The Bulwark Podcast - BONUS EPISODE with Jason Calacanis: The Civil War in Silicon Valley

Episode Date: October 15, 2024

Trump used to be considered an existential threat throughout Silicon Valley, but now the tech world is split between Mark Cuban and Reid Hoffman on one side, and Elon and David Sacks on the latter. Elon & David's All-In Podcast friend "J-Cal" is on the fence. He explains that the Trump side's grievance has to do with Elizabeth Warren, socialism, DEI, the 'self-made' being attacked for being rich—and having their feelings hurts since Elon wasn't invited to the White House. Tim Miller tries to explain to J-Cal how silly these complaints are in this special bonus episode.

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off your first month. That's betterhelp, H-E-L-P, dot com. This is an ad by BetterHelp Online Therapy. October is the season for wearing masks and costumes, but some of us feel like we wear a mask and hide more often than we want to, at work, in social settings, around our family. Therapy can help you learn to accept all parts of yourself, so you can stop hiding and take off the mask. Because masks should be for Halloween fun, not for your emotions. Whether you're navigating workplace stresses, complex relationships, or family dynamics, therapy's a great tool for facing your fears and finding a way to overcome them.

If you're thinking of starting therapy but you're afraid of what you might uncover, give BetterHelp a try. It's entirely online, designed to be convenient, flexible, and suited to your schedule. Just fill out a brief questionnaire to get matched with a licensed therapist, and switch therapists at any time for no additional charge. Take off the mask with BetterHelp. Visit betterHelp.com today to get 10% off your first month. That's BetterHelp.com. Hey, y'all. I had a little special bonus interview with Jason Calacanis. For those of you that don't know him, he's a massive angel investor, a big early investor in Uber, and he has this podcast called The All In Podcast with co-host David Sachs, Chamath Palhapatiya, and David Freeberg. Jason's kind of like the squishy centrist on this podcast. Sachs and Chamath have gone all in with Trump. I posted a video, which you'll get to hear on this episode, on Twitter of the four of them talking after January 6th.

And they all sounded quite a bit like the Bulwark Podcast. And Jason was the one who wanted to defend himself and defend his honor and say he hasn't changed his views on all of that. And so I invited him on and we wanted to have a wide ranging conversation that got a little bit into his view of politics and the Silicon Valley view of politics as well as a couple of burning questions I have about Silicon Valley. It went way longer than I thought, in part because Jason took the mic and started asking me questions. And so rather than try to shoehorn it into our existing daily podcast, we just wanted to put it out as a bonus. And for those of you who cannot stomach listening to somebody that is on the fence between Kamala Harris and Donald Trump, you can maybe skip this one. But for the rest of

us, I think it was a very interesting exchange that shed a lot of light on these tech bros who are getting weak in the knees for Donald Trump and why that is. And I think that some of Jason's answers and some of his non-answers were pretty revealing on that front. So I hope you enjoy it. Once again, his name is Jason Calacanis, at Jason on Twitter. So if you have positive or negative reviews, you can reach him there. Up next, Jason.

All right, I'm here with Jason Calacanis. I must just say to start, we didn't have to do this. J-Cal, they call him, over in the All In podcast. I took a little swipe at the All In boys, at some of his besties, his podcast co-hosts on Twitter. And Jason engaged in good faith. And so let's do this. Let's hash it out. And I'm grateful that he did it. So here he is on the Bullwark podcast, a little crossover. How are you doing, Jason? up the clip from was it episode 16 or something four years ago and it was our reaction to january 6th i hadn't seen it since then so it was great the edit was a little dicey but overall i thought it's great that you linked to it because it is good to see how people's opinions have changed over time about that day yeah i want to we'll get to that on this on the january 6th let's let's you know we don't need to start with old trump we'll talk about a few other things i was actually

an early i don't think episode 16 early but pretty early listener of all in because I was mostly interested in, I just am like looking for ways to consume information outside of my little bubble. Right. And so kind of learning about tech stuff. You guys are a bunch of VCs and you're an angel investor. And so I was learning things about, you know, kind of what was happening in the tech world that I wasn't getting from my other media. And then David Sachs made the whole podcast about politics. So I've started to tune out lately, I have to admit. But you don't have to comment on that if you don't want to.

The balance has shifted a little towards politics. Oh, I'm not a politics guy. And so I find it, you know, it's actually very educational for me because I, we have a very first principle thing in Silicon Valley, right? We like to go to first principles. We like to, you know, argue both sides. We like to steal man stuff. And then it comes to politics.

People become incredibly partisan and that kind of goes away. So it's been interesting to watch my friends, David included, who really care, who are partisans, you know, and then Reid Hoffman on the other side and Mark Cuban, who I've been friends with both those guys for a long time, over 20 years. So watching this civil war in Silicon Valley as a moderate independent from New York, uh, who's voted, I would say I voted democratic two out of three elections and you know voted for pataki giuliani you know when you live in new york you don't really have much choices my people the rhinos back when giuliani was a rhino you know that was my type yeah exactly and he was great

mayor but anyway i'm kind of independent socially liberal and fiscally conservative and kind of like and i don't know where i fit in the spectrum anymore uh but it was it's been really fascinating to watch what's happened in silicon valley where you generally were quiet about your politics because it didn't help business and in fact it hurt business to pick aside and generally it's 95 percent left-leaning democrats and that's changed radically yeah for people who don't know just give us a a real quick reader's digest on the show. We've got some listeners who probably just don't care about tech news, don't follow it, so might have no idea who you are.

What's the shorthand? So, yeah, 14 years ago, I started, I'm a former journalist, publisher from New York. I did a magazine in the 90s called Silicon Alley Reporter. I did a blog company, Assault AOL, which did Engadget, Autoblog, and competed heads up against Nick Denton and Gawker. I made a bunch of money selling that. I became an angel investor in startup companies. And when I did that, I started a podcast 14 years ago, and I've done 2,000 episodes of something called This Week in Startups, just about startups. And then two of my frequent guests and friends, David Sachs and Chamath Palihapitiya, who are capital allocators as well

and entrepreneurs. We created this new podcast during COVID because we couldn't see each other called All In. It's just a Zoom. I named it All In after the fact that we used to play poker every Thursdays and during COVID we couldn't. So it was just a way for us to chew the fat and it became extremely popular extremely fast and now when the episode comes out on the weekends if you were to look at the like apple charts or something you know sometimes it breaks the top 10 episodes typically the top 20 episodes it's once a week we've done 199 episodes there's a conference that goes with it called all in summit and um we've been doing that for three years and this year was kind of a high watermark for both the pod and for the event in that

like Trump came on, JD Vance came to the event, Elon was at the event, Sergey Brin was at the event, Travis from Uber was at the event. So if you were in the tech business, you would listen every week. If you're not in the tech business or finance business, might have heard about it but probably not yeah and you know the flashpoint i guess for the five this year and as i said you said you had trump on but of your co-hosts you mentioned two of them you also have i have david who's like kind of yeah free bird and uh token lefty though maybe not that left but um and then but sax and shamath both had a fundraiser for Trump earlier this year. Yeah, that was a big seminal moment, I think, in the history of Silicon Valley and politics.

Because, you know, if you were to actually come out in public support of Trump in Silicon Valley, that would be, I don't want to say career ending, but it would be damaging to your startup, you would lose employees. So during the, you know, let's call it the hyper woke era of Silicon Valley, it was, you know, Trump, like in New York, Trump was considered an existential threat to democracy, capitalism, America. And, you know, he was so toxic that to even say you would vote for him was kind of crazy. Now, that doesn't mean people weren't voting for him, but you would never in 2016 or 2020 host a fundraiser for Trump. To your point, since you led us right there about this change, right?

Like that this is something has changed, right? Where being for Trump would have been verboten and now it is not. I mean, that was, I i guess the fundamental point of the video that i that i had put up but that nothing has changed with trump right like trump hasn't changed i would agree with you that trump hasn't changed yeah i mean i think there was a moment when people felt he was changing and i called that trump 2.0 or all-in trump uh some people called it because he had an appearance where he was fabulously normal on all-in and you know people came to me and said wow you're gonna vote for him like i mean seems like he's actually learned a lot he's like maybe matured he's you

know he's uh evolved and you know he's different and then of course after the first assassination attempt we watched that rnc speech and people were like hey first half of the speech he seems like a changed guy like i guess almost dying would do that to you in the second half he went right back to insult comic you know name calling and so i think he should be up right now 10 points at least if he was that trump 2.0 and maybe jd vance is that you know in my mind which is somebody who believes in traditional American values, free markets, less spending, doesn't believe in identity politics. But Trump has obviously reverted back to full insult comic grievances, you know, adjacent to kind of racist, sexist stuff, right? So what do you think explains the change in attitude towards Trump and about your co-hosts specifically, but I guess maybe Silicon Valley broadly, right? Because

you said that now there's more things, like, so you don't have to speak for them specifically, but like why? So that's hard for me to wrap my head around because... Oh, I think it's pretty simple, actually. It's not so much, obviously elections, you're into politics more than I am, but it's a choice, right? So it's binary. So you have to pick A or B. It's not so much, obviously elections, you're into politics more than I am, but it's a choice, right? So it's binary. So you have to pick A or B. It's not like you get to write somebody in and have a chance of them winning. So, you know, if we look at Biden and his performance and what happened in San Francisco over the last decade, I think people are very nervous in the capitalistic part and free market part of the economy. I'm not speaking for

David Orchamoff, but just in general, what I hear from folks is they don't want socialism, and they don't like identity politics, and they like meritocracy. So there was a moment where DEI kind of was the main focus in Silicon Valley. Everybody had a DEI department. Everybody was obsessed with it. And now founders have started talking about merit, exceptionalism, and intelligence, MEI, I think is their counter-trolling. And so if you have Elizabeth Warren and Bernie Sanders attacking capitalism, success,

that is how I think a lot of folks have been flipped by the Republicans. And if you look at Joe Rogan, Elon, Chamath, and a number of folks, they all voted for Biden. They all voted for Obama. They voted for Hillary. They, in some of these cases, ran fundraisers. And then that party then set a test, I think, you know, a purity test for, you know, people who are moderates and capitalists in the middle, and we all failed it. And I think that's when people looked at Trump as the better option. They felt, and you know, really, losing Joe Rogan and losing Elon is like the most ridiculous, self-inflicted wound of the Democratic Party. They had them.

All they had to do was just say like, hey, we might disagree about, I don't know, taxes, meritocracy or whatever, but there's room in this tent, this Democratic tent for capitalists, for billionaires. And they kicked him out. Yeah, I guess I don't, that's the part I don't really get. I mean, Bernie Sanders and Elizabeth Warren lost in the Democratic primary to Joe Biden, who did not institute any type of socialism, who passed a lot of bipartisan bills, frankly,

on the chipsack and infrastructure, type stuff that Elon would have liked. I think it's the general tone of the Democratic Party is what people were picking up on. But Kamala is not running on DEI or socialism. I mean, her platform does not include anything related to socialism. There's no threats to capitalism. I dug him off on the podcast last week, and he called himself a capitalist a capitalist yeah most people believe she's lying in her move to the center okay well even if you believe that like her like her 2019 platform even her the most left version of

herself i think we can all agree kind of the democrats got caught up a little bit and the sort of lefty what woke wokeification if you will at the party during 2019 but like she never ran on socialism she never ran on socialism like i i guess i just don't understand it i think that's people's perception is that there is a hatred of entrepreneurship and i'm not saying this is real i'm just telling you the perception in silicon valley my brother-in-law works for uber her husband was a corporate lawyer you're making a great counter case i'm just telling you you asked me how it happened okay sir this is how it happened you don't invite elon to the ev summit that's kind of like not inviting michael jordan to the all-star

game you you kind of get the message loud and clear as entrepreneurs you introduce a wealth tax you put a tax on people selling their homes in la or in san francisco for over five million dollars and if people feel like you're constantly under attack for building and creating jobs that's that was what the democratic party did to capitalists in their minds i'm not saying it's true you can make counter arguments for it i'm telling you about the perception i hear from inside the room where people discuss these things they feel like the democratic party is absolutely anti-capitalist and i think the process in which you know they hid biden's you know mental capacity and then kamala not having to you know do a proper primary they consider all that part of this deep state machine of elitists and we i see you smirking

like i think it's come on i mean you're you're on a pot you're it's a four pockets of four billionaires so like the deep state elitist i'm not a billionaire yeah okay for but i mean that's like a superficial i would say that's a superficial way of describing us we're actually three of them are immigrants and we're all self-made so you can be dismissive and say oh four billion i'm just saying like you're you're talking about other elites like there's some elite cabal like i mean elon runs uh runs the biggest one of the biggest social media platforms like they're all so the thing you're missing yeah tim is self-made people versus ivy league elites who had it handed to them and journalists that's the perception in

silicon valley now again i'm not saying this is necessarily my take on it but you asked like what's what's what's driving it you take a bunch of people who are self-made and then you start attacking them and you're you just sort of take over the democratic party and you don't have a primary and you hit this guy who is obviously in mental decline. That's the kind of stuff that kind of counters how Silicon Valley and how capitalists think. They think about performance, think about meritocracy. They think about radical independence and being self-made. That's their worldview and then when a bunch of elite people and by elites the derogatory comment is ivy league educated working as journalists working in think tanks working in politics but having created jobs and then that's the tension

that i think led a lot of them to flip to trump. And so that's the answer to your question. Why did they flip there? I think the Democratic Party and that elite machine kind of made them feel like, even though they were donating money, that they were hated. Does that make sense? No, I mean, no. And yes, it makes sense that they think that,

but the argument doesn't make sense. I mean, Kamala went to Howard and she hasn't attacked self-made people, I don't think. Her argument for her campaign is that she wants to have an opportunity economy. If you just look at her economic proposals, there's nothing in there that is an attack on self-made people. Oh, when it comes to Kamala, that's a different story. They just think she's dumb. They just think she's dumb. I mean, that's not what I think, but I think generally people think she's not that bright and not well-spoken. And they think that Donald Trump is, what, smart? I think they think he's a better option.

And they think J.D. is very smart. So the people who have flipped, that's their perception. Let's just go back to your perception for a second, because you sent one tweet we really agree with, and I want to have one agreement here for a second. You wrote this. I like this a lot. You wrote, my lord, what a run-up.

The last two administrations added $8 trillion each to the debt, and the stock market has ripped. Entrepreneurs in the U.S. are violently and consistently building amazing, humanity-changing products. Unemployment is at record lows, and wages are rising faster than inflation. You can learn anything, anytime, for free. And y'all are miserable. This is the golden age, so soak it in.

It can be a lot worse. I totally agree with all of that that is the thing that's so flummoxing to me is like you just there are plenty of little criticisms you could make of biden or kumla or their policies or all this but like we are not in american carnage right now we there is not an attack on entrepreneurship it's never been better i don't understand why this is the moment to look at to to say we really need a radical shake-off of the system i don't i don't get that yeah so what the counter argument that these folks make is so um there is a new phenomenon that people perceive the economy and this manifested itself after bill clinton and it

happened during obama and i'm not sure i'm not a political science expert but people's perception of the economy bifurcated and became inversely correlated with their political party so during a republican uh you know like during trump publicans thought the economy was great democrats that was terrible and vice versa and there's a psychological phenomenon here of this tribalism that's been talked about, and they've written about it, but it didn't exist actually during Clinton and Obama and Bush and other presidencies. It was minor, like maybe 10% difference of perception of the economy. Now it's just become totally tribal. So if you point out to a Republican who's voting for Trump and supporting them, lowest unemployment of our lifetime, highest stock

market of our lifetime, and 60% of Americans participate in the stock market. So almost everybody benefits, or the majority of Americans are benefiting from that. Inflation has been tamed and looks like we're going to have a soft landing. Then they immediately go to, yeah, but the border and the immigrant crisis. And the truth is, there's really actually not that much difference between these two past administrations. If you actually looked at it from brass tacks, they both spent an enormous amount of money and put us into massive debt. And they both will do the same in their next administration, I predict.

They both had relatively, if you take COVID out, the same GDP, similar unemployment. I mean, everything's been basically the same. So any perception you have of this, or when you talk to partisans, you can tell who a partisan is, is because they'll look at it and say, oh my God, people are suffering. There's always people suffering in the world. That's the nature of human existence. But the amount of suffering in the United States, we are the envy of the entire world right now, who are still suffering from 5, 6, 7% inflation, 10, 15, 20% unemployment in other countries. And so there is an argument to be made that obviously printing money has created a lot of this and government spending is not healthy at this level. If we do this for two more administrations, it'll be cataclysmic. One more administration,

we might survive it. This happens for eight years of Kamala or eight years of Trump and then Vance. This country is going to have really seismic level problems. It will be cutting services at a rapid rate and raising taxes at a phenomenal rate. All right. I want to get to January 6th, but just to put a button on that. So we agree. We both agree that the deficit is a big problem that neither party is taking seriously. But we both agree that the entrepreneurship, capitalism, the economy during the Biden-Harris administration has been basically fine. Been great. has been basically fine been great the policies that they have put in place have like maybe they they did some they goosed inflation i think probably by spending a little

too much at the beginning but besides that it's hard to come up with specific policies that are attacks on entrepreneurs yeah it's more the vibes people feel you, that they are not. If people donate a bunch of money to your party, and then you spend a decade criticizing them, they might, don't be surprised if they flip parties. So their feelings are hurt. Chamath and Elon's feelings are hurt. I don't speak for that. They just didn't get invited to the parties.

Once again, Tim, I don't speak for Elon or Chamath. I've never been invited to the light. I'm just telling you how entrepreneurs feel writ large. That's how they feel. They feel when they hear the Democratic Party, which I would say Bernie Sanders, Elizabeth Warren coming out and saying ban billionaires and all that rhetoric. Yes, that is. And being anti-free markets and then the government spending is what I would say I hear most of

all from people who've switched parties. That would say I hear most of all from people who've switched parties. That's what I hear most of all. This message comes from BetterHelp. Can you think of a time when you didn't feel like you could be yourself? Like you were hiding behind a mask? BetterHelp online therapy is convenient, flexible, and can help you learn to be your authentic self so you can stop hiding. Because masks should be for Halloween self so you can stop hiding. Because masks should be for Halloween fun, not for your emotions. Take off the mask with BetterHelp.

Visit BetterHelp.com today to get 10% off your first month. That's BetterHelp, H-E-L-P.com. Landlord telling you to just put on another sweater when your apartment is below 21 degrees? Are they suggesting you can just put a bucket sweater when your apartment is below 21 degrees? Are they suggesting you can just put a bucket under a leak in your ceiling? That's not good enough. Your Toronto apartment should be safe and well-maintained. If it isn't and your landlord isn't responding to maintenance requests, RentSafeTO can help. Learn more at toronto.ca slash RentSafeTO. Let's do January 6th really quick. Well, not really quick.

It's impossible to do really quick, but we'll do it. And we'll do it in a way that you can feel that you have a full-throated context for your argument. I guess, actually, before we do the January 6th, because we haven't answered that. So, Saxon and Chamath, because we're going to hear from both of them in this clip that I played that you said was a lot of context. And so, they're both for Trump and fundraise for him. Have you said who you're voting for? I'm a double hater. You're a double hater.

Are you going to decide? Do you think, or do you, or I'm a resident of Texas. So my vote doesn't matter. Um, might do a write-in vote. Can I work you over?

What about all red Cruz? Do you have an all red Cruz vote yet? I don't know what that means. The Senate race in Texas. Oh yeah. I haven't actually given him a slot. I just became a, I just moved here this year. You're a Texas resident? Okay, well, I don't really think it's

probably the best use of our time for me to try to convince you to vote for Colin Allred over Ted Cruz, but we can do that off. We can do that in the green room if we still like each other at the end of this. Alright, so this is what started all this. We went back to, as you've said at the beginning, this podcast from right after January 6th obviously emotions are running high and we put out a one minute version of it obviously an hour

long podcast and so i want to replay that and then then you can tell us what what you think was missing from it but uh let's listen i would rather take every single person arrested and give them zero days in jail and add it all up and give it to Trump. He is a complete piece of shit fucking scumbag. He's garbage. Is Trump responsible? Yes. I mean, clearly. 100%.

100%. Yes, because he is the one who put forth this theory that the election was stolen and was constantly repeating it for the last two months. If you want to see this mob as a gun, I think he loaded the gun. He pointed it in a certain direction. And I think most of his political career. I think he's I think he's disqualified himself from being a candidate, you know, at a national level. Can I ask you guys what you think of this? Basically, Pelosi has told Pence, you have to invoke the 25th Amendment, or they're going to take up impeachment. What do you guys think about that?

I think it's the right thing to do. He's a maniac. I mean, this is insane, deranged, criminal, lunatic behavior. It's completely possible that he could do something more dangerous in the last 14 days. Okay. Naturally, I agree with all of that. Yeah. So I stand by my statements 100%.

Yeah. The biggest blocker for me with Trump has always been, you know, his behavior on January 6. I come from a family of law enforcement, and I was going to be a cop and then an FBI agent, and I just happened to get accepted to night school and didn't go into the forest. And my brother went into the forest, and he's a cop and retired now. You know, anybody who's got members of their family in law enforcement understands exactly how bad that day could have been and the fact that those cops did not for some law enforcement i mean some got injured yeah but if in those moments they when when a cop's getting beaten like that if one of those cops had done what other cops told me would have been absolute proper

protocol which is shoot their guns and defend themselves against people spraying them with bear spray and beating them savagely we would have had 50 dead americans 25 dead americans and i think that that is the thing that anybody who is voting for Trump has to really deeply consider, is that he could do this again. And the fact that he didn't accept, you know, the election results, and that they're still on about like, the election wasn't a clean election, despite them doing everything they could to fight it and every lawsuit getting turned over by Trump judges half the time. And then Pence, his own vice president saying like, you're lost, bro. That's it.

It's over. And then his own family saying, hey, call off the hounds. You know, you sent these people there. You said fight like hell. But, you know, I think for partisan people, you know, they've reframed their position on Trump. They've re-underwrote it. I have not re-underwritten my Trump position.

You said you're a double-hater. And so I just don't like, how do you get from a place where somebody is criminal, insane, deranged, a lunatic, possibly liable to do another insurrection, and then say, well, I don't know, even Stephen. I don't like Kamala because Bernie Sanders said something mean about, well, I don't know, even Stephen, I don't like Kamala because Bernie Sanders said something mean about billionaires. I don't understand. Why not just be for Kamala? No, I just don't know that. I don't think she's qualified for the job is my honest opinion. I mean, she's been an attorney general, a senator, vice president. Yeah. I am not impressed by her at all. Sure. But I mean, there are plenty of people I'm not impressed by that I would vote for over Trump. I mean, I guess I disagree with you on Kamala.

Yeah, I mean, you're making a strong Trump. I don't understand what, like, how do you go from saying this person should be jailed, he's disqualified, he's a maniac to being like, well, I don't know. Well, I'm not a fan of either person, and I'll probably do a write-in vote. But I don't think Trump's going to win, if I'm being honest. I think women who had their rights taken away by Roe v. Wade, which is my second major blocker with Trump, you know, January 6th being number one and overturning Roe v. Wade number two. I think women are going to come out in force

and he's going to get shellacked. But I could be wrong, you know. I'm no political expert. Sure. You had him on the podcast, though, and you didn't even ask about January 6th. So this is the other thing I don't understand. Like, Chamath wanted to be jailed.

He called him a piece of shit fucking scumbag and then he comes on the podcast and you don't even ask him you can ask chamath about that i was going to ask him about it and we ran out of time and i am only 25 of the questions but i did get my two questions in about abortion which went national news and uh visa uh you know visas and immigration which went national news so i had three questions i wanted to ask and i in my interview technique was going to increasingly go with the more difficult ones and then when we got to january 6th they they pulled the plug on it yeah i just but no sincerely tim you're laughing but i don't know i'm laughing because it's just like i don't

did you hear my other questions i did they were fine they were tough questions they're tough questions i mean i'm the only person who asked tough questions. Yeah, you're the only one. And I followed up three times on this. Why don't you look at your colleagues? In the post game, though, then I listened to the post game. And it wasn't like you were mad at them for not asking them or you didn't say like, hey, Chivas.

No, I mean, they're not journalists. You thought he should be jailed. I just don't understand how you get there. I thought he should be jailed to I'm going to host a fundraiser for him. You'd have to ask them. Does he no longer think he should be jailed you'd have to ask them it just seems like well why don't you ask him though you guys have a podcast you meet every week isn't that aren't you a little curious actually we've had the debate many times so then do you understand what what changed i mean again trump has all the things that led to january 6th

yeah i mean chamath did a whole episode where he talked about his re-underwriting of it. So you can listen to that episode. Yeah, okay. Like I'm saying, like, you know, I'm here to talk about my opinion. I don't, can't tell you about theirs. That's fair. Yeah.

Well, but your opinion is still neutral though, which I'm struggling with. Like I just, I struggle with how a maniac- I think Trump's- Is Kamala an existential threat? I think if she spends a ton of money, I think they're both existential threats if they spend another $8 trillion, yes. This message comes from BetterHelp. Can you think

of a time when you didn't feel like you could be yourself, like you were hiding behind a mask? BetterHelp online therapy is convenient, flexible, and can help you learn to be your authentic self so you can stop hiding. Because masks should be for Halloween fun, not for your emotions. Take off the mask with BetterHelp. Visit BetterHelp.com today to get 10% off your first month. That's BetterHelp, H-E-L-P dot com. Landlord telling you to just put on another sweater when your apartment is below 21 degrees? Are they suggesting you can just put a bucket sweater when your apartment is below 21 degrees? Are they suggesting you can just put a bucket under a leak in your ceiling?

That's not good enough. Your Toronto apartment should be safe and well-maintained. If it isn't, and your landlord isn't responding to maintenance requests, RentSafeTO can help. Learn more at toronto.ca slash RentSafeTO. So you said you weren't a politics guy, so maybe I can, I'm going to try to win you over here. Okay, go ahead. The Senate right now is 50 to 50, 51 to 50, 51 to 49, excuse me. And Joe Manchin is one of the Democratic senators.

He's not running again. So the Republicans are going to win that state. That's West Virginia. So that's, so the Republicans have at least 50 senators. They're almost certainly going to win the Montana Senate senate race which is john tester he's running nice guy lost a couple fingers but um it's just montana's pretty red these days and so republicans are going to have 51 senate seats like if the threat to trump is he might try another insurrection he's going to mass deport people he might unilaterally put in a tariff and the threat

to kamala she might spend a lot of money but there's going to be a republican senate it just seems like i got risk you you're a risk assessment guy right when you're deciding what to invest in isn't it like general risk analysis part of the this thing yeah i think she's a bit of a neocon and i think the one thing the one thing i do like about trump was a neocon yeah i think she will start worse and i don't think she will be able to handle those geopolitical situations as well as trump this is the only thing i can say for trump that i appreciate about him is his ability to bond with dictators and he does quite well with them communicating with them and he doesn't like to start wars and he's you know i think that he will

do better on that issue so that was that where your risk is because that's really what kind of lands for me i just like even if i were a double hater which i'm not like my risk assessment is i look at the two sides and it's like it's like we've established that the things are basically fine in the country right now even good and it's like we could continue that path with mixed washington with supreme court being republican with the senate being republican with with Kamala Harris as president. Or we can take a flyer on Donald Trump unleashed. We've already seen what happened at the Capitol.

Who knows what would happen in a second term? Like, doesn't the risk, isn't it just a, isn't like a basic risk assessment? I think your analysis is excellent. So have I won you over? Have we done it right now? You have breaking news? I'm in Texas. Your vote kind of matters.

You just said at the beginning, you have a lot of people that listen to your podcast. I'm sure there are a lot of Jasons out there. I'm sure there are a lot of people that are annoyed with Saks and they're like listening to Jason and they're like, I don't know, I'm on the fence right now and I live in Atlanta and I'm an all-in fan and maybe you can nudge them in one right direction.

Yeah, I'll take it under advisement. Okay. All right. That was a good try. I mean, I Yeah, I'll take it under advisement. Okay. All right. That was a good try. I mean, I also, I tell you the other show I have with Kamala is not her not going on any adversarial podcasts or talking to people who are adversarial. She's doing Fox this week. I finally, finally, yes.

I give her credit for doing Fox this week. Yes. That's the other big thing. Like, I really feel like there should be three debates and agree anybody who's a presidential candidate should have to do three primary debates and three regular debates you know presidential debates and like I think Trump did two debates and Kamala did one and they neither of them did any primary and then Kamala had no primary process so what do you think of that not having a primary process for her I wish there was primary but also parties picked presidents like this for a long time and so i don't like really see it as a grave start to democracy would you rather have than

kamala if you had like your yeah um i mean kamala has grown on me to be honest and i don't like so why i well for the part maybe part of the reason that you don't like her the comma is a neocon thing i like i feel like her foreign policy comments have all been directly in line with where i'm at basically on foreign policy so she all been directly in line with where I'm at, basically, on foreign policy. So she's grown on me in that sense. I thought her convention was really an appeal to the big middle and to, you know, kind of the American tradition, particularly when it comes to, you know, immigration and speaking about, you know, kind of the diverse backgrounds of her and Tim Walz and giving people opportunity and protecting freedom. I just think all of her rhetoric's been right in line.

What do you think of Tim Walls? I didn't like that pick. I wanted Shapiro. Me too. I like Shapiro a lot better. Why didn't she pick Shapiro? It makes no sense to me. Like, is it this idea of like, you don't want somebody who's a little bit brighter in terms of shining bright, not brightness, intellect, shines brighter. I have on pretty good authority. i think that the reason was simply vibes that like her and walls clicked

that walls was more of like a cheerleader type like i'm here for you i'm going to be your second command also the like kind of the vibe of bringing a little bit of balance like shapiro despite the fact that they're different like they both are still like coastal lawyers thing right like i think shapiro is still like was a lawyer you know and yeah so it's kind of a double lawyer thing versus a lawyer and a guy that's like a teacher and a veteran so i think that i just think that was really the reason why but yeah i don't know it would have been interesting to have a whole primary policy i think that she's really like stepped up and exceeded expectations in the big moments in the debate at the convention speech

i mean just to be candid like back before it was all i was my argument was just solely focused on beating trump and i was like you know if we could move on from biden and get a shapiro and whitmer situation where they both are popular in their home states and and center-left democrats that that would be like the safest way to beat trump if she loses why will she lose and if trump loses why will she lose? And if Trump loses, why will he lose? I'm curious. Your take. It's a good question. If she loses, it will be in part totally out of her hands because globally incumbents have done horrible since COVID and inflation, despite the fact that, you know, Republicans want

to make this all about like America, like we've had actually the best inflation and inflation hits people, particularly working class people hard. And so we've seen incumbents lose all around the world. And I think that if she loses, it's because she loses with non-college, you know, kind of middle and working class people that had traditionally been democratic voters and there's bleed there. Like, I don't think that there's going to be a ton of bleed among my people, like the center college educated folks. I kind of feel like the, your Silicon Valley people, a little bit of a weird outlier for some of the unique reasons we discussed, but I think You're Silicon Valley people are a little bit of a weird outlier for some of the unique reasons we discussed. But I think mostly- Can confirm. Silicon Valley people

are weird. Can confirm. I think mostly the suburban, yeah, the suburban types that Democrats have continued to do better with will continue to do better with. So I think it would be a bleed among working class Hispanic voters. And I think that would be the reason why she'd lose. And I think it would have hurt that she would have had um such a short runway to do a campaign and i think the biden unfortunately will have some culpability with that so i think that i think those would be the main reasons i guess i have a darker reason about what it says about the nature of our country but i don't know maybe this podcast probably isn't race or gender yeah yeah i mean i just again i just just to my same perplexion how perplexed i am asking you about how people could go for trump a third time i think if the

country goes for trump after seeing what happened on january 6th it's hard to come up with irrational interesting how people who you know had reactions where they're like, hey, this is terrible, have now re-framed it in their minds as it was like an outing that got out of control and that Trump had nothing to do with it. And if you look at the Oath Keepers, you know, we've had this debate many times online, you know, the Oath Keepers came there explicitly to take over the Capitol and they brought guns to the hotels around it. Like those individuals are highly qualified in many cases, ex-military and ex-law enforcement individuals. And they could have made, they obviously would not have overturned the government, but man, you could have had a lot more than this being a riot that got out of control

kind of situation. Or imagine if Mark Milley would have been Michael Flynn. Or imagine if instead of Brad Raffensperger in Georgia, Marjorie Taylor Greene was the Secretary of State and actually did try to find the votes. I mean, like there were so many catastrophic, and again, this just circles me back to the risk assessment. Like there were so many catastrophic potential outcomes. And it's like, I had a debate with Dan Crenshaw last week. Can I use this analogy? I was like, it's like when I listen to Saks, Troth, and some of these people who've come

around and changed their views, and Dan for that matter, it's like saying that I got hammered at the bar. I drove 100 miles an hour from LA to Vegas to go gambling for the night. I spun out on the highway and flipped around three times and landed going straight and ended up in my hotel in Vegas. And meanwhile, my friend over here was like following the rules and got t-boned. And the lesson that I take away from that is that I should get hammered and drive a hundred down the highway again. It's just like, just because we survived, it doesn't mean it was okay.

Like it was an extra, it was wildly, and there were a ton of them. What do you think of the lawfare, I'm curious, accusations? Like, this first case that they did against Trump, obviously, with, like, election, the hush money case, and, like, kind of extending. That one felt like, to me, the weakest of all the cases. It felt like a little bit like it was lawfare and political, whereas the other don't seem as much and and their claims you feel like they're weaponizing i agree i mean i agree that it was weak the weakest of all the cases but again like we have a system of i mean john edwards was charged with a similar thing and got off and he was a democrat i just but as for the january the lawfare thing this again i know you don't speak for chamath but i

want to go back to the podcast. He said that he wishes that all of the people that stormed the Capitol, we added up all those sentences and gave them to Trump. That was a current Trump donor's view. I agree with that. It was Trump's fault. lost including people i hate like if it was ron desantis or ted cruz or bernie sanders that had lost like they would have just conceded and there wouldn't have been a rally that day and nobody would have charged the capitol like the only reason anyone is in jail is because trump lied to them and so then to say it's lawfare i don't get that like it's trump it's obviously trump's fault it was plain that it was trump's fault from the moment that it happened so i don't i don't see it as lawfare yeah i i'm in total

agreement that he was culpable that day i think if he had just said we're gonna go there and it's peaceful be peaceful and don't fight like hell and if he had actually like you know not told the oath they shouldn't have been gone there though this is all it takes us to like he lost like he lost clearly right there shouldn't have even gone there, though. This is all it takes us to. Like, he lost. Like, he lost. Just clearly, right? There shouldn't have been a rally. He should have been working with the Biden team on the transition, like every other president in history.

Yeah, and they will bully you into saying that you're overreacting about January 6th. I know. And that's what I face. Yeah, they're underreacting. Constantly online, people are bullying me, like, oh my God, there was just a guy in a shaman outfit. I'm like, yeah, the mentally ill guy in the shaman outfit is different than the guys who brought long guns to their hotel and then were acting in formation to breach the barriers and

a woman jumped through a window with a pistol in her face from a secret service agent who begged her not to jump through the window and she decided she would breach that window with multiple guns trained on her saying do not jump through the window we will have to shoot you and she still did it i mean you want to talk about trump derangement syndrome that's the definition of it amen brother okay we've gone too long i want to but you picked my brain up politics i get to pick your brain about one thing that you're an expert on that i know nothing about i was excited to see this when i was googling you you tweeted this last year about crypto for a decade i said most crypto projects were a scam and i got brigaded with laser eyes saying have fun being poor as a non-silicon valley person as a

total neophyte on all this stuff i just like i've tried to get into crypto i've looked at it i've considered it i've had smart people talk to me about it and everything that i look at i'm just like this is a scam it's a fake it's nothing it creates no value and i don't get it so have you changed your view on that or do you also share that view when executed it's 99 of the time a giant scam or incompetence or a combination of those two things incompetent people running a scam which is why it looks so weird there are a collection of underlying technologies like blockchain or nfts and decentralization that are real and that could have applications it's just if you created a global casino where there was absolutely you know no oversight what do you think would happen bad actors would take it over and it would become

a scam and that's what's happened yes and there should be some reasonable regulation absolutely this is the other thing the crypto people get mad about kamala about and she's actually been more pro-crypto on her leg than than biden once but like yeah right there should be some regulation it's crazy that there's no regulation it's really simple the regulation in this space is super simple there's something called accreditation six percent of the country are accredited investors which means they make over 200 000 a year they have over a million in net worth you could create an accreditation test like a test to own a firearm or drive a car or cut hair and be a barber where people should get rid of the cut hair chat test but i'm with you on all the rest of it yeah and

you just do 50 questions and people take a three-hour course they answer 50 questions if they pass that test and it doesn't have to be onerous like a series seven which takes you know weeks and you know a couple of hours to take a test if they pass that test, and it doesn't have to be onerous like a Series 7, which takes weeks and a couple of hours to take a test. If they pass that basic test, they could invest in crypto. And then on the crypto side, they should have to have insurance be registered. But they should be allowed to let people buy NFTs and trade them and go crazy. As long as the people coming in are sophisticated enough to understand diversification, do not put your entire net worth into it. And then they could look at it alongside gambling on draft kings or going to vegas sure and it would be part of that which is the reason

there's a little bit of tension here is there's a group of people who do look at it as like draft kings and they look at it like going to vegas and then there's another group of people who think they're investing in the next uber or the next google and they don't realize they're actually at a casino and that's where education would know, be something the SEC could do really easily. And then if you took a course, and you knew there were no customers, and there was no revenue, and there was no profits, and you were still invested in a project, you would be an angel investor like I do. And you would take small bets, and then increase the investment size as they proved the product

and the use case. So yeah, I'm hoping that's some reasonable legislation. And there has been some around a path to becoming a sophisticated investor is the term I use. So it's a term in Australia, as opposed to accredited, which is just a nebulous term. Sophisticated is like a really good term, an educated investor. We've ended with several agreements. Thank you so much, Jason Calacanis. And if I've won you over, you're going to think about this. You're going to sleep on it tonight. And if I've won you over, like we're not airing this podcast till tomorrow, I'd be happy to have breaking news that Jason has agreed with me and he's going to reluctantly vote for Kamala Harris. I would love to, I would love to be the person to

break it. I plan on announcing my vote on the all-in live stream on election night. Okay. Well, maybe you don't want to do it before. A little guilt will come in place. You'll think about those cops at the Capitol. Everybody should make their own decision. All right. We'll see you.

Thank you so much, Jason. We'll talk to you soon, man. My pleasure. Okay, so your heart is broken You're sitting around moping, moping, moping Crying, crying You say you're even thinking about dying Well, before you do anything rash Baby, listen to this

Everybody plays the fool Sometimes There's no exception to the rule Listen, baby It may be factual, it may be cruel I ain't lying Everybody plays the fool Listen, baby, it may be factual, it may be cruel. I ain't lying. Everybody plays a fool.

Falling in love is such an easy thing to do. But there's no guarantee that the one you love is gonna love you Oh, loving eyes they cannot see A certain person could never be Love runs deeper than any ocean You cloud your mind with emotion Everybody plays the fool sometimes There's no exception to the rule Listen, baby It may be factual, it may be cruel

I lie Everybody plays a fool The Bulwark Podcast is produced by katie cooper with audio engineering and editing by jason brown