When Elon Went Broke, the Dark Side of Podcasting & Tales from the Tech Trenches | Jason Calacanis

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Check your eligibility today at joinvoy.com slash podcast. Treatments will only be prescribed if deemed appropriate. It's what I told Elon when I got him on Twitter. It's just a big mistake. Like I literally, my friend Billy and I at dinner got him to use Twitter. Oh, God. And he shows me the clay models of the Model S. And he's flipping through it. You know, in the BlackBerrys, he used to have that little trackpad thing. And he said, I think I can do it for $50,000.

that if you can do that for $50,000, you'll change the... world. I have an uncanny ability to look at a person and I will see above their head winner in a neon sign that they can't even see. That's your mutant power. That's my mutant powers. And so when I made my first couple million, I was sitting

there with my wife after i sold the company she goes are you okay and i said what do you mean this is incredible she goes you're crying i said i'm crying wow what happened in san francisco is they just had the best deal in the world the lowest economic price for fentanyl five dollars a hit with the least policing there's a

bunch of liberal guilt you know and people hate entrepreneurs they hate billionaires they hate people who've made money who wants to build a bridge who wants to do that who's capable of doing that you know there's a group of people who are capable of doing that they're called entrepreneurs how many people can we reasonably have seek asylum here all right at jason that's what i'm going to call you at jason

Jason on Twitter slash X. I thought I was going to start this by talking about the ear things that we were going to have in because this is your studio. We have very fancy professional grade earbuds. And I thought I was going to sit in the host chair and then I was going to have your earwax in my. year it was a very strange could have gotten it could have gotten weird real quick uh but welcome to austin

Thank you. It's good to be here in Austin. Yeah, you got a lot of friends here apparently. I have done 87 shows today. Absolutely. But I feel like you've done probably 20 shows and a couple business deals and sold some things and how's your day going? How is my day? I always like to answer this question sincerely. Yeah. We'll get to the instance here. We'll get to the instance later. You know, I said when Uber stock hit 88 that I would retire. And it hit 88 the other day.

Because it's just a lucky number in Chinese culture and gambling. So I sometimes buy in for $8,800 when I'm at a casino, $8,888 just for fun. It had nothing to do with the DeLorean and 88. No, but that's also part of the lore, I guess. And then, you know, I'm a big Knicks fan. As we were talking about, we both have a passion for basketball. And here we are on the cusp of beating the world champion Celtics and Jason Tatum, I guess.

ruptured his achilles in the last minute but we would have beat him anyway um and so we would have been up 3-1 and like this is like the one there's like two things i always wanted to be in life is to see a knicks championship and and be really Rich, and one of those things has happened and the other hasn't.

Yeah, but there have been moments. We were talking, so we'll do a little basketball stuff and how it connects us. And you were born in Brooklyn, too, right? Born in Bay Ridge, Brooklyn, which is the last exit on the R train, like literally before.

Staten Island, which is the fifth borough. Everybody knows Brooklyn's the best. But you're a Brooklyn boy, too. Yeah, so I was born in Bensonhurst. You've got a couple years on me, but we basically come from the same area. Same place. We were saying when I did your show just here a few hours ago, we come... this, this thing that brings us together from opposite positions, because I was kind of a politics guy that ended up doing tech. You're a tech guy and an investor.

I guess ended up doing politics. Got dragged into it. And yet it seems to me very clear that both of our love really is basketball. So we're clearly still in the wrong line of work. Absolutely. You and I should be doing commentary. We should just be doing sideline reports. You could be, I could do the color. you could do the play-by-play. You know, there was an incredible startup years ago, years ago. I...

I don't remember what it was called. It was like Simulcaster or something like that. Yes, I know this. And it would basically, you could watch the game on TNT or NBC, but then you could broadcast your audio. It was such a great idea. I did it a few times and then it just, you know the... I know the company. I looked at investing in it. The problem is the sports leagues are pretty particular. In that time, they were. So there was a whole fan culture.

uh, with soccer football in the UK and everywhere in Europe, um, where they have fan TV and this broke out on YouTube and there's one called Nick's fan TV. And I'm friends with CP who, who runs it. And. You know, like local sports radio you used to listen to. So after every game, he has three, four, 5,000 diehard Knicks fans who listen to commentary after the game. And maybe five or six years ago, the Knicks were...

winning 15, 16, 17 games a year. There were a couple really. It was pretty brutal. You know, we would all be just... It'd be like 200 of us on YouTube in this little community. And then over time, we got Jalen Brunson and Julius Randall and they traded him and got Kat and the team got better and better. And it's just been a passion of mine. But it really is interesting. audience becoming part of the show yeah and

For the fans, by the fans is what CP calls Nick's Fan TV. And it's become like a little business. And it very much reminds me of what you were doing, like with your fan base or our fan base here at This Week in Startups and all, and is the democratization of this. which started really in the internet in the late 90s, has actually come to fruition with the tools, the bandwidth, and the monetization has all lined up perfectly. And it's really beautiful. You know, anybody at any time.

has the platform and create a show and can be as famous, notable, affluent, rich as their talent will take them. Talent, little hard work, little bit of luck. Do you percentage those out? Like talent, hard work, good luck, connectivity, location? Yeah, that's a great question. You know, I have always been obsessed with media. And so my first business was getting into the zines. I was online for dial-up computers in the 80s into the 90s.

And then I saw zines at Tower Records on Lower Broadway in Manhattan, and there was a little section in the magazine section. Is that still there? It's got to be gone now, right? Oh, that's been gone for decades. It's been long gone. But that place where people would go and look at the records and you'd meet people, it was like a...

kind of like the original Tinder, you go there and maybe if you're in the goth section, you meet somebody in your case, you're in the Frankie Valley section. Exactly, there you go. I thought you were going to make a gay joke. It was okay. I wasn't a gay joke. It was a 50s dork joke. I like those better. In the Frank Sinatra section, you might be no bitty. You never know. But there was a zine section, and there was a zine called Mondo 2000, and there was another one.

called paper magazine which was a zine at the time and they became a glossy yeah and uh there was one uh 2600 about hacking and i really got obsessed with that and i had started a zine called cyber surfer about dial-up services then silicon alley reporter play on words and um

There was very few ways to break into media back then. You had so many gatekeepers. And what I realized was those zines, even though they were 16-page... photocopies that were folded a certain way you can look it up online how to make a zine yeah they were next to spy magazine and esquire and the new yorker and it just it was like an epiphany for me oh

I could create my own magazine. And then who's going to stop me? And I did it. And I put $1,800 on my credit card. And I went up to the Village Printers on 43rd and 6th. I took my first issue of Silicon Valley Reporter. And I went to Roseland where there was an internet party happening.

Total New York, one of the first internet websites. And there were probably 200 people there. And I had about 300 or 400 of these printouts on a luggage cart. And I went there and I started giving out this zine. And I handed it to people.

And then by the time I had handed out like the 200th one, I turned around and I looked at the party. The entire party had stopped. And 100% of people in the party were looking over each other's shoulders, flipping through the magazine. And I looked at it and I said, This kid who's, you know, dad's a bartender and mom's a nurse from Brooklyn who goes to school at night at Fordham. I just took over the entire internet scene. All 200 people are reading my words.

And it just— You wrote the entire thing. I had a couple of friends write a couple of stories. Yeah. But, you know, I realized at that time, wow, if you control the medium, you have that, like, power, you can define reality, you can— could own the scene and like i really think like content is really about community and i kind of saw that very early on when i was 23 24 years old and i kept pulling that string and pursuing it as a career and uh i combined live

events parties with the zine and then it grew to conferences and radio and email newsletters and then i wound up starting a blog company when i had seen all these blogs you know in the early 2000s started to get

You know, a lot of attention. There was one called Pay Content. That's somebody who worked for me and started. There was one called Boing Boing, if you remember that. I remember that. Shani Jardin, who worked for me, started doing it. And then I had seen Gawker that Nick Denton had started.

So I saw that and I was like, I'm going to start a, I was at the Patrick Ewing Retirement Center ceremony at Madison Square Garden with my friend, Brian Alvey. And I said, I think these blogs are going to become a thing. And he said, why? I said, because.

if you're a really good writer you don't have an editor and so you can write things that the editor would have stopped you from writing it's like very punk rock it's very much like i was into dylan i was like it's kind of like acoustic like it's kind of like going down to like you know bleaker street you just Take out your guitar and you go. And so again, it like clicked in my brain. Oh, no gatekeeper, no gatekeeper. And that is really what.

podcasting is about as well podcasting is about no gatekeeper nobody telling you what you can say or not and then talent comes from reps and understanding every nuance, every detail. So I can tell you in this studio that we're sitting in, the lights, the cameras, the microphones, the audio software, the lighting, you know, these cables, I have set all that up.

You mean all the stuff's plugged in? All the stuff that's plugged in. I don't know what's going on here. I see a lot of wires. Yeah, yeah. It's an audio setup. But anyway, the point is, like... Media is really about details, whether it's filmmaking or magazines and their collaborative efforts. So I just became obsessed with every nuance and learning each of them to about 50, 60, 70 percent. And when I did the magazine, I knew how to do the layout.

I took the photos. I did the writing. I did the editing. I sold the ads. And it just clicked in my brain. If you know every... single aspect of the production nobody can fuck with you you're kind of unstoppable so every time i did a different medium and podcasting came out of um the podcasting revolution came out of blogging because dave weiner and adam curry decided to add to blogs an attachment. And the attachment could be a PDF, an image, or an MP3 file.

And so I was maybe the fourth or fifth block, fourth or fifth. So what year was that? 2003 or four. Yeah. Cause I started a podcast around 2000. five or six and that was still very I didn't even know what when I had a guy that I was doing it with my on-air partner who was like let's do a podcast and I was like okay and we would sit and do it so we'd have mics like this sitting at a table

And then he'd be like, okay, I'm going to put it up now. But I didn't know where it went or like, I think it was maybe even. before the iPhone or the iPhone had just come out. And I was like, I just don't know what, or iPod, right, sorry. I was just like, I don't even know what the hell this is, but I knew I could do this. Yeah, you're a good talker. Podcasting, the name isn't from like Pods of Wows.

people think. It's from the iPod. And what they did was the iPod, Dave Weiner and Adam Curry, who don't get enough credit for this, they just had this insight. If you plug the iPod into your computer... And then at night, they ran a script that went to the RSS feeds. And every night, it would look to see if there's any new files. And then would put it into a podcast artist, an album, and then a track. And so it hacked.

the original thing and the original iPod. And then you would take your iPod with you on the subway and you'd have a couple of talk shows. And I think that's when, you know, a lot of like interesting people. started to understand there might be something here because a lot of the podcasters were fans of talk radio. Whether it was Charlie Rose or Howard Stern, there was a lot of like...

I want to be those guys. How do you become those guys? Well, you got to get somebody to give you permission. And here was a permissionless. you know, way to just go publish. It's interesting because timing wise, that's also probably around when Stern was leaving AM radio, right? And Sirius is coming out, but he went the other route, but it still had the same bones of you'll basically be free. And Adam Carolla gets a lot of credit.

he took adam carolla took stern spot in la for a year or two and then he got into podcasting very early and then who was the guy who had the web show that Joe Rogan was on and kind of blew it. Oh, Green. Yeah, Green. Tom Green. Tom Green was doing... webcasting so webcasting predated it so you could stream video with a webcasting server at that time and so yeah just watching all that was like very mind-blowing for for me are you nostalgic for those old days like when it was all so

new and like you didn't really know what you were doing but you knew you loved something and you were just trying to do it where now it's like you can walk into rooms and people know who you are and you can make deals happen more easily and yeah I mean it's There was something very charming about the early days of it when there was only 100 people or 1,000 people listening because it was much more freewheeling, you know? And, you know, heavy is the head that wears the crown kind of situation.

Be careful what you wish for because when you do become popular and you get to the top of the mountain, which arguably you are and, you know, all in is, very strange things start to happen. you know, fame, even the micro fame that we have, I consider like podcasting fame, micro fame, even if it isn't. I don't want any more fame. I always, I'm just like, whatever I have right now is good enough. Not everybody's built for it is what I've learned.

at Billford because I like people. I'm a super extrovert. When I took the Myers-Briggs, which is known as astrology for men. Right. I knew you'd like that joke. I was like ENTJ. Yeah, yours must have been off the charts. Well, I was 94% extroverted the first time I took it 20 years ago. And then 10 years ago, I did it at an offsite and I was 100%. To the point at which the proctor was like, did you do that on purpose?

And I was like, no, I don't know how to do it. She said, have you taken the test? I was like, yeah, like 10 or 15 years ago. And she goes, oh, it's changed. She goes, I just, I've only seen that one other time, like 100% extroverted. So I love. What happened to that guy? I don't know. I think it's Donald Trump. Look at you. You have more in common with him than you think. Perhaps. Perhaps.

Yeah, you'd have to be careful because, you know, it does create a house of mirrors. If you're not grounded and then it happens to you, then, you know, you might have a hard time. understanding that who you are and what you believe is different than how people perceive you, right? And I think you probably have had this experience. People will project their fantasies, their anger, their joy, whatever.

into an individual that they are fans of or that they listen to and what's particularly interesting about podcasting as a medium which i didn't anticipate was there's something about being in people's ears like we are right now for a regular period of time. And you got to Delhi. And there's something about getting to Delhi, which Howard Stern did, Charlie Rose did. I did for a while here. I'm four days a week, three days on This Week in Startups, one day on.

All in. And when you start hitting daily and you become a habit for people, now they have this experience of asymmetrical intimacy, which is another way of saying fame. They know everything about you. They know you have a kid or two kids. They know your dog. You like to ski in Japan. They know all this stuff. You've never met them. So when they come up to you, it's this cathartic moment like.

We went to summer camp together and we haven't seen each other for 20 years or we fought in like some war and then we saw each other again at a 50th reunion of something, you know, a D-Day. It just opens up this incredible emotional experience for people. I find that.

absolutely pleasant and joyful. It's incredible, yeah. It's incredible. Sometimes it can be a little bizarre when they remember something about you that you don't even remember. Of course. You're like, wait, I said that, I did that, I was there. Yeah, yeah, yeah. I have to brace for impact because people say, you don't remember this, but you had to.

profound impact on my life and i'm always like i hope in a good way yeah right and it's actually quite charming because i have always been so effervescent and enthusiastic about entrepreneurship and people quitting their jobs and just following their dreams. Have given people that roadmap. I can't tell you the number of times it's thousands that people have stopped me at an airport over the last decade and say, I heard you say this to this founder on your podcast.

And yeah, I wound up starting a company. I quit my job and I put all my money into it. I said, oh, how'd it go? I lost everything. And I'm like. okay, I'm sorry. And they're like, no, I did another company and I sold it for $50 million. And now I'm married. I have three kids and I'm independently wealthy. I'm like, great. Did you ever think of calling me to angel invest? And they're like,

Yeah, I did actually, but I never did. Or even worse, I did and you never responded to me. Or how often do you get hit up at the airport where they try to pitch you right then and there? I love it. When people say, can I pitch you? I'm like. That's my greatest joy. You can pitch me as long as you are cool with me giving you my candid feedback. Right. So I just always have permission to be candid.

And they're like, or would you like me to sugarcoat it? And what are the percentages here? How often do you- 100% do they want me to be candid? No, no, no, of course, I get that. But I mean, how often does someone randomly approach you at Starbucks or at an airport, pitch you something, and you're like, wow, we're going to have a call about this? Oh, to have a follow-up call, that could be...

5% of the time. Yeah. That's pretty decent. That's pretty decent, I would say. And then probably 1% of the time I actually wound up investing, I would say. Yeah. I mean, I don't invest in movies. I don't invest in pizzerias. Things outside of high growth companies like Uber or Robinhood or Thumbtack, you may have heard of some of those or use them. You know, those kind of crazy ideas are the ones that are non-consensus.

Most people don't think they're going to work. And you have to ask yourself and rewire your brain as an angel investor. I'm really like, I have a fund and I have 11 people who work on this with me. But we're investing in year zero. Half the time people haven't incorporated yet. Half the time it's two or three people with a prototype. So we're really making investments with a very thin amount of information. 80% of the time, 90% of the time, the investment goes to zero. But when it hits. Yeah.

It's 100, 500, or in the case of Uber, 7,000 times our money. So not 7,000%. $1 turns into 7,000. Yeah. 1,000 turns into 7 million. The brain chemistry you have to have for this job is like going up to, you know, an archery setup and you split the arrow. right, on your second hour, and you say, give me another hour. Yeah, let's keep doing this. I'm going to do it a third time. Like, that's the odds. One in...

200 wind up having these kind of crazy outlier, 500x, 5,000x. And you hit one in a lifetime, maybe two, and I've hit seven. So I've gotten pretty good at it, pretty predictable about it. Every 50 to 100 or so investments, I hit what's called a unicorn in our business. The great paradox is 99% of my time is spent with... The people who don't hit them. So I literally spend my time with people who are destined to quote unquote fail at their startup. Now, there's no success like failure.

It's incredible. You learn so much from it, and then they usually hit it on their second or third try. But I spend a lot of time with people working extremely hard and sacrificing their entire lives for a project that results in no outcome.

So what ends up being the win for you at this point? I mean, you have enough money. So if you never made another dollar, that would be fine. And if some of the companies disappeared, that would probably be fine. Like, do you, is it just, oh, can I get the next unicorn? Or is it like, I want to find someone who I see something in? And how often does that happen where it's like you're not sure about the product, but you just love the person?

Yeah. It's like two really good questions in there. I only get three per episode. So this is it. The rest are all going to be. So we used a lot. We burned through two of them real quick. You know, I have. An uncanny ability to look at a person and I will see above their head winner in a neon sign that they can't even see. And it's just blinking. And I look around the room and I'm like. This guy's a fucking winner. This gal's going to crush it. Nobody else sees the sign. I think it's like.

Almost like being a mutant, like an X-Men or something. That's your mutant power. That's my mutant power is like, I don't have some crazy superpower myself other than I can identify the other mutants. And I can help the other mutants. So it's kind of like a Professor X, like a Cerebro kind of thing. Because the people who do change the world, they are very difficult people.

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we don't believe in one-size-fits-all solutions voice medication is personalized based on what's right for you you'll have a full care team behind you from voice clinicians checking in on you to a personal coach keeping you motivated. And with the VOI app, your team is always just a tap away. Anytime, anywhere.

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People would describe them as assholes or difficult, but they're incredibly competent. And when you hear them talking, you hear their passion, it's not an empty can making a lot of noise. It's like... It resonates. It's deep. It's like, yes, this will echo in eternity if it works. Like when Travis showed me Uber, I was like, yeah, there's...

Absolutely no doubt in my mind that a billion people around the world will be taking out their phone and using Uber. Even though we grew up at a time where everyone was told, don't get in a car with a stranger. Of course, yeah. Don't get in a car with a stranger went from get in a car with a stranger. Yeah. And when, you know, when I asked him pressing questions, every time I asked a pressing question, he would.

I would see him processing it like a Terminator, you know, like in Terminator 2. And he's processing it, even if he hadn't thought about the issue. And he would have like a very clear... vision for how that might execute. And we had this like argument over tipping. You know, I'm from Brooklyn. Everybody gets tipped. You know, my first time I ever took a flight, I was 15 years old.

And the waitress, I'm sorry, the flight attendant, stewardess at the time, flight attendant came to me. And, you know, it was a... idiot Brooklyn kid. And she said, what do you want? And me and my friend, and I said, well, take two Coca-Colas. And she brought the Coca-Cola. So he said, here, this is for you, sweetheart. And I handed her two bucks. She took the two bucks and she looked at me and she goes, wait, we don't take tips.

Dropped it in my lap. Wow. At which I said, I'm so sorry. I'm from Brooklyn. We tip everybody. She goes, it's quite charming. You don't need to tip us. And I said, it's my first flight. I mean, this is like the opening scene of my movie is like this idiot kid who doesn't understand the world. Did you ever see My Blue Heaven with Steve Martin? Yes. When he plays a mafia guy in Witness Protection and he goes, I don't tip, I over tip. So the way you did your hand right there.

That's the way he did it, yeah. It's hilarious. And now I live in Austin where everybody calls me sweetheart again or honey. And I'm like, well, this is quite charming. We're back to the 80s. Anyway, I kind of can identify those people. But the first part of your question is like, well, what makes you tick?

right like what makes johnny run you know there's like that famous book in hollywood like what makes that kid run i forgot the name of it but everybody in hollywood reads it um and uh it's kind of about ambitious youth. And I think, when I look back on it, we're all the product of our childhoods in many ways. And I was just a kid in Brooklyn who was irrelevant.

who had no power, no money. We were just poor kids in Bear Ridge. And I just thought to myself, someday I want to go to Manhattan and be famous and rich and powerful. And it was like a... Was famous first? That's the way you said it there. I think it was. I think it was more... money because I just thought, my God, we never have any money. And every fight my parents ever had was just about trying to pay the bills, right?

We were living paycheck to paycheck. My dad had a bar at one point. That was just financially super difficult. The worst business you could ever be in. And so I just always had this fear of running out of money. And so when I made my first couple of million. I was sitting there with my wife after I sold the company.

And I was sitting there waiting for the wire to come through from AOL, and I'm refreshing my Bank of America screen because they said the wire's been sent through. Refreshing and refreshing. You know, this is online banking in the early 2000s, and it takes like, you know, a couple seconds.

I made it for it to load, and it loads, and I see this millions, tens of millions of dollars show up in the bank account. She goes, are you okay? And I said, what do you mean? This is incredible. She goes, you're crying.

And I said, I'm crying. Wow. And I felt my chin, and I was like, oh, my God, I'm crying. She goes, why are you crying? You're giving me all this money, and we're set for life. I said, oh, I never have to worry about money again. It was just like incredible cathartic release to say. oh, I don't have to have that fear, right? Like a primordial fear. And then I also thought like, well, wouldn't it be interesting if like...

You were relevant and people listened to your opinion or you knew people and your friends were super relevant and you like got to do what all these rich people are doing in Manhattan. When you and I grew up in the boroughs, there was a term, B&T. Yeah, bridge and tunnel. And if you went to Manhattan, when I went to Manhattan and I tried to go to Palladium or Limelight.

Half the time you went and you showed your Brooklyn ID, they would hand it back to you and say, no B&T. They wouldn't let you into a club if you were from Brooklyn. Literally. They would just go back to Long Island.

In your case, right? You're in Long Island? Yeah. Like, that's even worse than being from Brooklyn. That's where you're at. Yeah. You just throw your ID back in your lap. Exactly. Of course, I got a fake ID, an NYU ID from a St. Mark's place for $10, and that solved that problem. But, you know, I wanted to... try to be in charge. I wanted to have control of my destiny because every, the first two or three jobs I had, I kept getting either fired or told to wait in line.

Just infuriated me. But once I figured out how to hack stuff, I was like, oh, the world's a video game. There's a solution to every level. I'm just going to route around anything in my way. Anything that's in my way, I'm just going to find the back door. Because in New York, we kind of, like when we went to the movies, one person would buy a ticket.

They'd go to the back of the Fortway, they'd open up the emergency exit, and six kids would run in. Like, that's how we went to the movies. We didn't have the money to go to the movies, so one person bought a ticket, went in. We just always had an angle. We had an angle. And so, you know, that's what...

got me through the first 20 years. But, you know, after that, you're going to wind up. And I tell this to entrepreneurs because I've seen it happen over and over again. And once you've made much more money than me, you know, you see the bank statement.

And then you all of a sudden regret selling your company. You have no purpose. They own your company, the brand, the baby, the team doesn't work for you anymore. And you're sitting at home with all this money and all this time. And I've seen people get really depressed, you know, drugs. suicide, depression, you know, they realize, oh, that does nothing to solve whatever it was that put that battery in. And then you have to.

Oh, the shark has to stop moving and you have to actually examine, okay, well, what actually gives you joy? And what is your purpose? And that I was really able to see, like I actually really enjoy building things with people who are different, who are mutants. How did it change you? So you go from not having anything and it did take some time, but now, okay, you refresh the Bank of America.

you see all this money like it has to fundamentally change you at that point because you're crying without even realizing yeah i think it's not just that you have more it took the edge off and it took a couple years but then i realized okay now i'm dangerous like i don't need Even when I was an entrepreneur, I needed some permission. I needed to make money. I needed to get an investor. You know, there were costs associated with it. Then I was like, oh, I can just.

start a project now and just do it i don't need to go to an investor i can just build the prototype or get started and you know in today's day and age young people who have skills product designer developer a sales executive, they can start a project on the weekend. And we have something called Founder University where we teach people over 12 weeks how to build a company and all the little secrets that people don't know.

And some of it's like obvious stuff, like legal issues around cap tables, which you probably had to learn as a comedian. Yes. And it was like the funnest part of all of this. We, as Elon and I. Called it in the early days, like, how's it going on this or that? And we'd be like, yeah, I got to do some chores today. What chores are you doing today? Oh, the cap table, legal, accounting, HR. But we all have to do our chores. There's fun stuff like launching rockets or building pods.

And then there's chores. Hiring people, firing people, you know, all that kind of counting stuff. But, you know, then the fundamental change, I think, is I. realized, oh, there's like no upper limit to this. The world is rooting for entrepreneurs. They're rooting for creators and everybody can create, but it's just, I think the learned helplessness in society.

is such that people have been told to wait in line. And, you know, these are the safe routes. And then there's another side, which is, you know, pursue your dreams. And both of these are equally bad advice. Pursue your dreams is like. Well, you're going to need some skills. Right. You're going to need a target. What's the destination? Is there a market need for that? Are there customers who you're solving a problem for or delighting? Like there's a lot of blocking and tackling.

between you and follow your dreams. Right. And it's also, there's going to be a lot of work you got to do outside of your dream to just survive while you're pursuing the dream. The amount of stupid jobs that I had when I was doing standup, like. Oh my God. What was the worst? Oh.

God, I mean, well, I mean, I did everything from bartending and waiting tables and all that kind of stuff, like some of the worst. Well, this was, I wasn't even paid for this, but to get on stage as an early comic, I used to have to stand outside for two hours a night in Times Square, rain, sleet, nor snow.

with those flyers. We call it barking, barking. That's what it was. And then eventually you'll love this as a, as a founder. I was like, wait a minute, why am I doing this every night for someone else? And I opened up two clubs and started my own comedy club sits six nights a week. I gave one to once.

second one became super successful i gave the first one to the guys that were kind of beneath me i kept a little piece of it but let them run it and then i ran it was the largest tgi fridays in new york city and on 49th and broadway yeah i know we took over the

downstairs yeah we turned into a six night a week two show a night comedy club and i split the profits with the other comics and genius and and that was purely as we discussed on your show earlier it was purely out of necessity i needed to get on stage and then i figured out a way to make And this is the sort of, like, you can just do things, which is now a catchphrase in Silicon Valley. You can just do things. Yeah. Like, there's generations who have been told, like, can't do that.

You can just do things. Now, I'm not suggesting you do things like Elizabeth Holmes and Theranos. You can bet rules. Right, right, right, right. You can even break rules. But if you do go the route of bending and breaking rules, like I have a sort of golden rule I have to teach young founders because they're like, oh, Uber broke the rules and Airbnb broke the rules. And I'm like, when they bent the rules, I'll go with bend.

And they bent the rules. Who benefited? You know, if you bent the rules on ride sharing, well, the people in Brooklyn who couldn't get rides or... If you were a black person in Brooklyn, in Manhattan, and you tried to get a ride to Brooklyn, you weren't getting picked up. You weren't getting attacked. You weren't taking the subway. It was like a known thing to the point at which they did reality TV shows, like showing this example. And if you.

were somebody who wanted to, you know, get an Airbnb or rent an extra room you had. Well, when Airbnb bent the rules around that, they reinterpreted the rules. They said maybe these rules don't. apply to this new category of inventory, well, who benefited?

People who couldn't afford to go to Tokyo got to go for the first time in their lives. Or people who could only afford to go to Manhattan for two days got to stay for 20. And the person who had the extra room got to make money and hit their rent or pay their mortgage. So you have to be careful.

You know, that you're bending the rules for the betterment of not just yourself, the enriching of yourself, but the enrichment of society. And you look at Elizabeth Holmes, when she broke all these rules around blood testing. She was putting people's lives in danger, sociopathic, insane, and it was to benefit herself. And she was lying to her investors, so she wasn't even to benefit her investors. It was strictly to maintain her own narcissism. And at the...

cost of, you know, the people's potential health. Like there are people who got low cholesterol readings or perfectly fine cholesterol readings who then got prescriptions for drugs based on inaccurate results. So imagine you...

took a blood test with some Silicon Valley company. Not to say, though, if you break the rules for the, you know, let's say the right reasons as you're laying out, you could still end up in a lot of trouble because you got taxi companies with their medallions not happy with you guys or you got big... Got the mob. Probably...

I mean, New York City real estate, probably not so thrilled about certain things. Yeah. You can still step into it. I would say, you know, Vegas was the one city that was like really shaky for Uber and Airbnb. It was, I think, New York. Like both of those, the hotels in New York, they really did not like Airbnb. And they blocked them to this day. And then Vegas was the last city to fall. And London. London was a hard one too, I think, because they had this great tradition with their...

you know, cab drivers who knew every nook and cranny of every little backstreet and had to take these tests. So there were a little resistance. Right. So the next thing you know, you basically have anyone, not anyone, but someone that passes. Was it a test originally? I think it was.

driver's license insurance so they didn't necessarily know every in and out of the i mean you know how to use google maps right like good enough that worked out pretty well i mean yeah you didn't have to like be good at small talk so

Okay. So you succeed in all these things. And then there's a whole bunch of you that all kind of came up at the same time that everyone sort of knows their names. And obviously you're on all in with some of these guys and everything else. One of the things that I've found super interesting over the last couple of years. is that when I was sitting down with...

tech people, particularly, and VC guys and just this other world that I wasn't in. I would sit down with these guys because they had built all these things. And what I always thought was interesting, and this was probably before you guys had all in, I was always like, all these guys kind of want...

And I don't mean that as a pat on my back, but I always thought it was odd. I sense that what they really want is a show. They made money, which is awesome. And a lot of times I was talking to guys when I had no money and I was like, God, you have the great... But then they would walk out of my house and I'd be like, I'm pretty sure what they really want was to have what I have.

Now you have both of those things and there's a lot of you guys that have both of those things. What do you make of that just sort of premise generally? I mean, one of the things that happened was our industry was under the radar.

So when I would go out in Los Angeles and I had the blogging company and this podcast, people would recognize me, you know, in tech or whatever. And I was like very micro, micro celebrity. But like, you know, one out of 100 people at a party might have heard of what I was doing.

In your world, you were known. Yeah. And, you know, one time I was out with Elon and they're like, oh, what does your friend do? And I'm like, oh, he's working on a car company and a rocket ship. And they're like, does he make movies? I'm like, no, I don't. Elon, do you make movies? He's like, no, I don't make movies. And they're like, okay, fuck you guys. And they just walk off.

These are known celebrities or whatever. And so our industry was very, you know, bespoke, tiny, in a large way irrelevant. Like you had Steve Jobs, who was larger than life. Larry and Sergey at Google were becoming...

A little bit of household names, but then they kind of went underground because they really didn't want to be, you know, public facing. They were more introverted, you know. What about Paul Allen? I really only know him through because he owned the Blazers. Yeah. And he liked to play guitars.

And he had like a bunch of people come over to his house and play dead shows and stuff like that. So he was awesome. I could definitely see that. That was like a Bill Walton connection there. Yeah. I just know musicians who used to go and play at his place in Beverly Hills. He had all these guitars and he just liked to jam with people. He was smart, you know, like I think he realized, oh.

I only have a certain amount of times around the sun, and I'm just going to make the best of it. And he had gotten sick early in life, so he valued life. And he was like, yeah, I don't need to be here for the 12th release of Windows. I can go do some other stuff. was largely under the radar. And the way we sort of integrated with the world was Steve Jobs would do a keynote, but not many people did that. You know, Steve was a showman.

And then you would speak at a tech conference, you know, once a year, there would be a tech conference twice a year. And then TED started. So, you know, it's like a third tech people at that. So we go to TED and there'd be 600 people there. It was still underground. It wasn't shared online.

And you got to press once in a while. So you had a PR person or you went to John Markoff at the New York Times or Wired and they wrote a story about you. And that was like the extent of it. And people were rooting for tech because tech was cool. Like, oh, I got an iPod. I play music on it. But it wasn't.

Your whole life wasn't mitigated by the tech industry. And really, you know, all of a sudden Google, you're like, yeah, I kind of live in Gmail. And, you know, I'm using Google all the time and they own YouTube and I'm kind of into that. And then really, I think Facebook was a major. moment in time when you know that people started to see the dark side of tech like oh this is like resulting in bad things this is taking a lot of people's time and

This guy doesn't seem to have the great intent with people. And you start hating people that you were so excited to reconnect with this person. Next thing you know, you're fighting with them about nonsense. Marriages are getting broken up. People, it's getting contentious. And really, social media, Facebook.

book, specifically Instagram, it started having like a certain toxicity to it. And then the world kind of started to turn on tech a bit. We went from like these nerds who are making cool shit that people could enjoy, but, you know, generally made people's lives better too. is this actually making my life better? It's kind of not. And I don't trust that guy.

And really, Zuckerberg was that guy, I think, that a lot of people were like, I don't know if I trust that guy. Now, Elon was a hero to people. Like, oh, it's making this electric car. It's going to save the planet. And yeah, wow, we're going to go to Mars? Cool. You know, it's just like very simple. People that hate him now thought he was the same.

I mean, I think, yeah, because he really, when he was doing Tesla, I mean, he went bankrupt, basically. He's been public about this. I'm not speaking out of school. He basically went bankrupt and a friend of ours was loaning him money to keep him afloat. And I famously had dinner with him one time and he showed me the Model S car on his phone. He was getting in the middle of his divorce and he's told the story publicly. And I was like.

I have a couple of million dollars I can loan you. He's like, don't bother. I'm done. Tesla's going to go out of business in two weeks. And I was like, really? And he's like, because I had seen in. gawker they said it was going to go out of business next month i said is it true and he's like no it's not true i was like oh thank god he's like we have two weeks not four

And I was like, whoa. This is like right before Christmas. Who did you take the money from? I don't know how I don't know this story. Well, we were at Bowie eating a steak, just the two of us. You were at Bowie on Sunset? On Sunset, yeah. It's literally the only thing from L.A. that I missed. That was my favorite restaurant. And it's the only place.

i go back two of us went there in our roadsters he had p1 or p2 the prototype and i had number 16 and he just had texted me like hey on our blackberries like to date this conversation let's have dinner um feeling kind of blue i need some company so i went in a dinner with him and he was like

Yeah, it's kind of like, what's going on with the rocket ship company? It's like, yeah, well, we blew two up. I said, well, what happens? When's the next launch? He's like, oh, the launch is coming next month. And I said, what happens if you blow that one up? He's like, SpaceX is gone. And I'm like, okay, well.

I got a couple of million dollars. I'll ship it to you on Monday and whatever. I'll loan it to you. And he's like, don't bother. Not necessary. I said, well, Elon, there's got to be some good news. And he said, yeah, actually, I got some good news today. I said, okay. And he takes out his black bracelet. Don't tell anybody. And he shows me the clay models of the Model S.

and he's flipping through it on, you know, and the black breaks, he used to have that little tripod thing and the ball. Yeah, that little thing. Yeah, and he's flipping through it, and I looked at it, and it literally was clay models, you know, like little clay, but I'm looking at it, and I'm like...

that's nicer than the Porsche. It's like, I've never seen a car. It looks kind of like a futuristic tourist or something. It's like, what is it going to cost? It's four doors and it's like a sedan. He's like, yeah.

He said, what should I call it? And I was like, I don't know. You call it like the Model T. He's like, yeah, we can't call it the Model T. He's like, we can call it the Model S because T is still, Ford still has the trademark. He actually looked into that. I was like, yeah, that's a pretty good name. Model S is good. Like ST, whatever, sedan.

i said what's it going to cost and he said i think i can do it for fifty thousand dollars i said if you can do that for fifty thousand dollars you'll change the world This company has to survive. And he wound up over Christmas in St. Bart's closing some funding from some friends of ours, and he kept the company alive. But when I got home, I went to my wife, Jade. I said, give me the checkbook.

And I wrote two $50,000 checks. And I said, dear Yolanda, great looking car. I'll take two. Love, Jason. And when did those get delivered? I sent it to him. I kid you not. He put it in his desk drawer. He didn't cash the checks because he didn't want to take the hundred grand and blow it. And I knew that would, like, maybe give him an extra day in payroll. And I told Jade, that hundred's done. We're never going to get it. But I wanted to, like, let him know I was in his corner.

And I kid you not, like three or four months later, the checks get cashed. He had handed them to somebody and said, here's the first orders. I got the first orders. Literally three years later. Your serial number reservation. 000001. 000073. So I called him and said, hey, Lon. I can't take number one. You got to take number one. Take number one. I got four of these prototypes. I got no garage space left. Right. He's probably don't have a number on them. And he said.

I want you to have it because you were the first person to order it. And it's like very important for me for you to have it. And then I had the 73 and I gave that to my friend, Sky Dayton, who had supported me. How did you drop all the way to 73? Well, he had other people who were investors in the company.

You were the greedy with the two. Yeah. Getting one and two would have been a little over the top. Anyway, I think he just said, like, put this at the end of the other orders. Right. So maybe there were another. Actually, that was probably what happened. You know, I don't know exactly. And I still have that car. And the car's worth like a million dollars. And it's going to go in the. Smithsonian. If the Smithsonian's listening, I got to find somewhere to put it. So that...

Well, that story actually perfectly kind of explains the thing that I was asking about, which is this weird thing of like, so it's successful builders who are good at these things and can take these risks and do all these things. And then the fame component has now come.

Yeah, I mean, it's the most famous person in the world. Which is, by the way, terrible. I mean, people, I think... you know oh i want to be elon musk it's like no you don't yeah he can't even go out to dinner like i'm like let's go to dinner i have this new place or let's go on a hike it's like his life is

like, living in a cage now. Like, it really sucks. And then with all this hate because he just wants to make the government more efficient, I can tell you, like, he has got a very... highly ethical moral mission he is on, which is he, like many of us on All In and other, you know, people who have, you know, been in and around this administration, I'm not part of it, but, you know, I'm around it.

I mean, we identified pretty early on the existential crisis for America is running out of money and this debt load. And thank God, you know, Trump and J.D. and everybody and Peter Thiel and everybody in that circle kind of. had the maturity and the courage to say, yes, that is an existential. Putting aside how you feel, Democrat, Republican, never Trumper, always Trumper, MAGA, none of that matters. We have a balance sheet that is upside down.

If you've ever known anybody or your family members who've been upside down with their mortgage payments or underwater or no job on, you know, that's America. And there's only one way out. Cut expenses or raise income. Austerity or income. And, you know, if we try to take too much taxes, then people stop working and, you know, we need more money to be going in the economy. And then if you stop government spending, well, that's not good for the economy. This is not going to be easy.

Just like losing 50 pounds is not going to be easy, but you got to do it at a certain point or you're going to die. There's a lot of comorbidities that could happen from all this. So I just think, you know, the stuff he's doing with Doge is. Unbelievable. And we really need to carry on that Doge spirit, you know, beyond this administration. The government should really be effective and it should not waste money. And the amount of corruption and grift.

from all sides of the aisle is unbelievable. What they found is going to be talked about for a long time. And yes, they're going to make some mistakes, cut too many people here, not cut enough people here, but you got to start somewhere.

Do you fear that him walking away, or at least maybe, I guess maybe he's doing one day a week or he'll always be somewhat involved, but that the bulk of him walking away at this point, that because he looms so large over everything, even though I've seen a lot of interviews with the dojo. guys and it's a really eclectic mix of what seemed like hyper capable people that you need someone like him and there's no one else like him to like actually continue the mission properly i think he can

parachute in and inspire people and keep them focused. It's going to be on Trump and JD to keep it a priority. And, you know, there are people around Trump. who I worry about. There were people in the first administration who I definitely worried about and what their motives were. And, you know, now I'm...

I kind of like Lutnik and Besant and Elon and Sachs. I was a close friend. You know, there's a group of people, Tulsi, who are around Trump, I think, who are either incredibly highly qualified. and or have incredible intent and don't need to be there

And so I'm rooting for them in a major way. You know, there's some people I think are like weird choices and suboptimal and picked for loyalty, of course. But, you know, overall, it's going to be up to Trump to decide what he wants his legacy to be. Does he want his legacy to be? you

you know, creating strife in the country and, you know, chaos? Or does he want it to be actually balancing this budget and getting the country fiscally back on track and uniting the country? Do you think there's any risk? This is not my position, but this is what you hear a lot.

that there's some sort of risk in having all of these like hyper wealthy people around. I'm like, this is the oligarchy magically appearing. One of the things that I loved from Linda McMahon, who took over Department of Ed, she gets up there in the first day, you know, she's a billionaire.

was like, I'm here to put myself out of a job. I thought, what a great thing for a public servant to say. But, you know, if you listen to the Bernie class or whatever, they're upset that, you know, he's got all these rich people around him. As if the Democrats wouldn't have done it or didn't do it. If you were talking about people who, you know, were the heirs of Walmart, and I don't know them, but I'm sure they're fine people.

If, you know, you are the second or third heirs of the Rockefeller family, I don't know, you're old money in some way. Like, yeah, maybe you'd be worried about that. Maybe they're entitled. Maybe they're not effective. Trump likes self-made people around him, people who started with nothing and kind of got there. And those kind of people tend to be, in my experience, very principled, and they're doing things for a reason.

I, you know, there are some things that have bad optics. You know, we're sitting here at the time when the Qataris are giving up, you know, giant plane that's worth 400 million. So there are things like that that the press makes a lot about. There's the Trump coin. Terrible optics. There's a bunch of things that have bad optics that I think they should clean up. And I think you probably agree. And many people in Trump land are like.

Can we please stop doing those weird things? Yeah. Well, as I said, there's all there's stuff on the margins, which I'm just willing. I think actually what I've learned now spending a couple hours with you, I think what it seems to me are like main differences. I'm a little more forgiving on the margin stuff than you are.

which I think is fine. It's just like a prism that you look through. The most charitable way to look at it is like Trump's going to Trump and, you know, it's going to be fine. Let's just look at the totality of the presidency. Fair enough. And, you know, I think the other side is like, oh, my God, he's Hitler. And, you know, we're spinning into this, you know, what's going to be Putin, you know? And it's like.

No, it's not going to be. Obviously, we survived Trump one. We survived Biden one. Well, some survived Trump two. But really, it's the opportunity. Is there an opportunity here to make government much smaller? As I've gotten older, I've started to appreciate this concept of states' rights. That there's this incredible feature in how this experiment known as America was constructed, which is the states compete with each other. And.

If you think California is devolving like I did, and I think you probably did as well. You're giving the Dave Rubin story now. Yeah. And I was like. This place is not where I showed up 20 years ago. When I got to California in 2002, I was like, this place is incredible. Look at the nature. Look at the people. Look at the opportunity. And then it was like, oh, yeah, we hate capitalism. We hate entrepreneurship. We're going to just let this.

cities burn. We're going to allow, you know, junkies to take over. And they're more important than the safety of your children and the safety of businesses. Like, it just doesn't make any sense. And you're like, what's going on here? And it's like, oh, yeah, there's a bunch of grift going on, whatever. And then you come to a high functioning city like Austin or you go to Miami and you're like, oh, my God, this is like, wait, a city can have less crime and you could run the city for the.

taxpayers and the citizens and the parks can be clean and oh yeah i i think i prefer this and watching new york devolve has just been tragic for me i grew up in the 70s and 80s And I remember it peaking under Dinkins, how dangerous it was. Yeah, I remember that. Then you had Bernie Getz shoot a bunch of kids on the subway because people were carrying illegal guns in the subway in Manhattan because it was so dangerous. And I was like a... going to school at that time in college or Fordham.

I was just like, I went back there with my kids and they wanted to take the subway and see how I got to Brooklyn or whatever. I took them on one subway ride. It was chaos. Homeless person, another person screaming and yelling. Three police went running down the... You know, platform, it stunk like urine. I'm like, we're going to get back in an Uber. Like, this is too risky for me to have three daughters on a subway platform where these people are high out of their skulls on meth or fentanyl.

What's going on here? And the cops have given up and the city seems to have given up on any just modicum of policing or stability. What do you think turns these things around? Because obviously.

A huge amount of people have left Cali. San Francisco was the hub of everything you're talking about. I mean, when I met with Elon the first time there, we stood in his office. I think I told you about this off camera, but we stood in his office, in the corner office, so he has a nice view of the city, and he's literally...

just do he was doing play-by-play it was kind of funny the way he was doing it as if he was watching a sporting event basically like they get the drugs there they do the drugs there they wander over there they fall asleep over there yeah it's like That's not supposed to be. I think people have to get sick and tired of being sick and tired. And then when you see the tax basis change over time, which has happened in New York and New Jersey already, from what I understand, all those folks moved to.

Florida because they were already going for a couple of months in the winter anyway. So it's like if you're down there for two or three months. No, the snowbirds just stayed. The snowbirds were like, yeah, I could just stay here and not deal with like the crime in Manhattan and this chaos. I guess.

My understanding is New Jersey and even Connecticut are having problems with their tax bases because there were some hedge fund people there who were paying a billion dollars in taxes. They're not there anymore. And that actually affects services. People have to get sick and tired, but I think it's a 10-year process and it's not a two-year process. And like this Karen Bass, you know, in Los Angeles and watching her operate in the world when she came back.

from her trip and she couldn't even answer questions from the press and she didn't come back in time. And then they could have had Rick Caruso, like the guy who created. The Grove and the Pacific Palace. It's like, these are beautiful institutions that I took my children to. Who had his own private fire department keep his freaking thing going. It's still standing when... Yeah, I mean, here's the crazy idea. Water. Yeah. Yeah. Like, and...

A private citizen can get 10 fire trucks filled with water and carrying basses in another country, like in, I don't know where she is. Ghana. Ghana. And like, what does that have to do?

with Los Angeles. Los Angeles has got serious problems. And she had been warned about the Santa Ana winds kicking up before she left. I mean, it's just complete disgraziade, as we would say, in Brooklyn. And like, it's so disgraceful. And I think people have to get sick of it. And you look at Rick Russo, why didn't...

Didn't they vote for a cruiser the last time around? Because he's a rich billionaire white guy. Yeah. Let's just call it what it is. Yeah. There's a bunch of liberal guilt that, you know, and people hate. entrepreneurs they hate billionaires they hate people who've made money guess what like are we like is this atlas shrugged who do you think built society right who's left who's left who wants to take the task of

building the fire department? Who wants to build a bridge? Who wants to do that? Who's capable of doing that? You know, there's a group of people who are capable of doing that. They're called entrepreneurs. They're fearless, dogged. 12, 14 hour a day people who just work and do the work and who are qualified. And we hate those people as a society. Like, open your eyes, folks. Do you think that's shifting the psychological part of that? It is. Yeah. I think once, you know.

Things can only go so far to where people say, like, that's enough is enough. And I think for Los Angeles, it's different for every city. Los Angeles, it was the incompetence of the fires. They could have avoided a lot. I mean, thank God people didn't. die at a much higher rate it was only a handful of deaths is what i understand yeah thank god but you know the the loss of property could have been avoided in a lot of cases i mean especially with like

And kind of make fun of me and Trump for this, but like Trump was right about raking. Yeah. It's so dumb. But like in California, I have a house up in Lake Tahoe. The brush just got out of control there and there would be fires.

Then Trump does this whole thing. There's a bunch of fires. He says, hey, you know, in Norway, they rake everything up. You know, it's like it's forestry, it's called. He's exactly right. Like, why are we doing that? It's like, oh, yeah, because we're incompetent. Then after all these fires and Trump says this, I go up to Tahoe. There are people in the woods around all the different ski houses and towns raking up.

Giant piles of stuff doing control burns and chipping it out. Same thing in Los Angeles. I saw it over and over again when I lived in Brentwood. People were letting their brush go crazy. And like you just have to change the roofs and everything and you can solve these problems. And for, I think, San Francisco, it is when your car is broken into for the third, fourth, fifth time, when you go to the store and you can't buy deodorant and it takes 20 minutes to buy a razor.

need to get a shave. And it's like, is this like some crazy dystopian Gattaca world or something? Yes. Or you're in New York. Yeah. And you get on a subway platform and like literally the week before I got there, three people were stabbed by one guy in one week. And I'm like, I can't go to my hometown. Someone literally raped a dead man on the subway. You heard that one? literally it was an illegal thought he was just mugging somebody and a guy turned out to be dead dead and then he raped him

I mean, trying to put that together. I mean, it just sounds like something from a horror flick. It doesn't even sound real. Yeah. And then somebody was lit on fire. I mean. What do you think that says about people's like slow motion ability to accept horrible things? Because the same day that I met with you on.

that first time because he's so busy he kept delaying the meeting i was so i got there at like two and every hour i was getting a text from his assistant it's gonna be an hour an hour an hour yeah finally i was starving it's about eight o'clock and i'm looking for a restaurant i was like anything but i could not find anything that looks safe. No tenderloin, no. So I texted Sax. Yeah. And I said, hey, I can't, I went to, what's a fancy steak?

chain that's over there. Not Ruth Chris, fancier than that. They have one in Malibu on the water. Oh, well, yes. That one, I'll get it in a second. Mastro's. Mastro's, great. So I see a sign for Mastro's, so I'm like...

all right, I'll go to Mastro's. Can't be like a homeless. They were literally making meth or Coke or cooking something outside. I was like, I can't do this. So I text Saks. I was like, is there anywhere around here that I can just get a meal without feeling I may be killed? He said, yeah, come to my house. And that's what I did. But that like.

That feeling that you're just, but yet you see people that are walking around as if this is all normal. There was like a contingent in San Francisco, which was very different than Los Angeles. You know, people were like... On the fringes, I think, incredibly liberal. And, you know, like I remember when I moved to Santa Monica in 2002, 2003 timeframe, they were like having a big fight over.

can homeless people sleep on somebody's storefront in their store, well, in the, in the well, like, you know, in the little, the vestibule, the vestibule basically. Thank you. And, uh, like all these, like, and they basically said yes, right? Yes. And it was like, well,

my dad owned a bar like that's ridiculous i gotta come out and clean the place and then chase the person so that's like a weird like liberal guilt kind of like oh like well what's the core problem here like they're addicted to drugs so if you treat them like homeless

You're not going to solve the problem because there are beds available. There's more beds than they need. This is about being on like a super drug. So you have to actually – it's mental illness. It's addiction. There's like other things you have to address. And so – you know, you accept when you pay for something, somebody told me this one time, incentives matter. And if you pay for something, you get more of it.

And what happened in Santa Monica, what happened in San Francisco is they just had the best deal in the world, the lowest economic price for fentanyl, $5 a hit, with the least policing. And I remember when I was looking into this because Sachs and I collaborated on getting rid of Chesa Boudin.

Oh, yeah. He started this or he worked with the recall program and I hired an independent journalist to write stories about the victims. So we kind of attacked it from our different skill sets. His was political. Mine was journalistic. And we just kept harping on like this issue over and over again in the early days of the podcast. And we got Chesa Boudin removed or the people there voted for it. But, you know, when you were watching this happen, you know, you're just like.

how on earth could anybody like allow this to happen? And San Francisco is filled with not just like liberals, but there's actually socialists and communists, like quite literal, like who believe. That capitalism is bad. One of them's running for New York City mayor right now. This guy Zohan or whatever his name is. So, you know, I.

I listen to some of these folks. There's a couple of podcasts like that are super anti-tech, super anti-capitalist. I listen to it to try to understand it and it makes no sense. Like they're literally like people who believe that. capitalism has to go away and i'm just like okay you're doing that from a podcast studio with an iphone and you're like got an internet connection like

None of this would have been possible without entrepreneurship and capitalism. But people are getting sick of it and people... This is the great thing. Back to that, like states' rights. I can live in any number of states. And what people also don't realize is the truly affluent creators in the world can move countries. And so...

If America doesn't solve this problem, and if a state doesn't solve this problem, people will move from one state to another. California, in our cases, to Texas and Florida. Great. And then people are also moving to Nashville. They're moving to Boulder. They're looking at places and saying, is there a higher quality of life? And for entrepreneurs to go to San Francisco is absolutely crazy. It's $3,000 or $4,000 a month per bedroom in the Bay Area.

People come here and they could own a home for $500,000, like a nice three or four bedroom home, just 30 minutes from where we are. So we're just starting to see people make more thoughtful decisions, I think, you know, and I think. overplaying your hand, which we're seeing like teachers and administrators and this grifting, like it is all true, you know, like it's all true. Like these cities are being run by incompetent grifters.

What country are the rich people going to go to if America doesn't work out? I mean, pick a country. Yeah? Really? Is there a list at this point? I mean, it's not like many countries are doing it better. I travel, and I can tell you, if you go anywhere— There's probably a secret one that they don't talk about.

I would say like, you know, like Peter Thiel's very publicly got land in New Zealand, right? So New Zealand is easy, like great place to be. But they were terrible under COVID. Yeah, I mean, they... Sure, they lock things up. But in terms of like delightful place to live where you can buy some land, great. And it's isolated. Yeah, if there was a nuclear holocaust, pretty great place to be. Pick one of the islands far away from everybody else. But, you know, putting aside like Armageddon.

You know, places like Italy and Spain and the MENA region, Dubai, Saudi, Singapore, they are all more than willing to offer you like a golden visa, a 1% tax rate, etc. Now, if you gave up your U.S. citizenship. And some people have. One of the founders, Eduardo Serevin, if I'm pronouncing this correctly, who left Facebook and he went to Singapore and he gave up his citizenship. So that's an extreme example. And you don't see many people giving up.

the passport. I don't think we're there yet. But if Florida and Texas don't hold, if Boulder and Nashville don't hold, and we see chaos in those places like we saw in those other cities, and those other cities don't turn around, I would not be surprised if people say, you know what?

I'll just live in another country. I mean, I love to spend time in Japan. It's like a pretty great place to be. But I want to see America work. Not that easy to get into Japan. No, but they will give you a 10-year visa, but you can't be a citizen.

You'll never be a citizen. Literally, the only way to become a citizen in Japan, from my understanding of it, is if you have some heritage, in which case they would love to have you come back because they're in population. Sounds pretty racist. Protecting their own culture. How weird. Yeah, I mean, if you want...

To fix immigration, it's pretty straightforward. It is. Like, they have a monoculture there. And you could describe it as racist, protectionist, I guess. I was being sarcastic. But it is. Yeah, but they're entitled to protect their culture. Sure, exactly. Putting aside race.

And like is citizenship a right to be a citizen of another country? Like in Saudi, you can't just go to Saudi and be a citizen, but they will give you a 10-year visa to work with them. So like there are other options. Other people would love to have people be citizens as is their right.

But, you know, the point-based immigration system is such an easy solution. That's something, like, when I watch Republicans and Democrats fight, I'm like, this is so silly. Like, just pick a number, guys. It's just a number. How many people do you want in each category? High skilled, no skill, and people who need asylum. Let's just pick three numbers, folks. You can debate the number, high, low, average it out. Just pick numbers.

It's not, doesn't need to be as charged as it is. How many people can we reasonably have seek asylum here? 250,000 a year, 0.1% of the population, 1% of the population. I think we should be trying to get to 500 million Americans. through immigration and through, you know, population. Well, since you went there, so then what do you want to do with the, let's say, 12 to 16 that are here that are illegal? If they are great citizens, I would give them a path to citizenship.

I would have them pay a fine for each of the 10 years they're here, and they can pay it off over 10 years. And if they speak English proficiently and they understand the Constitution and they... Pass all those tests. We allowed them in this country. And in fact, it was the Republicans who allowed them in this country by far. So you can complain all you want about Biden opening the border. They were all horrible. I mean, I don't know that it was more horrible than the last four years.

under NAFTA was to have an open border with Mexico so that we would have seasonal workers just pass through the southern border in order to work in fields. Like, literally, this was the Republican position, but 15 years ago, you can look at articles in the Wall Street Journal arguing

for the virtuousness of like, why wouldn't we let these folks? It's a constant underclass. Yeah. Yeah. How many Americans do you know that want to just get down on their knees and pick strawberries for us? You know, this is an entry level job.

that, you know, Americans don't want to take. Right. We have the lowest unemployment of our lifetime. And then ironically, you have Democrats now saying, OK, we need them to pick our fruit. But it's like the robots are starting to do that. And then what are you going to do with all these people? It's a very simple thing.

The idea of deporting 20 million people is farcical. It's a lie by Trump. It's a lie by Bannon. It's a lie by Steve Miller. They're just doing that to feed the MAGA base. It's red meat for them. They're deporting a couple of hundred people a day, which is...

thousand or two a week. At the end of this year, they'll have done no more than 500,000 in their first year. That means they'll probably do an Obama-level deportation of a million or two million people, primarily people who have felonies or misdemeanors.

have done bad things here. The rest of them are immigrants like us. You might have been here, your parents might have been here for five generations. I'm seventh generation. Great-grandparents on both sides. Great-grandparents, yeah. And it's like... Yeah, this is a country of immigrants for immigrants. When Stephen Miller says America is for Americans and Americans only, that's like the kind of trolling that this group does to kind of trigger people. America is for immigrants.

by immigrants and should be welcoming of immigrants. And if we welcome these immigrants already under multiple presidencies across multiple parties, the compassionate thing to do is give them a path towards citizenship. And if they are good actors and they're willing to pay because they're already paying into Social Security, they're paying for Medicare, they're paying for a lot of these services that they're never allowed to tap unless they become citizens. So let's give them a path, right?

I don't want to end on politics. What do you think? Tell me why I'm wrong. No, I'm largely there. I'm not for kicking out somebody. Well, no, I'm not. I would say this. I'm not for kicking out as a blanket rule someone that's been here for 20 years that's law-abiding, that has a family. About five years. Yeah. Or even... I don't know. You have to pick a cutoff at some point. So it's all sort of arbitrary. So I don't know. Let's say five years. If you've been here five years.

I'm not fully proposing this right this second. But if you've been here, let's say, five years and you've been here and you haven't broken any laws and you have a job and you, let's say, have a family and you've paid taxes and something, there's something that we can do. I like what you said about that.

been here a certain amount of years, then you can pay it back a certain amount. So there's something that has to be played with there. And what we're not good at as a country really is dealing with the nuance of that. Am I just going to like kick out everybody? Like I know. Do you know how much of a cost? Well, the cost.

The chaos afterwards and the shredding of a portion of our social contract, even if there are illegal. Yeah, it's messy. It's messy. We have 7 million open jobs right now. We have... The lowest unemployment of our lifetime. It's 4%. The only reason everybody in this country doesn't have a job is almost universally, you know, aside from people who don't want to work. Right.

or don't want to work in certain jobs. It's because their job is not in their geography and they don't have the money to move. And that is actually an issue in the country. Like if you could move people to a different region. you could get them employed. So there is, there should be some, actually, there could be some opportunity there to pay for people to move from one region to another if they, you know, and they could get a job or giving them a loan to do that.

Putting that aside, then it tends to be skills. And skills are freely available on YouTube and, you know, Gemini and Grok and ChatGPT. It's almost no skill you... can't learn in a couple of days or weeks on uh you know the internet so we are doing so well if we were to deport you know

Even 10 million people or 5 million people would cause massive chaos, massive expense in this country. And it would be completely against the soul of America to allow these people to come here, to use them for their labor that we're unwilling to do. and then to savagely deport them because, I don't know, you don't like Biden and you think he did the wrong thing by opening the border?

America did that. You know, it's interesting. I think most Republicans, by the way, I think would get on board what you just laid out there if they saw the crime and the drugs drop. So if the Democrat run cities, if New York and Chicago and L.A. and Portland and Seattle, blah, blah, blah. If they could get that more under control, which they still, even now, Eric Adams, who's kind of coming around, he's still doing so much wrong.

Yeah. So it's like, if they could get that more under control and then people could get back to that more normal life, I think a fairly moderate plan like you just laid out there or a thoughtful plan actually would make sense. But until... people don't see the crazy subway videos anymore or dead people don't get raped on the subway, et cetera. I just think there's just no chance for that. Americans commit far more crimes than immigrants.

Immigrants almost universally keep their heads down. I know they say that. It just doesn't matter. It doesn't feel that way optically. Yeah. You see these. Yeah. It feels worse to people when they see an immigrant commit a crime. You know, if an immigrant speeds or steals it.

Hurts more than to most people than maybe, you know, an American doing it, which I understand to a certain extent, like maybe you feel like you have a little more rights here to break or bend the rules and whatever. But, you know, there's. I think what's nice thing about you and I talking is like there is a moderate.

path forward, you know, and that's what I've tried to do on all in as like the most left of the group. It's like three people who are either in the administration around the administration or super right wing. And, you know, I'm I think people try to make me into a lefty, but. kind of living in Texas on a ranch with a, and I carry a gun. I mean, I'm kind of not a, I'm not carrying a gun right now. Right, right.

I mean, I might be. You never know. It's my right. No, no. Whatever you want to do. It's fine. It's fine. I mean, you can carry a gun. I'm not ending on immigration and I'm also not ending on January 6th. So I'll give you just like an open one to end this on. And we will definitely do this again, which is.

So what, what is exciting to you now? Like, what are you, what are you looking at right now that you're either business or personal or just that you're just like, yeah, this is awesome. And I want to be part of this. The entrepreneurial spirit is alive and well with like this new generation, I think, and people are starting to reverse COVID. We have a generation now.

got lost in COVID and social media. And it really polluted their brains. And it really impacted them in a negative fashion, missing college, missing formative years in high school, being too addicted to Instagram and Snapchat or whatever. But I'm seeing a lot of young folks who are saying, you know, I want to be in an office. I want to build something. I want to be part of something. And so I encourage young people.

to start companies with like-minded people, to start projects, and to just have the courage of their own conviction to build things in the world. And I think there's like a renaissance coming of young people who realize, oh. Elon created a rocket ship company. I can do that. Oh, Shane created Polymarket. I can do that. I can go out and just create things. Travis created Uber. Vlad created, you know, Robin Hood. You created your media empire.

There's nothing stopping you. And I think this group of young people, we're going to see entrepreneurship and capitalism and the celebration of creation and even wealth accumulation. There's nothing wrong with that. In this country. But overwhelmingly, when somebody gets rich, you know what they do with their money? They give it away. That's the tradition in America. The tradition in Europe and other countries is, I have to create a family wealth system and it's got to trickle down.

In this country, people were like, yeah, I don't want to give my kids. I don't want to ruin my kid's life by dumping money on them. They can either work for the family business or they can. Right. They usually become a drug addict. Yeah. I mean, everybody knows it's like not a good idea. Yeah. The amount of money given away and the amount paid in taxes by our billionaire class, by our great companies is extraordinary. It dwarfs what everybody else has given.

What Bill Gates will give away is greater than 90 percent of the country's given way. His should probably be taken away. Well, I mean, listen, you could have your issues with him. I don't know what's in the Epstein files. That's up for you. I actually meant that more just because of his COVID stuff. There's probably some others out there too. I don't know all the details of that. That's all speculation.

man, just be excited, you know, for young, I'm so excited for young people to be able to use all these new tools, AI, et cetera, and to look at Gen X and our generation. We started with that, you know, on my podcast when you came on and we were talking about being Gen Xers. We were these free range kids.

who had a doggedness in the world, a fearlessness, and we were a little bit punk rock and we wanted to create things. I'm seeing that in this next generation. I'm meeting 20 year olds, 15 year olds, 25 year olds who are like, you know what? Yeah, I'm going to go for it. I'm going to make something. I heard about this. company, I can do better. That spirit's coming back to America. I don't think it ever left. I think we just had this weird fever dream for a decade where we didn't...

understand how valuable the creator class was. And now it's coming back and it's stronger than ever. And if you're creating a company, just email me, Jason at Calacanis.com for life. Tell me what your idea is. I'm happy to hear it. All right, wait. Now the bonus one is, why don't you at least partly own the name? Thanks.

Here's the problem. As my net worth has gone up, the value of MBI branches have gone up faster. You couldn't get the Mavs when Cuban was selling or something? I mean, listen, these things used to cost a couple hundred million. I could have made a play to own a piece of one, but, you know, I don't know.

The Boston Celtics went for six billion dollars. Is that right? Yeah. So is it not worth it to you to own like some tiny percentage just to be like, you know, if I could buy one percent of the Knicks, I would do it. Yeah, sure. I mean. And I guess I could technically. So, you know, if James Dolan is listening, if I could buy one. Were you just waiting for someone to give you that idea? I mean, it seems fairly obvious. Right now, I like to keep it very simple. I...

You know, you asked me before, like, what's next in your life? I love working with founders because they have this great energy. And then just selfishly, there's only like, you know, outside of my family and my professional life, there's only two things I do for myself. I like to go skiing. In Japan, I do like 30, 40 days a year of skiing. And yeah, I like to see my necks in the playoffs. And you got that right. And I got both this year.

One of the most important things in life is to, you know, if you're working hard with a group of friends and you happen to make it, just. Enjoy yourself a little bit on the margins. Like you work pretty hard. I hope you do something that you really enjoy. I disappear every August. I told you. I mean, it's so great. Your August disappears like such a great thing. And when your kids are a little older, it's going to become so special. Like when they.

Those memories, I always talk about, like, at the end of our lives, I think what we have is like a collection of memories. You know that scene from Blade Runner when Rucker Hauer's on the roof and he says— I just watched it again, like— It's incredible. And he just says like, you know, all of these memories will be gone like tears in the rain. Like, that's how I live my life. I just think, what are the memories I can create?

This week with my friends, I have like some of the most epic memories of these things. And yeah, they're all going to be gone. So you might as well just accumulate a bunch of them and enjoy them. And, you know, I think like I'm taking notes on your August concept. I think I'm going to do it in January. I'm bored, man. I'm going to do it January in the second. When's the last time you did three days without a phone? Three days. Two days.