I... [1:41:28] I make sure that no one is individually accountable for our losses. [1:41:33] I remember... [1:41:35] one of our early employees who I dearly love and we wouldn't have been able to build this [1:41:39] Without him... [1:41:41] Listen to a podcast about Bessemer. [1:41:43] where it's eat what you kill, where everyone's compensated on their specific deals. Right. [1:41:48] And he came to us and was like, I want to do this here. [1:41:51] And I was like, I don't think you do. [1:41:53] 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 awesome. [1:42:05] Recognized as the seventh best place to work in America. [1:42:08] 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. But anyway.

[1:42:15] It was the seventh best place to work in America. I was a first year associate. I needed help on something. [1:42:19] And I went two doors down to a fourth year associate who is smarter shit. Very successful. [1:42:23] And I said, hey, man, can you – I was like, hey – [1:42:27] Hey, Sarah, can you help me on this thing? [1:42:29] And 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. [1:42:34] I was like, wait, we work at the same business, right? Crazy. But 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. [1:42:45] 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, [1:42:51] 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. [1:42:58] I hated that feeling. Google was constructed the other way. When I first got there, I shared an office with Urs Hulsel, their very first engineer. [1:43:06] One of the most brilliant minds of all time and a wildly successful person in Google wouldn't be Google without worse. [1:43:11] By the way, there was a time when [1:43:13] I mean, he owned a real part of the company and was worth a lot of money. And [1:43:17] Somebody showed me a picture of one of the first TGIFs, like Friday gatherings of all the employees when there was like seven people there. And it was wearing the same shoes that he was wearing post IPO. [1:43:28] It was amazing. But here's a fun thing. There was an alias. [1:43:33] 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, [1:43:41] And then somebody on the legal team will be like, all right, I got this one and review the contract and send it back.

[1:43:45] um, [1:43:46] And one of the ways I learned the business is by just watching every single contract come through there, every type of deal from business. [1:43:52] The ads deals to the real estate deals. But one that went through was our company ski trip to then Squaw Valley up in Tahoe. [1:43:59] 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 Orz 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. It's like, I mean, multi-billion dollar budget, like in charge of all this engineering. He's like, what the? [1:44:15] He's like, what's the phone number on that? [1:44:18] And I'm like, and he just... [1:44:20] 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 and is like, great. And yeah, [1:44:29] I was just like... Radical ownership. We were all... [1:44:32] He was a Googler, right? One among many. And he's like, I can impact this. I'm going to do it right now. Yeah. [1:44:38] And so, [1:44:39] Every single person who works at lower carbon has a piece of the upside. [1:44:43] And every single person shares. [1:44:45] in each deal. I really needed a culture of where everyone was incentivized to high five. [1:44:50] And where everyone, if you went to them for help, they had every reason to help you. [1:44:54] or to volunteer to help you. [1:44:56] Um, [1:44:57] You know, one of the days I became... [1:44:59] I'm using these air quotes, ironically, like powerful at Google. [1:45:04] 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. [1:45:11] And my work partner wrote, [1:45:13] Chris doesn't know what to do about this.

[1:45:16] 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. Like everyone's going to 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, the emperor has no clothes. [1:45:33] The next meeting, Larry Page showed up. A guy you couldn't get scheduled to show up showed up because he had an idea. [1:45:39] And so did maybe like nine other engineers. [1:45:42] all there to help me. [1:45:45] Even though they weren't formally assigned to me. [1:45:47] I mean, what's the scarcest resource? It's human capital and building that stuff. And suddenly I was like, whoa. [1:45:52] Like I got backed into accidentally, regrettably, angrily backed into more power and influence and the ability to get shit done. [1:45:59] And so I wanted to recreate that environment of, [1:46:03] You can ask any single person for help and they want you to succeed. [1:46:07] In parallel, though, [1:46:09] I wanted to make sure that every single investment decision we made, like we have an investment committee. It's Clay, Crystal and I. [1:46:16] um and chris and i are the largest lps in the fund so we really have [1:46:20] hundreds of millions of dollars riding on everything we do. And I'm a capitalist and I have no allergy to making money and [1:46:25] I do think what we do is [1:46:27] It's not concessionary. It's not philanthropy. It is the biggest business opportunity. It's the biggest transformation in the economy right now. [1:46:33] 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 circular like that. But [1:46:43] I... [1:46:44] I want to make sure that every person in the company has a voice in the decision making process.

[1:46:50] that 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 hominem attack or anything really different [1:47:01] devolve into actual fights. [1:47:03] But if the debate isn't fierce enough, I'll be angry and upset about it and let down. [1:47:11] um because we i think the role of your colleagues is to push them but when we make a decision [1:47:17] Even though there might be a lead on that deal or somebody who brought it to us or somebody who's like responsible for that. [1:47:22] You know, like we had a deal where we took a $27 million loss. [1:47:27] And I know the person leading that deal took it personally. And I'm like, you can take it personally. [1:47:31] I think it's, I'm not going to tell you not to feel all the feelings about [1:47:35] What that was... [1:47:37] But that's not on your tab. That's not on your account. We're not keeping score, right? [1:47:42] You're... [1:47:43] you're a helpful person across so many other things and you wouldn't be here if we didn't think that. And so, [1:47:48] It's a bummer we took the L on that. [1:47:50] But... [1:47:52] That person wasn't capable of making those decisions unilaterally. That was a, that was, [1:47:56] Ultimately, like we signed the check, but that was a group. [1:47:59] decision, right? And I won't let anything get hung up in committee and it doesn't have to, nobody, [1:48:04] There aren't a lot of votes. Like it's not a democracy. Yeah. [1:48:07] And we don't have a system where like, [1:48:09] Someone gets a budget to like override everything else. Bullshit. Like we are the decision makers. It's 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, invite on podcast, go do it.

[1:48:25] Get your reps in. And, you know, Google did everything they could to shut me up. Um, and, um, [1:48:33] You're like that blog you're talking about. [1:48:35] The excerpt you wrote got me emotional about a particular event in my life, but at the same time, I'm thinking about how, [1:48:40] Elliot Schragge, [1:48:42] 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. [1:48:51] to like, [1:48:52] mind me and to tell me to stop talking to people. [1:48:55] And, um, [1:48:56] And every now and then I would say something like a very pivotal moment of my career. I was in Oxford. [1:49:02] Being interviewed, I was on a panel, and there was a... [1:49:06] Someone from the press, I don't even remember which newspaper, in the audience, [1:49:09] And they said, hey, [1:49:11] How come I can't? [1:49:14] Download Google Maps onto my phone. [1:49:17] 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. [1:49:31] By the time I woke up the next morning, that was all over every newspaper. Google versus the carriers. [1:49:37] And to be clear, [1:49:39] I was not a senior executive, but when you say something like that, it's senior executive Chris Sackett. I'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 so senior executive Chris Sackett has declared war on the carriers. [1:49:55] I am summoned back to headquarters.

[1:49:57] where my boss lets me know, um, [1:50:01] This guy, David Drummond, lets me know, like, [1:50:04] Yeah, so you should probably look for another role. [1:50:07] And I'm like, like in the company, [1:50:09] Like maybe I work for Jonathan Rosenberg and product or something. And he's like, oh, no, no, no, not not at Google. [1:50:14] And so he was like marching me to... [1:50:18] uh, [1:50:19] to the executive management group meeting where all the honchos were, right? [1:50:24] And one particular guy was responsible for mobile. [1:50:28] who I've since made up with, so I'm not going to call him out, but he's... [1:50:33] become very successful in his own right, but [1:50:35] He's like, I need... [1:50:37] a sacrificial lamb. I need to throw meat to the carriers to say, we killed this guy. [1:50:43] And this is not how we feel. Right. And so they were basically it was a foregone conclusion. I was dead. [1:50:49] And they were going to talk about how to message in front of me. Right. Like what, what do we say at his anti eulogy and Larry Page, [1:50:57] It was on his BlackBerry. He didn't even look up and make eye contact. And he said... [1:51:03] But what did Chris say that wasn't true? [1:51:07] And... [1:51:08] You know, there were, I mean... [1:51:10] It was already decided that I was gone. And he's like, I'm serious. [1:51:14] Tell me the thing that Chris said that wasn't true. [1:51:17] And, [1:51:18] It was silence for a while. And he's like, [1:51:20] They are inserting themselves between us and our users. We've never stood for that. [1:51:25] Everything we do is... [1:51:26] to keep Internet Explorer from resetting your search default so we don't have a direct relationship with our users there.

[1:51:32] Like everything we do with, [1:51:34] 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. [1:51:44] Like, [1:51:45] It may have pissed people off because it's true. Wow. [1:51:48] Thank you. [1:51:48] I left that meeting [1:51:51] with a multi-billion dollar budget, [1:51:53] to go scare the shit out of the carriers. Cute, which you need to pull off. And so, by the way, that was a huge hand of poker. Wow. We went to the Spectrum auctions. [1:52:02] A guy who worked for us, Rick Witt, [1:52:05] came up with this idea. [1:52:06] What if we attach, what if we convince the FCC to attach net neutrality rules to wireless spectrum? And so... [1:52:13] It was genius. This jujitsu movie did. [1:52:16] 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. [1:52:24] So, [1:52:24] So, [1:52:25] we decided, you know what we'll do? [1:52:27] We will say, Adam, you guys valued it at like $4 billion. We promise we'll bid $4.6 billion for it. [1:52:34] And look, we had the money. [1:52:38] But that's not what Eric wanted to spend that money on. He actually knew we were hiding. It was 2007, but he knew we were hiding into a recession. [1:52:45] He just knew already. And so he's like, I would prefer not to put... [1:52:51] $4.6 billion in this. [1:52:52] We had a plan for what to do, and part of my job was to [1:52:55] make sure Verizon knew we were serious enough. So I was out. [1:52:58] doing tower deals. And I mean, I and my team were doing tower deals, getting trucks ready to roll.

[1:53:04] We had Android in parallel. By the way, Android is pissed off at me because... [1:53:08] They had a clause like Andy Rubin is going to make like another $150 million or whatever if he signed up two carriers. [1:53:14] And now the carriers are like, why the fuck would we work with Google? I hate you. But we needed to build this net neutrality. There's no other company in the world that would let somebody roll $5 billion dice like that. And we want... [1:53:25] Verizon had to eat the spectrum. They couldn't afford to let us buy. [1:53:28] this incredibly valuable 700 megahertz, it penetrates concrete, et cetera. But, [1:53:32] but they bought it. And so your phone is essentially net neutral. [1:53:36] Like, and that was not the case back then. [1:53:38] But what I learned, and do you remember Marissa Mayer? Yeah. She's... [1:53:43] We were usually work rivals, but we've become friends since, and I really like her, but [1:53:49] She just said, oh, yeah. [1:53:51] My loneliest days at Google. [1:53:53] or when one line is taken out of context of what I said and used in a hit piece, [1:53:58] And then I walk around and it's like it's a ghost walking through the halls. Like I am... [1:54:03] Vilified, ignored, despite she was a senior executive and had earned that. Right. She was a total badass. [1:54:09] And so one of the things we've done when codified for our team is, [1:54:14] Take any invitation you have to be on a stage, a podcast, practice your storytelling, tell the story. [1:54:20] And if you sincerely believe the words that come out of your mouth, [1:54:24] They're not hateful or not toxic, but if you sincerely believe the things you say, [1:54:28] We will forever have your back. Like now you're friends with Ryan Orbach. That dude's got hot takes. I mean, just sizzling hot takes.

[1:54:35] But he can just go out in the world knowing we got him. [1:54:37] Right? [1:54:38] 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. [1:54:46] And so, [1:54:47] You know, one of our... [1:54:49] 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, [1:54:55] I like... [1:54:56] She's just an incredible outperformer. [1:54:58] She's accelerated her career by using an army of AIs, but also to simulate technology. [1:55:03] situations for herself to like [1:55:05] build board experience, et cetera. 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, [1:55:16] But like, I, you know, I think my own bias is like, all right, we need to add some 40 somethings to this company with a little bit of... [1:55:22] Deal experience. It's probably like HR. Yeah, it's probably HR illegal to say that. But we need some more experienced people here. [1:55:28] And then it turned out the call was coming from inside the house. Like it was... [1:55:32] Like Kai had this particular skill set we needed. [1:55:36] When I talked about the tyranny of relevant experience, one of our best investors right now is Lauren Forbes O'Connor. [1:55:41] who is a [1:55:42] Formerly a Chief Sustainability Officer for Los Angeles, she'd been in [1:55:46] government and policy a lot of her life. [1:55:48] And, [1:55:49] zero, zero indication that she could be an investor on her resume. [1:55:54] But God damn, does she make companies more valuable as a result. And so she came on as like an operating partner and very quickly became a partner partner. [1:56:02] Crystal, my wife, was... [1:56:04] wildly successful in the advertising world.

[1:56:08] like won all the awards for her creative work. [1:56:10] working at the coolest agencies and with the best partners. [1:56:13] But she was the one who didn't go to art school. [1:56:15] Like we met at the School of Foreign Service basically like, [1:56:18] precursor to CIA. [1:56:21] But she found her way into that. Nice parallel life path for Chris. [1:56:27] She just ended up being [1:56:28] You know, she would stay all night, literally sleep at work. She would overhear something that needed to be done, pick it up. [1:56:34] Taught herself. [1:56:35] photography, taught herself all the suite of tools you need. [1:56:39] Like already, cause she grew up all over the world and loved art, already had an eye for composition and, [1:56:44] and storytelling and [1:56:46] because she was a third culture kid, knew how to relate ideas to everyone. So it was great at tags and humor. [1:56:52] She's also the only person I've ever known who can just [1:56:55] I'd be like, hey, do you want to go to dinner? She's like, I need to write ads for an hour. [1:57:00] You can just sit down and be funny. [1:57:02] Like she could just decide, like, I need to be funny for an hour. [1:57:05] 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 [1:57:23] 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 onto this yet? I'm like, dial, bro. No, um, I haven't actually tried one. I know. Cause I won't be able to put it down, but like, but like, [1:57:35] I think that lack of relevant experience might be the superpower.

[1:57:39] So we look for those people more and more now. I want to pull on that. I mean, we only have a few minutes left, so we'll zag across a bunch of ideas quickly, but one big one, um, [1:57:49] You... [1:57:50] have walked away many times in your life. I see you as a particularly... [1:57:56] 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, [1:58:10] mom and dad's kitchen table and cried and was like, what have I done? It really was the greatest job in the world. [1:58:16] 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. Why does anyone walk away from that? You have this Minnesota speech. You gave the commencement speech. And one line in that is you talk about control-deleting and this being a rare opportunity when you're 22 to actually reset [1:58:32] You become a beginner again. Nobody does that. [1:58:35] Um... [1:58:36] in many ways is almost like different chapters. [1:58:39] 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. [1:58:48] And yet you keep doing it because it's what you need to do. [1:58:53] Yeah. Remember that book, The Fourth Turning, where they say the whole history is in these 20-year blocks? I've seen Van Nyset's videos. Van Nyset's video is fucking cool. All his videos are cool. But this one was really cool, the book report he did. [1:59:06] Are they called seculum or something? I forget. Anyway, these 20-year blocks...

[1:59:11] Thank you. [1:59:11] I did an exercise where I wrote my life out. [1:59:14] And it fits in seven of your blocks. Seven? Seven. [1:59:18] Not by design. It just always has. [1:59:20] Oh, looking back. Yeah. Wow. Yeah. Retrospectively, it's always been seven. Wow. I literally, I think there was one that went eight. [1:59:27] How far are we into this walk? [1:59:31] uh... [1:59:32] Seven. [1:59:34] And so, um... [1:59:36] Like, [1:59:37] The thesis started in 2017 and the execution started in 2018. [1:59:41] And so... [1:59:44] I didn't mean for there to be a regular pattern to it. [1:59:49] But I think there's a few things at play. [1:59:51] One is... [1:59:54] Emerging curiosities for other things when I think I've kind of gotten a subject matter dialed. [2:00:00] You know, it's funny. I got a chance to hang out with Questlove the other night, and... [2:00:05] Yeah. [2:00:06] Questlove is... I shared with him a story that he didn't remember at first, but... [2:00:11] A gazillion years ago, I'm standing with Evan Williams and Tony Hsieh. [2:00:15] The Zappos guy is no longer with us, but we were in L.A. and the roots were playing. [2:00:20] And I was like, you guys, you know, Questlove randomly follows me on Twitter. [2:00:24] I didn't have a big following yet. I don't know how he followed me, but... [2:00:28] um he just did maybe it was like a mutual friend or something maybe it was janina gavankar or someone put us [2:00:33] Yeah, but... [2:00:35] I DM'd him. [2:00:37] While he was playing. [2:00:39] He his phone buzzed. He reached down while still playing drums with one hand, saw the message.

[2:00:46] and wrote me back. No way. And then put it back in his pocket. And we were [2:00:50] The giddiest school children ever. [2:00:52] That I remember like Twitter, [2:00:55] 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. [2:01:04] And remind him of that story. He's like, oh, shit, I do remember that. That was funny. [2:01:07] And but I 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. [2:01:15] His playlists are sick. He's a crate diver. I like to crate dive, but that guy goes all the way. [2:01:20] Um, [2:01:21] You know, he teaches music. I mean, he's obviously a performer. It's just he produces. He's a film director. [2:01:27] Just incredible dude. So I felt like I was fanboying a little bit. [2:01:31] But... [2:01:31] We were at a discussion with a bunch of fancy, unbelievable people. [2:01:35] And it was about climate. [2:01:37] And he came up to me and said... [2:01:40] Um, [2:01:42] Damn, you remind me of the treasure of not being the smartest person in the room because often – [2:01:47] 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, [2:01:55] I know how unfulfilling it is. [2:01:57] And he's like, and so sitting here and listening to you talk about what you're up to and [2:02:02] and um and posing provocative questions other people in the room who are in the space and challenging them and [2:02:07] Reclaiming the moderate middle like I'm a climate investor who drives an F-150 Raptor and eats meat because steak is fucking delicious, right? [2:02:14] I tried being a vegan. There's a hole in my life.

[2:02:18] As he said that, my reaction was... [2:02:21] Yeah, this is why this discussion to me, like tonight... [2:02:25] It was fun. [2:02:26] but a little empty. [2:02:28] Because I wasn't being challenged. [2:02:31] And so I missed that. [2:02:33] We recently hired... [2:02:37] I didn't ask for it to be a young person, but we hired a very young person. What I said was, so I read three to four hours a day. [2:02:43] I track my time at 15 minute increments to see where it goes to make sure like to know who's wasting it really or how I'm wasting it. And so but it's three to four hours a day. I read every day. I'm obsessed with the eye. [2:02:55] 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 [2:03:07] The powers that be. Yes. 40 of them. Uh, [2:03:12] You would know the name of every single person there. Your audience would know the name of every single person there. [2:03:18] And 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. [2:03:26] I'm the least influential person in the room. Absolutely. [2:03:28] And maybe the poorest. 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 [2:03:39] Um, [2:03:41] lack of concern for humans, for fellow humans and stuff that I think is now [2:03:46] um the overton window has shifted on like what our responsibility is to other people so that's

[2:03:50] painful for me. I usually come home from this meeting a little depressed. A lot of depressed, actually. [2:03:56] But... [2:03:57] This particular year, [2:03:59] The moderator said, all right, everyone stand up. [2:04:02] We're going to do this thing where I'm going to pose a question and over this side is strongly disagree and over this side is strongly agree. [2:04:09] And so, um, [2:04:11] By the way, I should give credit. This is hosted by... [2:04:15] uh, 50 years fund. Uh, I forget what they call the event, but, um, [2:04:20] uh, [2:04:21] Seth Bannon and, and, uh, this is, this event is, is kind of spearheaded by, um, [2:04:27] 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, [2:04:38] The reason it's such a high-powered event is everyone respects him so much. [2:04:41] he can get them all to show up, you know? [2:04:44] Um, [2:04:45] 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... [2:04:51] Okay. [2:04:52] Do you believe there is a... [2:04:54] greater than 10% chance that within five years, AI has killed more than 50% of humanity. [2:05:03] All I'm going to say is every single person who works on AI full-time stood in the Strongly Agree column. [2:05:10] Like, [2:05:11] This was beyond even the job losses. [2:05:14] even the unavoidable disruption to the economy. [2:05:19] Um, [2:05:20] To the...

[2:05:21] I mean, you talk about like... [2:05:22] Yeah, I'm great at calculating odds, but I have... [2:05:26] No fucking idea what education looks like for our kids anymore. What skills I need them to be. I watched them write a paper. [2:05:32] 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 and like, [2:05:40] sit in that shit. Like that is some middle school shit you need to grind through. [2:05:44] And yet, [2:05:45] Is that, am I teaching them how to shoe a horse maybe? [2:05:48] Like, is that an outmoded skill? [2:05:50] I mean, I stood there and I typed in a chat GPT or a clot or something and showed Crystal and I was like, [2:05:54] 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. [2:06:04] But I've never been more uncertain about anything in my life. [2:06:07] 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? [2:06:15] So we hired this... [2:06:17] I was like, I need an AI person to work here. [2:06:20] And I don't know. I mean, AI is the biggest customer for what we do. [2:06:24] But I was like, I don't know if we'll ever do a deal on pure play AI, but we have this person who, [2:06:29] This incredible line is her name. [2:06:31] I think she's 21. I just found out. I had no idea. It wasn't specced for like, I need a, [2:06:36] 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. [2:06:42] about what certain emojis mean in Slack. [2:06:45] Like, I mean, you don't understand how much time I'm like, I don't... [2:06:49] I want to adapt, but I am old. [2:06:51] So you're becoming a minority. One thing, one thing I would love your audience to react to.

[2:06:55] is what the... [2:06:57] Thumbs up emoji means when used in Slack. So... [2:07:01] I'm... [2:07:01] I'm like informed enough to understand that thumbs up on an iMessage. [2:07:07] to another peer is like, whatever, bro. It's kind of dismissive, right? Do I have that right? Yeah. Yeah. I'm 31, so I still use it normally. But I think if you're 25, it's... How do you use it? Does thumbs up mean kind of like... [2:07:22] dismissive right okay so i had 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 did like just kind of like [2:07:39] banging on each other a little bit and [2:07:41] No, I was, I was, it was clarified to me that thumbs up in Slack means like, yeah, I agree. Hack. Okay. But the one that's really wild. [2:07:49] You know the big eyes? Just the eyes? Yes, the looking... Yeah, and they're kind of looking to one side. [2:07:57] 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 informative. [2:08:04] 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. [2:08:10] By the way, I high-five things, other people sparkle them and shit. And I'm like, I'm clearly... All right, just know that my high-five means high-five. So... [2:08:17] 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. I have a very limited repertoire. Oh,

[2:08:25] Um, but, but I got this lecture in like, [2:08:28] 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, [2:08:36] Whatever you just read is suspicious and bullshit. [2:08:38] Other people, I was with one of our founders last night, Julia from Vaulted, who's just fucking badass. [2:08:45] And she said, no, no, when I use it, [2:08:48] And they use Teams at their shop. She's like, when I use it, it means I know what I just said is a hot take, but I stand by it. [2:08:54] Okay. And so I was like, okay, that's a whole thing. [2:08:57] Um, [2:08:58] But, but like having that energy, um, [2:09:01] like a complete immersive AI expert who is among [2:09:06] the people, the earliest founders. And it also speaks this language of youth. I know that makes me sound even older to say youth, but like to just speak that language. [2:09:19] has been like the biggest fucking boost for me. I've loved having that energy and that, [2:09:24] And that's where my curiosity is. So, [2:09:27] So look... [2:09:28] Climate is the least creative thing I've ever done. [2:09:31] Like you're with me for a much more creative phase because we're building stuff. [2:09:35] where we had to [2:09:38] We had to look into the crystal ball about what are these people... [2:09:43] What will they care about? Will they use it? Why will they use it? We are creating stuff that was first impression. Almost everything we do in climate is a substitute good. [2:09:51] 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.

[2:09:59] that they'll buy out of greed, not shame and guilt. [2:10:02] do that across the board like i'm 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 right still yeah and so um it's way faster now but [2:10:21] So they might be doing that, but I'm not. [2:10:23] And so... [2:10:25] I started to feel like a little empty in that. And so Crystal and I, [2:10:29] Actually last year, um, [2:10:32] came up with the idea for a comedy feature film. [2:10:35] Went to a great friend of ours, Steve Brill, to write it. He's a really accomplished director and writer and filmmaker. And you've seen so much of his shit, you didn't even know it. But... [2:10:45] But, and he... [2:10:47] We loved being in that process. He was the writer, but we were [2:10:50] 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, [2:10:58] He gave us notes on the third act. [2:11:00] Then the female lead, who's like, I can't even believe that she wants to do it. [2:11:06] gave us third act notes and it took us a while. I mean, Braille... [2:11:09] rewrote that and stuff with some of our reactions to it and stuff. So we'll, he's the writer where the story by, 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 and then I consider, uh, [2:11:23] Raising kids like a creative outlet. [2:11:25] But... [2:11:26] I will end up doing more of that. I want to write.

[2:11:30] I have been writing. I do feel like ChatGPT is pretty good at it. And every time I kind of ask it for reminders, I'm going to ask it for [2:11:36] I actually... [2:11:37] ChaiGBT was pretty good at script writing. [2:11:39] There was a time where we got notes from this famous star. [2:11:43] And I had an idea. [2:11:45] 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... [2:11:53] I quickly typed into Claude. It did not have the script. [2:11:56] I just said, [2:11:58] Scene concept. [2:11:59] He walks in, she's on her cell phone. This guy comes around the corner, almost catches her. [2:12:03] He makes a lot of loud noises to cover for her. Like, these are the names. Just a bunch of contacts. Write it. [2:12:08] And it came up with enough funny... [2:12:11] Dialogue. [2:12:12] 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. [2:12:18] Like how to, how did not have any eye content in there? Because it was pretty fucking good. Not great. It wasn't, it wasn't brill level. It's going to 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, [2:12:36] I could phone it in. [2:12:38] And it'd be pretty fucking good. Like I, it's literally really fucking good. And when you're me, [2:12:43] The Internet. [2:12:44] has read a lot of what I've said and written. You can say, do this in Chris's voice. [2:12:50] We trained an internal bot on everything I've written. [2:12:53] And it's really good at being me. [2:12:56] Like I could kind of step away. [2:12:58] And I think most of our investors wouldn't know that I didn't write that thing. It knows my cadence of like,

[2:13:04] fact, fact, fact, fact, punchline, you know, fact, fact, fact, sigh. And, you know, they're like, [2:13:08] 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 [2:13:16] But [2:13:17] So I worry about that. [2:13:19] But I do think [2:13:21] I've been trying to [2:13:23] Give. [2:13:24] the organization even more, the lower carbon, even more room, [2:13:28] 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 [2:13:38] And, um... [2:13:39] We'll have to check back on this in a few years. We will. I mean, 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... [2:13:50] Either I didn't have a competitive advantage, [2:13:52] Like with lowercase. [2:13:54] I realized I wasn't [2:13:55] going to be the best again if we'd raise another fund. [2:13:58] And I also didn't care about the shit we were investing in. [2:14:01] Like, [2:14:02] Bless you and your e-gaming past, but I was never going to go to Staples Center and watch guys play League of Legends. I just didn't care. [2:14:09] It's not a judgment on anybody else when I'm like, I didn't give a shit. And like these dating apps and like... [2:14:13] 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? [2:14:19] And so, and if you're going to do this job, you have to give a shit. [2:14:22] Like, [2:14:23] Bye. [2:14:23] Somebody had to remind me. I have to tell you any job. At this point, if there's any antidote to the AI thing, if there's any optimism, it is you better find the thing you care about more than somebody else. And when you're... [2:14:33] When you're starting a venture fund, 996 would be a holiday.

[2:14:37] 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. [2:14:43] And when somebody calls... [2:14:45] I mean, I was on the phone... [2:14:47] late the other night with an entrepreneur who we backed in 2009. [2:14:51] who was having board issues, you know, and like, [2:14:55] you're married to these companies. They're, they're, [2:14:57] 15, at least 15 year commitments. And so each time we raise a new fund, I have to do that analysis. [2:15:03] From scratch. [2:15:04] Do 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. [2:15:10] I have to do it because I know we can change everything. [2:15:13] And, um... [2:15:15] And so I'm just constantly reevaluating that. [2:15:17] And so, you know, in case of walking away from lowercase, it was weird. 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 Bannister, [2:15:29] I had... [2:15:30] Barely ever met her. I'd seen her on TechCrunch before. I think we had once... [2:15:36] Shaking hands. I got her email address. [2:15:39] And I sprayed and prayed to every rich person I'd ever met. [2:15:43] She wrote us a $300,000 check. It was the largest individual check [2:15:49] Uh, [2:15:50] to lowercase. That worked out. [2:15:53] She's maybe the most successful angel investor ever. I think so. [2:15:56] And so I don't think anyone knows who she is. [2:15:58] um or like as that like how impactful she is i genuinely think yeah and so um [2:16:04] But... [2:16:05] And she's weird too. And her story is like she would be traditionally unqualified. That's kind of weird. And like irrelevant, you know, irrelevant for this. And I think that's why she's been so successful. But.

[2:16:15] But yeah, like I... [2:16:19] I think about this journey and... [2:16:21] Um, [2:16:22] And there was a time where I was just like, okay, everyone's throwing money at me. [2:16:26] But really, truly, for everyone... [2:16:29] No one realizes the only person who really knows their scorecard. [2:16:32] Is them. [2:16:33] Hmm. [2:16:34] I could sit here and give you [2:16:37] the most well-intentioned career advice ever. Jackson, like you are family to us. [2:16:42] Okay, wait, I have to go to an aside really quick. [2:16:45] You had... [2:16:47] the [2:16:47] Best, worst... [2:16:49] first day of work that anyone in history has ever had. I won't go into the details, but it was the fucking... [2:16:55] Worst day ever. I mean, it was just one failure after another, cascaded, cascaded, cascaded. [2:16:59] legendary. I know you've never forgotten it. [2:17:02] But the thing... [2:17:04] that Crystal and I talk about every time. [2:17:06] And just so you know, we don't share the details of how bad it was. It was fucking amazing. I mean, there should be it should be a script. [2:17:13] Because it was just the worst first day of all time. Like, dude, seriously. [2:17:19] But... [2:17:21] You wrote... [2:17:22] the most accountable follow-up email in history. I would put it up against anyone else's email, [2:17:28] After a fuck up. [2:17:30] First of all, you... [2:17:32] 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... [2:17:38] I reread it this morning. So you prep for this podcast, but I reread one thing. [2:17:43] And it was that note. [2:17:45] You...

[2:17:46] headlined it, outlined it, you bolded the subject matter titles, you... [2:17:51] The narrative was really good. It was chronological. [2:17:54] Then it had like what I could do differently, how I'll improve this. [2:18:00] And then like an overall, like I know the impact it had on you and the risks that it had like and so. [2:18:05] It's poetry, man. Nobody does that shit anymore. And I totally forgot to bring it up, but I think it's, [2:18:13] 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. [2:18:20] I was flattered by the invitation here. [2:18:22] I do think you are one... [2:18:24] of the most [2:18:26] self-aware [2:18:28] constantly working on yourself and accountable people I've ever met. [2:18:32] And you, and to do that at such a young age originally was just really special. Uh, [2:18:38] 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. But yeah. And so. [2:18:46] But, [2:18:47] 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. [2:18:53] And as someone who cares about you, I could... [2:18:55] 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, [2:19:00] all these great people are like, why? I mean, you're good at it. You did, you know, there's so much money and this and that, but, [2:19:05] We're the only people who just knew like it, [2:19:08] The meaning wasn't there for us anymore. [2:19:11] You know, and [2:19:12] The Aspen Institute Crown Fellowship I'm in likes to say about pivoting from success to impact.

[2:19:17] 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 in. [2:19:25] you know, souls go to die and stuff like that. But we just saw there was this, it was, it was priced wrong. [2:19:30] And so we knew we could go in there and shake shit up and have a massive impact. But [2:19:35] But it wasn't really, this might be a surprise to a lot of people, I'm not a climate zealot. [2:19:39] Like, um, [2:19:41] You know, my personal carbon footprint is inexcusable. On the other hand, the term carbon footprint was... [2:19:47] coined by Ogilvy and Mather, [2:19:49] at the behest of British Petroleum. [2:19:51] to take the spotlight off of the industrial carbon economy and put it, [2:19:55] put all the guilt and shame on individual users, you know, individual people make like, hey, it's up to you to take a shorter shower. [2:20:02] 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. I am like... [2:20:07] Look, we would not have the lifestyle we enjoy today if it weren't for oil and gas. Yeah. Right? Right? [2:20:12] I was in a meeting the other night where we got to stop the oil and gas fraud, you know, the mafia. And I'm like, how the fuck did you get here? [2:20:19] Like, look at the room. Look at what we're eating. Look at the furniture we're sitting on. Like, [2:20:23] we're just going to quit oil tomorrow. Like, [2:20:25] 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. [2:20:31] 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... [2:20:38] People feel that like I there's nothing I hate more than the activists. [2:20:43] And we call them the soup throwers. People go and fucking throw soup on a painting. I'm like, really?

[2:20:47] 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. [2:21:04] Like it doesn't fucking work. Like, [2:21:06] 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, [2:21:17] the most productive geothermal wells at the lowest cost ever, like some just incredibly clean, ubiquitous 24 seven power, like, [2:21:26] Those guys are all riggers who come over from... [2:21:30] 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 [2:21:41] 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, [2:21:53] is making people feel bad about their choices, how they live, despite their intentions, [2:21:57] Like it's an exclusionary purity test thing. [2:22:00] then we are not going to get anything fucking done right now. And no, I'm not running for anything. Fuck that. But I... [2:22:05] We have one last thing. We are sadly out of time as much as I, I I'm sure I could let you go forever and I'm going to, I'm going to change gears slightly, but it feels, um, very aligned with what you were saying. And, and, [2:22:15] I found something in your blog that really, again, I used the word authenticity earlier.

[2:22:22] 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. And it's called Manifesto of the Mad Farmer Liberation Front by Wendell Berry. [2:22:41] 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. [2:22:46] Love the quick profit, the annual raise, vacation with pay. [2:22:51] 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. [2:23:02] When they want you to buy something, they will call you. When they want you to die for profit, they will let you know. [2:23:07] So 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. [2:23:17] Denounce the government and embrace the flag. [2:23:19] 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. [2:23:36] that you will not live to harvest. Say that the leaves are harvested when they have rotted into the mold. Call 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.

[2:23:53] 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? [2:24:05] Will this disturb the sleep of a woman 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. [2:24:25] who makes more tracks than necessary. [2:24:27] Some, in the wrong direction, practice resurrection. [2:24:33] I feel like I forgot. I forgot I quoted that. [2:24:38] Again, [2:24:40] That's one of those writers where you're like, how could I consider myself? [2:24:44] an organizer of words, but, um, [2:24:49] My reaction is like, I feel like you just found another one of those letters I wrote to myself. [2:24:55] That became Prophecy. [2:24:58] Do you listen to Matthew McConaughey's book? I haven't. Green Lights? Oh, you've got to listen to it. You can't read it. [2:25:03] It's like six hours of [2:25:05] gelling with one of the most interesting storytellers of all time, but [2:25:09] And he's got the perfect accent, perfect stories. [2:25:13] Just amazing. [2:25:15] But in the end, [2:25:17] one of the reveals is, uh, [2:25:20] This isn't a spoiler, but it's a letter he wrote to himself with his life goals in it.

[2:25:26] when he had no business writing that letter. [2:25:29] And he'd kind of forgotten about it. [2:25:32] And then he rediscovered it and realized they'd come true. [2:25:36] 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, [2:25:45] But, [2:25:46] You know that when I was 41, I found a letter I'd written. Not even a letter. It was honestly, I was going to school in Ireland, and I was... [2:25:55] I only went to this one class to basically try to get closer to this one girl. [2:26:00] And [2:26:01] We did this little thing in the back of the class where we would write five questions for each other. [2:26:06] and pass the booklet to the other person to answer those questions, pretending to pay attention. [2:26:10] And then answer them. And she said, what do you want to be when you grow up? [2:26:13] And I wrote this response. I think I've written down or shared somewhere, but it was basically like, [2:26:18] I don't know what it's called. [2:26:20] I just know it's going to have a lot of high stakes, high risk, high reward. [2:26:24] Uh... [2:26:25] A lot of talking on the phone, a lot of negotiating. [2:26:29] I'm going to do it halftime from the mountains, halftime from the beach. [2:26:33] Um, [2:26:34] 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. [2:26:41] Whatever it was, I don't think I ever even ended up with that girl at all, but I ended up with The Notebook. [2:26:47] And it was in my garage. [2:26:48] And Crystal and I were cleaning up my garage. [2:26:51] our garage and, um, [2:26:53] You know, when I was 41. [2:26:54] And we found it and I was flipping through it and,

[2:26:56] I came across that [2:26:58] reading it with her and she's like, [2:27:00] my God, you're late. [2:27:03] Every single bit of it. We lived in Truckee and had a house on the beach in L.A. [2:27:07] 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... [2:27:14] is trying to import Ferraris in this warehouse and he's just got multiple phones going and it's sparse. There'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 [2:27:28] That to me is the kind of business that a not rich kid with no network [2:27:32] could just do with the power of ideas and thought and speaking. That was kind of what I had in mind. And I didn't know what that job was. [2:27:40] I knew I didn't want to like bill hours or anything like that, but... [2:27:44] when I look back at what I made happen, [2:27:47] I'd forgotten I'd written it. [2:27:49] 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. [2:27:54] But... [2:27:55] You know, when you read that, [2:27:59] I get a little emotional because I think I... [2:28:02] I'd forgotten about that for sure. I'd forgotten about that, but, [2:28:08] I think a lot of my... [2:28:09] journey has been trying to get

[2:28:13] My biggest goal for myself is hoping that my drift is closer to real, is back to the real me, the me that hopefully I've been or – [2:28:24] that was covered in layers of [2:28:25] either pretense or inauthenticity or striving or [2:28:29] I was in college. I didn't [2:28:31] I didn't have, I didn't, I didn't, [2:28:33] Talk about my politics. [2:28:35] Because I thought I would offend half of my future potential employers. [2:28:41] At each stage, I have found the opportunity to speak my mind, be more real, dress the way I want to dress. [2:28:49] live the way I want to live. [2:28:50] Bill Clinton invites me to this meeting every year here. [2:28:54] Basically, it's a room full of suits, world leaders, unfortunately, and he throws it to me to... [2:28:58] say the things that nobody else wants to say, [2:29:01] swear while doing it, drop a cowboy phrase in there, but just like [2:29:05] Just stir it up. Yeah. [2:29:06] And, [2:29:07] We've developed a fun friendship over the years because I just stir it up and... [2:29:12] you know, [2:29:12] 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, [2:29:18] that's not a good job for you. [2:29:21] Being an ambassador is not about saying what you actually feel. He's like, that, that I'm kind of glad that didn't work out for you. Yeah. He's like, I'm kind of glad that didn't work out for you. But, but I do try to drift. [2:29:32] And there's rapids along the way, and I got to get a paddle out and push. But I do try to drift back towards... [2:29:38] Real. [2:29:39] And real for me was I did grow up laying down in the field.

[2:29:43] I dig her up with [2:29:45] artists and performers and writers and actors in our family. I did grow up with my mom and dad who constantly were [2:29:52] introducing the arts as well as science to me. [2:29:55] who [2:29:56] We're teaching us. [2:29:58] about love, [2:30:00] and collaboration and openness. [2:30:02] and about our responsibility to other people. [2:30:06] And about... [2:30:07] the real privilege of raising kids. I mean, the thought and the heart that I can see in retrospect that my mom and dad put into the, [2:30:14] raising and nurturing us while also [2:30:17] not being pushovers and like having real, [2:30:21] Real values, communicating values, but also boundaries and edges and consequences and responsibility and hard work. [2:30:30] And, um, [2:30:31] and accountability and just... [2:30:33] and how I try and reflect that and what I do now. [2:30:37] I tried not working for a bit and that lasted like 60 days. [2:30:42] I... [2:30:43] I've tried stepping back and I suck at it. [2:30:46] The only... [2:30:48] I get a real pleasure from hopefully... [2:30:50] helping raise the people who can [2:30:53] do it better than I can lower carbons getting there [2:30:56] like get into the place where but [2:30:59] 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. [2:31:04] You know, I've had to teach people don't be so nice, you know, don't be so cooperative. [2:31:10] And so... [2:31:11] Don't be submissive. Like the world needs a little more alpha.

[2:31:15] And, [2:31:17] You know, the most expensive employees in an organization like that aren't the ones you pay the most. They're the ones who [2:31:21] drag the most on everybody else. Maybe they come in like Eeyore from Winnie the Pooh just sad every day. [2:31:26] or they're toxic, or they just... [2:31:28] can you reread this email for me before I send it? I'm like, just fucking send the goddamn note. Like, [2:31:33] What are they going to say? You know? [2:31:35] And, um, [2:31:36] And so I... [2:31:38] There is an inflection point coming for me at some point soon. [2:31:42] Um, [2:31:43] But... [2:31:45] But it's fun that you read that because it reminds me. [2:31:48] Bye. [2:31:49] That's kind of a scorecard I'd like to measure myself against a little bit. I think I've done some of that. [2:31:54] I don't know if I... [2:31:56] I remember like there's a lot in there about women and birthing. [2:32:00] When Crystal and I first got pregnant, she asked me to sit down and watch a pregnancy movie. [2:32:05] I... [2:32:06] Grew up in a Catholic town where the day they teach girls about periods, they let the boys play connect for. [2:32:13] And they told the girls, don't show the boys that pamphlet. [2:32:17] on the bus ride home. It was like a secret. [2:32:20] That was the level of stigma around like... [2:32:24] female reproduction, like just didn't grow up in a place talking about cycles or any of that. [2:32:29] And so, [2:32:31] When we got pregnant and Crystal's like, watch this movie, I'm like... [2:32:34] Wait, really? Are you sure? [2:32:36] Like I can have a couple of drinks first. Like I really expected to be grossed out. Hmm. [2:32:42] And it was this cool movie by Ricky Lake, of all people, 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...

[2:32:51] 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 that, [2:32:58] Much less safe than that's happening in the United States, but how [2:33:02] essentially embrace that woman [2:33:07] as someone built to do this not a patient the united states treats women giving birth as patients [2:33:12] Put you in a hospital, don't trust your body, drug you up, put you in stirrups, which is the least natural way to... [2:33:17] 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, [2:33:31] like, um, 4.30 p.m. and at, like, 9.30 p.m. So, 4.30 is so the doctor can get home for dinner and 9.30 is so they can get home and sleep that night. I mean, they all... It's a fucking... [2:33:41] Scan. [2:33:42] But... [2:33:45] But I just... [2:33:46] I didn't have an... [2:33:47] 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 [2:33:54] lobby with the cigars, not in the room doing it. [2:33:57] But... [2:33:59] You know, three babies in, it became kind of part of my identity. [2:34:04] How much I... [2:34:05] Felt. [2:34:06] Like the fatherhood journey starts way before that baby comes out, but definitely while that baby's coming out and all the way through. [2:34:14] 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,

[2:34:22] And so anyway, Jackson, I got to say, I really like, I love listening to you. By the way, I told my team last night I was coming here. [2:34:29] 50% of them listen to you. [2:34:31] And the one who knows you is Jackson. The other people raise their hand. I'm like, no, no, I just listen. I'm like, no. [2:34:36] how the fuck do you know about Jackson doll? It's amazing. Um, [2:34:40] But I love listening to you. I told you before we started rolling, I asked ChatGPT what you would ask me. [2:34:45] It was pretty fucking good, man. Those are some B plus, A minus questions. [2:34:49] And I want to go back and answer those just for myself. It's like form spring crystal is like that form spring. Yeah. Um, [2:34:55] But I like, I think the depth and originality of your questions. [2:34:59] I think what you pull out of people, but more than anything, the guests you curate. I, [2:35:04] I felt a little bit of imposter syndrome coming on here because – [2:35:07] I think you've got some incredibly... [2:35:09] dynamic creative challenging people doing stuff and i [2:35:14] I looked this morning, I scrolled through Spotify, and I... [2:35:18] knew the names of four of your guests before they got here. [2:35:22] Um, [2:35:23] Lux Capital Guy, Cyan. I don't know. There were like a couple I was like, all right, yeah. [2:35:27] Even then, it's still an interesting discussion. I'm learning new things because of the way you talk. But [2:35:32] you know, I bought Nadia's book, which was in our company color. So it was even better. But, um, [2:35:36] You know, I learned about Stripe Press, which as close as I am to the Cosmo Brothers and the Stripe, I didn't know about that culture there. [2:35:43] And so I'm just really grateful for the work you're doing. And I was just... [2:35:48] Awesomely thankful to be here. [2:35:51] And I hope I lived up to your expectations, man. Yeah, more than I could have asked for. Thank you, sir. This was really a pleasure. Right on, brother. Good to see you. Hopefully not in another eight years. Yeah, we'll do it a little quicker this time.