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. org, I think? 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,, 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,