E23: Radical DAs, breaking down FB/Google vs. Australia, sustained fear post-vaccine & fan questions

Chamath Palihapitiya 0:00 JK, are you going to do your Trump impression? We're going to do your, your Trump-

Jason Calacanis 0:02 Okay.

Chamath Palihapitiya 0:03 Yeah.

Jason Calacanis 0:04 Everybody, (music playing) I'm getting my Twitter hammer back next week.

David Sacks 0:06 Don't give him derangement syndrome right before we start the pod.

Chamath Palihapitiya 0:09 We want to warm him up.

Jason Calacanis 0:09 Going to be like Ted Cruz.

David Sacks 0:10 This doesn't warm him up, it gets him deranged.

Jason Calacanis 0:12 Get your show notes up, bitches.

David Friedberg 0:15 I'm going all in.

David Sacks 0:16 Let your winners ride.

Jason Calacanis 0:19 Rain Man David Sacks.

David Friedberg 0:21 I'm going all in.

David Sacks 0:23 And I said- We open sourced it to the fans and they've just gone crazy with it.

Chamath Palihapitiya 0:27 Love you,

David Friedberg 0:28 Queen of quinoa. I'm going all in.

Jason Calacanis 0:33 Hey, everybody. Hey, everybody. Welcome to another All In podcast. With me today, of course, the Dictator, Chamath Palihapitiya, the Queen of Quinoa, David Friedberg, and of course, yeah, definitely the Rain Man is here, David Sacks, who's an excellent driver in the driveway. Yeah. Okay, boys, uh, I guess we made it to episode 22.

David Friedberg 0:59 Your- your intro, your intro becomes one second longer for every episode we do. It's just so-

Jason Calacanis 1:04 (laughs)

Chamath Palihapitiya 1:04 But people love it. And people- the fans love it.

David Friedberg 1:06 It's so laborious actually. (laughs) You know, they don't. They think it's so stupid. He was-

Jason Calacanis 1:08 I am... You have to understand persuasion. What I'm doing is I do the same intro and it warns people about the discussion.

Chamath Palihapitiya 1:13 Oh, okay. See, we're still, we're still talking about the intro.

David Sacks 1:15 (laughs)

Jason Calacanis 1:15 Okay, let's just... You, and see, everybody's obsessed about it. You proved my point. All right, guys, are we going to address...

Chamath Palihapitiya 1:23 Elephant in the room.

David Friedberg 1:24 The elephant in the room.

Jason Calacanis 1:25 ... the elephant in the room or do we just move on to topics?

Chamath Palihapitiya 1:27 I will say-

David Friedberg 1:27 Elephant in the room.

Chamath Palihapitiya 1:28 ... after the last show, um, I fought very hard with the three of you to not post that episode.

Jason Calacanis 1:37 You wanted to can- you wanted to spike the episode.

Chamath Palihapitiya 1:39 I wanted to spike the episode and I'll tell you why. Um, I thought it was not good content. I don't think Vlad said anything new or remarkable or interesting. I don't think we had good analysis, and I think the whole thing kind of fell flat and felt like a PR stunt. And I felt that truly and honestly, and I, you know, I made the case to you guys that we should cancel. Um, obviously I lost.

Jason Calacanis 1:59 Okay.

Chamath Palihapitiya 1:59 Uh, and I think going forward we should have a veto right, but, you know, we can talk about that offline.

Jason Calacanis 2:04 Did you quit the show or did you threaten to quit the show?

Chamath Palihapitiya 2:07 I threatened to quit the show.

Jason Calacanis 2:07 And are you quitting now?

Chamath Palihapitiya 2:09 I'm, I'm gonna... After this, I'm going to propose to you my rules, my ground rules for, for going forward.

David Sacks 2:14 (laughs)

Chamath Palihapitiya 2:14 One of which I think should be no more PR bullshit from Jason's portfolio.

David Sacks 2:18 (laughs)

Chamath Palihapitiya 2:18 But, um, you know, besides that, I think I might be able to-

Jason Calacanis 2:21 Oh wait, I think I hear a bestie guestie. Is that calm.com at the door?

Chamath Palihapitiya 2:24 (laughs)

Jason Calacanis 2:25 Ding-dong. (laughs)

Chamath Palihapitiya 2:27 (laughs) And I, I don't think that we're journalists.

Jason Calacanis 2:29 Have you guys met any of get ...

Chamath Palihapitiya 2:30 And I, by the way, I don't, I don't, I don't think that the journalism thing works for us. I think we're like analysts and commentators and, you know, we have opinions. And so to bring someone on and try and interview them with a four-on-one format, it just feels weird. It doesn't seem to work. It doesn't create an opportunity for discourse. And frankly, you know, um, when you try and do journalism in this context, you either appear like you're softballing or you appear like you're doing gotcha journalism, and I think both are bad. And so I think it works really well when the four of us just kind of chat and analyze and, and shoot the shit and have opinions and talk and debate. Um, and so my vote is to kind of avoid doing bestie guesties unless, you know, it's something pretty amazing and critical and we can all kind of build a dialogue with that person around a topic. But, um, yeah, so that's kind of m- where, where I'm sitting and, and how I feel about it, but-

Jason Calacanis 3:17 Nice.

Chamath Palihapitiya 3:17 ... we've had a lot of debates obviously since, uh, since the last episode about it.

David Friedberg 3:21 Can, can I, can I build on what you're saying? Um, you know, i- this is, like, kind of like that really, uh, famous Teddy Roosevelt quote about sort of like the man in the arena with the dust on his face, right? Um, I feel like all four of us are in the grind doing things. And I think what makes the podcast good is it's almost like there's like, you know, in a basketball game of four quarters, there's a timeout and you come off the floor and you can actually just take a second to observe what you're seeing. And then the ref blows the whistle and you go back into the game. And I think for me, what makes this thing so fun is I feel like every Friday for these two hours, you know, it's basically the ref calls a timeout or the coach calls a timeout and we can just kind of take a breath and just observe, all right, what's happened, bef- before we get back in the arena. And so, you know, just to your point, um, I don't think we're journalists, and I don't think we should try to be, because I don't think that's the point of what this is. It should be four friends talking about things that are important. And then to the extent that it's important and interesting for other people, they'll listen or not listen. And I think these last few weeks, we got caught up a little too much in, you know, ratings, where is it ranking, how can we go higher? And it's that, the gamification of people's reactions that I think caused us, you know, to do that. Um, whereas the episode before I actually kind of liked because Draymond is legitimately one of our really good friends. You know, we see him-

Jason Calacanis 4:42 He's a bestie.

David Friedberg 4:44 ... we see him, we see him many, many times, obviously less during basketball season, but a ton when he's outside. We play poker together. We all hang out together. So it's, that to me, I think is sort of in bounds. Um, last week... And then also, you know, last week I wa- I think we were all supposed to be on point. I'll just tell you personally for me, I had an extremely crushing two weeks of work. I was extremely tired. Um, I ended up literally unplugging and not doing anything for three days straight and sleeping. Um, and so it... Well, I didn't even do my best even just to be either supportive or, you know, uh, argumentative with Vlad. So I don't think I got anything out of it myself.

Jason Calacanis 5:22 Okay. Coming around the horn, Sax, do you... How do you feel that episode stands on its own? Obviously, it's very polarizing. We got barbecued in the comments. We got barbecued on Reddit. We got barbecued on social media. But then there were a large number of people who said they really liked it. Uh, my mom.

Chamath Palihapitiya 5:38 (laughs)

Jason Calacanis 5:39 Robin Hood.

David Friedberg 5:39 A job letter. (laughs) Robin Hood PR.

Chamath Palihapitiya 5:40 David Blaine. (laughs)

Jason Calacanis 5:42 My portfolio manager.

Chamath Palihapitiya 5:44 Right. Sequoia.

Jason Calacanis 5:44 I mean, there were people who liked it.

David Friedberg 5:45 Sequoia thought it was excellent.

Chamath Palihapitiya 5:47 Yeah.

Jason Calacanis 5:47 (Laughs) Right. There's 12 people in the launch.

Chamath Palihapitiya 5:51 Yeah.

Jason Calacanis 5:51 Fun.

David Friedberg 5:51 Sax-

Chamath Palihapitiya 5:52 Give us your candid assessment because you weren't as hard as these other two.

Jason Calacanis 5:55 ... on it.

5:56 Yeah, I wasn't as hard as these other two, and I do feel like that if they felt they... that we were soft on Vlad, then they should've brought it harder. And they should've gone after Ve- Vlad and challenged him more. That being said, I completely, uh, understand and agree with what Freeburg is saying, that, look, we're not journalists, we're not playing a game of gotcha. It's not our job to go after Vlad. Um, I think a lot of the, you know, th- the, the comments on Twitter, that's what they wanted us to do. But that's not who we are. You know? Um-

6:27 Well, it's difficult for business, too, Sacks. I mean, if you're attacking Vlad, and then the next day, we have to go into supporting founder mode, it's kind of a bad look, isn't it?

6:38 Yeah, I mean, it's not what we do, right?

6:40 Right.

6:40 I mean, we, we, we are... Uh, l- like Chamath was saying, we are in the arena. We're doing things. We're not critics sitting on the sidelines pointing out, you know, what the doers of deeds did wrong, you know? And so it's not our job to, you know, run an inquisition on, on Vlad, you know? And so we're not really equipped to do that. I think, I think Freeburg is right that it doesn't really make sense to have guests on the show if the job is to, you know, to get to the bottom of something as investigators, you know?

7:09 Yeah.

7:09 We're not, we're not investigators.

7:11 And it was, you know, a big story, uh, just to sort of put a cap in it from my perspective. You know, I, I'm always supportive of my guys. I try to be supportive of whoever I invest in, and I try to give them the benefit of the doubt. And this is a situation where, you know, people are upset. There were mistakes that were made, and so I, I think anything other than demolishing Vlad is considered by some constituency as a failure, right? And, and so what are we supposed-

7:38 Totally.

7:38 ... to do here? I can't be trashing my own company that I'm an investor in and a supporter of, and, and founders who I believe in. It just... Would that wouldn't be authentic either.

7:44 Well, I think there, there was a moment... There was a moment in the pod, Jason, where I think actually, uh, th- so on the whole, I thought Vlad did a, did a good job in accomplishing his objective on our pod, which was the same objective he had in front of Congress, which was basically to run out the clock without saying very much, you know? And, uh, you know, he, he actually... Uh, whoever prepped him for, for Congress did a pretty good job because he testified for five hours and said nothing quotable, you know? (laughs) Which, which is pr- pretty much the best-

8:13 Kind of the goal, right? Yeah.

8:14 ... you can do in that situation. It's kind of the goal for, for him.

8:15 Keep your head down.

8:17 Yeah, exactly. So, uh, but there was a moment in the pod last week where I think Vlad got himself in a little bit of trouble. Freeburg did ask actually a pretty tough question about the guy in the street who, who had lost all of his life savings. How would Vlad respond to that? He made this claim, "Well, I saved that person money because I shut down trading at the high." And, and then we pointed out, "No, I mean, it, it, it was a high because you shut down trading. You have the causation backwards." And then you, you ran and said, "Whoa, whoa, whoa, whoa, whoa," you know? Uh... (laughs)

8:47 (laughs) Well, my guy was on the floor. I gotta pick him up. I, I... What are you talking about? I called a timeout. I got in there, but let's-

8:53 Yeah, exactly.

8:54 Yeah.

8:54 All right, let's move on. Let's move on.

8:55 Do we talk about the insanely high profile guest that was planned for March 5th that just-

David Friedberg 9:02 Yeah.

Jason Calacanis 9:02 ... canceled on us?

David Friedberg 9:02 No, no, no. We should, we should talk about that too.

Jason Calacanis 9:03 Do we put it on the ta- 'cause I... You know, I... This, this... The other thing about protocol, I'll just say, Freeburg, is if we have a guest on, you cannot just spike the guest if they took the time to be on. That was my understanding also.

Chamath Palihapitiya 9:14 Unless you tell them before they come on, "I may spike you."

Jason Calacanis 9:16 That we might spike it if it doesn't go their way.

Chamath Palihapitiya 9:18 If you don't... If, if we don't like it.

David Friedberg 9:20 Yeah, I think, I think-

Chamath Palihapitiya 9:20 Do they get that right?

Jason Calacanis 9:21 None of us do this for a profession. None of us are getting paid to podcast.

David Friedberg 9:23 But do they get that right, Freeburg?

Chamath Palihapitiya 9:24 We don't have any advertisers. Like-

David Friedberg 9:26 I completely agree.

Jason Calacanis 9:27 See, I disagree with you.

Chamath Palihapitiya 9:27 We're not here to be a PR machine for people. I mean, Vlad had his frigging PR woman sitting on the Zoom call while we were doing it last week. You know, like, I just don't think that's a-

Jason Calacanis 9:35 That's a little inside baseball that got interesting, I think. Explain what happened when you laughed and came back.

David Friedberg 9:38 Well, no, we don't need to go there, Jason. I just think, I just think what Freeburg says is right. Like, we, we do this. We don't make any money from it. We do it because we like to talk. We... I think we all learn from it. I think other folks enjoy it. They learn from it. But I do think that Freeburg's right. We're not gonna be used as a shill.

Jason Calacanis 9:55 No, I don't think we should be.

David Friedberg 9:56 I think we're learning as this goes. I think we're, we're learning what the ground rules should be, just like any other business. Vlad's made mistakes. He's gonna change. We've made some mistakes, and we're iterating. And I think one positive iteration that Freeburg has proposed is if any one of us don't like an episode 'cause we think it's basically moving away from our values, we should be able to spike it. And I, I support that.

Jason Calacanis 10:16 I support it generally, but I don't like the idea of inviting a guest on, and then it doesn't go well, and then telling... You know, from our perspective, it makes us look bad, and then we tell the guest, "Well, you came out good."

David Friedberg 10:27 No, but I think, I think what Freeburg-

Jason Calacanis 10:28 "And we came out down, therefore, we're killing your appearance."

David Friedberg 10:30 No, no, no. I don't, I don't think that's the point. I think what Freeburg says is like, "Look, this is not for... to be a marketing thing. And so-

Jason Calacanis 10:36 Right.

David Friedberg 10:36 ... we're gonna ask things that are exposed... that are about having a real conversation, where there's real-

Jason Calacanis 10:42 Sure.

David Friedberg 10:42 ... honesty." And if you're gonna just be there and bat around, as Sacks said, to run the clock out, then we're just gonna spike it.

Jason Calacanis 10:48 Uh, fair enough. Fair enough. Uh, I think if that's communicated ahead, I'm okay with it.

David Friedberg 10:52 By the way, come with your A game. And this is a great segue to talk about what actually we were... A person that was gonna come on and realized that they probably were gonna get so pilloried, um, that they basically spiked themselves, uh, is-

Jason Calacanis 11:06 Yeah, they opted out.

David Friedberg 11:07 ... Chesa Boudin, the, the District Attorney of San Francisco. Tell, tell the guys what happened, Sacks.

Jason Calacanis 11:11 Well, no, we, we invited him to come on the podcast-

11:14 No, no, we didn't invite him to come.

11:15 ... to talk to us.

11:15 He... An intermediary said that she could get him on the pod, would we like to have him on the pod? We said... We discussed it, we said, "Sure, have Chesa Boudin on and then go from there," Sacks. We didn't like seek him out. He was-

11:28 Well, okay.

11:28 ... back channeled to us.

11:29 Got it. So he, he agre- great. So he... But he agreed to be on the show, and then-

11:33 Yes.

11:34 ... you... Our scheduler got an email out of the blue, like a day or two ago saying, "Sorry, he's not coming on the show." No explanation, right? Isn't that what happened?

11:42 Yeah, that's basically it.

11:44 I mean, so look, here's what I would say is, um, Chesa, Mr. District Attorney, you don't have to come on the show, but I will challenge you to a debate-

11:53 (bucks)

11:53 ... any time, any place, any format-

11:55 (bucks)

11:56 ... on your policies in San Francisco.

11:59 (bucks)

11:59 So if you have, if you have the huevos-

12:02 (laughs)

12:03 ... to engage in a debate-... I am ready.

12:06 Bok-bok-bok.

12:07 And I thought Chasen was a guy who had a little bit of courage. I mean, there was that night-

12:10 Hah.

12:11 ... when people were discussing the situation in, in San Francisco and... on Clubhouse, and he jumped into the room. So I thought this was a guy who had some cojones. So Chasen-

12:21 Some chutzpah?

12:21 ... if you have... If you have the chutzpah, if you have the cojones, if you have the huevos, let's debate.

12:28 Let's debate.

12:28 Let's talk about your policies. San... And by the way, he's an expert. This is what he does, you know-

12:35 For a living.

12:36 ... he's an expert.

Chamath Palihapitiya 12:36 Isn't he a defense attorney, Sacks? You're gonna have a...

Jason Calacanis 12:39 He was a public defender. He should, he should mop the floor with me. I'm just some shallow-

12:45 Schlong.

12:46 ... tech bro.

Chamath Palihapitiya 12:46 Yeah. Tech bro.

Jason Calacanis 12:47 Tech bro.

12:47 Who doesn't know anything, who he can easily demonize. So I would say, come on-

12:51 Chest pain.

12:51 ... let's go. Let's do a debate. I'll agree to whatever format you want, but we need to talk about what's happening in San Francisco because crime is out of control and it's his fault.

Chamath Palihapitiya 13:02 Trigger the young Spielberg Rain Man song right about now.

Jason Calacanis 13:04 Here he goes (laughs) . Drop it. Boom.

David Sacks 13:06 (singing) Baby, I'm the rainman.

Jason Calacanis 13:08 (laughs)

13:09 With me cackling in behind-

13:11 Sh-

13:11 I'm like Sacks' hype man.

13:12 ... should we, should we talk about it? Let's talk about it.

13:13 Facts.

13:14 I wa- We should talk about what's happening in San Francisco, okay? So since, since the last pod, there, there has been another victim, um, Sherya Mat- Matsyoka, who was a, a young, a young man from, from... originally from Kenya who... He came to the United States for college, just like Hannah Abe, uh, who w- who was killed on New Year's Eve. Uh, he went to Dartmouth. All of his advisors said he was brilliant. He had a young wife and a three-year-old baby. He was in San Francisco for 10 days, goes out running, and gets hit, gets, gets killed by another drugged out hit-and-run driver who had be- uh, named, um, uh... Let's see. I think it was, uh, Jerry, Jerry Olee-Adams or something like that. Um, I don't have the, the, the guy's name, but he was arrested four or five times in the last year, and he was released every single time by Boudin's office. It's, it's just like the New Year's Eve story where you had this repeat offender, Troy McAlister, hit... You know, he was... He had stolen a, a car. He was fleeing another crime he had committed. He was on drugs, and he killed Hannah Abe and Elizabeth Platt. And this was, this was another case where he was caught five times over the past year, and every single time, he was not charged by Boudin. He was just let go. And so we have this case. We have a, a district attorney who doesn't wanna prosecute people. His agenda is decarceration. It's like a fire chief who doesn't believe in using water.

14:44 Yes.

14:44 And, and-

14:45 Bu- He, he is part of the burn-it-all-down party.

Chamath Palihapitiya 14:49 Let me challenge you with the argument he might make, which I think I've heard him make a few times, um, which is really, um, uh, a position on the criminal justice system, not necessarily on local prosecution. But really, what he says is once, um... You know, once someone ends up in the criminal justice system in the United States, it causes this cycle of recurrence and this cycle of repeat that is very difficult to get out. It, it basically minimizes the opportunity for reform, uh, for an individual, uh, for a criminal to, to reform themselves and to have a shot at being a successful member of society again in the future. And the objective is find other ways to, to, to kind of, um, accelerate reform and not use incarceration as the only tool in the toolbox. What is, um... You know, what is the, the argument back to him when he makes that point? 'Cause I've heard him make that point a number of times and how do you kind of move past that, uh, that point with him?

Jason Calacanis 15:45 Yeah, so, so the, the, the... I'm not saying that incarceration is the only answer, but Boudin's only answer is decarceration. He doesn't want to prosecute anyone, he doesn't want to lock anybody up, and we see the results immediately in this community. You have these repeat offenders now killing people. They should have been locked up. Um, it's... You know, uh, I... Boudin's always putting forth these elaborate theories. This is, you know... The, the San Francisco Chronicle had an article about it, about why these crimes occur and he never wants to put the fault on the people who are actually perpetrating the crimes. It's always economic desperation. He just put forward a, a theory that a decline in tourism is causing, uh, people to commit more, uh, home invasions.

16:29 What?

16:29 You know, he, he never wants to... Yes. This is in the, uh, San Francisco Chronicle article. Here, I'll pull it up on the, on the screen.

16:34 Sorry. I mean, it's crazy. I mean, the other thing you left out, David, I'll say, is... And this was really, you know, hits home to anybody with kids, is a food driver for DoorDash... Uh, not that it matters which service, but, uh, was in San Francisco's Pacific Heights neighborhood, which is the safest and most elite neighborhood, uh, in... It's, you know, the Beverly Hills or Bel Air of San Francisco. Um, and his car was carjacked with his four-year-old daughter and two-year-old boy inside. Now, of course you should not be leaving two kids in the car. Putting that aside, that mistake, which I'm sure this father is suffering over, but he needed to make deliveries obviously. He made a mistake leaving the kids in the car. But the... We all got an Amber Alert last week on our phones. I mean, this is the law- level of lawlessness. It's turned into Escape from New York level-

17:25 Right.

17:25 ... Gotham City level chaos here.

17:27 So let's-

17:27 And the criminals know they will not be prosecuted. And this is the key criminal justice problem here. If you say you are not gonna prosecute crime and you demonstrate to the hardest core faction of criminals that you don't prosecute, they're gonna take advantage of that weakness. And, and that's what's happening.

David Friedberg 17:45 Yeah. Let me take the counterpoint just for a second, just so we can construct what the other side of the argument looks like. The other side of the argument says, okay, these folks are largely, you know, engaged in an enormous amount of petty crime to support their drug habit, right? I think that's probably the... And that, you know, underneath that is just an explosion, uh, of opioids and fentanyl and whatnot, uh...... underneath that is sort of economic uncertainty that's been compounding and just basically crusting over. Um, and so folks would say, "Okay, these guys are a victim of a much broader economic malaise that needs to get fixed." I'm just, I'm just ... You know, you're shaking-

Chamath Palihapitiya 18:23 Yeah.

David Friedberg 18:23 ... your head, Jason. But I'm just saying, I think that that's where the trail of breadcrumbs grows in the counterf- in the counterfa- in the, in, in the counterargument. So-

Jason Calacanis 18:30 Well, th- but the, th- these are, these are the types of arguments that Chesa makes in order to, um, obfuscate and disguise that his real agenda is basically radical decarceration. You know, he's got this, this childhood background where his parents went to jail when he was just a baby, and he grew up ... He says his earliest memories were visiting his parents in jail, and it profoundly affected his political views. I think he-

18:55 And now we have to suffer through this. (laughs)

18:57 We're suffering for all the-

18:57 Through his childhood trauma.

18:59 Through his childhood trauma. And so, so Tremath, you're right about deeper causes, but it doesn't excuse the need to lock people up when they are dangerous to the community. And it's not just petty crime. I mean, let, let's go through the, the actions he's taken as DA. Okay? So first week on the job, just about, he abolished the whole cash bail system. Okay? Which voters, in November, just voted, uh, in, with, uh, Prop 25 to affirm. So voters of California want the cash bail system because it keeps criminals locked up. What Chesa said is that he would replace cash bail with an algorithm. Well, what exactly is that algorithm? He won't explain. Well, he won't submit to third-party audit. There is no algorithm. They're just letting people go. Okay? Then, the next thing he did was fire seven veteran prosecutors in the DA's office who weren't on board with his agenda. These are people who s- have spent their whole lives prosecuting murders, rapes, I mean, hardcore crime. And it takes years of experience to learn how to be a prosecutor like that. So for him to just purge this office of these veteran prosecutors is a disaster for this city. I've been talking to people who used to work in the DA's office, and they tell me that the problem goes much deeper than that, that in addition to these seven veterans he purged, over 30 prosecutors, which is about a quarter of the whole office, have left under his reign because they don't like working for him. So h- you know, and he complains about being short-staffed. He says a lot that he can't, you know, prosecute everyone he needs to prosecute 'cause he's so short-staffed. The reason he's short-staffed is no one wants to work for him. You know?

Chamath Palihapitiya 20:36 By the way, I think it's worth highlighting, this guy was e- elected, right? So the, the, the city, uh, the voters in the city and county-

Jason Calacanis 20:42 In a runoff, I understand. Right?

20:43 He, he won by something like 2,000 votes. It was a tiny, tiny number of votes, and I-

Chamath Palihapitiya 20:47 Regardless, pe- people voted him in on a platform that he very clearly articulated and is now realizing in office. So, there is something about that platform, that I think is worth noting, was and is appealing, uh, and, and probably is to a large number of people-

Jason Calacanis 21:03 Large number.

Chamath Palihapitiya 21:04 ... in San Francisco, right? And-

Jason Calacanis 21:05 No, the, the, the, the part of it that's appealing, okay, is that, is that, is that we, we do believe that there are too many people in prison and that a better ... and a better way to deal with a drug addict who commits, say, petty theft, is to send them to treatment, okay, as opposed to putting them in prison.

Chamath Palihapitiya 21:22 Right.

Jason Calacanis 21:22 Right? So I think we can all agree on that. But, but his agenda is so much more radical than that. He just doesn't want to lock people up. Take, um, take Troy McAllister, okay? This is a dangerous person who, uh, he was o- he was facing trial for his third strike. Okay? He committed armed robbery. He robbed a store with a gun. Okay? He, he was facing a third strike for that, for that robbery, and one of the first things, uh, Chesa did when he came in was basically, uh, release him for time served. He basically pleaded that down. That was someone who was facing a life sentence. That is the reason why Hana Abe and Elizabeth Platt are dead, is because he didn't wanna prosecute ... That's a violent offender.

Chamath Palihapitiya 22:03 Zacks, I, I, I'm not disagreeing, by the way. I think, like, w- what is interesting to me is that so many people, um, have an eye on and agree with the notion that criminal justice system needs reform. The problem is realizing that reform with a radical district attorney doesn't really resolve to a solution. It resolves to more problems on a local level.

Jason Calacanis 22:25 Here's what's interesting-

Chamath Palihapitiya 22:25 And, and, and even Chesa said this publicly, which is like, you can't just solve this problem from the DA's office. It is a much bigger and broader problem. And the radical action he's taking isn't solving any problems. It's creating far more. And, um, I think it is worth noting though that there is, should, and likely will be, especially with, uh, Kamala Harris, uh, um, as vice president, some attempts at reforming on a federal level, um, uh, you know, how, how, how criminals are treated, how the system, um, realizes opportunities for them to reform and, and come back into society, uh, as productive members. But-

David Friedberg 22:59 I mean-

Chamath Palihapitiya 23:00 ... to your point, you lose all sense of safety and security if you try and do it solely on the local level.

David Friedberg 23:05 Well, let me, let me ask a question. Like, look, now we have basically political activism and judicial activism on not just the right, right? People used to pillory Trump for putting in all these, you know, extremely conservative judges who felt they were gonna just sort of like legislate their own point of view, um, you know, Supreme Court nominees who were gonna try to overturn Roe v. Wade, uh, but it turns out it's happening on the left as well, I guess just more at the local level. Um, how pervasive is this? Like, meaning the issues of San Francisco, are they, are these the same issues of other cities and towns in America?

Jason Calacanis 23:38 Yeah. Well, I mean, you've got Gascón in LA who's running the exact same agenda as Chesa Boudin. He's not prosecuting third strikes. He was just sued by, uh, an organization of deputy DAs, and the judge is now requiring him to uphold the law, which is three strikes. He will not bring third-strike charges on his own. He's also ... This is both Gascón and Boudin now have prohibited prosecutors from attending the parole hearings of dangerous convicts, murderers, rapists, whatever, and victims' groups are up in arms because they need a prosecutor to go there and explain to the parole board why this person does not deserve to be released. And so you now have recall movements forming-And, uh, by the way, they've also done stuff like take death penalty off the table, they've take- taken gang enhancements off the table. They're, like, voluntarily, they're unilaterally disarming their, their, the p- their prosecution teams. They're taking away weapons at their disposal to lock people up. And this is why you're already seeing recalls forming around Gascón in LA. There's now a recall of, uh, Boudin forming in San Francisco.

24:42 Okay. But David, David, go back to what Freeburg just said. They're probably not doing a bait and switch on their platform, so let's just... Like, what do you think it is about what they are saying that resonates on the way in f- with a plurality-

24:57 Right.

24:57 ... of people?

24:57 Yeah. Here, here's the thing that resonates. Um, a- a- a- and it's not that... A- again, it goes back to this idea that i- incarceration is definitely not the only answer, this is where I agree. The problem is, Boudin is on the other side of it, where decarceration is his only answer, right? We need to use, uh, multiple weapons or tools in our toolkit here. So, so hold on. So for, for example, okay, let's take the, let's take the drug addict who commits a petty, petty theft. We all agree that person should go to treatment, not to jail or prison, right? A non-violent-

Chamath Palihapitiya 25:29 Of course.

Jason Calacanis 25:29 ... offender. Okay.

Chamath Palihapitiya 25:30 Reasonable.

Jason Calacanis 25:30 But how are you, how are you gonna get that person to go to treatment? Because right now, there is no leverage whatsoever to get that person to go to treatment because Boudin's just not bringing charges. He's not prosecuting. The choice should be given to that person, "Listen, you can either go to jail or you can go to treatment."

Chamath Palihapitiya 25:46 Yeah, carry and stick.

Jason Calacanis 25:46 "What's it gonna be?"

Chamath Palihapitiya 25:47 Yeah.

Jason Calacanis 25:47 That's right. Right now, the- we have all these social services. Guess what? Nobody uses them because a hardcore addict is not gonna avail themselves of those services.

Chamath Palihapitiya 25:56 I, I would make the argument that we have a broader, bigger problem with the criminal justice system as it operates. And it is deep and it is complex and it is friggin' awful. There's a book from a few years ago, um, that this guy named Shane Bauer wrote. Um, I'm just trying to remember the name. I think it's called American Prison. And, uh, the guy goes undercover, and he goes and works in a, in a, in a, in a penitentiary in Louisiana. Um, and he reports on what the conditions are like. And these are these, these prisons that are run by private companies that are contracted by the state locally-

Jason Calacanis 26:26 We gotta ban that.

Chamath Palihapitiya 26:26 ... and what it's like to be an employee at one of these companies and what these employees do and how the prisoners are treated. There is no system for reform once you end up behind bars in most prisons in the United States. And that is, um, you know, he makes the argument, others have made the argument, that is a, uh, has a long history that dates all the way back to slavery in the United States. And in some cases, it's just about ineptitude. And in some cases, it's about unions, especially in California where we have a, a huge cost for, uh, for corrections and for the, uh, the healthcare and the pensions for corrections officers. Um, and so there's a lot of complex competing interests and history that relates to why this criminal justice system doesn't largely work on a moral and ethical basis, as we might all kind of, you know, wear our hearts and look at, like, at how things are working. And so the problem is everyone sees this, or a lot of people will see this. Voters will see this system, treating people poorly, being inept, being corrupt, and they wanna-

Jason Calacanis 27:22 Being racist.

Chamath Palihapitiya 27:22 ... being racist, and they wanna fix it.

Jason Calacanis 27:23 Yeah.

Chamath Palihapitiya 27:23 And the way they fix it is they see a guy who shows up and he's like, "I'm a sledgehammer, and I'm gonna fix it, and I'm gonna take care of all these people." And the reality is when you try and take a shotgun and shoot it inside of a room, it's gonna cause more problems than good. And I think that's really what he is. He is a manifestation-

Jason Calacanis 27:39 I think that's well-said.

Chamath Palihapitiya 27:39 ... of the anger of voters and the anger of people that look at how-

Jason Calacanis 27:43 Can I-

Chamath Palihapitiya 27:43 ... complex and racist the system is and how difficult it is to resolve these problems. And we're all looking-

Jason Calacanis 27:48 I-

Chamath Palihapitiya 27:48 ... for a simple big hammer answer, and he's got the biggest mouth around and the biggest hammer.

Jason Calacanis 27:52 Thank you ͝Able, Jason. And that's why people vote for him. All right, Chamath, and then we'll wrap it in.

27:56 Absent a few, uh, words, specifically racist, if you took that out, you could use that entire statement you said and describe Trump as well. Meaning the left and the right are moving to these poles where it's all about authoritarian, sort of, strongmen. At the federal, state, local level, folks, to your point, David, that just wanna go and take a sledgehammer to things. And depending on your political beliefs or depending on the biases or depending on your life lived, you're gonna gravitate to these two poles. And what's crazy is over the next 20 or 30 years, these polarizing figures will become crisper, sharper, smarter. You know, they'll find a way to foment all of s- all of the support without any of the long tail shittiness that Trump figured out. Like, Trump was, you know, he's like a beta test of an idea, right? He was like version 0.1. Wait till we see version 1.0 of the American strongman or strongwoman. It's really gonna be fucking scary. Well, yeah, I mean, and th- this is, this is a guy who, um, uh, w- was a fan of, of Hugo Chávez long after he revealed himself to be a strongman intent on ruling for life. And so, yeah, he is very much in that mold. He is a sledgehammer to the system. But, but, look, I think... And, and the problems are big and complicated. But look, we all have a role to play. The reformers have a role to play. Public defenders and defense attorneys have a role to play. And the district attorneys and prosecutors have a role to play. And the problem we have right now a- a- and the role of the district attorney is to prosecute, okay?

29:31 I don't think that this, by the way, Sacks, is a very difficult problem to solve. I think there are just so many misaligned incentives. It's very clear that we don't try to reform people when they go to prison, and that there's a weird incentive when it's a for-profit prison and the customers and the revenue is based on how many people you have in the prison. So if we just get rid of that, there's no private prisons where people have an incentive to keep people in there. And then if we made treatment free for everybody and had over capacity of treatment centers, and then we look at the drug schedule and say, "These are the drugs that are not h- these are the drugs that are not harmful, and these are the drugs that are really, really, really harmful," we're looking at a fentanyl issue like it's a cannabis issue, and that that's drugs. You know, cannabis versus fentanyl is like a nuclear bomb versus-... like a slingshot. It- it-

30:26 Sure.

30:26 There's no comparison-

30:27 Sure, but Jason, they're not gonna-

30:28 ... between these two things.

30:29 Ri- and, and, but here's the thing. No one's going to treatment when they're not forced to.

David Friedberg 30:33 Voluntarily. Yeah.

Jason Calacanis 30:33 Well, of course, right? But there's no treatment to go to, David.

David Friedberg 30:36 Maybe, maybe-

Jason Calacanis 30:36 The wait for treatment is six weeks, eight weeks, 12 weeks-

30:38 No, no, that's not true. That's not true.

30:40 ... in a lot of places.

30:40 That's not true. We, we, we have a lot of social services that aren't being used. There are, there is a lot of treatment available. People don't wanna do it unless they really have to.

David Friedberg 30:47 Let me bring it back to where we were before. Mo- maybe the right thing is to actually have a bunch of these sledgehammer folks go off for the next 10 or 20 years, you know? The Trumps and the Chesa Boudins, maybe they're all the same, and maybe what we're all just saying is, "Enough's enough. This system doesn't work, so let's just tear it down, every single brick of it, brick by brick, at the local, state, and federal level."

Jason Calacanis 31:11 It's chaos.

David Friedberg 31:11 Al- al- all I'm saying is, um, just, I would just wanna get your reaction to that statement, guys. Maybe, maybe that's what we're seeing.

Jason Calacanis 31:16 Well, people are... That, that is what Boudin is doing, is he is deconstructing the district attorney's office from the inside. He is destroying it. He is not bringing charges against people. He's driving away all the veteran prosecutors.

31:27 Number two, to Chamath's point, Sachs-

31:28 He's bring- he's bringing in his, he's bringing in all his, he's bringing in, in his own people who all were, uh, public defenders and have that mindset, and people are dying. Look, we can see the results right now in the streets. Innocent people are dying. Hana Abe, Elizabeth Platt, Sheria Muskogee-

31:43 All right, it's an emergency. But, uh, to Chamath's point, is there any validity, Sachs or Friedberg, to the burn it all down, cause chaos, and then people come in and say, "You know what?"

31:52 That's not gonna, that's not gonna make things better. No, we, we need, we need-

31:53 "This needs to be fixed. Let's have a nuanced discussion." Will nuance be added to this discussion, Sachs or Friedberg?

31:58 We, we, we need to improve things incrementally, okay? You're not gonna make things better by dismantling the whole district attorney's office. I mean, come on. We need to improve things incrementally.

Chamath Palihapitiya 32:07 Yeah, I mean, look, everything looks exponential until it cycles back. So, you know, you're, you're only gonna have so much, um, evolution to Gotham in San Francisco until enough people put their hands in the air and say, "Okay, you know, time for a change. Let's go back and let's start fixing this."

Jason Calacanis 32:23 They are. They are saying that. That's why we're having the, the-

32:26 I mean, there's a Recall Chesa Boudin movement.

Chamath Palihapitiya 32:28 Flexing a muscle and making it stronger, I think, you know, we're learning a lot about what approaches to criminal justice reform work and what approaches do not work. And it is clear that a local only, non-prosecution position is not gonna work with respect to both criminal justice reform and the satisfaction of the society at large. Um, and we're realizing that.

Jason Calacanis 32:47 I, I

Chamath Palihapitiya 32:47 think so.

32:47 And I think we, we are inevitably... I mean, there's so many people that are up in arms. We are inevitably gonna cycle-

Jason Calacanis 32:51 Yes.

Chamath Palihapitiya 32:51 ... back the other way at some point very soon here.

Jason Calacanis 32:54 Yeah, and honestly, I, I think you guys are over-intellectualizing this a little bit. You know? When, when Sheria, uh, died because he got hit by, by that repeat offender, they asked his, uh, wife, "Who's responsible for this?" She said, very clearly, "The DA, that is who's responsible," and she's right. Let's stop over-intellectualizing this. I know the problems are big and complicated. Frankly, people like Chesa prey on that because they can kind of obscure what they're doing with, you know, some nice-sounding obfuscation, some nice-sounding words. But the reality is, he's not prosecuting the way he needs to. We gotta stop this.

33:32 Yeah, and then y- it is possible to have nuance and to hold multiple ideas in your head at the same time, David. You could... There's a practical reality to people cannot murder people, people cannot drive in cars and run red lights on fentanyl while saying the criminal justice system is incredibly biased and racist. And people who are of color in Texas, you know, wind up in jail for five or 10 years for selling a bag of weed, and then we're investing in companies that are making weed gummies or people are buying stock in weed companies at the same time. You can't have one person who's a Black teenager in Texas going to jail for decades for doing what somebody in California or Seattle or Canada is getting an IPO for. I mean, this is a fundamental injustice in the world. And you're right, that's something that Chesa preys on. But there must be nuance here where we look at each individual situation and say, "What are the ways to solve the problem surgically, not with a shotgun," to David Friedberg's point, but with maybe a scalpel and a, and a sniper rifle. Do we wanna move on to questions from our audience? 'Cause they submitted hundreds of questions. Or do we wanna move on to the Australia news and Facebook backing out of publishing news if that's a good thing or a bad thing?

David Friedberg 34:43 Let's end... Let's end with the Q&A,

David Friedberg 34:44 I think. Sachs, what the fuck is going on with Facebook and Australia and climate change and... This is insanity.

Jason Calacanis 34:50 Yeah, so I think what's going on in Austr- Australia is, is contemplating a law that would require Facebook and Google, and I think just those two companies, to essentially pay royalties for hyperlinks to, to, to, to news publications. And I think this is mostly at the behest of some powerful, uh, newspaper magnates down there, I think like Rupert Murdoch and folks like that.

35:14 I love the way you say magnates. It's like ooh.

35:16 Well, they are. I mean, you know, um, and so, uh, it, but, but, but this issue's, is gonna be very closely watched by Europe and maybe even the US. Um, it's basically a tran- uh, like a, a wealth transfer from Google and, and Facebook to the traditional media and to traditional publishers. Um, this is an issue where I actually, um, side with, with Zuckerberg and Facebook on this. I mean, I kinda throw up a little bit in my mouth saying that. But, um, uh, but, uh, no, but look, Tim Berners-Lee has come out and said that it, it could really interfere with the open internet and the World Wide Web if you start to tax hyperlinks. I mean, historically, hyperlinks and the titles on hyperlinks were, um, were, were, were, were fair use. You could, you could use those things without violating somebody else's copyright or need to pay them a royalty. And so I think that it's, it's bizarre to me that, that Facebook and, and Google wouldn't now be able to use hyperlinks, and I'm kinda worried about where that goes.

36:22 Yeah.

36:22 And, uh, you know, I, so, so, yeah.

David Friedberg 36:24 Well, Facebook, Facebook said that they're not gonna publish links now for Australian news. And then, but then they followed that up with they were also going to start...

Jason Calacanis 36:34 ... uh, dismantling any anti-climate change content. I don't know if that's just, just in Australia or-

36:39 Well, there's labeling. So there's another thing going on, which is they've decided now to label any posts involving climate change, which is part of the whole censorship debate. And, um, and so-

36:49 Separate issue.

36:49 ... yeah, I mean... Well, it's separate but related in the sense that the traditional media is cheering on censorship, but then when Facebook es- essentially, uh, censors these links 'cause they don't wanna pay royalties to traditional media, then the traditional media is up in arms. And so, they're very selective in how they, how they view these issues. My, my principle is very consistent, which is I want an open internet. I'm against censorship in all of its forms. And I, and I, you know... And I'm, I'm worried that this new Australian law could really lead to some... le- lead to an overall re- reduction or shutdown.

37:25 He- here's what's really, I think, going on, is that with fair use, the doctrine of fair use, it's a four-part test. Uh, you're a lawyer, obviously you know all this, Sachs, but to sort of educate people in the audience who don't, there's no specific, uh, number of characters, no specific percentage of the original work that you, uh, can use you... to clear yourself of fair use. Fair use is a test. When it goes before a judge, a judge looks at this four-part test, the percentage of the work you used. Is the public confused? Um, is there some educational or criticism version of it? So if you were to use 10% of this podcast and you were to wrap it with, you know, put us in a picture window and you were 50% of it and there was no confusion that you were commenting on this, that would be fair use. Or if you were to use it in an educational system and if you were monetizing it. Now, if you were to just clip our podcast, like this one website clipped the podcast and made 60 clips of it, took our file, and I sent them a cease and desist actually and said, "Hey, don't do this. We're doing it ourselves." They fought us and they said, "We're fans." And I said, "I don't care if you're fans or not. You're not linking back, you're not giving us credit, and you're doing 60 clips." If you wanna do one or two clips and you wanna comment on it, that's fine, but you can't take all 60 clips and make a 60 clip version of this. Um, and so fairness is in the word fair use. The problem with Zuckerberg and with how Google has used journalist content is they are clipping out specific sections of it and putting it in something called OneBox on Google. So many of you might have said, "How many people... you know, how many pounds are in, you know, whatever?" Or "What time is this TV show on?" And then the content that was made by The Ringer or the New York Times gets clipped, and they put just that section, David, with an algorithm, and they give you the answer. So you don't need to go visit that website. This is tipping over into what I would call unfair use, because you're-

39:18 Okay. I think that's a great point.

39:18 ... eliminating the person linking. Now, let me finish.

39:21 Yeah.

39:22 If it was just the URL and you didn't pull the headline, you didn't pull the abstract, and you didn't pull the photo, that would be fine. There is a very easy solution to this, which is if you wanna pull the link and the headline, you pay $0. But if you wanna pull anything else, uh, 100 characters, et cetera, you need to get a license from that person unless you are doing actual criticism. So there's nothing to stop anybody in Australia right now from taking a screenshot of a New York Times story or an Australian, you know, newspaper story and writing some commentary on it. You just can't wholesale take everything. And so what we're seeing here is a real-time negotiation between private parties into what is fair. And I think Google has a really rich history of sharing revenue. Uh, the App Store, they give 70% to app developers. YouTube, they give 55% to creators. And with AdSense, they let you put AdSense on your website and they give you 68 cents on the dollar or something in that range. They never actually disclose the exact percentage, but that's what I'm told it is. Facebook has given $0 to Instagram users, $0 to WhatsApp users, $0 to Facebook folks. They're too greedy. And what Facebook needs to do is either not use the content or come up with some reasonable payment and come to an agreement with these folks who are now banding together. And they're realizing the traffic we get from Facebook and Google is not worth what they're taking away from with us, which is all that revenue that, you know, they earned in the free market. And so this is a free market debate, and I think the government should stay out of it, to a certain extent, and let the free market work, which is all publishers should get together in the United States and confront Facebook and say, "Pay us unless you use anything more than the headline." But Jason, I think these things are interconnected though, right? On the one hand, if you... if you have an economic stake in distribution of content, but then you're also then going to decide under, you know, a- an opaque definition what is truth or not truth, you all of a sudden just become, I mean, the purest form definition of a publisher, right? And I think it just becomes a very treacherous place for both Facebook and Google to end up in. So it's almost better- Well, Google's paying the bill, by the way.

41:34 Yeah. No, G- you're right. G- Google's paying for it. Facebook decided not to. But Facebook, uh, they said something like only 4% of their, their, their posts involve this kinda content. So it's just not a big deal for them the way it is for, for Google. And I think-

41:47 Well, I think it is a big deal for Facebook. They're just trying to make a point here, because Zuckerberg's a, you know-

41:52 Yeah. Yeah. And they're, they're being-

41:53 ... hardcore.

41:53 ... they're being, they're being overly heavy-handed in their response.

41:56 Yeah.

41:56 There's no question about it. They're, they're throwing their weight around. It doesn't look good. But I'm not defending Facebook, I'm defending the principle. I mean, look, if this Australian principle were used, you wouldn't have the Drudge Report. You wouldn't be able to create-

42:07 Yeah.

42:07 ... a site, uh, uh, of, of news links. I mean-

42:09 No, you could if it was commentary. You could put the link-

42:12 But it's not-

42:12 ... and write commentary.

42:13 The Drudge Report's not-

42:13 It's when you just rip the links, people are objecting-

42:15 Understood, but Drudge Report-

42:15 ... to ripping the links without any commentary. Drudge Report-

42:18 Right.

42:19 ... re- rewrites the headline, puts his own spin on it, and then links, he would never get caught into this, and there is no publication that would ever object. What they're objecting to is taking the photo, taking the first paragraph, and the, the, this, the synopsis is 30 or 40% of the value. And so Facebook is a better, and Twitter i- with their algorithms, are better front pages than the New York Times front page.

42:41 But why isn't this applying to Twitter then?

42:44 ... I, I think it will ultimately. They'll, they'll go there as well. Um, I think this will become the test case which is, if you want to take more than just the headline, or- or- and like, you know, ba- basically that's it, or the URL, if you wanna have that little snippet, pay us. Pay us something. It doesn't have to be a lot. But this could-

43:03 Right.

43:03 ... actually solve, if these networks that are making tens to hundreds of millions of billions of dollars, if they just said, "You know what? 1% to the news organizations to keep them viable," just like anybody else would pay in the licensing fee for terrestrial, radio, or other things.

43:18 But why is, but, but why is, why is the Australian government setting the price? And why are they only applying this to Google and Facebook?

43:23 Well, the, I think they're gonna go right down the line. I think it's just a starting point. But to my point I said earlier is I don't think the government needs to do this.

43:30 Right.

43:30 I think the news organizations en masse should get together-

43:33 Yeah.

43:33 ... and put their foot down and say no. And if they did, they would get paid.

43:37 Well, I mean it's, it sounds, it sounds like what the government should do is clarify what fair use entails.

43:40 Yeah, just a link.

43:41 And then, maybe it's just a l- maybe it's a link plus a title. I, I mean, look, it- it's, it's never just a link, right? It's a hyperlink plus the, like-

43:48 The snippet.

43:49 ... plus the word. Yeah, exactly. So-

43:50 Yes, the snippet is the issue.

43:52 Right.

43:53 So-

43:53 So fine. So the government should clarify what fair use is, and then if Google and Facebook or whoever want more, they gotta go negotiate for it.

44:00 Exactly.

44:00 But, but Australia is doing more than that. They're setting the price, and they're limiting their overreaching policy just to Google and Facebook because they know that if they applied it to everybody, it would break the internet.

44:10 This is by the way we do that, we- we already do this in the United States, David, with local carriage of, uh, news organizations on terrestrial TV. So we already ha- we already mix it up with the FTC doing this with licenses and, and the public good. So it's the extent.

44:24 I think the other thing that, you know, is gonna happen with all of this is like on the other, on the other side of this, the actual media organizations themselves that theoretically could benefit from this are frankly just going out of business anyways. I, uh, I, there's a, you know, there's a Wall Street Journal alert, um, for the owner of the LA Times who's about to sell the Times. Like, it's very likely that the Times in four or five years doesn't even exist. So I don't really know where all of this goes, except that, you know, everybody's just gonna be an individual person blogging and tweeting whatever opinion they want. (laughs)

44:58 Right? So there'd be no money to pay anybody 'cause it won't really matter. But what will be left is then these rules on arbitration of fact and fiction, and I think that that's where we're gonna end up. That's gonna be a crazy place, because then those folks, those folks then really are the puppet masters.

45:14 Yeah. I- I- I- I- I- I agree that these traditional publications have like a fundamental business model problem, and it's not gonna be solved. Like, I think there's a, a, like a misplaced blame on Facebook and, and Google. I mean, the fundamental problem with all these publications are, you go search for a news article on something, and there's like 10 versions of the same thing, or more, 100 versions. And, you know, when- when newspapers, we used to have thousands of newspapers all across the country, and they had a, a local geographic monopoly. But once it all got digitized and moved online, you realize how much redundancy there was.

45:46 Yep.

45:46 You have thousands of reporters creating the exact same thing, and there needs to be consolidation. It doesn't make sense to have 100 articles saying different things.

Chamath Palihapitiya 45:52 Not, not only that, but a point we made last time which is, um, you know, facts have largely commoditized, or most facts. Like, you know, remember we used to open the newspaper and look at what the stock market prices were. We- we opened the newspaper and looked at the sports scores. We looked at what happened in this place and this place. Facts about events, facts about the prices of things, facts about sports scores. That's all completely commoditized. I mean, that's like 90% of the content of what people used to read the newspaper for has gone online. And so as we talked about last time, newspapers and publications uh, of the like have largely moved into, you know, different sorts of narrative. And, um, you know, it's created a, a, a marketplace that has a lot more competition because anyone can write that, as we are- we're seeing with Substack and Medium and-

Jason Calacanis 46:37 As we're seeing with our own podcast. Yeah.

Chamath Palihapitiya 46:38 As we're seeing with our own podcast. And I think that's, um, this feels to me like, you know, I went to a media conference back in 2008, and there was this huge battle, uh, between Google and, um, Viacom. And I- I was at the conference, and I think Larry Page was on stage or someone, one, or Eric Schmidt was on stage. And the Viacom CEO got up, and he's like, "When are you gonna start paying us for our content?" And, uh, I think that that, and he really screamed at him in a room of like 800 people. And I feel like that same kind of point of view has persisted until there's finally some legislation that they feel kind of gets them justice. Meanwhile, the world has passed them by. And, uh, you know, I think this, uh, this will be kind of some transitory, uh, legislation that ultimately the content is gonna democratize anyway, and the content creation is gonna democratize.

Jason Calacanis 47:26 Yeah. Last topic for me 'cause, uh, I really want Friedberg's answer to this 'cause I also just saw an alert how the federal government is opening up a vaccination site in Miami-Dade County. I actually saw Francis Suarez retweet it. Um, what the hell's going on with vaccinations? Are we gonna get vaccinated soon? (laughs)

Chamath Palihapitiya 47:43 So I said it in December, and I- I tweeted about it, and I've repeated it multiple times since, that the US has enough supply to vaccinate pretty much anyone that wants to get vaccinated (laughs) because we are producing and delivering three to four million doses per day in the US right now. And, um, there is a, just a fundamental issue, especially, like, I mean look at California, you know? They haven't opened up, quote-unquote, vaccination to people outside of tier, what they call tier 1A. Um, and so this is much more of a kind of policy issue than, uh, an administrative issue, um, than a supply and demand issue. There's enough people that want the vaccine, and there's enough vaccine. So just let people get fucking vaccinated. Um, and so I feel like the market forces are now kind of converging with policy a little bit more than they were a month ago. And the policymakers are no longer fighting and complaining about supply and complaining about constraints. You know, we've got mass vax sites now in California. The amount of money that's being wasted, by the way, in this process makes me want to vomit every time I read about it. That's a whole nother separate issue. But it feels to me like we're probably May, June.... when enough people are vaccinated, that we can have, you know, a circumstance where people are going to fly without masks and be comfortable doing so. But I'm sure there will be these over, you know, constraining rules around what people can and can't do in public for a very long time, like I mentioned would happen. I do want to say one thing that I've noticed. We- we were, we were all... We played some poker the other night, and we were with a- a friend who, uh, got vaccinated. And I was like... He said, "This is my first time playing poker with people," and I was like, "Well, you got vaccinated, like, why aren't you..." He's like, "Well, I don't know if other strains are gonna get me or, you know, if this thing's evolving and other people are going to get sick." And, um, if you think about what's happened over the last year, people have been conditioned to be afraid. And so even though we're getting vaccinated, even though this thing is moving and working, I'm concerned that we're not going to end up in a more civil state. Schools aren't opening. People aren't flying. People aren't doing stuff, even after vaccinations and science and data shows that these things are okay.

Jason Calacanis 49:44 Except in Texas and Florida, where people aren't opening. (laughs)

Chamath Palihapitiya 49:45 Maybe there's some, maybe there's some cases of it. But I... What I'm saying is like, you know, the human subconscious gets trained first, and then our conscious mind rationalizes what we feel. We've all now been-

Jason Calacanis 49:55 Yeah.

Chamath Palihapitiya 49:55 ... trained over the past year to be very afraid. And then we all-

David Sacks 49:59 But we have-

Chamath Palihapitiya 49:59 ... come up with these rational excuses about why I can't do X, Y and Z. And it's like, but you've been fucking vaccinated. You're fine. Like all the data, all the science says go do whatever you want to do. Go into a nightclub sweaty next to people.

Jason Calacanis 50:14 (laughs)

Chamath Palihapitiya 50:14 Throbbing beats and music.

Jason Calacanis 50:15 Keep going, Friedberg. Yes, tell us-

Chamath Palihapitiya 50:17 And enjoy. (laughs)

Jason Calacanis 50:17 Tell us about the throbbing nightclubs, Friedberg.

Chamath Palihapitiya 50:19 Yeah, it's like that scene from-

Jason Calacanis 50:19 I've never seen you so animated.

50:20 (laughs)

Chamath Palihapitiya 50:20 It's like that scene from Good Will Hunting. Remember, when he talks about the psychologist, he's like, "Drop in." (laughs)

Jason Calacanis 50:23 Tell us about your rave stories again, from the '90s, when you would get arrested.

Chamath Palihapitiya 50:25 Activating fourth emotion. Yeah. Throbbing rave, give up to the mom.

Jason Calacanis 50:31 Pulsating, pulsating music.

Chamath Palihapitiya 50:33 Pulsating sweating bodies and-

Jason Calacanis 50:34 Did the molly just kick in, Friedberg? Did you drop a molly at the start of the pod?

50:38 (laughs)

Chamath Palihapitiya 50:38 But my point is like, people are really afraid and I think, uh-

Jason Calacanis 50:41 I just got the best idea for an episode.

Chamath Palihapitiya 50:43 The biggest concern I have is frankly less about are we going to get vaccinated. I feel like the convergence-

Jason Calacanis 50:46 All right.

Chamath Palihapitiya 50:46 ... between market forces and government nonsense is now going to allow us to all get vaccinated.

Jason Calacanis 50:51 Do you guys-

Chamath Palihapitiya 50:51 But, uh, but the issue is really going to be like how do you break through these rules and the fear that, that basically-

Jason Calacanis 50:57 I want, but I don't understand. Where, where are the max vaccination sites in California and who's eligible? Like why aren't we just making this thing like a drive-thru?

Chamath Palihapitiya 51:05 We should... This is where we could absolutely-

Jason Calacanis 51:07 They're popping up right now. We just opened the East Bay.

51:09 It's ridiculous. You got to-

Chamath Palihapitiya 51:09 I think we all have absolute violent agreement that California is so messed up with respect to how we're vaccinating. We have so much supply. We're sitting on half our frigging supply right now in California City.

Jason Calacanis 51:18 There's 30 million vaccines sitting on shelves. We are now at 75% deployed, 80% deployed.

Chamath Palihapitiya 51:23 California's got like four or five million vaccines sitting in storage.

Jason Calacanis 51:26 Right. It should be a drive-thru and you just get in line and you go.

Chamath Palihapitiya 51:29 In some places it is, yeah.

Jason Calacanis 51:30 And instead what we're doing is... No, but it's... What we're doing now is you got to schedule an appointment.

51:34 Oh yeah, scheduling is bullshit.

51:35 Because you first you got to qualify, then you got to schedule an appointment and then the, the clinic or whatever is only open from 9:00 to 5:00. And so, like, how many doses are they really administering when you got to make an appointment? Probably one every half hour. So maybe they get through 16 people a day or something like that.

Chamath Palihapitiya 51:50 And cruise, cruise qualifications.

Jason Calacanis 51:52 Yeah, and they get fined a million dollars and lose their medical license if they inject the wrong person. So I mean, you're talking about 16 people per day at a site when they could be doing a couple of hundred. I mean, it's crazy.

52:03 Well, Johnson & Johnson is coming and that's refrigerator stable, right, Friedberg? So-

Chamath Palihapitiya 52:08 You don't even need it. We have, we have everything we need.

Jason Calacanis 52:09 ... we now have bought 1.2 billion vaccines.

52:11 But let me, let me go back to Friedberg's point about when will life get back to normal. I'm not as pessimistic as you are, Dave, about th- this idea that life won't go back to normal. And part of the reason why is I'm seeing so much outrage about school closures right now. California is one of the only states in the country that still completely closed all the schools and people are absolutely up in arms. I'd say it's as big an issue as this exploding crime issue. Crime is a big issue in the cities and school closures is the big issue in the suburbs. And if these two things don't turn around, I think Gavin Newsom's going to get recalled. I mean, people are just on fire about this.

Chamath Palihapitiya 52:47 Yeah. But I mean, my point was like our, our wealthy conservative, you know, uh, friend that lives in Florida was afraid to go do stuff even after he's been vaccinated.

Jason Calacanis 52:59 Yeah. There's, there's like-

Chamath Palihapitiya 52:59 And I think that's what's permeated everywhere, is just like there's this-

Jason Calacanis 53:02 It's like a shark... Friedberg, it's like a shark attack. You know, if there's a shark attack, you know, at Half Moon Bay or whatever, people don't swim there for a couple of weeks and then somebody swims and they're like, "Oh, the water is great." People will jump back in. I think it's April, David, to your point, of when this goes back to normal. Because if you look now, people have been saying... Friedberg, correct me if I'm wrong, would you put a 5X multiplier on the confirmed COVID cases, a 4X multiplier at this point?

Chamath Palihapitiya 53:25 Oh yeah, 5X, 5X I think is the right median, median, yeah.

Jason Calacanis 53:27 Okay. So if you have 30 million people who've had the vaccine, uh, had COVID, you're looking at five times that is 150. Now you have 60 million people who have been vaccinated. We're at 210. There are 330 million Americans, 70 million are under... are kids. So, you know, we're- we're basically getting to herd immunity and if you look at the slopes right now, what is causing the drop in cases this massively, David? Is it herd immunity, vaccine or people suddenly wearing masks? What is it?

Chamath Palihapitiya 53:54 There, there's complexity because everyone assumes that there's one thing that affects the whole population but remember, the way viruses work is they're hyper-local. And so the local population dynamics looked at on a scale is where you see the statistical results of the scale and so... You know, we saw this in North Dakota. A bunch of people got really sick. They got to herd immunity in communities and then all of a sudden, it dropped off the curve. When you zoom out and that's happening combined with behavioral changes, combined with vaccines, then you start to see these statistical things happen at scale so it's not a simple answer, but the answer generally can be we are coming down the slope, we are getting to a point of, you know, general like low case counts, low death counts, low fatality and we should be living a normal life allowing our economy to kind of progress again, um, and we're still caught up in this kind of fear, fear, uh, cycle.

Jason Calacanis 54:42 Pick a date. Let's just end on this. Pick a date when you think all four besties are vaccinated. I'm going to say April 1st.

54:50 June.

54:51 June? Okay. What do you got, Friedberg? I say April 1st we're all going to be vaccinated.

Chamath Palihapitiya 54:54 It's literally a choice. I mean, any one of us could go get vaccinated in the next month. I mean...

Jason Calacanis 54:58 How? We- none of us are over 30 BMI. I mean, Sax was for a minute.

Chamath Palihapitiya 55:03 California's opening 1B. A lot of the states are opening broadly. If any of you wanted to get on a plane and go get vaccinated somewhere else, you could. I mean, there's enough places now that have open vax, or will in the next 30 days, you can go get vaccinated, so you-

Jason Calacanis 55:13 Okay, so you say 30 days, which would be March 15th or something like that.

Chamath Palihapitiya 55:16 Yeah, that, I think that's a choice for the four of us. If you guys wanna hop on a plane, we can go get vaccinated.

Jason Calacanis 55:20 Does anybody have access to a plane?

David Friedberg 55:22 But sorry, but doesn't that kind, you're, you're, you're saying in an open vax state, anybody can show up without proof of residency-

Jason Calacanis 55:28 No, you have to have a driver's license. I've looked into this.

Chamath Palihapitiya 55:30 There have been different ways that this has played out, but generally speaking, there are market forces at play where, you know, where there's a will, there's a way. Not saying that you're cutting line and screwing people over, but there are vaccinations that are happening all over the country now with people that want to get vaccinated.

David Friedberg 55:44 Uh, you know-

Chamath Palihapitiya 55:45 And, and by the way, in California next week, tier 1B opens up. So anyone-

David Friedberg 55:48 But what does that mean? What is tier 1B?

Chamath Palihapitiya 55:50 It's a total BS definition. It is absolutely ridiculous. I absolutely think this is the biggest waste of time and money ever. But tier 1B definition in California is healthcare work, sorry, childcare workers. So anyone that's a teacher or works with children-

Jason Calacanis 56:04 I have kids.

Chamath Palihapitiya 56:04 Uh, if your nanny or your daycare, uh, people, um, you know, wanted to, they could go in and get vaccinated.

David Friedberg 56:09 Wait, oh wait, our, our nanny can get vaccinated?

Chamath Palihapitiya 56:12 Starting next Wednesday.

Jason Calacanis 56:13 Oh, my, uh-

Chamath Palihapitiya 56:13 In California-

Jason Calacanis 56:13 Oh, my God.

David Friedberg 56:14 Oh, my.

Chamath Palihapitiya 56:14 And so all you need to do is go get to a vax site with vaccines. And, and by the way, they all, a lot of them have vaccination, um, supply now, uh, or they will this weekend. There's apparently a big shipment going out. Um, and also, all food and agriculture workers, loosely defined, so people that work in grocery stores, restaurants, farm workers, if you're saying-

Jason Calacanis 56:32 You're saying if I had a chef they could get-

Chamath Palihapitiya 56:34 If you have a chef they can get vaccinated. No, no, just kidding.

Jason Calacanis 56:35 (laughs) I think two people out of four on here might have chefs. I think two of us definitely don't. I'm still-

56:40 So, so if you take care of your own kids and cook your own food, you can't get vaccinated, but if you do that for somebody else, you can.

56:47 So wait, you're saying if you have a chef and you have nannies, you get vaccinated? (laughs)

56:51 No, you don't.

56:52 You don't?

56:52 What I'm saying is, is, you-

Chamath Palihapitiya 56:53 Yeah, if you're a chef or a nanny for someone else, you can go get vaccinated next week.

Jason Calacanis 56:57 Right, but if you-

56:58 David, what do you want for dinner? I'm coming over right now to make whatever you want.

57:01 (laughs)

57:01 I'll watch your kids this weekend, David. Get me a shot. (laughs)

57:05 It's so insane. We have all these ridiculous job categories and distinctions. It's just like with the lockdown policy. They had 10 pages of exceptions for essential workers. Listen, if you've got a policy with 10 pages of exceptions, the policy doesn't make any sense.

57:19 It's not a policy. Yeah.

Chamath Palihapitiya 57:20 Like all the, like, and this caused all the controversy in LA, like anyone that works in the movie business is an essential worker.

Jason Calacanis 57:25 Right. Well, there's-

Chamath Palihapitiya 57:26 But people that work, but people that work in restaurants and bars are not essential.

Jason Calacanis 57:29 Let's see this for what it is. It is payoff to Newsom's political supporters, uh, that the politicians are using, they use essential worker exceptions and now they're using vaccines as political capital. They dole them out to their supporters so that, you know, in exchange for, you know, votes down the road.

57:49 Also, the, remember the exception, David, if you serve more than seven courses in your prix fixe, you can get a vaccine.

57:56 (laughs)

57:56 So that is the French laundry, if you add an amuse bouche and an intermezzo, you qualify for the vaccine. Um, there are people going to states, renting houses, and getting driver's licenses-

58:09 Vaccine tourism.

58:09 ... and getting vaccines. I know about this.

58:10 Yeah, it's called vaccine tourism.

Chamath Palihapitiya 58:12 By the way, think about it this way. In six weeks, I think a lot of those restrictions are gonna fall by the wayside because the supply is gonna completely outstrip the nonsensical, you know, restrictions and prioritization methods we put in place. And hopefully, God willing, these idiots who have the ability to vaccinate people open up their sites 24/7 and drop all the bullshit questionnaires and registration requirements, let people drive in, get a shot, wait 15 minutes and leave, and have just some basic principled people on site that can take care of people if they have a, uh, uh, adverse allergic reaction, and get shots in arms. We have the shots. We have the supply. We are gonna be oversupplied by May. We are gonna have far more shots than there will be demand. And so, you know, we just need to get this, this kind of nonsense thrown out the window.

Jason Calacanis 58:57 All

Jason Calacanis 58:58 right, straight to Q&A. This is from, uh, Fadesh. He says, "Where are you investing your money over the next 10 years?" So Friedberg, you wanna start? And then we'll go to Sax and then, uh, Mr. Palihapitiya.

Chamath Palihapitiya 59:11 I've talked about this pretty largely, uh, you know, uh, on the podcast. I mean, two areas that are super interesting to me that, um, I'm spending a lot of time on is obviously biomanufacturing, so the idea that we can kind of move away from traditional animal-based agriculture and systems of production, um, to systems where we use, uh, genetically engineered, uh, microbial organisms to produce molecules and materials and food. And that, that, uh, that system of production can have a radical impact on, um, uh, on the environment, on the opportunity for jobs, on the cost of goods and, uh, and things that humans want and consume. Um, and that's, that's a primary area, uh, of interest for me.

Jason Calacanis 59:53 Love it.

Chamath Palihapitiya 59:53 And I think it's a multi-decade. I think by 2050, you know, we should see, um, most of our goods that are manufactured rather than being made in the traditional sense, which is basically old technology scaled up, uh, which is what the Industrial Revolution did, uh, but really shift to a new model of manufacturing where we, uh, use a smarter machine, which is a, a genetic, a biologic organism to make stuff. So that's, that's my interests.

Jason Calacanis 1:00:16 Sax.

1:00:17 Yeah, so I'm, I'm focused on the area of bottom-up SaaS, which is basically business software that can go viral, uh, very much in the mold of Yammer, which was a company I founded and sold back a, a dozen years ago. It was, it's, it's-

1:00:30 It was the precursor to Slack, let's be honest.

1:00:32 Right. Yeah, yeah. (laughs)

Chamath Palihapitiya 1:00:33 Mm-hmm.

Jason Calacanis 1:00:33 It could have been 27 billion, but you did not ride your winner. You took the quick billy and that was-

1:00:39 No, I mean, look-

1:00:40 ... not a mistake because it let you invest in the other 20 unicorns, correct?

1:00:44 It, it, kinda. I mean, so, so-

1:00:46 So, oh, you do have a chip on your shoulder about selling too early. No, let it out, David.

1:00:49 No, no, it's not, it's not, it's, it's not a chip. I, I would say that around the time that PayPal hit a $200 billion market cap and Slack had a $27 billion outcome, I started realizing, you know, if I just stuck with my ideas longer...... you know, I probably would, would, would do better. And I'm like, "You know, I don't really need to come up with a new thesis or a new idea. I already came up with the idea 12 years ago, which is to make business software viral. I'm just gonna keep investing in that thesis." So it's not that original or new for me, but-

1:01:16 Hmm.

1:01:17 ... um, but, but it is, it... You know, bo- bottom-up has become the, I would say, almost the, the dominant mode now of, of, of SaaS.

1:01:24 Explain that to somebody who doesn't understand what you mean, bottom-up.

1:01:27 Yeah. So, so bottom-up means that the entry point for the software is any employee in the company. They can just start using it. They go to your website, they start using it, they spread it to their coworkers. As opposed to top-down. Top-down is like the Oracle sales guy who carries a bag and goes to meet with the CIO and-

1:01:43 Right.

1:01:43 ... you know, sells him a big expensive implementation. That's the... And that's traditionally what business software used to be, is a bi- is a big top-down IT sale. Bottom-up is, um, is just going in through the rank-and-file employees.

1:01:55 All right. Chamath Palihapitiya, for the next 10 years, where are you putting your money?

David Friedberg 1:02:01 Uh, two areas. Uh, inequality... Well, uh, i- it's not even 10. I would say for the next... For the rest of my life. Um, so it's... I think it... These are actually multi-decade, but, uh, inequality and climate change. And so, um, you know, the inequality side, what does that mean? It's any business-

Jason Calacanis 1:02:18 By the way, the second you said inequality and climate change, Sax left.

David Friedberg 1:02:22 Oh, he went to throw up. Yeah, yeah.

Jason Calacanis 1:02:24 He's just like, "What is this nonsense?" (laughs)

David Friedberg 1:02:27 He, he went, he went to throw up. No, no, no.

Jason Calacanis 1:02:27 "He just read."

David Friedberg 1:02:28 He went to throw up. No, no, no.

Jason Calacanis 1:02:29 He's like, "Oh, God."

David Friedberg 1:02:30 Yeah.

Jason Calacanis 1:02:30 "Here we go."

David Friedberg 1:02:31 Oh, there, he's back now. Okay.

Jason Calacanis 1:02:32 He's back.

Chamath Palihapitiya 1:02:33 Sax, did you throw up when Chamath said inequality and climate change? (laughs)

Jason Calacanis 1:02:36 No, I...

Chamath Palihapitiya 1:02:36 Out of your back? (laughs)

Jason Calacanis 1:02:36 When he said his woke nonsense, did you just go throw up?

David Friedberg 1:02:39 (laughs)

Jason Calacanis 1:02:40 No, I, I, uh, I'm, I'm, I'm just, uh-

1:02:41 You burnt your sigils and you threw up.

Chamath Palihapitiya 1:02:43 He had to polish his Glock. (laughs)

Jason Calacanis 1:02:45 (laughs)

Chamath Palihapitiya 1:02:46 He just called a security detail.

David Friedberg 1:02:48 He went, he went and he kissed his gold bricks that he keeps in his house. Like... (kissing sounds)

Jason Calacanis 1:02:52 (laughs)

David Friedberg 1:02:53 Uh, no, inequality basically means, uh, anything that evens the starting line. So the... If that's-

Jason Calacanis 1:02:59 Love it.

David Friedberg 1:02:59 ... healthcare software that solves a chronic condition or if that's financial software that drives inclusion, um, and then climate change is pretty obvious, but the, the panoply of things that we need to do to basically, you know, slow the warming of the earth, those are the two areas.

Jason Calacanis 1:03:15 Huge opportunity, yeah.

David Friedberg 1:03:16 Huge.

Jason Calacanis 1:03:16 And I've... Uh, for Videsh, if you even care, I take a remora-like approach. Um, if you don't know what a remora is, you ever see like a big shark and then there's like a bunch of things stuck to it and it's like following the shark and it just eats whatever? So basically what I do is I'm getting behind these three guys (laughs) and I just draft on these three sharks and just try to weasel my way onto their cap tables. It's a, it's a living, you know.

David Friedberg 1:03:37 It works.

Jason Calacanis 1:03:37 Basically, I just go to the poker game and try to... No, uh, in all sincerity, I am stay... I am vertical agnostic because I think the great companies, um, m- make the verticals. They create the categories, and the categories don't exist for the outliers.

David Friedberg 1:03:51 At, at your stage particularly.

Jason Calacanis 1:03:52 Yeah.

David Friedberg 1:03:52 What's that? The early stage.

Jason Calacanis 1:03:53 At your stage particular- yeah, exactly.

David Friedberg 1:03:54 Yeah. And so what I do in the early stage is I am focused on the process, and the process I'm trying to master here is what I do at thesyndicate.com, which is find great companies and share it with now 7,000 accredited investors and let them decide, you know, how much they want to invest in each deal. And just to give people an idea, we are on a $60 million run rate this year of deploy capital via The Syndicate. In other words, it'll be four times, five times what my fund will do. The fund has access to 100% of deals, but The Syndicate has access to 60% roughly.

Chamath Palihapitiya 1:04:28 So now that we've broken our no advertising rule...

Jason Calacanis 1:04:30 Yeah. No, I mean, I'm... We-

Chamath Palihapitiya 1:04:31 (laughs)

Jason Calacanis 1:04:31 ... we're all talking our book here. Let's take another question.

1:04:33 (laughs)

1:04:34 Um, and, uh, Angel is available from HarperCollins Business. Uh... (laughs)

Chamath Palihapitiya 1:04:38 (laughs)

Jason Calacanis 1:04:39 (laughs)

1:04:40 Uh, what... Oh, here's a good one. What's the biggest-

Chamath Palihapitiya 1:04:42 By the way, if you want to save money on car insurance, metromile.com. Sorry, go ahead. (laughs)

Jason Calacanis 1:04:46 Metromile.com. (laughs) Absolutely fantastic. Also, the ticker symbol. (laughs) Uh, what's the biggest investment/venture miss you had early starting out that would have been a ridiculous return?

Chamath Palihapitiya 1:04:58 Oh.

Jason Calacanis 1:04:58 What is our anti-portfolio looking like?

Chamath Palihapitiya 1:05:00 Oh. Oh, my God.

Jason Calacanis 1:05:00 Freedberg, we'll start with you then go Chamath and go Sax. Freedberg?

Chamath Palihapitiya 1:05:03 Oh, I was with, um, Jack Dorsey-

Jason Calacanis 1:05:05 Oh, this is painful.

Chamath Palihapitiya 1:05:06 ... in, um, in, uh... at this conference and he went around and did a pass the hat on who wanted to invest in his new startup called Square.

Jason Calacanis 1:05:15 Oof.

Chamath Palihapitiya 1:05:17 That's my story.

Jason Calacanis 1:05:18 What, what is that? A 50... Is that a $50 million miss?

Chamath Palihapitiya 1:05:23 Um, yeah, I'm not gonna say. It, it, it would have been big, I mean, you know.

Jason Calacanis 1:05:27 You would put 50K in that 10 million.

Chamath Palihapitiya 1:05:29 But, I mean, the pro-... Here's... By the way, an interesting thing going back to the s- the point Sax made earlier and that we've said in the past, you know, when Square went public, there was a lot of questions and trepidation around its valuation. Big fund managers were pooh-poohing the company. And what's the market cap of Square today? Sax, you might know.

David Friedberg 1:05:45 100, 100, 120.

Chamath Palihapitiya 1:05:47 120 billion?

Jason Calacanis 1:05:49 Wow.

Chamath Palihapitiya 1:05:49 I mean, 125 billion today. That's incredible, right? Because like when they went public, people were kind of pooh-poohing it saying this thing is a... this is a sub-billion dollar company, you know, it shouldn't be worth anything more than a billion dollars. And look at it just a few years later.

Jason Calacanis 1:06:02 Mm-hmm.

Chamath Palihapitiya 1:06:02 Um, anyway, yeah, I missed it... I missed that one on the, uh, seed round and, um, and I've just watched with, with awe what Jack has-

David Friedberg 1:06:08 By the way, the-

Chamath Palihapitiya 1:06:09 ... continued to, to innovate, to, to build that business.

David Friedberg 1:06:11 It troughed. As a public company, it troughed at a $4 billion valuation.

Chamath Palihapitiya 1:06:15 It did, right?

David Friedberg 1:06:15 Um, it did-

Chamath Palihapitiya 1:06:16 Yeah.

David Friedberg 1:06:16 ... like five years ago. And so within five years, it's gone from 4 billion to 124 billion.

Jason Calacanis 1:06:21 I, I was in a venture capital fund that invested in it. They distributed the shares, I sold half, and I was like, "I'll just keep half, I like Jack." I sold half at 72 and now it's at 276. And so ride your winners, folks. Uh, Sax, anti-portfolio, which one is the most painful?

1:06:38 I made... Honestly, I haven't missed that much just to be perfectly frank.

1:06:40 Okay, there you go.

1:06:41 Uh-

1:06:41 Jesus Christ.

Chamath Palihapitiya 1:06:42 But-

Jason Calacanis 1:06:42 Uh... (laughs)

1:06:44 ... what a douche.

David Friedberg 1:06:44 What a douche.

Chamath Palihapitiya 1:06:45 What a fucking douche.

Jason Calacanis 1:06:47 Well, actually-

1:06:48 Okay. I, I-

1:06:49 ... um, I, I analyzed my chess game with Peter Thiel and actually my check-

Chamath Palihapitiya 1:06:54 I am the best.

Jason Calacanis 1:06:54 ... my castle, uh, queen side castle was actually a brilliant move. Uh, if he hadn't pinned my rook...

1:06:58 No, I mean, look, I, uh, I, I, I tend, I, I t-

Chamath Palihapitiya 1:07:02 (laughs)

Jason Calacanis 1:07:02 Look, I don't overthink these things too much. I mean, it's why I'm in like 27 unicorns. If the company looks good, I, I invest.Uh-

David Friedberg 1:07:10 Is this Phil- is Phil Hellmuth here? (laughs)

1:07:12 This is unbelievable. You have to have a Phil Hellmuth-

1:07:14 Well, you know, I got my 16th ring.

1:07:16 Are you channeling the-

Jason Calacanis 1:07:16 Done.

David Friedberg 1:07:16 No, this is-

1:07:17 But, uh, I've won 29 of the last 30 sessions.

1:07:19 Now, what would you say your total, like, multiple is on all your angel investing? Like, do you have a sense of what that number is?

1:07:24 That's not the question, Sax. Answer the question. Come on. The audience asked what you missed. Can you just be humble enough to say you missed something?

Jason Calacanis 1:07:30 Yeah, yeah, yeah. No, no, no. I'll tell you. I'll tell you. So th- th- this was a se- sort of a semi-miss, is that, um-

David Friedberg 1:07:35 (laughs) Oh my god. It's not even a miss?

Jason Calacanis 1:07:36 This is a semi-miss.

David Friedberg 1:07:38 Well, here's how I made up for it. (laughs)

Jason Calacanis 1:07:39 No, no, no. Again-

David Friedberg 1:07:39 I only put in half my normal amount.

Jason Calacanis 1:07:42 No, no, no. Let me tell you what happened. I did miss it. So, uh, back in 2007, um, I thought Twitter was gonna take off. I had a, like, a former employee who wanted to sell secondary, and so, you know, I had a deal worked out to buy I think a couple of hundred thousand dollars of shares at, I don't know, a $40 million valuation or something like that? And, um, we submitted it to the company, and then they ROFRed it for... 'Cause I think Chris Sok- for Chris Sacca basically. I don't know if you remember, Sacca-

David Friedberg 1:08:08 Yep.

Jason Calacanis 1:08:08 ... had set up, like, some secondary fund.

David Friedberg 1:08:09 Secondary thing, yeah.

Jason Calacanis 1:08:11 So yeah. The, uh, the fact that, you know, I wasn't able to complete that transaction probably cost me, you know, a couple hundred million bucks.

David Friedberg 1:08:19 Uh, Chamath? Anti-portfolio, what sticks out? Well, I have a, I have a huge anti-portfolio. Airbnb.

1:08:23 Huge.

1:08:24 Robin Hood?

1:08:25 You know, Airbnb at a billion obviously. I actually did invest. I agreed to invest, but then I got into a huge public snafu with, with Chesky 'cause he was taking a bunch of money off the table, and then we ended up not even finalizing the investment. Uh-

1:08:38 And your letter was, your letter was published, your email that you sent him.

1:08:40 It leaked. My email was leaked, yeah. Um...

1:08:42 It was leaked.

1:08:43 So I was really pissed when they did that. But anyways, that was a decade ago. Not much has changed, I guess. Um, there is one thing that above all others, um, which is sadly also in my portfolio. So my portfolio and anti-portfolio is the same thing. You can guess what it is, but that's Bitcoin. At one point, you know, we controlled low single digits, mid-single digits of the entire float. And had I held onto that, that's talking about, you know, a mid-deca-billion dollar position.

1:09:13 Ieesh.

1:09:13 So my anti-portfolio, uh, in, in the unrealized loss, in unrealized gains or losses if you will on Bitcoin, is in the many tens of billions of dollars.

1:09:24 Yep, mine is clearly Bitcoin as well because I was reporting on it when it was 10 cents, and I was one of the first journalists