![[32-Chris_Sacca.jpg]] *Dialectic Episode 32: Chris Sacca - Drifting Back to Real - is available on [Spotify](https://open.spotify.com/episode/6o9q6GKgiphuyWK3KqZR1s?si=h8GRUk9_SxSAgzNRnBv-tw), [Apple Podcasts](https://podcasts.apple.com/us/podcast/32-chris-sacca-drifting-back-to-real/id1780282402?i=1000735330709), and [YouTube](https://youtu.be/acwhhgGGdX8), and all podcast platforms.* <iframe data-testid="embed-iframe" style="border-radius:12px" src="https://open.spotify.com/embed/episode/0BJ36Y79zfFNxYONp9EtZF/video?utm_source=generator" width="624" height="351" frameBorder="0" allowfullscreen="" allow="autoplay; clipboard-write; encrypted-media; fullscreen; picture-in-picture" loading="lazy"></iframe>  <iframe allow="autoplay *; encrypted-media *; fullscreen *; clipboard-write" frameborder="0" height="175" style="width:100%;max-width:660px;overflow:hidden;border-radius:10px;" sandbox="allow-forms allow-popups allow-same-origin allow-scripts allow-storage-access-by-user-activation allow-top-navigation-by-user-activation" src="https://embed.podcasts.apple.com/us/podcast/32-chris-sacca-drifting-back-to-real/id1780282402?i=1000735330709"></iframe> # Description [Chris Sacca](https://chrissacca.com/about/) is an investor and founder of [Lowercarbon Capital](https://lowercarbon.com/) and [Lowercase Capital](https://lowercasecapital.com/). Prior to becoming an investor, Chris grew up in Buffalo, NY; studied around the world by way of the Georgetown School of Foreign Service; turned his student loans in $12M in the tech bubble of 2000 before losing it all and then some; and broke into Silicon Valley before eventually landing at Google, where he won the founders award. Then Chris started angel investing, which led to his first venture fund, Lowercase I. Lowercase I is one of if not the best performing VC funds ever, by multiple, at 214x, and included Twitter, Uber, Instagram, and more. Toward the end of Lowercase, I had the pleasure of working with Chris. Around that time, he was also a Guest Shark on Shark Tank. Chris was heavily involved in both Obama campaigns and was a large supporter of Hillary Clinton in 2016. When Trump won, he wound down new investing at Lowercase and "hung up his spurs" to focus on political and democracy related efforts. Then, in 2018, Chris started Lowercarbon Capital to invest in "un-f\*cking the planet": carbon removal, climate science, cooling the planet, and eventually nuclear fusion. We talked about writing and storytelling, keeping people around who keep you honest, having a good taste in "weird," playing rigged games, taking the right kind of risks, and how even billionaires have imposter syndrome. We also get into how great founders embody inevitability, what makes the people at Lowercarbon special, how much Chris thinks about AI, and the many chapters of Chris's life, including whatever might be next. Authenticity is a moving target for all of us, but one of the things I most admire about Chris is his ability and desire to shamelessly play his own game. --- Thanks to Josh Kale for producing this episode. Please check out his show [Limitless](https://www.youtube.com/@Limitless-FT) on frontier technology and AI. And thanks to KG. # Timestamps - (0:00): Open: The Common Thread Amongst The Best Founders - (1:20): Intro - (3:42): Coast to Coast - (12:29): Leaning into Weird & Investing in Fusion - (24:35): Having People Who Keep You in Check - (32:00): The Power of Language and Stories - (1:03:03): Investing, Risk, and Wild Confidence - (1:27:57): Imposter Syndrome and Making Companies Better - (1:38:03): Lowercarbon's Team and Culture - (1:57:47): Chris's Life Chapters, AI, and Creative Outlets - (2:22:04): Drifting Back Towards Real # Links & References - Note: as we discuss, Chris's old blog What is Left went down shortly before this interview was recorded. - [Crystal English Sacca](https://lowercarbon.com/team/crystal-sacca/) - [Dean Karnazes](https://en.wikipedia.org/wiki/Dean_Karnazes) - [Augustus Doricko](https://x.com/adoricko) - [Rainmaker](https://www.rainmaker.com/) - [Dr. Scott C. Hsu](https://lowercarbon.com/team/dr-scott-hsu/) - [Clay Dumas](https://lowercarbon.com/team/clay-dumas/) - [Ryan Orbuch](https://lowercarbon.com/team/ryan-orbuch/) - [Bob Mumgaard](https://x.com/bobmumgaard) - [Commonwealth Fusion Systems](https://cfs.energy/) - [Alan Eustace](https://en.wikipedia.org/wiki/Alan_Eustace) - [Felix Baumgartner](https://en.wikipedia.org/wiki/Felix_Baumgartner) - [List of cognitive biases](https://en.wikipedia.org/wiki/List_of_cognitive_biases) - [Garrett Camp](https://en.wikipedia.org/wiki/Garrett_Camp) - [Sick in the Head - Judd Apatow](https://www.goodreads.com/book/show/23834688-sick-in-the-head) - [David Kwong](https://www.davidkwongmagic.com/) - [How to Fool Your Parents - David Kwong](https://www.goodreads.com/book/show/199531858-how-to-fool-your-parents?from_search=true&from_srp=true&qid=lHhH76V34a&rank=1) - [David Blaine](https://en.wikipedia.org/wiki/David_Blaine) - [Steve Martin](https://www.goodreads.com/author/show/7103.Steve_Martin) - [P.J. O'Rourke](https://www.goodreads.com/author/show/14549850.P_J_O_Rourke?from_search=true&from_srp=true) - [Chuck Klosterman](https://www.goodreads.com/author/show/375.Chuck_Klosterman) - [The Overstory - Richard Powers](https://www.goodreads.com/book/show/40180098-the-overstory) - [Billy Collins](https://www.poetryfoundation.org/poets/billy-collins) - [And, This Is Charlie Kirk - Gavin Newsom](https://youtu.be/9XJ6rQDRKGA?si=bY2okcSCkkNaHRNW) - [Ira Glass](https://en.wikipedia.org/wiki/Ira_Glass) - [Alex Blumberg](https://en.wikipedia.org/wiki/Alex_Blumberg) - [Gimlet 1: How Not to Pitch a Billionaire - StartUp Podcast](https://open.spotify.com/episode/5BAbYcpOFYzv2ED7bilzLh?si=Jw6kkPTzSWmUQeJF9uLhzg) - [Edward Norton](https://en.wikipedia.org/wiki/Edward_Norton) - [This American Life](https://www.thisamericanlife.org/) - [Cory Booker](https://en.wikipedia.org/wiki/Cory_Booker) - [Zanksar](https://zanskar.com/) - [Carl Hoiland](https://x.com/geologycarl?lang=en) - [Chris Sacca — The Tim Ferriss Show](https://www.youtube.com/watch?v=jIBo69EsAzw) - [Generations - Jean M. Twenge \| Goodreads](https://www.goodreads.com/book/show/61273798-generations) - [Jonathan Haidt](https://en.wikipedia.org/wiki/Jonathan_Haidt) - [Bourré ](https://en.wikipedia.org/wiki/Bourr%C3%A9) - [Addiction by Design - Natasha Dow Schüll](https://www.goodreads.com/book/show/13748038-addiction-by-design) - [Suhail Rizvi](https://en.wikipedia.org/wiki/Suhail_Rizvi) - [Caro's Book of Poker Tells - Mike Caro](https://www.goodreads.com/book/show/86523.Caro_s_Book_of_Poker_Tells) - [Emotions Revealed - Paul Ekman](https://www.goodreads.com/book/show/156462.Emotions_Revealed) - [Travis Kalanick](https://en.wikipedia.org/wiki/Travis_Kalanick) - [Formspring](https://en.wikipedia.org/wiki/Spring.me) - [Ryan Graves](https://en.wikipedia.org/wiki/Ryan_Graves_(businessman)) - [Melody McCloskey](https://x.com/melodymcc?lang=en) - [Loïc Le Meur](https://en.wikipedia.org/wiki/Lo%C3%AFc_Le_Meur) - [Blocks Podcast w/ Neal Brennan](https://open.spotify.com/show/6gx3bANm25DtKA3cnlBH1r) - [Neal Brennan: Blocks \| Netflix Official Site](https://www.netflix.com/title/81036234) - [Neal Brennan: Crazy Good](https://www.netflix.com/title/81728557) - [Hans Swildens - Industry Ventures](https://www.industryventures.com/team_member/hans-swildens/) - [Caie Kelley](https://lowercarbon.com/team/caie-kelley/) - [Pod Save America](https://crooked.com/podcast-series/pod-save-america/) - [Urs Hölzle](https://en.wikipedia.org/wiki/Urs_H%C3%B6lzle) - [Elliot Schrage](https://en.wikipedia.org/wiki/Elliot_Schrage) - [Megan Quinn](https://x.com/msquinn?lang=en) - [David Drummond](https://en.wikipedia.org/wiki/David_Drummond_(businessman)) - [Andy Rubin](https://en.wikipedia.org/wiki/Andy_Rubin) - [Marissa Mayer](https://en.wikipedia.org/wiki/Marissa_Mayer) - [Lauren Faber O'Connor](https://lowercarbon.com/team/lfo/) - [Chris Sacca's commencement address at the Carlson School of Management](https://www.youtube.com/watch?v=RskzYHPlh5U) - [The Fourth Turning - William Strauss](https://www.goodreads.com/book/show/670089.The_Fourth_Turning) - [We Are In A "FOURTH TURNING," What Does That Mean? - Van Neistat](https://www.youtube.com/watch?v=xeVyfiP0cLk) - [Questlove](https://en.wikipedia.org/wiki/Questlove) - [Fifty Years Fund](https://www.fiftyyears.com/) - [Seth Bannon](https://www.fiftyyears.com/team/seth-bannon) - [D. Scott Phoenix](https://www.fiftyyears.com/team/scott-phoenix) - [Julia Reichelstein](https://www.linkedin.com/in/jreichelstein) - [Steven Brill](https://www.imdb.com/name/nm0109359/) - [26. Cyan Banister - A Fool’s Dérive - Dialectic](https://dialectic.fm/cyan-banister) - [Henry Crown Fellowship - Aspen Institute](https://www.aspeninstitute.org/programs/henry-crown-fellowship/) - [Manifesto: The Mad Farmer Liberation Front by Wendell Berry](https://allpoetry.com/poem/12622463-Manifesto--The-Mad-Farmer-Liberation-Front-by-Wendell-Berry) - [Greenlights - Matthew McConaughey](https://www.goodreads.com/book/show/54771828-greenlights) - [‎Rain Man (1988)](https://letterboxd.com/film/rain-man/) - [Ricki Lake](https://en.wikipedia.org/wiki/Ricki_Lake) # Transcript ## [00:00:00] Open: The Common Thread Amongst The Best Founders ## [00:01:20] Intro **Jackson**: Chris Sacca. **Chris:** What's good, Jackson? It's been forever. **Jackson:** It's been like eight years. A long time. **Chris:** Right on, man. ## [00:03:42] Coast to Coast **Jackson:** I'm going to start in an unlikely place—not for you, but for people who've known of you only more recently. You are one of the best writers I've ever met in my life, and you don't write very much publicly anymore. You haven't written publicly much in the last decade or so. You once said, "Nothing can stop time and bring us together like words, done right." So I'm going to take you way back. **Chris:** Did I write that before AI? I can actually take credit for this. I think it was in the 2000s. **Jackson:** We're going way, way, way back for a bit of writing. You'll have to bear with me, but I'm going to read it in full from a section of a blog called "Coast to Coast." The title is "3,286 Thank Yous," from November 30, 2009. This is partway through the post, as you were riding your bike across America. The peak of my experience came, quite literally, in my push to the crest of the Newfound Gap—the 5,048-foot pass 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, and its rushing waters flipped a switch in me, and I pedaled with abandonment. If you know this road, then you are quite familiar with its singular direction: up. The more I spun, the sooner I climbed into a bracing, snowy canopy. 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. As the inches accumulated on the ground, I accelerated. With each fishtail of my rear wheel, I laughed and hooted with a carefree exuberance. Oh, to be alive in the snow! With a racing heart and heaving lungs, I made it to the summit a half hour before folks started falling and our guides collected everybody in a van, declaring the road unsafe. I felt so charged. The looks of disbelief on the faces of the tourists in their cars provoked cackles from me. Travelers would stop and ask about my ride and shake their heads when I explained the goal and admitted to having pedaled to that summit in the storm. 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 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. And in that moment, legs still surging with adrenaline, I finally knew that I would be there soon. Nothing would keep me from it. **Chris:** I gotta say something funny to distract from that. It makes me emotional. I really hope people are listening to this at 2x. That was a long clip. Jackson, I always appreciate how you ask things that nobody else asks. That's why I listen to you. Just last night, one of the people on our team was talking to me. He's a great young person, and he said, "I feel like I need an adventure. I want to take a little time and go on an adventure." It was fun for me because even as an employer, at no point did I think about it as PTO. I was just so excited for him to want to go do something. He was talking about the Camino de Santiago. Then I mentioned Crystal, my wife and co-founder and best friend forever. She went and did Machu Picchu and El Sangate multiple times at the height of her career. She left and went and did that. I was reminded of this bike trip. I started pretty fat and out of shape on the West Coast and was shredded and strong by the East Coast. It was essentially more than a hundred miles a day, just nonstop. What I loved about it was how few times in our life we have a very singular focus. I got up in the morning and I knew my exact purpose. I knew the only thing I had to do was get to the other side. I had a mantra: "Tonight, I will be in my bed." This is the same thing that got me through Ironmans. But even with Ironmans, it's just one day of pain, and there are lots of people on the side cheering for you. For riding, it was the last time I only had one thing to care about. The way that frees your head up to let other thoughts come in or not—it is the most meditative thing I've ever done repetitively. I would call Crystal at the end of the day and say, "All right, love, I'm going to bed." She's like, "It's five where you are." I'm like, "I'm definitely going to bed." I've never eaten more, because I had earned it. I'd have two chocolate shakes. When I got to South Carolina and dipped my wheels in the ocean, I cried a lot. 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. I had been sitting in a fucking seat going 100 miles a day. The other things that hurt were my shoulders and my Achilles. You don't even think about it. You think it's your quads; it's not. I dipped my bike tires, I made it, and I got on the plane. Then I was wildly depressed for the next month. I missed the dopamine that I'd had in my body every day. I've heard this about Dean Karnazes—I think that's his name—the guy who ran coast to coast. **Jackson:** Okay. **Chris:** He got to New York and almost committed suicide. He decided he would just run back to San Francisco because he was really chemically addicted to it, and he had that same purpose. I felt something like that. It was a real loss; I went through a sense of grief. In the meantime, I was just so distracted by everything else. I'd wake up in the morning, and if my purpose wasn't--by way if there's another human being in the room, I have to make eye contact with them. As someone who's done primetime television, you're never supposed to look into the lens, but Josh is sitting over here. I was raised right; I'm incapable of ignoring another human's presence. This is going to be weird because I'm looking right into the lens, breaking every rule of Hollywood, but I can't help it. Maybe Josh should just pull up a chair. **Jackson:** The audience is over there. **Chris:** Okay, cool. After that, I got back to this mode where I was reactive. What's in my inbox? We were texting by 2009, but I was just responsive to everything else, and it made so much less room in my head to actually think about things. I missed that. You remember we moved out of San Francisco up to Truckee near Lake Tahoe. I was doing 14 hours of coffees and brain picking: "Yeah, I'll meet and hear your pitch." At the end of the day, I was wildly over-caffeinated, hadn't worked out, and had lost my voice. I enjoyed it because I was helpful to their company, their product, and these founders, but I hadn't done anything on my own to-do list. I hadn't written, I hadn't reflected, I hadn't worked out. I hadn't even thought about the weekend and what I might do. Moving to Truckee helped. But even in Truckee, trying to start a business, as much as I wasn't doing daily meetings, I was still just building a business and reacting to it—yelling at people on the phone, getting yelled at. Crystal and I would look up and it would be 4:30. We were still in the clothes we slept in and hadn't been outside. We ostensibly live in the mountains to be in the mountains, so we'd hurry up and get outside before it got too dark. The bike ride for me was the most meditative thing I've ever done. Now, my biggest fear in the world is a 10-day Vipassana retreat. I'm not saying that to be funny; it truly is. I've reflected on this. Snakes, bats, whatever, surgery—all good. But a 10-day Vipassana retreat where you can't read, write things down, or listen to music... you're not supposed to really exercise. You walk and reflect and do chores and sit. **Jackson:** You're pretty good at facing your fear in most parts of your life. **Chris:** Sure, but then in the next hour, you're over it. ## [00:12:29] Leaning into Weird & Investing in Fusion **Chris:** Anytime I have a really strong reaction to something, that is a clue that we should do something. Have you met Augustus Doricko? **Jackson:** I know of him. **Chris:** Augustus has this company, Rainmaker. He's one of our most unusual founders. **Jackson:** I think it was important for you to invest in someone with a mullet after all these years. **Chris:** A mullet. Jean jackets lined with sheep. He has a huge American flag behind his desk. He will unironically quote the Bible sometimes in the work he's doing. I remember we were having a team dinner in LA with the whole team gathered, and two of our teammates had just come from a meeting with him. They were rolling their eyes. They said, "This guy is just a little too big for his britches. The shit that was coming out of his mouth was absolutely crazy. The ambition might be way out over his skis." Crystal and I both had the same reaction. We told them, "No dessert for you. Stand up right now and immediately go back to that meeting." They asked, "Wait, really?" We replied, "If we invest in normal people, all this money is going to go away. The alpha is in the fucking weirdos. Immediately go back there." They said, "Seriously? But what he's doing is crazy." I said, "Yes, he's literally trying to make it rain. That's exactly why we need to go talk to him." There might be political fallout, and we might be the target of conspiracy theorists. We knew that then. But that dude just sounds so unlike any other dude I've ever heard about. Go back there. All the things you're talking about were not toxic. They were just fucking weird. **Jackson:** Right. **Chris:** I don't want to invest in sociopaths. Sometimes you end up with them and think, "Oh, fuck, I misread these signals." But Augustus is the opposite of that. We had dinner last night, and he's fucking weird. But that is at the heart of his success. I was told recently that one of our teammates was speaking at a fancy school, one of those recruiting talks, and most of the questions he got were about Augustus. Not about our climate work, but about this guy. That was an amazing lesson. We got to this point in our life where we realized that anytime we have a disproportionately strong reaction to something, you have to train yourself that it's probably a reason to lean in. Now, sometimes you might find you have a disproportionately strong reaction to Trump, and it turns out I was right. What a piece of shit. I'm sure that'll get me killed, or at least jailed or indicted. I'm on the record. If I were writing for the AIs, it's already there. But there are other times where you think, "This seems like bullshit and makes no sense to me." And then you say that and realize, "Wait, I probably need to go talk to some people." You start to learn. We're huge investors in fusion. We have the only dedicated fusion fund in the world. We had a couple of small projects in fusion to learn; it was family office money. Everyone had always said, "Fusion is 30 years away and always will be 30 years away." It was the refrain for that space, and for at least 30 years, that was very true. But what had happened was the net energy gains from these had started going exponential—in fact, double exponential, where the exponent is also an exponent. As we started talking to other people outside of the fusion industry about it, they said, "That's where dreams go to die. All your money will just get lit on fire." And we thought, okay, except those of you who are saying that just haven't visited a lab recently. If you actually go and talk to the folks working on this and visit the companies... first of all, it's cool. It's the biggest magnets in the world, and they're achieving temperatures of 150 million degrees Celsius, hotter than the sun. Pretty badass. It's always fun to wear hard hats and vests, too. The strong opinion of the market and our initial skepticism ended up being this incredible clue to lean in. The signal to just go find out. "Do your own research" is now a stigmatized phrase for all the right reasons. And please, take your Tylenol. But going to the actual labs, talking to the actual scientists, and looking at the actual data revealed to us this anomaly in the market... **Jackson:** That partially started with a taste in weird. **Chris:** Absolutely. They're not normal people, because these are people who have gone into a thankless industry that was underfunded, ignored, and dismissed. **Jackson:** Your guy leading fusion was at Los Alamos for 20 years. **Chris:** Dr. Scott Hsu is great. He joined us this year to accelerate our fusion strategy. It was Clay's original idea to do this. He's our co-founder, but with no technical background. He was the one who said, "Look, we can get smarter on this space." I had taught him when he first joined a lesson Larry and Sergey had shared with me, which is: with the tools available to us today—and this was in 2003—there is nothing keeping you from being one of the 50 most knowledgeable people in the world on a subject within a year. It sounds ridiculous, particularly for those of us who didn't go to school for that thing. But if you're willing to exchange all your hours, read all the things, nowadays listen to all the things, and then literally go visit all the people who wrote those things and ask, "Can I come see you at your place?" **Jackson:** No one's asking to visit those people. **Chris:** Ryan Orbuch, who's a buddy of yours and works for us, once told me that his cherubic, youthful face meant that people would literally accept him into their lab, even though he was essentially gathering as much information as possible. People found him really harmless looking, so he could go there and ask any question. It was like, "Oh, look at this cute student who wants to know about my work." He's one of the best ever. I think I've mentioned before, he has a certain reflexive Tourette's for the word "why." He just can't help but interrupt you with, "But why? But why? What's that? What was that word?" It's awesome. No filter on that guy. Clay really started this. He read every book on fusion and started meeting all the authors, all the skeptics, and all the proponents. Then when we started meeting the founders, something really wild happened. Bob Mumgaard is the founder of Commonwealth Fusion Systems, which is the most respected company in the space, the most known, up in Boston. Alan Eustace, the head engineer at Google, was the first one to tell me, "You should go meet these guys." **Jackson:** Wow. **Chris:** That's a pretty strong signal. He's one of the greatest engineers of all time—also the guy who built his own platform to jump out of space from without telling anyone. Remember Felix Baumgartner did it for Red Bull? Cameras everywhere, lots of promotion. Then Alan came along and did it from higher on a project he built and funded himself. **Jackson:** Google engineer. **Chris:** The top Google engineer just did it. They filmed it and people found out about it later, but he did it all the time. After we went and saw what was being achieved there and the results that were happening, Bob Mungard said, "I want to introduce you to another guy who's trying to tackle the same problem but with a totally different approach and, ostensibly, a competitor." To be clear, Elon is not introducing you to Rivian. There are a lot of things Elon's not introducing you to today. He sent us to this other team, and we saw a completely different approach in terms of technology to the same problem. Before we knew it, we'd written two checks in the space. As we spent more time, that unlocked that these are people who actually care about fusion. We built more technical expertise within the firm to make sure we weren't just faking it. Then we started to see the facts on the ground had changed, and we built a dedicated fusion fund. We gave all our LPs an option to either opt into it or not, rather than forcing them into it or overloading our existing fund with too much concentration in this one thing. Now we're in eight fusion companies with probably four different approaches to the same problem, and we are also investing in the vertical stack. Some of these people just make magnets; some just make superconducting tape. The hockey stick is genuine. In our last investor update, we posted the first hockey stick we had shown people next to the current one. The peak of the first one is the blade of the second one. Humans suck at exponential curves. Tim Urban wrote the canonical blog post on this, but your nose is right up against it, and you're estimating progress by what's behind you. It's just a cognitive bias. We just started to see truly exponential stuff, so we're out with our second fusion fund now. We don't hold it against anyone who said no the first time; we get it. But these companies went from "not if, but when," and now "when" is much sooner. Even better, they have billions of dollars of commercial agreements. They're siting their plants. By the time this comes out, we will have just broken ground on a facility in New Mexico. I was with the governor of New Mexico here in New York two nights ago, and she's flying home for it. She said, "This is my obsession." **Jackson:** Wow. **Chris:** Making sure to look at things with completely fresh eyes is important, but I have strong opinions. I think our culture has been drifting more in the direction of trying to be more heterodox about ideas, at least in the world that we swim in. It's like, wait, that's been doctrine for a while; maybe I should dive in and question it. I'm close to the Collison brothers. I helped them get in the country when they were literal teenagers. Patrick visited Google when he was 15. Paul Graham brought him by, and I gathered a bunch of awesome people. **Jackson:** That guy is everyone. Literally, he finds them all. **Chris:** They were hacking on Lisp, which was Paul Graham's obsession, so they were known to him. They took their first communion money and bought a computer. Anyway, he brought Patrick to Google. I gathered a bunch of people who could independently assess that Patrick was one of the smartest people walking the planet. I just remember being like, "So what do we do? Do we hire you? Do we appoint a guardian? Do you live in a dorm or on campus?" I didn't get it. What were we supposed to do? You're asking him to decide? Clearly you should be here, but what do we do about that? I don't even know. Over the last few years, Patrick and John have emerged from people I used to think of as younger brothers to people I just deeply admire. I think they're doing it better than anybody else, and maybe it's because they keep each other honest. **Jackson:** They're really good at this weird taste thing, too. **Chris:** Yes. I've spent the last few years throwing hot takes out there, like, "This is some bullshit." And they're like, "But is it?" And I'm like, "You're right. Maybe I was programmed to think that was bullshit." ## [00:24:35] Having People Who Keep You in Check **Jackson:** This is really interesting. You brought up Elon and Tim Urban. Whatever you want to think about Elon, one of the most interesting things Tim ever wrote about was when somebody asked him what's so special about Elon. He said what Elon is so amazing at is that he can 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 reland a rocket; it's physically impossible until it is. It's the exact same thing you were saying about nuclear. I find that somebody like Patrick has this ability you were describing. It's this ability to filter out the total BS and let something enter the filtration system, while the rest of us just decide it's not worth our time. **Chris:** That used to be Elon. I've known him for 20 years. That used to be who he was. **Jackson:** For someone like Patrick, who is still really good at that, what causes it? **Chris:** I know exactly what causes it. The more successful you get, the more money you make, and the more you've built and achieved, the fewer people around you call bullshit on you. **Jackson:** Sorry, I meant what sustains it? **Chris:** My point is, Patrick and John have each other. And whether you call it dialectic—a word I had to look up because I'm not sure I ever knew what it meant—that's who those guys are. They keep each other incredibly honest in their thinking and who they are as people. 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. Three kids later, she is the very first person on a daily basis to say, "You're so full of shit," or "That is a tired idea," or "I disagree," or "You're missing the point." Or, "Are you fucking serious with that right now?" I've never seen anyone care less about celebrities. She's exhausted by questions like, "Are you actually friends with them?" and is so nonplussed about world leaders. I admire her for that as an individual, but it's also why I have been able to avoid the slope that would be so easy to slide down—where everything that comes out of my mouth is Bible and everything I do is infallible. If you look at some of the household-name leaders who we now consider off the rails, completely imbalanced, self-destructive, or outwardly destructive, you'll find people who almost invariably have no one around them who can say no. Everyone around them is either sycophantic or opportunistic or has made a living swimming in their wake. **Jackson:** Yep. **Chris:** And that becomes a self-reinforcing thing. My favorite Wikipedia page is the list of all the cognitive biases. It is all the absolute flaws in our code. We are the most hackable—the most self-confident but hackable—species. **Jackson:** When you read through those, you think, "Oh, I know somebody who's like that." **Chris:** You project them out. As you get older, things become less black and white and more gray, and you start admitting more of that vulnerability, fallibility, and fragility. But we see this just by virtue of making money. Trump knew early on he had to establish himself as a rich person. This is a guy who, if he had just taken the money he inherited from his parents and put it in index funds, he'd be a twelve-billionaire now. He excelled at losing money. He was horrible at deals, Wall Street wouldn't touch him, and he was just a mess. And yet, you can read about how every year he would fight with the Forbes folks to make sure he got on the list. He would submit documents that were likely false because he knew the validating nature of being rich in America. **Jackson:** It wasn't just a vanity point; it was actually utility. **Chris:** That's a really great way of putting it. Mark Cuban is actually rich, and I feel like he could be president because people take what comes out of his mouth as Bible. **Jackson:** You predicted this 10 years ago. Are you still on the bandwagon? **Chris:** No, his family won't. They've agreed as a family that they won't do it, and I can't disagree with the amount of danger and disruption. It's sad. I think he's wildly qualified to do it. But my job on Shark Tank was to keep him honest. What would happen is he would just say something, and to the American jury of the audience, it's just, "Well, the richest guy is the rightest guy." You should read the Reddit comments from when I used to fight with Mark. **Jackson:** I found a few. **Chris:** 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." There was no actual objective analysis of me being right. Sometimes, years later, you find out that the startup I was saying wouldn't work out, didn't work out, and I was right. But that didn't matter. Scoreboard. It was won by wealth. One of the biggest traps we all fall into is starting to believe our own bullshit. I saw a guy write the canonical Shared Economy blog post. Uber was "Shared Economy," right? It wasn't. At no point did Garrett have this grand thesis of shared economy. It started with a car 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. He loved going to dance music at night—EDM stuff. He makes his own music now. He would say, "I can't get a cab at night home from these places. I call, they don't show up," etc. Then he had this dedicated car and thought, "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." At no point was he thinking, "What if we could distribute the resource?" There was no thesis. It was solving a problem. And he's brilliant. **Jackson:** There's probably a lesson there. **Chris:** He's one of the all-time thinkers and way more reflective and philosophical than people ever give him credit for, partly because he doesn't self-promote or tell that story at all. He just lets his products speak for themselves. But I saw another guy write the shared economy blog post that went wild and got shared, and then he would get all the shared economy deals. Instead of evaluating each of them with fresh eyes, every single one of them inherently confirmed that his blog post was right. So he did a bunch of 85% okay deals. You can't invest in 85% good shit. And his money went away. ## [00:32:00] The Power of Language and Stories **Jackson:** On that note, while there are downsides to it, there's also incredible power in using language to organize or narrativize something for somebody. You've literally said, "I write things that raise billions of dollars." People probably don't know, but the lowercase and Lowercarbon LP updates might someday be published in a biography. You are clearly an incredible investor. I want to talk about talent later. You're incredible at spotting talent. You use language to do incredible things. You're obviously good at talking too. I had never really read your blog from 2004 to 2009. You were blogging constantly. **Chris:** Oh my God, you're reminding me. That might have just gone away. Typepad just went down on September 25. I was supposed to migrate it and I totally forgot. **Chris:** Did you access any of that this morning? **Jackson:** No, but you can. **Chris:** I think it might have gone away. Go to the website. **Jackson:** It doesn't show up, but you can find the archives on Google. **Chris:** No, I want them. I left it up there for a reason. I think I've been paying Type Pad a couple dollars a month. You're reminding me that I have this. **Jackson:** Whatisleft.org, I think. **Chris:** Whatisleft.org, yeah. **Jackson:** Why? When did you figure it out? And what is so powerful about written language? You have no need to write at this point. **Chris:** I grew up in a storytelling family. My mom was a teacher and professor, and sometimes, due to a lack of childcare, I would sit in the back of her university classroom at night. We didn't grow up with any money and didn't always have babysitters, so I would have to go with her to Buff State in Buffalo. Similarly, my dad was a small-town lawyer, handling everything that people would need help with, whether they got into trouble, needed to buy a house, or divvy up their estate. I would go with him to court and sometimes sit at the defendant's table. I was once mistaken for the defendant while doing my homework. I would also sit in the judge's chambers, and before you knew it, I was literally sitting side by side with a convict chained to the chair. I also grew up in a family that told jokes and stories. We were a skiing family, and the ski house didn't have a television. We would sit around the table with friends and just tell stories. My dad is a masterful storyteller, and I learned early on the joy of a hearty laugh from the whole table. I learned about the arc of a story, how to set it up, how to prime the punchline without giving it away, and the beauty of a real joke. My dad is an inherently folksy person. We grew up in a small town in New York. When I was 14 or 15, I was deputized by the district attorney in our town to be their first white-collar investigator, mostly because I was the only kid around who could use a computer. They needed to do a white-collar investigation involving forensics of some money flows, and I was the only person who could do it. I remember the district attorney went to the clerk to grab a couple of files, and the clerk couldn't find them and told him to come back next week. He was really frustrated, so I said, "Let me go see." I went down, and they gave them to me five minutes later. He asked, "How'd that happen?" And I said, "I think because of my dad." My dad learned to treat every human as a human. I still can't help but talk to every single person who touches the table, who opens the door, who you interact with at all. What Crystal's dad would say is that every single person has a story—give them a chance to tell it. You start to realize that we are all so hungry for narrative, for stories, for tales, for things to believe in that, done right, feel a little mystical and can provoke emotion and allure. **Jackson:** They're pointing at something, maybe. **Chris:** My mom and dad both wrote and told stories for a living. They weren't published authors, but that's what they did. They organized arguments and reasoning. I submitted my first story to a story contest when I was six years old, and I won. It was for Cricket magazine, a literature magazine for kids. As a result, I was in the newspaper as a published author at age six. The craziest thing about that was my mom used it to help me meet with any author who came through the Buffalo area. She'd pull me out of school. School for me was basically to be around other kids. I was six years ahead academically, but they gave me a computer in the back of the room, and I would just code and make stuff. Then I'd go to gym class and lunch and hang out. I tested out and could have skipped way ahead—I'm not unusual in your audience that I could have—but my mom and dad were very insistent that I didn't, so that I could go on dates and play sports with kids my age and just be normal in a normal town. So I would sit in the back of the class and do my own thing, reading college textbooks while being a normal kid. I feel really lucky for that. Along the way, any author would come to town, and my mom would pull me out of school to go meet with them. If they were hesitant, she would literally send them the article. She'd say, "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 and is a supporter of our work... I don't know if you've read his book where, starting at age 15, he started interviewing the great comedians. **Jackson:** Yes. **Chris:** He would say he worked for some station, and it was really the high school radio station. Then he'd show up and Seinfeld would be like, "Oh, what, it's a kid?" But he'd still answer the questions. I took advantage of that as a kid and would meet these authors. I realized words are free. You don't need art supplies; you don't need canvases. There's a reason I read college textbooks. My mom and dad had all their textbooks from college and grad school. When I was growing up, I had a bookshelf in my room, and they needed to fill it with something. We didn't have a lot of kids' books yet. Any books we would get, we'd go to the library to read and return them. So the only permanent books on my shelves for a while were all their old college textbooks, and I just read them cover to cover. **Jackson:** It seems like there was a mix of both deliberately and sometimes non-deliberately taking you really seriously as a kid. **Chris:** That's a really good point because it's something we've learned to do with our kids. Everyone thinks their kids are special, but I think our kids really are because we've given them the room to be as big as they are and as much as they are. We've never baby-talked to them. They're kids, so we don't foist the problems of the world on them. We give them the room to be kids, but at the same time, we entertain their deep questions. We joke that our youngest is always on mushrooms. She's 10 now, and we've said this out loud in front of her, and she's kind of run with it a little bit. But her questions... it would be so easy for me to dismiss them, but I'm like, "Yeah, why did that happen in the universe? Maybe I have to ask ChatGPT." **Jackson:** ChatGPT, saving parents everywhere. **Chris:** We've just given them the room to be as full as possible. That is absolutely something my mom and dad did. They really were insistent that I didn't feel trapped in this small town we grew up in and that I felt like the world's my oyster, without any real budget to do it. Starting at age 12, they were insistent that we had really hard manual labor jobs at home—character building, just shitty jobs. Literally, one was in septic, so we were digging out septic lines. It was actual shit. But it was just construction-type stuff, equipment-yard-type stuff. They also sent us to stay with friends of the family who had white-collar jobs in Washington D.C., for example. I'd wear the same tie every day and just shadow them around at age 12. Then I tried to write—I remember writing a lobbying leave-behind. I was at some lobbying firm for consulting engineers that a friend of the family worked at. I read everything to try and get smart on what their platform was. Then I would tail along to some senator's office. It was some high-quality swearing from some of those guys. Howell Heflin from Alabama—that guy could spin a yarn. Then I would hand over this leave-behind that summarized the points. Part of it was because I knew how to use a word processor and could format bullet points and stuff. But I just remember, wow, the power of this one thing. **Jackson:** To get something passed when you're 12 or 15. For most people, writing is some chore you do when you're a kid, or for their whole life. Then you turn 22, and it's over. You never really learned the power. **Chris:** I also learned something really early on. Let me give you this example. I came home from college once. I was ostensibly going to college and law school, but I was just showing up for the exams. I took some time to come home while we were building a house for my mom and dad. My mom had some health issues that required her to live on one floor. We moved out of our childhood home and were building a house. The way we could afford it sounds crazy, but when you pay cash to contractors under the table, they don't have to declare tax on it, so you get massive discounts. They're also used to people not paying them or messing around with them. We went to the bank, took out basically all the money my parents ever had, and had an actual pile of cash. We would say to a guy we knew in our town, "Hey, we need a foundation." He'd quote us 40, and we'd say, "15 cash." He'd say, "I'll be here Thursday." We were building this house for cash. We were also using people who owed my dad favors. My dad is obsessed with doing pro bono work. I always used to ask, "Wait, we're broke?" He'd say, "Yeah, but I know this guy's dad and his family, and they need help." I'd reply, "I get it, but we have no money." I helped install my dad's first credit card reader in his office when I was a teenager because I thought, "Let them take the credit risk, not us." It's probably why I became such a capitalist. There were just people who owed my dad favors because he'd helped them with a situation. I was working with one of those guys once. His name was Todd—I won't say his last name—but he had started going to a megachurch in town. We had one of those big Christian evangelical churches that had come in. We were a Catholic town until then, and they just wiped it out. Everyone was going to this church. He is your prototypical Trump voter today: a hardworking, blue-collar laborer who felt excluded from the elitist system. We were laying brick and making small talk, and I asked, "What do you learn in that church?" He said, "Oh, man, last night was amazing. The preacher told this story. He said down in the South—I forget where—you go to this one town, maybe Arkansas, and you'll find this huge, massive statue of Thor." The preacher explained that in the soil at the base of that statue are all the naturally occurring elements you would need to make a watch. You've got the iron that you could make into the metal, and you've got the glass in the dirt that you could melt to be the face of the watch. And the preacher said, "If you believe in evolution, then you should be willing to stand at that statue, wait for lightning to strike, and a Rolex to pop out of the ground." My brother was there, and we looked at each other like, "Holy shit." How many hours, days, or weeks would it take us to undo that metaphor? How much science, how much evidence? How the fuck are the dinosaurs here? **Jackson:** Right. **Chris:** I got to the point where I realized maybe you can't. I started to realize that good metaphor, simile, and analogy are the true weapons of mass destruction. It was another lesson in the power of language. Later in my life, I was briefly an attorney. I was general counsel at a company where one of our founders was arrested based on false accusations from our main competitor. They were trying to put us out of business. They had concocted this story about how he had accessed an anonymous FTP server, which is the standard of file sharing. There were millions of these servers in the world, and they all had the same username and the same password: the word "anonymous" and the word "anonymous." It was the opposite of a private or secure server. And yet this company, Akamai, had gone to the Justice Department and the FBI and said, "This guy just hacked a server." We knew that it was bullshit. It was my first time helping out in federal court, in front of this judge. We get there, and the judge is old as dirt. 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 bullshit. My eyes glazed over. I'm sure yours did, too. So I'm just going to make this easy for you. What the defendant did here was akin to..." And he reaches in his pocket and pulls out a combination lock, the kind you put on your locker in school. He says, "We all know what this is. A combination lock, right? What the defendant did here was akin to just trying every combination on the lock until he got the one that popped it open, then stealing everything inside." And then he sat down. I was like, "Fuck." All I've got are the literal inventors of this standard. The guys who created the anonymous FTP servers were in the room—not even paid—just on the basis that this is some bullshit. Why is this guy in jail? We were powering 2 to 3% of the internet at the time, and they seized our servers. So I'm thinking, how do I undo that? It was a false metaphor, but how do I undo that? I undertook the study. I dove deep into colloquialisms, idioms, and cowboy language. Years ago, I taught a master class at Oxford called "Business Language of the American Cowboy." I already grew up in a place that had a different dialect and parlance than anywhere else. Now I worry that TikTok has homogenized how we all talk. My kids in Montana don't have phones, but they learn it all on the playground from the other TikTok kids. They have the same exact slang as kids in Seattle and kids in St. Louis. It's all the same as the young people on our team. I don't know whether it's "mid" or "sus" or whatever. Those are dated now. It's definitely not "skibidi" anymore. It's "giving." Whatever. It's all the same. I started to realize the power of those things, so I really dove into how we make things accessible when we communicate and how we help people file those in a way that they get comfortable. I got my head around that idea. One of the coolest things to do with ChatGPT—and by the way, I also use Claude and Gemini, I'll just use chat as the shorthand for it—is to talk to it about a real idea. Talk to it about a serious scientific concept, which we do all the time in the hard science business, and then ask it to explain it to somebody with declining reading levels. So start with high school, go to middle school, and go to elementary school. When you start hitting third and fourth grade, the metaphors it comes up with are genius. They're genius. This is how I would explain it to somebody at the bar. It's really cool and powerful. Thanks for calling out my writing. Those update letters you talk about? It is wild. I wish the world saw more of them. They usually contain a bunch of confidential information, so the audience is about 200 people. But we work on those for a couple of months. Even as you were reading that blog post, I saw I used the word snow twice in successive sentences. **Jackson:** I remember editing those letters. Get out the thesaurus. **Chris:** Crystal and I are both type A plus plus. Inside of our wedding ring, it says "in violent agreement." If you've worked in our home, you know how we go at each other because we fight over every pixel. Every pixel, every word has to be perfect. **Jackson:** Who can captivate you in a way that really makes you shut up? Anybody? **Chris:** Crystal made a joke last night at dinner. We had David Kwong, the nerdiest magician of all time. He's a cruciverbalist for the New York Times. He's a magic historian. He wrote this incredible book called \*How to Fool Your Parents\*. It's a magic book for kids. He's come and stayed at our house, and our kids have signed the Magician's Oath, so they work on tricks together. I love bringing magicians to meet engineers because to an engineer, a computer scientist, or a scientist, everything has a clear, linear, causal explanation. And then when their senses betray them, they just stop. I used to bring David Blaine to Twitter; he's an old buddy. And I would just watch the smartest people I know go blank. Crystal always jokes about how I've become an obsessive student of magic. Last night I knew how eight of the 10 things were done, but she watched me and was like, "Oh, he doesn't know this one. He can't figure it out." And she's like, "David Kwong might be one of the only people who can shut up, Chris." I love a good listener. **Jackson:** Talk about a type of storytelling, too. **Chris:** There are authors who make me stop: Steve Martin, P.J. O'Rourke, who's passed away, Chuck Klosterman. There are authors—and I'm forgetting a dozen, I read too much—where I'll read a sentence and just think, "Man. How can I ever..." **Jackson:** Have you ever read Richard Powers? The The Overstory. You could hang those sentences on a wall. **Chris:** Oh, the Overstory. I didn't remember that. There are people who write substacks or poetry I like. I've reread Billy Collins. His poetry is incredible because it is such accessible, normal, everyday language communicating incredible ideas from a completely familiar life. I constantly reread it and am intimidated by it. I don't know if I see it in speech as much. I love good orators and powerful speakers. **Jackson:** And your writing is like that, I would add. **Chris:** I watch a lot of evangelical speakers. I watch a lot of ultra-populist Republicans. I tell our people that if you're not diving into it... The whole Charlie Kirk thing is a horrible tragedy. I don't think he had the best intentions, and I think a lot of what he was arguing was insincere, but I listened to it constantly. He went on Gavin's podcast. I think Gavin is a great person with good intentions, but Charlie ate him alive. This is a rhetorical master. This is a person who knows where they want to get to in an argument and can take people there, making them feel empowered along the way. There's no denying the effect he had and the relationship his viewers and listeners had with him. That power of debate makes somebody feel invested, like they followed the chain of reasoning to that endpoint. **Jackson:** More like a story. **Chris:** We have to not run away from that. We have to understand why people crave it and why it makes them feel like a co-author of the story. I talked to Ira Glass about this 10 years ago. I was on primetime television. I was out there; I was exposed. But the people who come up to me and have the strongest reaction were people who heard me on a podcast. That Startup podcast with Alex Blumberg, season one, episode one. I still get stopped in New York. **Jackson:** I think that's how I found out about you. **Chris:** It's 2025, and I still get stopped in New York because of that. I talked to Ira, who is the greatest audio storyteller of all time and wildly intimidating as a result. When you talk about speakers, I would put him there. So is Alex Blumberg. Alex Blumberg, who co-created \*This American Life\* with him, is just incredible. I think about why people feel they have such an intimate, deep relationship. I could walk down the street in New York with Edward Norton—one of the great, you've been there, one of the great all-time performers and a genius in his own right and so sui generis. He's a CEO and a founder and all the things. But if we walk down the street in New York, people come up to him and stick their arm out. "Oh, Mr. Norton." Literally, "Mr. Norton, I loved you in..." And it's wild to see—was it \*Primal Fear\* or \*The Hulk\* or whatever? **Jackson:** He's not really a person. **Chris:** No, he's a series of characters. I have always played myself. I've tried acting twice, and I'm miserable. Both times, they had me play myself, but they scripted the lines. I thought, "This is not actually what I say. Or if I said it, this sounds weird the second time." I'm a shitty actor. Because I play myself and because I tweet about myself, people are convinced they know me. They come up and get right in my personal space and talk to me like we're pals. When I am on a podcast and I try to be as real as possible and talk about things people don't expect me to talk about, then they believe we know each other. **Jackson:** Yep. **Chris:** this came full circle for me when I met Alex Blumberg for that episode to tape it. I was not convinced that podcasts were a business yet. You were there; you were working with us at the time. But hell yeah, I was going to take a meeting with Alex Blumberg. He'd been in my ears. \*This American Life\* was kind of like my church. **Jackson:** Yeah. **Chris:** I'm not a religious person, but that was a spiritual thing for me. It came out on Sundays. At first, I used to listen to it on the radio, and then when podcasts were a thing, it was my go-to. It was top of my list. When Alex Blumberg wanted to meet me, I was going to pretend like I'm not fanboying. **Jackson:** He's doing the thing. It's amazing. I just listened to it back—it's incredible. He's so nervous, and then you're telling a story back to him, and it's awesome. **Chris:** But I show up, I go to walk into our favorite sushi restaurant, Mori, and as I'm putting my hand on the door handle, I think, "Wait, I don't know what Alex Blumberg actually looks like." **Jackson:** Right. **Chris:** I have spent so many days with him. **Jackson:** His voice is in my head. **Chris:** I have a picture of what he looks like because I hear his voice, and it sounds just like Ira's. I don't know if they influenced each other that way. I walk in and start panning this restaurant, panicked, trying to figure out which of these people is Alex Blumberg. Then I look all the way right, and there's a guy with a big boom mic and earphones on. It's clearly my guy. I had been building the story. I had been setting that stage and costuming it. The long-form nature of it is very rewarding. I think there is a lot of reward with an audience for being real and being yourself. Not everyone adheres to that; they're playing a character or saying something they don't actually mean because it's opportunistic, advantageous, or manipulative to do so. The power of podcasting is significant. I have this theory that if the Dems ever have a president again, or if we even have free elections again, it won't be a current politician. I think it has to be someone that comes out of podcasting or sports. **Jackson:** Stephen A (Smith) is waiting in the wings. **Chris:** Years ago, I told Cory Booker—he's an incredible person and a true public servant—"If you want to shatter the glass ceiling of your relevancy to America, you played football at Stanford. Go on College GameDay." **Jackson:** Chalamet did this. **Chris:** Yeah, **Jackson:** he crushed it. **Chris:** I told him, "Just go and do not talk about politics. Don't even have them introduce you as Senator Cory Booker. Just talk about football. You know it." Maybe two years ago, I talked to Gavin here in New York and said, "I know you, and a lot of people know you, but most people think you're just a slick politician. They don't know who you actually are, why you do this, and all the other opportunities you'd have." So I told him to have a sports podcast. "You care about sports. I know you know how to talk about sports, but you never do. You're a good orator about politics, and you've got all the facts, but America doesn't give a shit about facts anymore." He came back to me later. I saw him at the Super Bowl when the Niners were playing, and he said, "Hey, I'm doing it." I asked what he was doing, and he said, "I got this thing. It's me and Marshawn Lynch." I'm like, "Fuck, yeah! You're going beast mode. You're going to take care of your mentals and your chickens. That is amazing." Then he said they put it on Sirius. I'm like, "That is the opposite of amazing. You might get to a few truck drivers." And then they talked about politics. I love what he's doing now. I think Gavin's only hope is to shake it up and break every norm, so I love what he's doing with his content right now. There's no downside to it. There's just a limit on what he could be politically if he doesn't build that connection with an audience and motivate people. I think George Clooney could have been president some years ago, but I don't think it's going to be a traditional star now. It's got to be someone who has a recurring, connective, vulnerable, authentic relationship with an audience. Today, that's podcasters and athletes. **Jackson:** You gave up on having an audience, and you don't write publicly anymore? **Chris:** I miss it. It's a drug, though. You can get addicted to it for all that self-reinforcing stuff. **Jackson:** Yeah. **Chris:** People would scream about me on the internet, on message boards and Twitter. I didn't love that. Everyone says, "Don't read the comments," but you can only read the comments. Twitter is only the comments. It goes back to cognitive biases. We're built to find the one. There can be 20 flattering things, and then there's the "fuck you." I saw a comment where somebody said my eyes turn down at the corners and that's associated with some level of retardation. I was like, "Wait, what?" **Jackson:** You think about it for four days. **Chris:** I started Googling it to understand. How do you look away from that? It's like, "Those eyes are associated with..." **Jackson:** John Mulaney has this old joke where you walk by middle schoolers on the street and they know exactly the one thing to say to you that just devastates you. It's the internet. **Chris:** Last night I was out late in New York with our team, talking to one of our founders, Carl, who runs Zanskar, which is this incredible geothermal company. I said, "You know, it's funny because…" and a guy walks by, goes, "It's not funny," and just keeps walking. I just turned around, like, "Dude, you just made me laugh. That was actually funny." You saying my thing wasn't funny was actually funny. I loved it. The timing was perfect. New York is amazing. ## [01:03:03] Investing, Risk, and Wild Confidence **Jackson:** I want to talk a little bit about investing and risk. Famous line: "It may be lucky. It's not an accident." Classic. I've repeated that to many people. You also are very thoughtful about stacking the deck, playing a game you can control. You have a really strategic and successful relationship with risk. My sense is that most people wildly overrate risk or are afraid of risk. I'm curious how you've used risk broadly in your life and maybe why it's less scary than people think it is. **Chris:** There's a couple of components to this answer. I'm going to tie this back to what you were just asking about, but I do miss having an audience, and I'm writing something right now for an audience. But I really worry that ChatGPT has diluted the power of words and taken a lot of the soul out of writing because it's pretty fucking good. It's not great, but it's pretty fucking good. In the same way that Instagram cheapened photography and took a lot of the soul out of it, AI is doing it all over again. AI image editing is doing it, and maybe Sora is doing it for video. I have something I'm really obsessed with right now. I talked about it a little bit with Tim. He knew I was working on this idea and forced it out of me. It was really preliminarily baked, and since then, I have someone I'm working with on it. We all tease this generation. I'm decidedly Gen X. I'm 50—I use a good skin cream, but I'm definitely 50. And I'm 50 from Western New York, a banged-up place in the Rust Belt. I'm still really close to my friends from high school, some of whom have had hard paths. Guys like Chuck Klosterman, who've written about our generation, and Jean Twenge's book about generations have made me prouder of being Gen X than I ever was. I think we were taught to be ashamed of ourselves because we were slackers. I've become pretty proud of who we were, or are. I've started to take responsibility in the same way that we think boomers need to take responsibility for how they fucked up our planet and economy. We need to take responsibility for how we fucked up kids. I have trouble talking about this without feeling like I'm characterizing an entire generation of people as broken. You're going to yell at me. I'm not on social media, so I'm not going to see you yelling about me anymore. So go ahead, say it. I worry we see too many people—not all people, but too many—who have no agency, no resiliency, no adaptability, and take no initiative. My friend Matt from Bozeman said they ask for permission to solve a problem. Crystal and I lit up. **Jackson:** They ask for permission to ask a question! **Chris:** In a 30-person Zoom, they let everyone know they're going to the bathroom. You're a professional, making hundreds of thousands of dollars a year, leading tens of hundreds of millions of dollars of investment. Go piss. 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. I've trusted you to run a part of the business. You really don't need to let us know the status of your bladder. You've now imposed that cost on 32 people. You've interrupted the discussion to let all of us know that you need to take a leak. Just go. What I really worry about is that we don't give kids a chance to fuck up anymore. We don't give kids a chance to take risks and make bad decisions, whether it's helicopter parenting or snowplow parenting, or robbing them of a play-based childhood and putting them in a phone-based childhood, which is way less safe. We overclock for physical safety and underclock for online safety, as Jonathan Haidt has written about extensively. I think he is one of the most honest brokers of truth about what's happening to kids. Originally it was girls, and now he's realizing men and boys are so deeply affected by this too. At the heart of it, we just don't give kids a chance to make decisions, let alone bad decisions. Good decision-making comes from bad decision-making and feeling the consequences of, "Whoops, that was stupid." There was a fight at our kids' middle school last week. I don't know the two kids who were involved. But unlike the fights we had, there are 10 different camera angles of this fight. I watched them. They were sixth graders. Two slaps landed. Other than that, you could see both kids were terrified of each other and of being in a fight. Their sixth-grade adrenaline was firing, so they were posing as punching, but there was at least five feet between them. Eventually, the fight got broken up. The school, a public school in Montana, suspended the core witnesses to the fight for a day and then suspended the participants for two months. **Jackson:** Oh my gosh. **Chris:** In hockey, you get five minutes to reflect on that, and then you're back out on the ice. Crystal and I have worked extensively to help people. We've worked on helping California use brain science to pass a law that allows anybody who is sentenced to die in prison for a crime they committed under the age of 25 to be eligible for resentencing. They're not necessarily freed—not everyone should be freed. But there are some people who did horrible, inexcusable things when they were 16, usually as a result of horrible circumstances. We now know your frontal cortex is not fully formed until you're 25 or 26. There's clear science on that. We do dumb shit. Sometimes that has mild consequences, and sometimes it's life-changing for yourself and others. Do you know what suspending two kids from school for two months does to their trajectory, their social development, and their academic progress? It wasn't hate or racial or anything like that. It was just two kids who had beef that got out of control in the hallway, and people talked it up. By comparison, I had this buddy in school we called Hawkeye. He knows who he is. He would see a fight start to break out in the hallway. I went to a huge public school with fights all the time. I lived in fear of the hallway. I was a nerd, an easy target. I had to make friends with protectors, like going to jail where you have to find the big guy to be your ally. He would see a fight start to break out, immediately go in and break it up, and say, "Let's settle this after school." He would find a kid who lived near school and have the fight in his yard. He would bring a video camera, charge admission to the backyard, and give a cut to the kids who were fighting. He would make so much. **Jackson:** You're giving the TikTok kids some ideas. **Chris:** He would make so much money doing this. I admired his entrepreneurship. In school, I sold Blow Pops. So did Hawk; I think he pioneered it. I didn't deal drugs, I dealt sugar, and it was totally against the rules. I had a secret pouch in my backpack. 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 that we would buy those Blow Pops for seven and a half cents wholesale, but you could buy a box of sour apple. There was way more supply of sour apple in the market than anyone thought. They thought they were getting the one. I also ran a card room in school. We played a game called Bourré that no one listening has ever heard of. It's mostly played in NBA locker rooms and on flights right now. It's a game that originated in Louisiana. Any pro ball player has played Bourré. It's a progressive pot game, and the stakes are really high. I ran a spades room too. That endeared me to President Obama—he throws spades. I had a teacher, Mr. Maine, and I paid him a cut. I gave him a piece of the vig, a piece of the rake. I ran a tab. I loan-sharked. I did shit like this all the time. I would get busted and there would be some consequences, but it was enough to shut it down for a week or two. **Jackson:** All of this is table stakes. People aren't taking enough risk. You're also the guy who wrote a $25,000 credit card check into Photo Bucket. **Chris:** You see the relatedness of this. By the time I wrote a $25,000 check to Photo Bucket, a few years before that, I had lost millions of dollars trading on crazy margin online. **Jackson:** You were down $4 million. You had to work yourself out of. You came out of Google not that rich because you had to work yourself out of $4 million of debt. And then somehow you also had enough conviction... You are using risk as your ally. There's a broad-based fear of risk that culture has today, and then there is how you have the balls to... Part of it is that you're taking less risk than it looks like from the outside looking in. **Chris:** You talked about playing rigged games. As a kid, I was fascinated. I started going to university for math in sixth grade. I would sit with college students at night, so I was a math kid. I could calculate pot odds in my head. I could do expected value calculations. I loved books on casino science. Just before I was leaving to come to New York, a new one on casino design for addiction showed up on my desk. **Jackson:** "Addiction by Design." **Chris:** That's it. **Jackson:** My friend Blake Robbins always talks about it. **Chris:** 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, and fascinated by lotteries—how everyone can attach themselves to the outcome of the lottery and that narrative. And how would you spend that money? A dollar and a dream, knowing it's a losing bet. I only play rigged games, and to me, venture investing is rigged. I am a horrible public markets investor. I get invited on CNBC, but I haven't done it in years. I would talk about a stock and then look, and it didn't move either direction at all. Volume didn't change, price didn't change. This sucks. I'm not a good picker of public stocks, and I can't affect the outcome. In venture, people have accused me of being self-promotional. If I don't promote myself, who's going to? I hope I've earned the right to take credit for things I'm good at and acknowledge the things I'm not good at. But I'm good at increasing the likelihood of success of a company. That's why people bring us their companies. That's why we put up the 214x on our first fund, the 17x on fund two, and the six-plus billion dollars of return to investors on just secondaries alone. It is not maybe lucky, but it's not an accident. I know how I've caused that. People say I might be lucky, and I say, "It's weird how I keep getting lucky, huh? Maybe 13 or 15 times I've been lucky. Weird, right?" The odds would be in the quintillions. **Jackson:** You said you're not good at public markets, but it's worth noting—crazy Lowercasee fund, people know you as this legendary angel and seed guy—you made a lot of your money 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. That maybe is the underrated part. **Chris:** But that's because the odds have shifted. My first check into Twitter was 25k, 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 I would just have somebody badge me in. I was a self-appointed business guy because this thing needed to make some money. **Jackson:** And you were working to make that happen. You were actually improving its outcome. **Chris:** I kind of did the first $30 million. **Jackson:** But later on, you weren't doing much to help Twitter, and yet you still saw what nobody else saw. A lot of early-stage investors believe in their companies, but they think, "I'm an early-stage investor; I have my multiple." You decided, "No, I'm going to go rally up with Rizvi and own the majority of this thing." **Chris:** Suhail Rizvi was an incredible partner on that and unlocked a lot of capital for me. But I knew at that point it was mispriced. People were still asking, "How's Twitter ever going to make money?" I'm like, "Are you fucking serious?" I ended up having this personal mantra: I'm no longer here to convince them; I'm here to take their stock. So I just went and rolled it up from people who didn't believe. By the time of the IPO, we owned about 16% of the company; 15.8 was the number. I do the same now. I just explained how the expected value calculation of Fusion had changed from the way the market prices it. So now we're into fusion for 10 figures. **Jackson:** When you have conviction, you are smashing the throttle. That maybe is the difference. **Chris:** I also know I can make Fusion more likely to happen. That's across all of these things. When you talk about having the stones to take risk, I think sometimes risk is mispriced. A lot of that is rooted in narrative, fear, imposter syndrome, and underpricing the ability to impact the outcome. I also believe... I think we were working together when somebody asked what all our most successful founders have in common. I was trying to find a thread. It wasn't how they grew up, but there's no doubt that immigrant kids, with the things they overcome to get here and build stuff, their hustle, their desire, their focus is insurmountable. People who grew up with single parents have that same fire, that same adaptability and resilience. They've taken on responsibility at such an early age. You can't deny that they're a disproportionate representation within successful entrepreneurial roles. But I kept looking. Are they scientists? Are they computer scientists? Did they all sell Blow Pops when they were kids? Did they have a hustle? A lot of them did, but not all of them. The single thing I found among every one of our most successful founders is that not only did they not prepare for the downside case, it just wasn't one of the options in the math. It wasn't. Zero was never a consideration or a possibility. **Jackson:** Success was inevitable. **Chris:** You know this. When I first sat with Kevin and Mikey, who were building Instagram, I was throwing out a product idea, and they said, "That's a great feature for when we get to 10 million users." And I said, you guys: " we are meeting in a coworking space. There are two of you." We were in the dark shadows offstage of some pitch event Calacanis was running. And I think, by the way, Travis pitched on that same stage that same night. "I said, what's with this 10 million users thing?" But Kevin wasn't trying to sell me. He just knew it. He literally knew it. You can just tell. You can tell in the body language. **Jackson:** When you say you can just tell... \*You\* can just tell. But I think a lot of people can't. What does that mean? **Chris:** Hopefully you get to a point in your career where you can tell if somebody's selling you, if somebody's hitting on you, or if somebody's trying to steal from you. Hopefully you start to get that read. If you can't, you should be spending way more time with people. You can try to train this. I remember being on a train in college and reading Mike Caro's book of poker tells. Then there was the micro-expression guy who trained everyone in the FBI and CIA on how to read eye wrinkles and micro-expressions (Paul Ekman). So you can train yourself a little bit, but it really comes from just knowing people and spending time with all types of people. Travis (Kalanick)—we haven't talked in a long time, and we don't agree on a lot of things, but he was my closest friend for a while. We spent a lot of time together. We worked on Uber for six months before it was incorporated, and he was an advisor to the company early on. A little-known fact about Travis: there was a point where he was weighing whether to become CEO of Formspring or CEO of Uber. Those were literally equivalents. Formspring was a flyer. **Jackson:** A lot of people listening probably don't even know what Formspring was, but it was big. It was the anonymous question-asker deal. Oh my gosh. **Chris:** Yeah. **Jackson:** I think the world lucked out on that one. **Chris:** TK is a wildly talented person, but one of the things that might have led to his imbalance was being so wildly successful that there was nobody around him who could say no to him anymore. I think Travis is one of those people. That might have been one of the things that pushed him to some extreme places. I remember being in a meeting where Ryan Graves had shown some analysis. Ryan was the first employee at Uber. **Jackson:** Wasn't he CEO briefly? **Chris:** Ryan was CEO in a time when it was a relationship business. He looks like the Marlboro Man—an incredibly handsome guy from a 1950s cigarette ad, but he also has a very high EQ. At a time when drivers were suspicious of us, Ryan could walk into a room full of very skeptical Armenian limo drivers, at risk of being pummeled and dropped in a back alley, and walk out arm in arm with these guys. That's still who he is. He is a guy you can build a relationship with and count on, and I think his EQ has gotten even higher. But there was a point where we started to realize it was a math company. It was the biggest yield equation in history, more than the airline pricing algorithm. We had more units and more data, and with surge pricing, it was just becoming a huge equation. Ryan didn't come from the world of cohort analysis and regressions. That's Travis's kink. He can do it in his head. I remember Travis saying, "Once you take 2.71 rides on Uber, you're a customer for life." That's the actual number I remember from an early board meeting. It stuck with me forever. Travis could just do that. We started to realize this is a math company, less about relationships. In the end, maybe we needed more Ryan and more relationships, and the company would have been in a different place. The reality was, turning all the math dials is what made it as big as it was. Maybe not as friendly as it should have been or could have been. Maybe not as accepted or embraced. Maybe it never could have been. I remember being in a meeting where Ryan Graves tells us the data show that Houston is the next city we should go to based on the black car market and cabs. And Travis says, "No, we're going to Paris." We're like, "What?" And he's like, "They hate us there. I'm going to win Paris." He went to Paris, stayed in a hostel, and won Paris. A lot of the original ideation for Uber happened in Paris. Travis, Garrett, and Melody McCloskey were there in the early days. It was at LeWeb, Loïc Le Meur's old conference, and it was hard to get a car there. There were a lot of late-night jam sessions, and that's where those guys really polished the idea for what was going to become Uber. Garrett had already had his own personal car that he let some of us use here in New York. But he's like, "I'm going to Paris." Normal people don't do that, but he just knew we would get it. To be clear, they set Ubers on fire and dropped rocks from overpasses through the windshields. And yet, he did it. Later, think about Travis going to China. He went up against a state-sponsored ride-sharing company. Everyone likes to characterize that as a loss, but he turned $2 billion into $17 billion. I'll take that trade every time. It was a genius move. He definitely got punched in the figurative face over and over again trying to do that. He was stalked and harassed. Can you imagine going into maybe the most authoritarian market where they don't like when somebody out there is rebelling? People get disappeared sometimes. When I take it to my own journey, when I lost $4 million in the 2000 market crash—by the way, I lost $16 million. I was 12 million up and 4 million in the hole. I'd never spent any of it and had nothing to show for it, but I was trying to pile into my geometric gains from my first couple thousand-dollar bets. It started with my student loans. I told the school the checks hadn't shown up. I went to a check-cashing place, paid a ridiculous vig to do that, and then kited them into the market. But when I was $4 million in the hole, at no point did I consider that failure, or that I'm out, or that I have to move back home. I was just so fucking angry that this was going to slow things down. **Jackson:** That's the difference, I think. An internal locus of control, maybe more than anything else. You've talked about this a lot: when you're up, it's all skill; when you're down, you're unlucky. But I think when people really get hit on risk, they probably internalize that they got super unlucky or got killed. There was never a point where you felt it was out of your control. It was just, "I'm going to make it back." **Chris:** Because I could impact that, I thought, "All right, I've got to just build a thing and work that much harder. Damn, I hate that the score has been reset." ## [01:27:57] Imposter Syndrome and Making Companies Better **Jackson:** Where did the confidence come from? Do you have any imposter syndrome in any context? **Chris:** Absolutely. All the time. If you don't listen to Neil Brennan's podcast \*Blocks\*, that's one of my favorites. Neil is a really cool person. He kind of pivoted stand-up comedy into that realm of vulnerability. He wasn't the only one, but he's had three very successful Netflix specials in which his comedy is rooted in just bearing his soul, talking about depression, talking about struggles. His most recent Netflix special was incredible. He's like, "For those of you who know me from \*Three Mics\* and from \*Blocks\*, you're going to be a little upset because I'm happy now." One of the things he talked about in this special, \*Blocks\*, was all his own things that have gotten in the way—obstacles he's either had to overcome or that still weigh him down. There was so much emotional response to it, not just among audiences but among peers, that he made it into a podcast where he brings on performers and creatives, and they talk about their blocks. This is a guy who is so deeply respected, and the nature of those conversations are so raw. He got Jerry Seinfeld to admit to imposter syndrome. Still. Jerry's still struggling with the idea, "I'm not a stand-up." Neil is uniquely good at this. It requires an incredible amount of courage to talk about the things that banged you up along the way. We had a culture that really shunned and stigmatized those things. Maybe we're opening up more about it. Maybe therapy and trauma culture has been a little overplayed among some people, but he gets people to talk about the real real. I have imposter syndrome. Until a couple of years ago, we didn't even have an office. We launched an office because we realized our young people weren't learning from our more experienced people. That sucked because a lot of learning happens in collisions in the office, overhearing a call, or being pulled in to take some notes, or at lunch. It just doesn't happen over Zoom. I work from the middle of nowhere, and there are definitely advantages to that: being in nature, being outside of the bubble, talking to real people all the time. I actually feel more in touch with real politics than almost anyone I work with because I am among real people. One of our daughter's best friend's dad drives an Amazon truck, or they coach sports, or they bartend, or work in the hospital. They are middle-class folk. Being out of the bubble is psychologically refreshing from a perspective, relationship, and raising-kids standpoint. We live in a free-range town. There are 150 bikes out in front of the middle school with no locks on them, so the kids can just roam without phones. They just go, and fingers crossed, they come back. They usually do. I think they have a hundred percent track record of making it back home at this point. There are three of them, so the odds are good. For me, not having an office... Do you remember when \*Shark Tank\* tried to film the opening reel of me? They're like, "Well, we've got to go somewhere that says Lowercase on the wall." We don't have that place. We borrowed a portfolio company's office, put a logo up on a projector, and then pretended to have a fake board meeting. Were you in that clip? **Jackson:** I wasn't in it, but I remember that. **Chris:** They said, "We'll come by your mansion." I have a 2,000-square-foot house; it's not going to impress anybody. Then they asked, "What about your boat?" For Lori, they rented a boat to make her look rich. They just sailed around Newport Harbor. When I said I don't have one, they asked, "How is America going to know you're rich?" It was really important for them that we look rich. I don't look the same as the other guys. We never had a big office or a big team. I didn't go to school for finance, wasn't versed in finance, and I was never really concerned with our IRR. I still can't tell you what it is or what it was. I know our multiples, because that's how you think about cards or sports gambling—how much money I put in and how much money I get back. When I get to New York, I can use DraftKings again. I can lay action on my Bills. I bet a little bit of hockey. Sports betting shouldn't be a thing, but I love it. I always felt like I wasn't a venture investor, even when making the Midas list. I would think, "What am I doing here?" **Jackson:** You just listed off a bunch of superficial stuff. Clearly, none of this imposter syndrome is getting in the way of smashing the throttle down. Chris I'm not a venture investor. I am a builder and a helper. And you have confidence in that. **Chris:** Yeah. I'll tell you one of the things I struggled with for a long time—and now I have enough data to show it—is the tyranny of lack of relevant experience. The most successful people I work with have no domain expertise in investing, and that's me. When one of my mentors, Hans Swildens, convinced me to launch a venture fund, I said, "I've never managed anyone's money. I'm not even good at managing my own money." I've had a collection agency after me at one point just because I forgot to pay the bill. I've also had them after me when I couldn't pay the bill. I asked, "How would I manage anyone else's money?" He said, "That's the easy part. We'll do that for you." I used Industry Ventures' back office for the first couple of years. He said the hard part is picking the companies and making them better. He might have just said "picking the companies," and I added "and making them better." **Jackson:** When people ask what I learned from you, I say that you don't want to bet on the things that need you. You want to bet on the things that are going to work with or without you. But you would always accompany that with asking, "Where is the deck stacked and I can have an impact?" **Chris:** At heart, each of us wants to be helpful. One of our daughters, CC, started volunteering recently in school, tutoring other kids. She's an academic superstar. Our kids are homeschooled for academics and go to school for orchestra, phys ed, lunch, and to play on sports teams. It's a perfect balance. Montana's amazing that they can do that. **Jackson:** Yeah. **Chris:** They were the ones who requested to homeschool. Academics for them weren't as compelling, and they were losing their curiosity and their thirst for learning. That's fed the way they get taught with these Zoom tutors, who are incredible and really help pace them, push them, and challenge them. But they also are regular kids: riding their bikes, wearing hoodies, goofing off, getting in a little trouble, mixing it up, doing dumb shit like I hope they would. Have you looked at the data? Kids don't drink, they don't hook up, and they don't want their fucking driver's licenses. And that's translating to the workplace now, as we talked about. So, I've watched her light up as a consequence of being helpful. It's a new thing she unlocked. She's a helpful kid around the house and helpful to friends, but being formally helpful to another person is unlocking what she's doing by tutoring kids who are English language learners and helping them catch up academically in their mainstream classes. Frankly, when I first started in Venture, the trap was people would come pitch me, and I would think I could make this better. But it wasn't already great. My first four or five deals were shitty. **Jackson:** Yes. **Chris:** They needed... **Jackson:** There's a me-shaped hole here. **Chris:** That comes from imposter syndrome. I left Google. I left a hundred million dollars on the table when I left Google. It was financially a dumb decision, and there were definitely days where I thought, "What was I thinking?" It wasn't 100 at the time; it grew to be 100, but I bet it was 20. It was stupid, and it took many years before that was the right trade. **Jackson:** Not that many years... **Chris:** When I first started showing up in Y Combinator or meeting with founders, I thought at first I was going to have to fake it till I made it, but instead I was immediately helpful. That was a great feeling. But I also had to build the feature of knowing that when you work for a boss at a company and they assign you something to do—you're working for Eric Schmidt and he says, "Hey, I need you to do this"—you can't say, "No, thanks. What else you got?" Whereas when you start playing poker, you realize that most hands get folded. Or maybe you just check, and then once it starts getting raised, it's just folded. If they actually showed the entire poker game on TV, it would take nine hours and it would be boring. They only show the super compelling parts, and that makes people go to Vegas and do dumb shit. They think, "Oh, yeah, I'm going to play the 2-7 and see how this goes." But I started doing each thing that was pitched to me because I thought, I can make this better. It was filling a hole of wondering, can I be an investor? I can make all these things better. I had to learn to build a filter. What I do for a living is say no. It's hard to be an optimist and say no all day. And then from that, I find things that are amazing and that hopefully I can make better. ## [01:38:03] Lowercarbon's Team and Culture **Chris:** What I'm confident about is my ability to make things better. And that's something we really work with our team on. You don't have to have gone to business school. We have some people who have, and we have one of the most brilliant analysts I've ever encountered in any industry: Caie we call her Caie GPT. She's special. But at the same time, really successful investors don't have that. Our co-founder, Clay, his resume betrays nothing that he would be an investor ever. He worked… **Jackson:** Incredible impressive person **Chris:** but... Let's be clear: when I was reference checking him, the Pod Save America guys got back to me within the hour: "Absolutely, yes." And then a person close to the president said, "Hold for the president." The president said, "Clay, hire him. you'll thank me later." They handed it back to the guy, and I thought, "Well, we're done with the reference check." **Jackson:** Clay worked in the White house. **Chris:** He was a chief of staff, to... **Jackson:** We overlapped for one month, two months. Very tail end of my lowercase. **Chris:** Oh at Lowercase, yeah. We didn't hire Clay to be an investor. **Jackson:** It was all the political stuff, right? **Chris:** Once you were gone, we had to write an update to our investors, to our LPs. We had 100 companies, and some of them were companies I'd never met because you did the deals. I didn't know any of these guys, so I said to Clay, "I have to write about this stuff, and some of these are young people things that I don't understand. I've never met these guys, so can you go check in with them so I can fulfill my duty to our investors?" He had 25 hours in his day at the time—no kids yet. He's got four now, four under six. He started talking to these entrepreneurs, and two things happened. One is they started calling us saying, "Clay's amazing. Can he be on our board?" That wasn't even his job; he was basically supposed to be taking notes. He was not hired as an investor. He was supposed to help us with politics and philanthropy. But two was, one of the quickest ways to learn this business was to get thrown into a portfolio that already had some age and some dents on it. It's cool to get exposed to Uber and Stripe, but it's even more helpful to get exposed to shit that's been going sideways or that is going to. **Jackson:** At the beginning, it's all possibilities, it's all dotted lines. **Chris:** It's so easy in the beginning. I see this in our team now. You can't lose. Most of the people we hire right now have never lost. **Jackson:** In life. **Chris:** They've all aced their SATs. They all were front-row kids in college. By the way, I actually think we hire fewer of these people than we used to. But if you're going to have a science-heavy team, these are the best scientists, and they've all gone to grad school and they all just never failed. 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. You have to digest that failure. It's funny, they struggle with it or they do the safe thing. And we have to teach that out of our teams often, right. **Jackson:** It's sort of like teaching risk. How do you actually teach that? You didn't have to do a lot of that in the Lowercase era. You've got a big team now. **Chris:** Here's one thing I do about risk: I make sure that no one is individually accountable for our losses. I remember one of our early employees who I dearly love, and we wouldn't have been able to build this without him. He listened to a podcast about Bessemer where it's "eat what you kill"—where everyone's compensated on their specific deals. He came to us and said, "I want to do this here." And I said, "I don't think you do." I appreciate challenging the model because everything we do is an evolution of something that we're reacting to that we've seen somewhere else. But 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 recognized as the seventh best place to work in America. A law firm. What? I don't know what kind of scam they were running, but I filled out that survey. It was the seventh best place to work in America. I was a first-year associate. I needed help on something, so I went two doors down to a fourth-year associate who was smarter and very successful. I said, "Hey, Sayer, can you help me on this thing?" He asked, "Can I bill on it?" I said, "No, I just need..." And he said, "Then get out of my office and close the door." Wait, we work at the same business. I probably took it personally, but I don't blame him. The incentives were such that he had to rack up hours. Every hour he was spending on my thing was an hour he wasn't with his S.O, he wasn't working out or having fun. So why would he fucking do it? **Jackson:** Yep. **Chris:** It's not a charity; it was a for-profit enterprise. I hated that feeling. Google was constructed the other way. When I first got there, I shared an office with Urs Hölzle, their very first engineer. He is one of the most brilliant minds of all time and a wildly successful person. Google wouldn't be Google without Urs. He owned a real part of the company and was worth a lot of money. Somebody showed me a picture of one of the first T.G.I.F.s, the Friday gatherings of all the employees, when there were only seven people there and Urs was wearing the same shoes he was wearing post-IPO. It was amazing. Here's a fun thing. There was an alias at Google that I subscribed to called "contracts@google." I was one of the lawyers there initially. Anyone in the company who had a contract would send it to that alias, and then somebody on the legal team would review the contract and send it back. One of the ways I learned the business was by watching every single contract come through there, from the ads deals to the real estate deals. One contract that went through was for our company ski trip to Squaw Valley up in Tahoe. I looked at it and it was $800 a person. I mentioned, "Whoa, that's a lot of money." Urs said, "Let me see that." He was sitting behind me, running the entire data center strategy with a multibillion-dollar budget, in charge of all this engineering. He asked, "What's the phone number on that?" He just picked up the phone, called the hotel, and said, "We're not going to be able to come unless this price comes down." He got it down to $400 and said, "Great." **Jackson:** Radical ownership. **Chris:** He was a Googler, one among many, and he thought, "I can impact this. I'm going to do it right now." **Jackson:** yeah. **Chris:** Every single person who works at Lowercarbon has a piece of the upside. Every single person shares in each deal. I needed a culture where everyone was incentivized to high-five and where, if you went to them for help, they had every reason to help you or to volunteer to help you. One of the days I became "powerful" at Google—and I'm using these air quotes ironically—was after something my work partner did. All notes in Google were available and public, and you could subscribe to notes from a meeting. My work partner wrote, "Chris doesn't know what to do about this," and it got published to everyone. I read the notes later, and we had a really big blowout fight because I thought, "You ruined me. Everyone's going to know I don't know what to do about this." Larry Page subscribes to these notes, as do all these other people. I felt like the emperor has no clothes. The next meeting, Larry Page showed up. A guy you couldn't get scheduled showed up because he had an idea. So did nine other engineers, all there to help me, even though they weren't formally assigned to me. I mean what's the scarcest resource? It's human capital. Suddenly, I had accidentally, regrettably, angrily backed into more power, influence, and the ability to get shit done. I wanted to recreate that environment where you can ask any single person for help and they want you to succeed. In parallel, I wanted to make sure that every single investment decision we made was handled correctly. We have an investment committee—it's Clay, Crystal, and I—and Crystal and I are the largest LPs in the fund. We have hundreds of millions of dollars riding on everything we do. I'm a capitalist and I have no allergy to making money. What we do is not concessionary. It's not philanthropy. It is the biggest business opportunity and the biggest transformation in the economy right now. People talk about AI, and I say AI is our big customer. AI accelerates every single one of our science companies. It's circular like that. But I want to make sure every person in the company has a voice in the decision-making process and that we have a "dialectic" environment with robust argument. Because we have a diverse team, I've never seen an ad hominem attack or anything devolve into actual fights. If the debate isn't fierce enough, I'll be angry and let down. I think the role of your colleagues is to push them. When we make a decision, it's a group decision, even if there's a lead on the deal. We had a deal where we took a $27 million loss, and I know the person leading that deal took it personally. I told them, "You can take it personally. I'm not going to tell you not to feel all the feelings about what that was, but that's not on your tab or your account. We're not keeping score. You're a helpful person across so many other things, and you wouldn't be here if we didn't think that." It's a bummer we took the L on that, but that person wasn't capable of making those decisions unilaterally. Ultimately, we signed the check, but that was a group decision. I won't let anything get hung up in committee. There aren't a lot of votes. It's not a democracy, and we don't have a system where someone gets a budget to override everything else. We are the decision-makers. I've been doing this a long time, and I feel good. And if **Jackson:** they get burned too hard they're probably not going to take any risk next time. **Chris:** Absolutely. Another thing we do—I have a rule: if you get an invite to a podcast, go do it. Get your reps in. **Jackson:** That's why he said yes. **Chris:** Google did everything they could to shut me up. That blog you're talking about—the excerpt you wrote got me emotional about a particular event in my life. At the same time, I'm thinking about how Elliot Schrage just hated that I was a voice out there. He would assign Megan Quinn, who is now a dear friend and an incredible executive and entrepreneur in her own right, to mind me and to tell me to stop talking to people. Every now and then I would say something. A very pivotal moment in my career happened when I was in Oxford being interviewed on a panel. Someone from the press was in the audience and they said, "How come I can't download Google Maps onto my phone?" I said, "That's because your carrier has inserted themselves between you and the thing you want. I think that has dangerous implications for the future of the web and mobile." By the time I woke up the next morning, it was all over every newspaper: "Google versus the carriers." To be clear, I was not a senior executive. But when you say something like that, the headline reads "Senior Executive Chris Sacca." I knew who all the senior executives were, and I was not one of them. When you say the right thing, it's "anonymous Googler," but it was: "Senior Executive Chris Sacca has declared war on the carriers." I was summoned back to headquarters where my boss, David Drummond, let me know, "You should probably look for another role." I asked, "In the company? Maybe I could work for Jonathan Rosenberg in product." He said, "Oh no, not at Google." He was marching me to the executive management group meeting where all the honchos were. One particular guy was responsible for mobile—I've since made up with him, so I won't call him out—but he said, "I need a sacrificial lamb. I need to throw meat to the carriers to say we killed this guy and this is not how we feel." It was a foregone conclusion I was dead. They were going to talk about how to message my departure in front of me—what to say at my anti-eulogy. Larry Page was on his BlackBerry. He didn't even look up or make eye contact. He just said, "But what did Chris say that wasn't true?" It was already decided I was gone. He said, "I'm serious. Tell me the thing that Chris said that wasn't true." There was silence for a while. Then he continued, "They are inserting themselves between us and our users. We've never stood for that. Everything we do is to keep Internet Explorer from resetting your search default, so we have a direct relationship with our users there. Everything we do with Firefox is so that users have a choice and can always come to us. We try to win on the merits of our product. That's everything we do. So tell me what's wrong with what he said? It may piss people off because it's true." I left that meeting with a multi-billion-dollar budget to go scare the shit out of the carriers. That was a huge hand of poker. We went to the spectrum auctions. A guy who worked for us, Rick Whitt, came up with this idea: what if we convinced the FCC to attach net neutrality rules to wireless spectrum? It was a genius jiu-jitsu move, so we did that. Then the carriers announced, "It's easy for Google to say that because they're not going to bid on it. You've just impaired the value of it." So we decided we would say, "You guys valued it at four billion? We promise we'll bid 4.6 billion for it." We had the money, but that's not what Eric wanted to spend that money on. He knew we were heading into a recession in 2007. He just knew already. He would prefer not to put $4.6 billion in this. We had a plan for what to do, and part of my job was to make sure Verizon knew we were serious enough. My team and I were doing tower deals and getting trucks ready to roll. We had Android in parallel. Android was pissed off at me because they had a clause where Andy Rubin was going to make another $150 million if we signed up two carriers. Now the carriers were asking, "Why the fuck would we work with Google?" 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. Verizon had to eat the spectrum. They couldn't afford to let us buy this incredibly valuable 700 MHz. It penetrates concrete. But they bought it, and your phone is essentially net neutral. That was not the case back then. Do you remember Marissa Mayer? We were usually work rivals, but we've become friends since, and I really like her. She said her loneliest days at Google were when one line of what she said was taken out of context and used in a hit piece. Then she would walk around like a ghost walking through the halls—vilified and ignored. She was a senior executive and had earned that right. She was a total badass. One of the things we've codified for our team is to take any invitation you have to be on a stage or a podcast, practice your storytelling, and tell the story. If you sincerely believe the words that come out of your mouth—and they're not hateful or toxic—we will forever have your back. You're friends with Ryan Orbuch. That dude's got hot takes—sizzling hot takes. But he can just go out in the world knowing we got him, and so he can act without fear. **Jackson:** Pretty cool. **Chris:** Everything we do is designed like this. The other thing Crystal and I encountered all the time was ageism. I talked about Caie. I think she's 29. I haven't looked in the HR files, but she's an incredible outperformer. She's accelerated her career by using an army of AIs by simulating situations for herself to build board experience by role-playing with AIs. She hasn't been in a lot of board meetings, but she can just build virtual board meetings and get the reps in. My own bias was that we needed to add some 40-somethings to this company with a little bit of deal experience. It's probably illegal to say that, but we needed some more experienced people here. Then it turned out the call was coming from inside the house. Caie had this particular skill set we needed. This relates to what I talk about with the tyranny of relevant experience. One of our best investors right now is Lauren Faber O'Connor, who was formerly Chief Sustainability Officer for Los Angeles. She'd been in government and policy a lot of her life with zero indication that she could be an investor on her resume, but God damn, does she make companies more valuable as a result. She came on as an operating partner and very quickly became a partner partner. Crystal, my wife, was wildly successful in the advertising world. She won all the awards for her creative work at the coolest agencies and with the best partners. But she was the one who didn't go to art school. We met at the School of Foreign Service, basically a precursor to the CIA. But she found her way into that space— **Jackson:** That's a nice parallel life path for Chris. **Chris:** She would stay all night, literally sleep at work. She would overhear something that needed to be done, pick it up, taught herself photography and the whole suite of tools you need. Because she grew up all over the world and loved art, she already had an eye for composition and storytelling. And because she was a third culture kid, she knew how to relate ideas to everyone, so she was great at tags and humor. She's also the only person I've ever known who can just be funny on command. I'd ask, "Hey, do you want to go to dinner?" and she'd say, "I need to write ads for an hour." She could just sit down and decide to be funny and creative for an hour, sketch something out, and then say, "All right, dinner time." I would just be like, "What?" And then that thing, six months later, would be in a funny global campaign. **Jackson:** Most of us need to sit for eight hours. **Chris:** Or it takes a week until I'm finally in the zone. You have to put it on "Do Not Disturb," you're feeling it, the caffeine's right. Or for most of the people we work with now, it's the Zyn pouch—getting their Zyn going. **Jackson:** You're not on to those yet? **Chris:** I haven't actually tried one because I know I won't be able to put it down. **Jackson:** It's like the TikTok thing. **Chris:** I think that lack of relevant experience might be the superpower. So we look for those people more and more now. **Jackson:** I want to pull on that. We only have a few minutes left, so we'll zag across a bunch of ideas quickly. ## [01:57:47] Chris's Life Chapters, AI, and Creative Outlets **Jackson:** One big one: you have walked away many times in your life. I see you as a particularly authentic person, and I think that's part of this. You left the Google job. Nobody's supposed to leave that. The New York Times wrote about you. **Chris:** They wrote something along the lines of, "Why would this guy leave the greatest job in the world?" I sat at my mom and dad's kitchen table and cried, asking myself, "What have I done?" It really was the greatest job in the world. **Jackson:** You have the journal from when you were 20, and you wrote about how you're going to retire at 40. You walked away from Lowercase. Why does anyone walk away from that? You gave a commencement speech in Minnesota, and one line was about "control, alt, deleting." You talked about this being a rare opportunity when you're 22 to actually reset and become a beginner again. Nobody does that. In many ways, it's like you have these different chapters. Maybe you're on the perpetual chapter now, maybe not. But what has caused that? It's irrational. It doesn't make any sense... and yet you keep doing it. Because it's what you need to do? **Chris:** Yeah... rememberer that book, \*The Fourth Turning\*, where they say history is in these 20-year blocks? **Jackson:** I've seen the Van Neistat video. **Chris:** Van Neistat's video is fucking cool. All his videos are cool, but this one—the book report he did—was really cool. Are they called a saeculum or something? I forget. Anyway, these 20-year blocks... I did an exercise where I wrote my life out, and it fits in seven-year blocks. **Jackson:** Seven. **Chris:** Seven. Not by design. It just always has. **Jackson:** Oh, looking back. **Chris:** Yeah. Retrospectively, it's always been seven. I think there was one that went eight. **Jackson:** How far are we into this block? **Chris:** ... Seven. The thesis started in 2017, and the execution started in 2018. I didn't mean for there to be a regular pattern to it, but I think there's a few things at play. One is emerging curiosities for other things when I think I've gotten a subject matter dialed. It's funny, I got a chance to hang out with Questlove the other night. I shared with him a story that he didn't remember at first. A gazillion years ago, I was standing with Evan Williams and Tony Hsieh, the Zappos guy who's no longer with us. We were in L.A., and the Roots were playing. Questlove randomly followed me on Twitter. I didn't have a big following yet. I don't know how he followed me, but he just did. Maybe it was a mutual friend or someone; maybe it was Janina Gavankar. I DMed him while he was playing. His phone buzzed. He reached down while still playing drums with one hand, saw the message, and wrote me back, **Jackson:** No way! **Chris:** And just put it back into his pocket, and we were the giddiest school children ever. We lost our minds. I got to talk to him the other night and remind him of that story. He said, "Oh, shit. I do remember that. That was funny." I had never spent time with him, but I've read everything he's written. I think he's one of the most talented and provocative people ever. His playlists are sick. He's a crate diver. I like to crate dive, but that guy goes all the way. He teaches music, he's a performer, he produces, he's a film director. Just an incredible dude. I felt like I was fanboying a little bit. We were at a discussion about climate with a bunch of fancy, unbelievable people. He came up to me and said, "Damn, you remind me of the treasure of not being the smartest person in the room." He explained that in music, as a historian, he often knows the most, and it wasn't coming from a place of conceit. He just knows how unfulfilling it is. He said, "Sitting here, listening to you talk about what you're up to, posing provocative questions to other people in the room, challenging them, and reclaiming the moderate middle…" I'm a climate investor who drives an F-150 Raptor and eats meat because steak is fucking delicious. I tried being a vegan; there's a hole in my life. As he said that, my reaction was that the discussion, while fun, felt a little empty because \*I\* wasn't being challenged. I missed that. We recently hired a very young person, though I didn't ask for it specifically. I read three to four hours a day, and I track my time in 15-minute increments to see where it goes and to know how I'm wasting it. I read every day. I'm beyond obsessed with AI, and I am worried about the existential threat. I was in a room recently under Chatham House Rules, so I can't be specific, but it was with **Jackson:** The powers that be. **Chris:** Yes. Forty of them. Your audience would know the name of every single person there. It's a very cool annual meeting, and it's the only time I go to San Francisco anymore. I go once a year for this thing. I'm the least influential person in the room, and maybe the poorest. The attendees are from across the political spectrum. Sometimes I'm shocked by the new fascism that I think has arisen and the new lack of concern for fellow humans. The Overton window has shifted on what our responsibility is to other people. That's painful for me. I usually come home from this meeting a little depressed. A lot depressed. This particular year, the moderator said, "Alright, everyone stand up. I'm going to pose a question. This side is 'strongly disagree,' and this side is 'strongly agree.'" I should give credit. This event is hosted by 50 Years Fund. I forget the name, but Seth Bannon is involved, and it's spearheaded by D. Scott Phoenix, who is a fascinating mind. I worked with him when his company was worth a couple million dollars, and now he is one of the godfathers of AI. He built and sold Vicarious. The reason it's such a high-powered event is that everyone respects him so much they all show up. It's often the first time I've met many of these people I've been reading about, so it's wild for me. He asks, "Do you believe there is a greater than 10% chance that within five years, AI has killed more than 50% of humanity?" All I'm going to say is every single person who works on AI full time stood in the "strongly agree" column. This was beyond even the job losses or the unavoidable disruption to the economy. I'm great at calculating odds, but I have no idea what education looks like for our kids anymore or what skills they need. I watch them write a paper and struggle with their bibliography, and that's a rite of passage. I love it when they've procrastinated, waited too long, are up too late, and are feeling stress. I tell them, "Sit in that shit. That is some middle school shit you need to grind through." And yet, am I teaching them how to shoe a horse maybe? Is that an outmoded skill? I stood there, typed into ChatGPT or Claude, and showed Crystal. Then I prompted it to "write it like an eighth grader." And it was just boom. And I'm like...? On the other hand, maybe teaching kids how to shoe horses is actually the more relevant skill to get back to. I've never been more uncertain about anything in my life. I have this hole in my learning because I read about these companies that have scaled and wonder how I haven't heard about a particular AI company, as obsessive as I am. So we hired an AI person to work here. AI is the biggest customer for what we do. I don't know if we'll ever do a deal in pure-play AI, but we have this person, an incredible woman named Lina. I think she's 21, I just found out? I had no idea. She's definitely Gen Z. I have to translate some of her Slack posts sometimes. It's amazing. We've had huge debates about what certain emojis mean in Slack. I want to adapt, but I am old. **Jackson:** You're becoming a minority. **Chris:** One thing I would love your audience to react to is what the thumbs-up emoji means when used in Slack. I'm informed enough to understand that a thumbs-up on an iMessage to another peer is kind of dismissive, like, "whatever, bro." Do I have that right? **Jackson:** I'm 31, so I still use it normally. **Chris:** Okay. **Jackson:** I think if you're 25, it is. **Chris:** How do you use it? Is it meant to be dismissive? Right. Okay, so I had to learn that. **Jackson:** Sorry, a tap back or the thumbs-up emoji? **Chris:** The thumbs-up emoji. **Jackson:** Yeah, that's dismissive. **Chris:** Yeah, okay [Laughs]. I had to learn that. But we had a big debate about what thumbs-up means in Slack. I started seeing it and thought, "Wait, are these people just banging on each other a little bit?" But no, it was clarified to me that a thumbs-up in Slack means, "I agree." **Jackson:** ACK. **Chris:** The one that's really wild is the big eyes emoji. **Jackson:** The looking eyes. **Chris:** Yes, and they're looking to one side. I have used that to mean, "Hey, I read your post." **Jackson:** Right. **Chris:** I acknowledge it. It's informative. It's not a post that I have to disagree with or celebrate with a high five or whatever. I just agree with it. By the way, I high five things. Other people sparkle them. Just know that my high five means high five, and my prayer hands mean thank you. I'll do some fire or the stock-going-up one. I have a very limited repertoire. I got a lecture about how I use it, and a massive debate erupted. To some people, it means whatever you just read is suspicious and bullshit. I was with one of our founders last night, Julia from Vaulted, who's a fucking badass. She said, "When I use it"—and they use Teams at their shop—"it means I know what I just said is a hot take, but I stand by it." That's a whole thing. Having that energy from a complete, immersive AI expert who is among the earliest founders and who also speaks this language of youth—I know that makes me sound even older to say "youth"—has been the biggest boost for me. I've loved having that energy, and that's where my curiosity is. Climate is the least creative thing I've ever done. You were with me for a much more creative phase because we were building stuff where we had to look into the crystal ball about what people will care about, if they will use it, and why they will use it. We were creating stuff that was first impression. Almost everything we do in climate is a substitute good for something that's already made. We're building clean steel. We know who buys steel, who wants steel, why they buy it, and how they price it. We just need to make better steel that they'll buy out of greed, not shame and guilt. Do that across the board. **Jackson:** Nuclear fusion is a little different I think? **Chris:** But I can't be like, "You guys, what if I had this idea for a crazy physics formula?" There's none of that, at least not coming out of me. Those guys might be really creative. **Jackson:** Long time horizons, too. **Chris:** Yeah, it's way faster now. So, they might be doing that, and I'm not. I started to feel a little empty in that. So last year, Crystal and I came up with the idea for a comedy feature film. We went to a great friend of ours, Steve Brill, to write it. He's a really accomplished director, writer, and filmmaker, and you've seen so much of his work without even knowing it. We loved being in that process. He was the writer, but we were giving notes, chopping it up, and coming up with jokes and hijinks. A household name gave us notes on the third act. Then the female lead, who I can't even believe wants to do it, gave us third-act notes. It took us a while. Brill rewrote that with some of our reactions to it. He's the writer; we're the "story by." That felt great, and I hope it gets made just to get it out there. **Jackson:** Yeah. **Chris:** I also do a lot of physical art at home, and I consider raising kids a creative outlet. I will end up doing more of that. I want to write. I have been writing. I do feel like ChatGPT is pretty good at it. ChatGPT was pretty good at scriptwriting. There was a time we got notes from this famous star, and I had an idea. I wanted to give them back in real time while they were in the meeting, before we lost attention and had to set another meeting. So I quickly typed into Claude. It did not have the script. I just said, "Scene concept. He walks in, she's on her cell phone. This guy comes around the corner, almost catches her. He makes a lot of loud noises to cover for her. These are the names. Write it." It came up with enough funny dialogue to just immediately go, "Here's what I have in mind for the scene." The challenge after that was how to write that out and not have any AI content in there, because it was pretty fucking good. Not great. It wasn't Brill-level good. **Jackson:** It's going to get harder. **Chris:** It wasn't Brill-level good. If it were up to me to write it, I would have had a really hard time. He would wildly eclipse it because this is what he does. What's demotivating about writing this book is that I could phone it in and it would be pretty good. It's literally really good. And when you're me, the internet has read a lot of what I've said and written. You can say, "Do this in Chris's voice." We trained an internal bot on everything I've written, and it's really good at being me. I could step away, and I think most of our investors wouldn't know that I didn't write that thing. It knows my cadence: fact, fact, fact, fact, punchline; fact, fact, fact, sigh; analogy, metaphor. It just knows it. It's a cadence and a verse that I didn't realize I had until I watched a machine replicate it. And I'm like, "Wow, I'm kind of predictable." So I worry about that. But I have been trying to give the organization, Lowercarbon, even more room to see how it operates without me—more autonomy to make decisions without me. Clay is a singularly capable and powerful force in this business. And we'll have to check back on this in a few years. We will. I am the largest investor, and there's no way I'm stepping away from this one. But all those other times you talked about stepping away, I started to realize I didn't have a competitive advantage. With Lowercase, I realized I wasn't going to be the best again if we'd raised another fund. I also didn't care about the shit we were investing in. I was never going to go to the Staples Center and watch guys play League of Legends. I just didn't care. It's not a judgment on anybody else, but I didn't give a shit. With these dating apps, first of all, if I install one of these, I'm going to get in trouble, but I just didn't fucking care. And if you're going to do this job, you have to give a shit. **Jackson:** I would argue that any job at this point, if there's any antidote to the AI thing, if there's any optimism, it is that you better find the thing you care about more than somebody else. **Chris:** When you're starting a venture fund, 996 would be a holiday. Just yesterday, somebody had to remind me that today's Friday. I had no idea which day of the week it was. I was on the phone late the other night with an entrepreneur we backed in 2009 who was having board issues. You're married to these companies. They're at least 15-year commitments. Each time we raise a new fund, I have to do that analysis from scratch. 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. I have to do it because I know we can change everything. I'm just constantly reevaluating that. In the 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 wanted to invest. **Jackson:** Everybody had just started to figure it out. **Chris:** One of your past guests, Cyan Banister—I had barely ever met her. I'd seen her on TechCrunch before. I think we had shaken hands once. I got her email address and I sprayed and prayed to every rich person I'd ever met. She wrote us a $300,000 check. It was the largest individual check to Lowercase. That worked out. She's maybe the most successful angel investor ever. I don't think anyone knows who she is (as that) or how impactful she is. **Jackson:** I genuinely think she is. **Chris:** She's weird too. Her story is that she would be traditionally unqualified and— **Jackson:** Best kind of weird. **Chris:** Irrelevant for this. I think that's why she's been so successful. I think about this journey, and there was a time where everyone was throwing money at me. But no one realizes the only person who really knows their scorecard is them. I could sit here and give you the most well-intentioned career advice ever, Jackson. You are family to us. I have to go on an aside really quick. You had the best, worst first day of work that anyone in history has ever had. I won't go into the details, but it was the fucking worst day ever. It was just one failure after another. Cascaded, cascaded, cascaded. Legendary. I know you've never forgotten it. The thing that Crystal and I talk about every time—and just so you know, we don't share the details of how bad it was—it was fucking amazing. It should be a script because it was just the worst first day of all time. But you wrote the most accountable follow-up email in history. I would put it up against anyone else's email after a fuck-up. You acknowledged fuck-ups I hadn't even noticed. I was like, "Oh my God, I didn't even know that one went down." **Jackson:** Just deepening the hole. **Chris:** I reread it this morning. You prepped for this podcast; I reread one thing, and it was that note. You headlined it, outlined it, and bolded the subject matter titles. The narrative was really good. It was chronological. Then it had what I could do differently and how I'll improve this, and then an overall summary of the impacts it had on you and the risks. It's poetry, man. Nobody does that anymore. I had totally forgotten to bring it up, but I think 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 was flattered by the invitation here. I do think you are one of the most self-aware, constantly working on yourself, and accountable people I've ever met. And to do that at such a young age originally was just really special. I don't know if you're raised right or you worked in the right settings or you had the right mentors, but that was really, really different and special. **Jackson:** Starts with parents. **Chris:** You're the only person right now who knows what you actually want to do with your life, what you care about, and how you weight those variables. As someone who cares about you, I could throw out ideas and be like, "You gotta do this thing, etc." So when we announced we were quitting Lowercase, all these great people were like, "Why? You're good at it. There's so much money," and this and that. But we were the only people who knew the meaning wasn't there for us anymore. The Aspen Institute Crown Fellowship I'm in likes to say, about pivoting from success to impact. It wasn't really what we were looking for, but we saw this hole in climate where it had a bad rap. People said it's where money and souls go to die. But we saw it was priced wrong. We knew we could go in there, shake shit up, and have a massive impact. This might be a surprise to a lot of people, but I'm not a climate zealot. My personal carbon footprint is inexcusable. On the other hand, the term "carbon footprint" was coined by Ogilvy and Mather at the behest of British Petroleum to take the spotlight off of the industrial carbon economy and put all the guilt and shame on individual users. "Hey, it's up to you to take a shorter shower, and it's up to you to not eat the shit you want." **Jackson:** I see why some people don't like you. **Chris:** We would not have the lifestyle we enjoy today if it weren't for oil and gas. I was in a meeting the other night where they were saying we got to stop the oil and gas fraud, the mafia. And I'm like, how did you get here? Look at the room, look at what we're eating, look at the furniture we're sitting on. Are we just going to quit oil tomorrow? My job is to give them a better, cheaper, faster, easier, safer alternative. It turns out oil and gas tend to blow up from time to time. But that's my job: to give you a choice that you choose out of pure self-interest. In the meantime, stop fucking making people feel bad. There's nothing I hate more than the activists we call the "soup throwers"—people who go and throw soup on a painting. Really? 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. By gluing ourselves to the floor of the US Open? That's how we're going to raise awareness and get people on our side. It doesn't fucking work. I honor the people in the trenches. And a lot of our best people come from oil and gas. If you want the best engineers and the best workers, if you want to drill like Zanskar is—the most productive geothermal wells at the lowest cost ever... Incredibly clean, ubiquitous, 24/7 power—Those guys are all riggers who come over from the oil pan, from the panhandle of Texas. And they come over and drill these wells. It's the same fucking pipes, the same tools, the same trucks, the same gun racks, the same beer at the end of the day. It looks like a goddamn Chevy ad. That's what's happening. That's what the clean economy actually looks like. **Jackson:** Tell me how you really feel. **Chris:** And if you make these people feel bad, which is how Democrats have rooted their politics for years—making people feel bad about their choices, how they live despite their intentions, this exclusionary purity test thing—then we are not going to get anything fucking done. And no, I'm not running for anything. Fuck that. ## [02:22:04] Drifting Back Towards Real **Jackson:** I have one last thing. We are sadly out of time, as much as I'm sure I could let you go forever. I'm going to change gears slightly, but it feels very aligned with what you were saying. I found something in your blog that really felt like you. And I think despite sometimes the rants or the strong opinions, you are a pretty soulful dude. I wanted to read it to you. **Chris:** Oh, my God. I'm going to end up crying. **Jackson:** It's not something you wrote. It's something somebody you enjoy wrote. It's called "Manifesto: The Mad Farmer Liberation Front" by Wendell Berry. **Chris:** Oh, okay. **Jackson:** This is on your blog in 2009. "Love the quick profit, the annual raise. Vacation with pay. Want more of everything ready made. Be afraid to know your neighbors and to die. You will have a window in your head. Not even your future will be a mystery anymore. Your mind will be punched in a card and shut away in a little drawer. When they want you to buy something, they will call you. When they want you to die for profit, they will let you know. 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. Denounce the government and embrace the flag. Hope to live in that free republic for which it stands. Give your approval to all you cannot understand. Praise ignorance, for what man has not encountered, he has not destroyed. Ask the questions that have no answers. Invest in the millennium. Plant sequoias. Say that your main crop is the forest that you did not plant, that you will not live to harvest. Say that the leaves are harvested when they have rotted into the mold. Call that profit. Prophesy such returns. Put your faith in the 2 inches of humus that will build under the trees every 10,000 years. Listen to the carrion. Put your ear close and hear the faint chattering of the songs that are to come. Expect the end of the world. Laugh. Laughter is immeasurable. Be joyful, though you have considered all the facts, so long as women do not go cheap for power. Please women more than men. Ask yourself: Will this satisfy a woman satisfied to bear a child? Will this disturb the sleep of a woman near to giving birth? Go with your love to the fields. Lie down in the shade. Rest your head in her lap. Swear allegiance to what is nighest your thoughts. As soon as the generals and the politicos can predict the motions of your mind, lose it. Leave it as a sign to mark the false trail, the way you didn't go. Be like the fox who makes more tracks than necessary, some in the wrong direction. Practice resurrection. **Chris:** I forgot I quoted that again. That's one of those writers where you're like, how? How could I consider myself an organizer of words? My reaction is that you just found another one of those letters I wrote to myself that became prophecy. Do you listen to Matthew McConaughey's book \*Green Lights\*? You got to listen to it; you can't read it. It's six hours of chilling with one of the most interesting storytellers of all time, and he's got the perfect accent, perfect stories—just amazing. In the end, one of the reveals is a letter he wrote to himself with his life goals in it when he had no business writing that letter. He'd forgotten about it, and then he rediscovered it and realized they'd come true. One of them was an Oscar, when basically all he'd said on film was, "All right, all right, all right." When I was 41, I found a letter I'd written—not even a letter. I was going to school in Ireland, and I only went to this one class to try to get closer to this one girl. We did this little thing in the back of the class where we would write five questions for each other and pass the booklet to the other person to answer those questions, pretending to pay attention. She said, "What do you want to be when you grow up?" And I wrote this response: "I don't know what it's called. I just know it's going to have a lot of high stakes, high risk, high reward, a lot of talking on the phone, a lot of negotiating. I'm going to do it half time from the mountains, half time from the beach. Whatever it is, I'm going to do the best there was at it. And I'm going to quit when I'm 40 and do something else I really want to do." I don't think I ever ended up with that girl at all, but I ended up with a notebook. It was in my garage, and Crystal and I were cleaning up our garage when I was 41. We found it, and I was flipping through it and came across that, reading it with her. She said, "My God, you're a year late." Every single bit of it. We lived in Truckee and had a house on the beach in LA. Every single word of that. One of the things I had in mind when I wrote it was the scene in \*Rain Man\* where Tom Cruise is trying to import Ferraris in this warehouse. He's got multiple phones going and it's sparse—a desk, a couple of chairs. He's trying to balance these phone calls and deals are falling apart. I literally wanted that, not Ferraris. That, to me, is the kind of business that a not-rich kid with no network could just do with the power of ideas and thought and speaking. That was what I had in mind. I didn't know what that job was. I knew I didn't want to bill hours or anything like that. When I look back at what I made happen, I'd forgotten I'd written it. I knew I wrote it for me. I don't think I was writing it to impress anybody; I don't think it was particularly impressive. But when you read that, I get a little emotional because I'd forgotten about that. My biggest goal for myself is that my drift is back to real—back to the real me. The me that hopefully, I've been, or that was covered in layers of pretense or inauthenticity or striving or... when I was in college and didn't talk about my politics because I thought I would offend half of my future potential employers. At each stage, I have found the opportunity to speak my mind, be more real, dress the way I want to dress, and live the way I want to live. Bill Clinton invites me to this meeting every year. It's a room full of suits and world leaders, and he throws it to me to say the things that nobody else wants to say, swear while doing it, and drop a cowboy phrase in there. Just stir it up. We've developed a fun friendship over the years because I just stir it up. I was up to be an ambassador if Hillary got elected. I was going to be an ambassador, and I remember President Obama being like, "That's not a good job for you. Being an ambassador is not about saying what you actually feel." He said, "I'm kind of glad that didn't work out for you." But I do try to drift, and there are rapids along the way. I have to get a paddle out and push, but I do try to drift back towards real. And real for me was growing up laying down on the field. I grew up with artists, performers, writers, and actors in our family. I grew up with my mom and dad, who were constantly introducing the arts as well as science to me. They were teaching us about love, collaboration, openness, our responsibility to other people, and the real privilege of raising kids. I can see in retrospect the thought and the heart that my mom and dad put into raising and nurturing us, while also not being pushovers. They had real values and communicated those values, but also boundaries, edges, consequences, responsibility, hard work, and accountability. I try to reflect that in what I do now. I tried not working for a bit, and that lasted 60 days. I've tried stepping back, and I suck at it. I get a real pleasure from helping raise the people who can do it better than I can. Lowercarbon is getting there. But sometimes the thing I think is missing is the freedom I found to be able to say exactly what I want to say. I've had to teach people, "Don't be so nice. Don't be so cooperative. Don't be submissive. The world needs a little more alpha." The most expensive employees in an organization aren't the ones you pay the most. They're the ones who drag the most on everybody else. Maybe they come in like Eeyore from Winnie the Pooh, just sad every day. Or they're toxic, or they ask, "Can you reread this email for me before I send it?" I'm like, "Just fucking send the goddamn note. What are they going to say?" There is an inflection point coming for me at some point soon. But it's fun that you read that because it reminds me that's a scorecard I'd like to measure myself against. I think I've done some of that. There's a lot in there about women and birthing. When Crystal and I first got pregnant, she asked me to sit down and watch a pregnancy movie. I grew up in a Catholic town where the day they teach girls about periods, they let the boys play Connect Four. They told the girls, "Don't show the boys that pamphlet on the bus ride home." It was like a secret. That was the level of stigma around female reproduction. I didn't grow up in a place talking about cycles or any of that. When we got pregnant and Crystal said, "Watch this movie," I was like, "Wait, really? Are you sure? Can I have a couple of drinks first?" I really expected to be grossed out. It was this cool movie by Ricki Lake, of all people, the old sensationalist talk show host who took this on as a personal issue. It was about how women are built to do this. How right now, hundreds of thousands of women around the world are giving birth in conditions much less safe than in the United States. Essentially, embrace that woman as someone built to do this, not a patient. The United States treats women giving birth as patients. Put you in a hospital, don't trust your body, drug you up, put you in stirrups—which is the least natural way to deliver a baby. It keeps your tailbone from flexing out; it's built to flex out. A lot of women break their tailbones in birth, or there's nowhere for the baby to go. The whole industry is tilted towards cesareans because that's where more money is. The cesareans are all done at 4:30 p.m. and at 9:30 p.m.—4:30 so the doctor can get home for dinner and 9:30 so they can get home and sleep that night. It's a fucking scam. But I didn't have in mind that that was a path for me. It was one of those things that I had the strongest rejection of: fuck that, I'll be the guy in the lobby with the cigars, not in the room doing it. Three babies in, it became part of my identity how much I felt the fatherhood journey starts way before that baby comes out, but definitely while that baby's coming out and all the way through. I like that it's reflected in that verse because I don't think that was part of my identity at all for a while. Anyway, Jackson, I have to say I love listening to you. I told my team last night I was coming here. 50% of them listen to you. The one who knows you is [Ryan]. The other people raised their hand and were like, "No, I just listen." I'm like, how do you know about Jackson Dahl? It's amazing. But I love listening to you. I told you before we started rolling that I asked ChatGPT what you would ask me, and it was pretty good. Those are some B-plus, A-minus questions, and I want to go back and answer those just for myself. It's like Formspring. Crystal said, "That's Formspring." I think the depth and originality of your questions, what you pull out of people, but more than anything, the guests you curate... I felt a little imposter syndrome coming on here because you've got some incredibly dynamic, creative, challenging people doing stuff. I looked this morning, scrolled through Spotify, and I knew the names of four of your guests before they got here. Lux Capital guy, Cyan... there were a couple. Even then, it's still an interesting discussion. I'm learning new things because of the way you talk. I bought Nadia's book, which was in our company color, so it was even better. I learned about Stripe Press, and as close as I am to the Collison brothers and Stripe, I didn't know about that culture there. I'm just really grateful for the work you're doing. I was awesomely thankful to be here. I hope I lived up to your expectations. **Jackson:** More than I could have asked for. Thank you, sir. This was really a pleasure. **Chris:** Right on, brother. Good to see you. Hopefully not another eight years. **Jackson:** We'll do it a little quicker this time.