The Exchanges

Q think that I'm a very logical and representable speaker. After a couple of Heinekens, when I was about 18 years old, I was not so solid as I should be. But I do, I do want to start with a little bit of context. I always love this question, which is like, fundamentally, how did you make your first move into investing, and what was the first check for you?

A Yeah, the first check for me, I mean, I'd been doing deals on behalf of Google for a while. Uh, and, and even before that at a company called Spadera, so where I was general counsel and I don't tell many people I'm a lawyer, so we'll keep that between us, but, uh, but general counsel and head of biz dev and corp dev and stuff like that. And so, and then even before that, as a lawyer, I was adjacent to all these deals. I was watching other people do deals. I'd be in the room taking the notes when John Doerr was, uh, was receiving a pitch and stuff like that as his outside counsel. Uh, And so, so I was always close to deals, but the very first one I did on my own, uh, was a company called Photobucket, which we ultimately sold for three hundred thirty million dollars, which sounded like all the money in the world at the time. You know, Flickr had sold for like 25 to thirty five million dollars, and so to be able to 10 x that with Photobucket was insanity. Uh, and, and we felt just so lucky to have gotten that deal done. But that check I wrote was literally a credit card check for me. Uh, I didn't have any cash on hand. I was at Google, and I was vesting, but I hadn't sold any stock yet, and so I literally, um, I went into that one with 50,000 dollars of credit card checks. My second investment was Twitter, and that one was funny because Evan Williams was, I'd already been working …

AI assessment note: “the very first one I did on my own, uh, was a company called Photobucket”

Q friends for me there with that, with that one. Um, but no, I, listen, I love a good opinion. I want to finish though, Chris, on the most important, which is like, what are the next 10 years hold for you and for lower carbon? Like, how big do you want to make this? Do you want to make this like BlackRock style? Is this, what does that look like?

A I mean, I never want to run a huge org, and so there'll be a breaking point at which, you know, when the slack gets unmanageable, and so, you know, we're single digit number of people right now, I think I can see hiring two or three more heads. I don't really want to be bigger than that. Clay's a really good manager, and so it might be able to scale. It's working really well, but that's not my personal aspiration. My aspiration is just to be a big fucking lever. You know, like I get excited when I am able to go to Goldman Sachs and say, don't go guarantee drilling finance in the Arctic. Instead, go do deals with us. And that those guys who, you know, look, I'm, I'm close with David Solomon, the guy who runs the bank, and I know he cares, but he also has a fiduciary to manage money, and they seek profit, and so when those guys walk away from the Arctic and instead do clean energy deals alongside us, that makes me happy. I mean, I had, I, I said this when we announced our fund is like that, while I loved having a bunch of LPs, and we had like billions of dollars of interest for our fund in just a few, a few days, and so that was overwhelming, but when I, We actually made room for some people who are sheer greed-based investors, not just the folks who had a climate mandate, because I was like, I want you here, and I want you to put this in your for-profit pocket of capital, and I …

AI assessment note: “I never want to run a huge org”

Q to ask is I had Doug Leone on the show recently, and his first three investments were three IPOs, and he said it actually distorted his mindset having three big hits early. When you look at your big hits very early on, Twitter being your second ever investment, did it distort your mindset? And, and did it make it almost challenging actually moving forward to having such success so early?

A No, I was lucky, and I'm going to use some air quotes around lucky. To have had my ass completely handed to me in the public markets before then. So I very famously took my student loan checks for law school, told the school they hadn't shown up, cash them, and use them to day trade in the market. And so this is one of the reasons why I get so nervous about what I see in the Robin Hood phenomenon. You know, like even as we tape this, the market's crashing and I worry about so many people trading on margin because I was that guy. Um, and at the time they hadn't built the margin requirements back into the online trading platforms yet. So I would take a thousand dollars worth of equity And buy a million dollars worth of stock and hold onto it for a week. And so the swings were insane. And, um, and at one point I was up twelve million dollars after about 18 months. And along the way, you start to think you're a genius. And then when you put your buddies into the stock, you know, they'll come back and be like, hey, I bought a boat, man. You're the guy, you know, like, you've got it figured out. And you really start to believe that shit. And one buddy said, hey, you need to diversify. So I had two stocks. That I traded. And, um, ultimately those came crashing down one week in 2000. Left me totally on my ass. Four million dollars in the hole with nothing to show for it. And so I had a…

AI assessment note: “No, I was lucky... To have had my ass completely handed to me”

Q Chris, we both know many VCs. Do you think VCs are actually helpful?

A Uh, some definitely are like, all right, we'll just, we'll make this the Bill Gurley fan club show, but, but I have a very specific example that comes to mind with Bill sometimes. And, and by the way, there are a lot of guys like Josh Koppelman and Rob Hayes, and, um, uh, fuck, I'm going to piss people off by not naming a bunch. So I'm going to stop and just focus on Bill. We were in an early Uber board meeting once, and we needed a CFO. And I kind of, I, I, I, They said, okay, we need a CFO. And I stopped and I think, okay, like who could be a CFO? And I'm thinking of like old Google people who were like director of finance and maybe ready for a CFO level. And Gurley just opens up this dossier and it has the resumes of six public company CFOs who are vetted and who want the Uber job. And I was like, that's what fucking Bill Gurley does. Like that's one of his many things. He does lots, but that's, that guy just, Materially increase the likelihood of success of this company on that fucking day. I can point to it. Like that guy, you know, will go in. Uber was obviously becoming a huge marketplace. That guy will go in and do a ton of marketplace analysis, connect us to other big marketplaces to understand lessons learned and things they did wrong. And he will materially move forward the likelihood of success of the company by influencing the business strategy. And so there's no f…

AI assessment note: “some definitely are”

Q Do you think success is cyclical in venture? You get, you do Uber, and so you get Instagram, you do Instagram, so you get Docker, you do Docker, so you get, and it just continues and continues. Do you think that success really is cyclical?

A Doug Leone was like, fuck no, people don't just come to me with deals, but, um, I think, I think Doug was bullshitting, uh, but you know, like Instagram came to me, but like Kevin Systrom literally said, I want three angels, you, Adam D'Angelo and Jack Dorsey. And so he pitched me. I, I literally was not seeking photos. I, it sounds fucking hilarious, but I thought it was spent. I thought it was done. And so he came and pitched me why he wanted me involved. And it was specifically because I was helpful and it was specifically, um, things he'd seen that I had written to that influenced him. And specifically when he was at Google, he was kind of a junior guy who'd seen the work I would done. And he's like, so I want you in my deal. And so that does happen. Like, that reputational thing matters. And by the way, to, to investors who are up and coming, I think you need to consistently remind other investors of how you're helpful. So, you know, people are like, you know, Saka, you're self-promotional. I'm like, fuck yeah, I am. Like, that's part of the job is I have to continue to remind people why I matter, because I need other investors to bring me their deals too. Like, this is inherently collaborative business. If we're not going to see all of them, Like we see the most, but I'm not going to see all of them. I need somebody like I needed someone at first round capital to be like,…

AI assessment note: “that does happen. Like, that reputational thing matters.”

Q What makes you and Crystal such a great partnership?

A Well, knowing each other since we were kids is definitely helpful. Um, we've, and I think seeing each other grow up at similar paces and rates in our respective fields has been incredible. You know, Crystal doesn't take, um, any public credit for anything because it's just, she's just a much more balanced human who doesn't need external validation at all. Um, but Crystal's been, you know, she was there in the room to choose the, to, to hear the Uber pitch and decide we should do the deal. Um, and has been an instrumental part of everything we've ever done at Lowercase. And so, um, but, but with that, I mean, it's, um, uh, inside of our, of our wedding rings, we have these two things engraved. Um, one is mutual weirdness forever. Um, so we try and encourage each other to stay our, our just weird, um, our weird selves, you know, and pursue those quirky interests and not try and smooth the edges, like be a little rougher on the edges. Um, and then the other thing we have engraved in our rings is in violent agreement, because we can really go, like, we can, we're both very type A strong personalities, and our kids laugh, because we can really get going, um, and often, you know, we'll be like, look, we're seeing the same fucking thing, we're just nuancing the words right now, but, um, but I think having, having a dynamic, worthy, robust debating partner who, who has, A very strong c…

AI assessment note: “knowing each other since we were kids is definitely helpful.”

Q to ask is I had Doug Leone on the show recently, and his first three investments were three IPOs, and he said it actually distorted his mindset having three big hits early. When you look at your big hits very early on, Twitter being your second ever investment, did it distort your mindset? And, and did it make it almost challenging actually moving forward to having such success so early?

A No, I was lucky, and I'm going to use some air quotes around lucky. To have had my ass completely handed to me in the public markets before then. So I very famously took my student loan checks for law school, told the school they hadn't shown up, cash them, and use them to day trade in the market. And so this is one of the reasons why I get so nervous about what I see in the Robin Hood phenomenon. You know, like even as we tape this, the market's crashing and I worry about so many people trading on margin because I was that guy. Um, and at the time they hadn't built the margin requirements back into the online trading platforms yet. So I would take a thousand dollars worth of equity And buy a million dollars worth of stock and hold onto it for a week. And so the swings were insane. And, um, and at one point I was up twelve million dollars after about 18 months. And along the way, you start to think you're a genius. And then when you put your buddies into the stock, you know, they'll come back and be like, hey, I bought a boat, man. You're the guy, you know, like, you've got it figured out. And you really start to believe that shit. And one buddy said, hey, you need to diversify. So I had two stocks. That I traded. And, um, ultimately those came crashing down one week in 2000. Left me totally on my ass. Four million dollars in the hole with nothing to show for it. And so I had a…

AI assessment note: “No, I was lucky... To have had my ass completely handed to me”

Q friends for me there with that, with that one. Um, but no, I, listen, I love a good opinion. I want to finish though, Chris, on the most important, which is like, what are the next 10 years hold for you and for lower carbon? Like, how big do you want to make this? Do you want to make this like BlackRock style? Is this, what does that look like?

A I mean, I never want to run a huge org, and so there'll be a breaking point at which, you know, when the slack gets unmanageable, and so, you know, we're single digit number of people right now, I think I can see hiring two or three more heads. I don't really want to be bigger than that. Clay's a really good manager, and so it might be able to scale. It's working really well, but that's not my personal aspiration. My aspiration is just to be a big fucking lever. You know, like I get excited when I am able to go to Goldman Sachs and say, don't go guarantee drilling finance in the Arctic. Instead, go do deals with us. And that those guys who, you know, look, I'm, I'm close with David Solomon, the guy who runs the bank, and I know he cares, but he also has a fiduciary to manage money, and they seek profit, and so when those guys walk away from the Arctic and instead do clean energy deals alongside us, that makes me happy. I mean, I had, I, I said this when we announced our fund is like that, while I loved having a bunch of LPs, and we had like billions of dollars of interest for our fund in just a few, a few days, and so that was overwhelming, but when I, We actually made room for some people who are sheer greed-based investors, not just the folks who had a climate mandate, because I was like, I want you here, and I want you to put this in your for-profit pocket of capital, and I …

AI assessment note: “I never want to run a huge org... we're single digit number of people”

Q to founders because they don't want the founder to say something bad. They're worried about their reputation. The power has swung so much that no one is willing to say anything bad at all, and I'm sitting in board meetings going, what the fuck? Someone needs to speak up. And no one says anything. Like, does this worry you as well? Because it seems like VCs just lost their voice.

A It's an, it's an exceptional point, and it's true. One thing I want to counterbalance it with is VCs actually have way less power than people think they often do. You know, I go back to when everyone was like, why didn't you fire Travis? And I was like, there was no fucking way we could. You know, ultimately we'd come up with some kind of crafty ways that we could convert our stock from preferred to common and maybe take over the board. That was risky, and we weren't totally sure. In the end, what pushed Travis out was when his team held him accountable. It was when the, you know, his 13 senior managers all wrote a letter that said, dude, you've got to stay out of the company. And so, you know, that's, that's really the only force that Silicon Valley leaders are accountable to. I mean, Zuckerberg doesn't, has zero fucks left to give. In fact, I think he might even drive pleasure from public criticism of him. You know, it might reinforce his worldview that the rest of us don't fucking get it. And, and so, but when his employees start pushing back on him, that is the number one hardest resource in all of, of tech is if you can't recruit and retain good talent, you're powerless. And so, you know, it'll be interesting now that Mike left, I, well, let's see what that meant actually. Was he just, you know, did he want to go hang out on a beach or was there something greater to that? …

AI assessment note: “VCs actually have way less power than people think they often do.”

Q Chris, we both know many VCs. Do you think VCs are actually helpful?

A Uh, some definitely are like, all right, we'll just, we'll make this the Bill Gurley fan club show, but, but I have a very specific example that comes to mind with Bill sometimes. And, and by the way, there are a lot of guys like Josh Koppelman and Rob Hayes, and, um, uh, fuck, I'm going to piss people off by not naming a bunch. So I'm going to stop and just focus on Bill. We were in an early Uber board meeting once, and we needed a CFO. And I kind of, I, I, I, They said, okay, we need a CFO. And I stopped and I think, okay, like who could be a CFO? And I'm thinking of like old Google people who were like director of finance and maybe ready for a CFO level. And Gurley just opens up this dossier and it has the resumes of six public company CFOs who are vetted and who want the Uber job. And I was like, that's what fucking Bill Gurley does. Like that's one of his many things. He does lots, but that's, that guy just, Materially increase the likelihood of success of this company on that fucking day. I can point to it. Like that guy, you know, will go in. Uber was obviously becoming a huge marketplace. That guy will go in and do a ton of marketplace analysis, connect us to other big marketplaces to understand lessons learned and things they did wrong. And he will materially move forward the likelihood of success of the company by influencing the business strategy. And so there's no f…

AI assessment note: “some definitely are like, all right, we'll just, we'll make this the Bill Gurley”

Q the better, but VC now is less collaborative than ever. It's more transactional than ever. Tiger do more deals than I do fucking podcasts. Um, it's not, it's not the same place that it used to be when you, do you know what I mean? It's so different. I'm like, I don't know, I almost feel like a jaded soldier, and I'm like, oh, do you get jaded by that?

A I mean, yeah, but remember, there's part of the market that, um, So I encourage you to kind of go back and read the success stories of people. Like when they like read the series B stories, right? It's fun to read the IPO stories. Like how did that deal come together? But to your point, those are, those were funded in a slightly different era. So read the series B postmortem. So, Hey, how did that deal come together? And what you'll see is the most selective, the best founders are still looking for quality, not building party rounds. And so they may have more leverage in the situation. But they know that they want an actual helper to help them build a company. You know, so, so it was interesting. We recently, um, in, in Lilac, uh, co-led around with T. Rowe. And so T. Rowe has this incredible expertise in, uh, in minerals. And so, you know, we're in the lithium mining business, right? Their expertise is wildly complimentary to our company building expertise. And so for us, It made perfect sense to split the round with them, and the founders of the company were excited to have us come to terms with, ah, in a way that we could split the round evenly with T. Rowe, because it's like, look, we can help you build out your team. We can help you build this company from here. We can help you work on strategy. We can help you. I can help counsel you on your worst fucking days, right? Whe…

AI assessment note: “I mean, yeah, but remember, there's part of the market that”

Q don't want the founder to say something bad. They're worried about their reputation. The power has swung so much. That no one is willing to say anything about it at all. And I'm sitting in a board meeting and he's going, what the fuck? Someone needs to speak up. And no one says anything. Like, does this worry you as well? Cause it seems like VCs just lost their voice.

A It's an exceptional point. And it's true. One thing I want to counterbalance it with is VCs actually have way less power than people think they often do. You know, I go back to when everyone was like, why didn't you fire Travis? And I was like, there was no fucking way we could, you know, ultimately we'd come up with some kind of crafty ways that we could convert our stock from preferred to common. And maybe take over the board. That was risky, and we weren't totally sure. In the end, what pushed Travis out was when his team held him accountable. It was when the, you know, his 13 senior managers all wrote a letter and said, dude, you gotta stay out of the company. You know, that's really the only force that Silicon Valley leaders are accountable to. I mean, Zuckerberg has zero fucks left to give. In fact, I think he might even derive pleasure from public criticism of him. You know, it might reinforce his worldview that the rest of us don't fucking get it. But when his employees start pushing back on him, that is the number one hardest resource in all of, of tech is if you can't recruit and retain good talent, you're powerless. You know, it'll be interesting now that Mike left. Well, let's see what that meant actually. Was he just, you know, did he want to go hang out on a beach or was there something greater to that? It'll be interesting. And we'll see if there's more departure…

AI assessment note: “It's an exceptional point. And it's true. One thing I want to counterbalance”

Q a couple of friends to me there with that one. But I, listen, I love a good opinion. I want to finish though. Chris, on the most important, which is like, what are the next 10 years hold for you and for lower carbon? Like, how big do you want to make this? Do you want to make this like black rock style? Is this, what does that look like?

A I mean, I never want to run a huge org, and so there'll be a breaking point at which when the slack gets unmanageable, you know, we're single digit number of people right now. I think I can see hiring two or three more heads. I don't really want to be bigger than that. Clay's a really good manager, and so it might be able to scale. It's working really well, but that's not my personal aspiration. My aspiration is just to be a big fucking lever. You know, like, I get excited when I am able to go to Goldman Sachs and say, don't go guarantee drilling finance in the Arctic. Instead, go do deals with us. And that those guys who, look, I'm close with David Solomon, the guy who runs the bank, and I know he cares. He also has a fiduciary to manage money, and they seek profit. And so when those guys walk away from the Arctic, and instead do clean energy deals alongside us, that makes me happy. I mean, I had, I said this when we announced our fund, it was like that, while I loved having a bunch of LPs, and we had like Billions of dollars of interest for our fund in just a few days, and so that was overwhelming, but when I, we actually made room for some people who were sheer greed-based investors, not just the folks who had a climate mandate, because I was like, I want you here, and I want you to put this in your for-profit pocket of capital, and I want to put up the returns for you that …

AI assessment note: “I never want to run a huge org... single digit number of people right now.”

Q Okay, so you mentioned a couple of books, but what's the favorite book and why?

A All right. I've said this before, but it's, it's still not fade away. A book of this guy, um, who was, uh, well, our lives are similar. He was a ski bum. He became a massive exec executive at Liberty media and, uh, and right at the height of his success found out he, uh, had incurable stomach cancer and started writing the book then reflecting on his life, reflecting on meaning, because I think one of these things is so easy to get totally obsessed and consumed by our industry. It's, it's easy to forget. And as we talk, as we touched upon multiple times in this interview, Um, that balance in life, those relationships, those friendships, that time to take care of yourself. And so, um, you know, you'll cry. So anyway, not fade away.

AI assessment note: “it's, it's still not fade away.”

Q I can do that, that's a lot of money, and then now, How do you think about your relationship to money? Because, you know, it always changes. How do you think about your relationship to money today, Chris?

A Yeah, I, I think I'm lucky in that I don't feel competitive with other investors or other rich people. So I, I have a lot of friends who are tortured by it. Um, and they just, they have countless, countless dollars at hand, but feel like they're, that the goal, the goal line's always moving and they need to keep up with somebody else. So, uh, I certainly look at it as what can I do with the money we have? And, um, and luckily, Um, we have all the stuff we want and you get to this point where like in the beginning I made a bunch of money and I bought houses for family and, um, and multiple houses for ourselves. And then my wife and I turn around and we're like, fuck, we're property managers. Like that's all we do now is like our inbox is like, Hey, this broke and this is happening. And what do we do? I was like, so we're just prisoners to our stuff right now. And, uh, and so again, it was lucky that I kind of got into that early and realized like, oh my God, like, And then you start to realize, you know, we're fortunate enough to go on vacations, but we don't need to own that chateau. It's amazing. There's some incredible places in Europe where we love to spend time that you can rent. And then when you're done, you walk away from them. And so, you know, you can live luxuriously and then not have to own it. And so, um, and luckily we're also not into big boats, thankfully. So tha…

AI assessment note: “I don't feel competitive with other investors or other rich people.”

Q What did, what did you learn from that? I'm sure it was some, like, fascinating takeaways that actually impacted How you think about your lifestyle today, your relationship with Crystal. What did you learn from that, like, interrogative process?

A Yeah, one of the things I think we learned was that, uh, couples that work are couples where both people are growing, no matter, like, in which vector, which direction, uh, or, and not by necessarily traditional, you know, business measures, whatever. They're just growing in some way that matters to them. Whether it's, um, artistically, um, Uh, philanthropically, athletically, uh, building a startup or an organization that matters to them. You know, and that's obviously hard in the first couple years of raising kids, and I think that's one of the reasons why that ends up being a choke point for a lot of marriages is one spouse is off kicking ass in their career, and the other one is just taking care of kids. But, but I think we realize that the couples that worked where we're both, uh, both sides of the couple were getting better in some way at something. And had some kind of pursuit that was self-defining, um, that they could, that they could, um, you know, chase. That said, we also learned that helping other people get out of an anxiety zone was really rewarding for us. So, you know, I, I've heard people wrestle with like giving money to family. We, we gave a lot of money to family, but every time we oriented it around like, so what do you owe to credit cards? What's your goal? What do you need? You know, like what, like how stressed are you about your house payment kind of t…

AI assessment note: “one of the things I think we learned was that, uh, couples that work”

Q and then we really should do a quick fire, because I, I, I'm aware that the 20 minute VC is not 20 minutes. Um, but it's the final thing, which is, you've mentioned LP-ing into funds quite a few times. When you look back at the 75 or so that you've done, have there been some big takeaways for you from doing 75 LP checks and seeing 75 different managers?

A Yeah, I think the number one, um, thing is, I don't want to get credit for that as a philanthropic investment. Because in the end, I, I, I told everyone from the beginning, I was like, look, diversity in this industry, you can either, you can either hire diverse people for your firm, um, because you've, you know, acknowledged there's been hundreds of years of systemic discrimination and women are making 70 cents on the dollar, um, and, you know, entire races have been shut out of the industry, or you can hire diverse team members because the data are clear that diverse teams just outperform monoculture. So either do it cause you're a hippie or do it cause you're Scrooge McDuck, but either way do it. Um, and I have no allergy to money. And so I, I am like, I go into the LP situation and I say, look, I mean, we can either invest in these managers because you feel bad and you want to do something to help the industry and you feel like you owe it as a result of your privilege. And I'm not going to talk you out of that, but also do it just because, you know, in a time where everyone's chasing the same fucking deals, we're now backing a generation of entrepreneurs or of Of, of GPs who are seeing deals that we're not going to fucking see. And so that aren't bubbling up through our old boys network of white guys that aren't making it to Sand Hill Road, but have massive addressable mark…

AI assessment note: “our LP portfolio of diverse managers is running about a two and a half X”

Q Okay, so you mentioned a couple of books, but what's the favorite book and why?

A All right. I've said this before, but it's, it's still not fade away. A book of this guy, um, who was, uh, well, our lives are similar. He was a ski bum. He became a massive exec executive at Liberty media and, uh, and right at the height of his success found out he, uh, had incurable stomach cancer and started writing the book then reflecting on his life, reflecting on meaning, because I think one of these things is so easy to get totally obsessed and consumed by our industry. It's, it's easy to forget. And as we talk, as we touched upon multiple times in this interview, Um, that balance in life, those relationships, those friendships, that time to take care of yourself. And so, um, you know, you'll cry. So anyway, not fade away.

AI assessment note: “I've said this before, but it's, it's still not fade away.”

Q What makes you and Crystal such a great partnership?

A Well, knowing each other since we were kids is definitely helpful. Um, we've, and I think seeing each other grow up at similar paces and rates in our respective fields has been incredible. You know, Crystal doesn't take, um, any public credit for anything because it's just, she's just a much more balanced human who doesn't need external validation at all. Um, but Crystal's been, you know, she was there in the room to choose the, to, to hear the Uber pitch and decide we should do the deal. Um, and has been an instrumental part of everything we've ever done at Lowercase. And so, um, but, but with that, I mean, it's, um, uh, inside of our, of our wedding rings, we have these two things engraved. Um, one is mutual weirdness forever. Um, so we try and encourage each other to stay our, our just weird, um, our weird selves, you know, and pursue those quirky interests and not try and smooth the edges, like be a little rougher on the edges. Um, and then the other thing we have engraved in our rings is in violent agreement, because we can really go, like, we can, we're both very type A strong personalities, and our kids laugh, because we can really get going, um, and often, you know, we'll be like, look, we're seeing the same fucking thing, we're just nuancing the words right now, but, um, but I think having, having a dynamic, worthy, robust debating partner who, who has, A very strong c…

AI assessment note: “having a dynamic, worthy, robust debating partner who, who has, A very strong compass”

Q a couple of friends to me there with that one. But I, listen, I love a good opinion. I want to finish though. Chris, on the most important, which is like, what are the next 10 years hold for you and for lower carbon? Like, how big do you want to make this? Do you want to make this like black rock style? Is this, what does that look like?

A I mean, I never want to run a huge org, and so there'll be a breaking point at which when the slack gets unmanageable, you know, we're single digit number of people right now. I think I can see hiring two or three more heads. I don't really want to be bigger than that. Clay's a really good manager, and so it might be able to scale. It's working really well, but that's not my personal aspiration. My aspiration is just to be a big fucking lever. You know, like, I get excited when I am able to go to Goldman Sachs and say, don't go guarantee drilling finance in the Arctic. Instead, go do deals with us. And that those guys who, look, I'm close with David Solomon, the guy who runs the bank, and I know he cares. He also has a fiduciary to manage money, and they seek profit. And so when those guys walk away from the Arctic, and instead do clean energy deals alongside us, that makes me happy. I mean, I had, I said this when we announced our fund, it was like that, while I loved having a bunch of LPs, and we had like Billions of dollars of interest for our fund in just a few days, and so that was overwhelming, but when I, we actually made room for some people who were sheer greed-based investors, not just the folks who had a climate mandate, because I was like, I want you here, and I want you to put this in your for-profit pocket of capital, and I want to put up the returns for you that …

AI assessment note: “I never want to run a huge org, and so there'll be a breaking point”

Q don't want the founder to say something bad. They're worried about their reputation. The power has swung so much. That no one is willing to say anything about it at all. And I'm sitting in a board meeting and he's going, what the fuck? Someone needs to speak up. And no one says anything. Like, does this worry you as well? Cause it seems like VCs just lost their voice.

A It's an exceptional point. And it's true. One thing I want to counterbalance it with is VCs actually have way less power than people think they often do. You know, I go back to when everyone was like, why didn't you fire Travis? And I was like, there was no fucking way we could, you know, ultimately we'd come up with some kind of crafty ways that we could convert our stock from preferred to common. And maybe take over the board. That was risky, and we weren't totally sure. In the end, what pushed Travis out was when his team held him accountable. It was when the, you know, his 13 senior managers all wrote a letter and said, dude, you gotta stay out of the company. You know, that's really the only force that Silicon Valley leaders are accountable to. I mean, Zuckerberg has zero fucks left to give. In fact, I think he might even derive pleasure from public criticism of him. You know, it might reinforce his worldview that the rest of us don't fucking get it. But when his employees start pushing back on him, that is the number one hardest resource in all of, of tech is if you can't recruit and retain good talent, you're powerless. You know, it'll be interesting now that Mike left. Well, let's see what that meant actually. Was he just, you know, did he want to go hang out on a beach or was there something greater to that? It'll be interesting. And we'll see if there's more departure…

AI assessment note: “It's an exceptional point. And it's true. One thing I want to counterbalance”

Q I can do that, that's a lot of money, and then now, How do you think about your relationship to money? Because, you know, it always changes. How do you think about your relationship to money today, Chris?

A Yeah, I, I think I'm lucky in that I don't feel competitive with other investors or other rich people. So I, I have a lot of friends who are tortured by it. Um, and they just, they have countless, countless dollars at hand, but feel like they're, that the goal, the goal line's always moving and they need to keep up with somebody else. So, uh, I certainly look at it as what can I do with the money we have? And, um, and luckily, Um, we have all the stuff we want and you get to this point where like in the beginning I made a bunch of money and I bought houses for family and, um, and multiple houses for ourselves. And then my wife and I turn around and we're like, fuck, we're property managers. Like that's all we do now is like our inbox is like, Hey, this broke and this is happening. And what do we do? I was like, so we're just prisoners to our stuff right now. And, uh, and so again, it was lucky that I kind of got into that early and realized like, oh my God, like, And then you start to realize, you know, we're fortunate enough to go on vacations, but we don't need to own that chateau. It's amazing. There's some incredible places in Europe where we love to spend time that you can rent. And then when you're done, you walk away from them. And so, you know, you can live luxuriously and then not have to own it. And so, um, and luckily we're also not into big boats, thankfully. So tha…

AI assessment note: “I don't feel competitive with other investors or other rich people.”

Q and then we really should do a quick fire, because I, I, I'm aware that the 20 minute VC is not 20 minutes. Um, but it's the final thing, which is, you've mentioned LP-ing into funds quite a few times. When you look back at the 75 or so that you've done, have there been some big takeaways for you from doing 75 LP checks and seeing 75 different managers?

A Yeah, I think the number one, um, thing is, I don't want to get credit for that as a philanthropic investment. Because in the end, I, I, I told everyone from the beginning, I was like, look, diversity in this industry, you can either, you can either hire diverse people for your firm, um, because you've, you know, acknowledged there's been hundreds of years of systemic discrimination and women are making 70 cents on the dollar, um, and, you know, entire races have been shut out of the industry, or you can hire diverse team members because the data are clear that diverse teams just outperform monoculture. So either do it cause you're a hippie or do it cause you're Scrooge McDuck, but either way do it. Um, and I have no allergy to money. And so I, I am like, I go into the LP situation and I say, look, I mean, we can either invest in these managers because you feel bad and you want to do something to help the industry and you feel like you owe it as a result of your privilege. And I'm not going to talk you out of that, but also do it just because, you know, in a time where everyone's chasing the same fucking deals, we're now backing a generation of entrepreneurs or of Of, of GPs who are seeing deals that we're not going to fucking see. And so that aren't bubbling up through our old boys network of white guys that aren't making it to Sand Hill Road, but have massive addressable mark…

AI assessment note: “our LP portfolio of diverse managers is running about a two and a half X”

Q Can I be blunt? Why raise external money? You have enough money to fund it all yourself. Like, why take external money?

A I mean, look, I, I'm very lucky I have lots of money, but I don't have enough to do this all myself. I mean, to do this right is going to take billions and billions of dollars. These businesses are, the unit economics are there, but they scale faster than any businesses ever too. Look, when you and I invest in an app or a website, like, we can have the very best business plan and the best intentions, and we can spend A year, sometimes two years building that thing, pushing, moving the buttons around, getting excited about it. And then on launch day, nobody gives a fuck. And, and it's this very binary thing. And I mean, I, I get it. Like just some of this shit just doesn't work sometimes. What we're seeing in climate is our stuff works. And so it's a rush to, to scale it, to land those customers. Like by the time we meet with somebody, usually their science is already palpable. We can, it's tangible. We can touch it. And so as a result, it's like, how do we go to market? And so what's interesting is these companies are more capital intensive, but they also are able to tap project finance earlier. They're able to get loans and debt earlier in their life cycle than, you know, I think Uber was like a fifty billion dollar company before they were able to borrow money instead of the loot of financing. And so, but you need some deeper pockets to play in this stuff. And so, you know, w…

AI assessment note: “I don't have enough to do this all myself. I mean, to do this right”

Q know, Bill Gurley, um, was the one that told me, um, you don't want to be the guy that stops dancing before Mr. Brightside comes on at the party. I love that. Um, but, like, I'm like, I'm looking at the industry, I'm like, shit, I should have discipline, and then no one else has discipline. Like, how should I think about this, and how do you think about this?

A Yeah, it's not discipline, it's, um, it's, it's, okay, I think there's this fake discipline to these requirements that, that the industry somehow thinks have been imposed by LPs, and they may have been, and any, but any LPs who think like this are fucking backwards, and so, and I see this in decks, you know, my, Crystal and I are LPs in dozens and dozens of funds, Because that was one of the ways we paid it forward, you know, and, uh, to help kind of promote diversity in the industry, we backed literally dozens of first-time general partners who are women, people of color, and other underrepresented groups. And so, but we'd see these decks, and they'd be like, okay, this is exactly how much I'm going to own of each round. This is my deployment velocity. Um, these are the board seats I'm going to take, et cetera. And every time I was like, stop, like, take that slide out. You know, I, well, when I wrote my checks into Uber, They were out, they were too big, quote unquote, for my fund, and one of my LPs called me, and I was like, look, I have conviction about some things, but this one I fucking know. I mean, so much of Uber came together in my fucking kitchen. I'm going in, and like, if I, if I fucking crash and, you know, and, uh, crash and burn, then it's on me, but this one I fucking understand, and I'm betting the farm on it, um, and I was right. I mean, I shouldn't take much…

AI assessment note: “I think there's this fake discipline to these requirements”

Q Are you going to make more money from climate than you are from tech?

A Absolutely. I'll, I'll get way richer from this. I mean, we have, I have multiple companies in the portfolio right now that have the, the very, like they have a trajectory to being multi-trillion dollar market cap. And it's just, that's not like, like, yes, we, I mean, look, we are in the business of curved lines rather than straight lines. And a lot of the naysayers in the business are still extrapolating off of the straight lines. Like, look, here's, Here's where we are today. There's no way that I'll ever be big. And I'm like, yeah, but we are in the business of these, of these lines that bend upward at radical rates that some of the OGs in the space just can't wrap their heads around, you know, like fusion. So we have a handful of companies in the fusion space forever. People have said nuclear fusion is 30 years off and it always will be. And so, and I just, I got in a Twitter fight the other day with a guy who's like, it'll always be 30 years off. And I was just like, You know, I deeply respect all the work you've done in the space, but you sound like someone who hasn't visited the lab in a while, because that's not where it is, and I can't preempt any announcements coming from any of our companies, but I can assure you it's, I, fuck, I, I overstepped my bounds in terms of what we know, but I can assure you it is much, much more near term than 30 years, like imminent, um, …

AI assessment note: “Absolutely. I'll, I'll get way richer from this.”

Q Do you not feel like we're losing our humanity a little bit?

A Yes, that's the point is we've stopped giving a shit about other people along the way. You know, so, so I believe, I believe in a meritocracy, but I believe that, you know, often despite the circumstances people are born into, whether they're born, you know, on, uh, you know, into extreme poverty and, and, you know, or, or came from a first generation immigrant family. I mean, those are inspiring stories, but I also believe that there are people who were born on third base Who also have worked hard and created some of their own luck, but at the same time, like, I believe that, like I said, I may be lucky, but it's not an accident, but at the same time, the friends I grew up with who just didn't work as hard, maybe, you know, who like played cards on Wednesday night, you know, when I was going to university for math, they have absolutely the same fundamental human right to be happy and healthy and to have a family and to enjoy themselves right now. And that's the fucking part that I think our culture keeps forgetting is that I love when people go on their accelerated journey, and I do believe that those people who are that fortunate should enjoy some of the spoils of life. Like, whatever they, you know, if, if going to on a fancy vacation or drinking incredible wine or driving a super fast car is their thing, I'm actually not like a complete socialist, you know, that people shou…

AI assessment note: “Yes, that's the point is we've stopped giving a shit about other people”

Q How do you retain an optimistic mindset then? When you're wrong, and you lose money, or the deal doesn't go as planned, To not go, ugh, consumer social's crap, or healthcare's crap, or you name it's crap, because you've lost money there before. How do you keep that optimistic, fresh mind?

A Well, it's funny. It was, it was a lack of optimism that cost me some money in the beginning when I met the Airbnb guys and, and I pulled them aside and was like, look, somebody's going to get raped or murdered and the blood is going to be on your hands. And you know what? That's turned out to be true once they've had hundreds of millions of, of users of the site. Yes. And people are going to get hurt. It's the law of big numbers, but I had let the bad case get in the way of me seeing the most obvious case. You know, most humans are good. Most of these services are obviously going to work. I mean, we, You know, I, I once, we were, we were in an Uber meeting talking about how, um, there was this, you know, like, I mean, you see articles about this driver hurt somebody, and so we dug into the data. First of all, half of the time, it's passengers hurting the drivers, um, and so there's this even split, uh, but the reason those articles get written is because, thanks to Uber, we know about them. We know exactly who was involved, right? If you get assaulted by a cab driver, you'd never know. Um, but the other thing is, Just the law of big numbers. There's so many damn drivers and passengers out there now. So many collisions between individuals is going to lead at scale to some bad ones. And I, I once did some math and I, I can't make it up now, but it was like Walmart employees, som…

AI assessment note: “I had let the bad case get in the way of me seeing the most obvious case.”

Q we chatted before the show about things that you were most passionate about, and one of them, again, on the safety net, was raising kids to be happy, balanced, helpful people. I guess when you look back at that, and also the interrogative process, what have also been some of your big, like, lessons on what great parenthood means to you, and the type of dad you want to be?

A Yeah, so, so it's funny, one of the, one of the things I've seen, um, is how, And it's a strange correlation. It's obviously anecdotal, but the less formal education some of my friends have, the more obsessed they seem to be about getting their kids into the right schools and the right enrichment programs. And so, you know, I, I, I was lucky to go to a cool university. That's where I met my wife, um, and study the humanities and have this incredible, you know, education in the classics and all and other cultures and got to study abroad in multiple countries. And so I feel super lucky and privileged for that. But I definitely don't think it's the only way forward. You know, I, I have very close and successful friends who didn't go to college at all. Um, I have one friend who left high school, uh, and has been a wild success. And so I think there's countless paths to this really, um, to, to success, however you measure it, you know, not just in business, but in art and, um, and, and philanthropy and volunteerism and stuff like that. So, but, What I worry about is this race I see among too many of my friends to just push their kids on this path to Stanford. They have to go to the best school. They have to start coding early. They have to take all the enrichment classes. They have to take the IQ tests. And it just gets like this, it's this fucking insane treadmill. And I also see i…

AI assessment note: “What I worry about is this race I see among too many of my friends”

Q Do you not feel like we're losing our humanity a little bit?

A Yes, that's the point is we've stopped giving a shit about other people along the way. You know, so, so I believe, I believe in a meritocracy, but I believe that, you know, often despite the circumstances people are born into, whether they're born, you know, on, uh, you know, into extreme poverty and, and, you know, or, or came from a first generation immigrant family. I mean, those are inspiring stories, but I also believe that there are people who were born on third base Who also have worked hard and created some of their own luck, but at the same time, like, I believe that, like I said, I may be lucky, but it's not an accident, but at the same time, the friends I grew up with who just didn't work as hard, maybe, you know, who like played cards on Wednesday night, you know, when I was going to university for math, they have absolutely the same fundamental human right to be happy and healthy and to have a family and to enjoy themselves right now. And that's the fucking part that I think our culture keeps forgetting is that I love when people go on their accelerated journey, and I do believe that those people who are that fortunate should enjoy some of the spoils of life. Like, whatever they, you know, if, if going to on a fancy vacation or drinking incredible wine or driving a super fast car is their thing, I'm actually not like a complete socialist, you know, that people shou…

AI assessment note: “Yes, that's the point is we've stopped giving a shit about other people along the way.”