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

Summary

Podcast Summary: The Rubin Report – "When Elon Went Broke, the Dark Side of Podcasting & Tales from the Tech Trenches | Jason Calacanis"

Release Date: May 31, 2025
Host: Dave Rubin
Guest: Jason Calacanis

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1. Introduction and Early Interactions with Elon Musk

Timestamp: 00:00 – 01:12

Jason Calacanis recounts his initial interactions with Elon Musk, highlighting a pivotal moment where Elon considered shutting down Tesla. Calacanis offers financial support to keep Tesla afloat, emphasizing his ability to identify winners early on.

Jason Calacanis [00:30]: “If you can do that for $50,000, you'll change the world.”

2. The Emotional Impact of Early Success

Timestamp: 00:30 – 02:48

Calacanis shares a personal anecdote about selling his company and the emotional response it elicited. Despite achieving financial success, he felt an unexpected sense of overwhelm and vulnerability.

Jason Calacanis [02:13]: “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.”

3. The Evolution of Media: From Zines to Podcasting

Timestamp: 06:01 – 10:48

Calacanis delves into his passion for media, tracing his journey from creating zines in the 80s and 90s to recognizing the potential of blogging in the early 2000s. He credits the founders of podcasting, Dave Winer and Adam Curry, for revolutionizing content distribution by eliminating gatekeepers.

Jason Calacanis [09:54]: “If you control the medium, you have that power. You can define reality.”

4. Entrepreneurial Philosophy and Investment Strategies

Timestamp: 17:15 – 20:04

Discussing his role as an angel investor, Calacanis explains his approach to funding startups. He emphasizes the high-risk, high-reward nature of early-stage investments, where the majority fail, but a few unicorns can yield substantial returns.

Jason Calacanis [19:14]: “One in 200 wind up having these kind of crazy outlier 500x, 5000x returns.”

5. The Psychological Effects of Fame in Podcasting

Timestamp: 14:47 – 16:15

Calacanis reflects on the concept of "asymmetrical intimacy" in podcasting, where listeners feel a deep personal connection to hosts. This relationship can lead to fans projecting significant emotional impact onto the host without having met them.

Jason Calacanis [15:51]: “It's this cathartic moment ... an incredible emotional experience for people.”

6. Building and Leading Teams with Diverse Talents

Timestamp: 21:54 – 23:18

Calacanis discusses the challenges of leading teams composed of highly competent but sometimes difficult individuals. He praises Elon Musk’s ability to process complex issues swiftly and outlines the importance of having a clear vision.

Jason Calacanis [21:54]: “He has got a very highly ethical moral mission.”

7. Reflections on Wealth, Purpose, and Personal Growth

Timestamp: 24:03 – 27:38

Calacanis shares his personal journey from financial insecurity to wealth, highlighting the psychological shift that accompanies financial stability. He emphasizes the importance of finding purpose beyond money and staying grounded despite success.

Jason Calacanis [24:55]: “I felt my chin, and I was like, oh, my God, I'm crying.”

8. The Decline of Major Cities and the Rise of Alternatives

Timestamp: 37:59 – 53:25

A significant portion of the conversation centers on the socio-economic decline of major cities like San Francisco and New York. Calacanis critiques the mismanagement and policy failures leading to increased crime, homelessness, and economic instability. He contrasts this with the rise of cities like Austin and Miami, which offer better quality of life and opportunities for entrepreneurs.

Jason Calacanis [53:37]: “Who do you think built society right? Who's left?”

9. Immigration Policies and Economic Impact

Timestamp: 61:02 – 68:59

Calacanis presents a nuanced view on immigration, advocating for a balanced approach that includes a path to citizenship for law-abiding immigrants. He argues that immigrants contribute significantly to the economy and fill essential roles that are often unfilled by native-born citizens.

Jason Calacanis [65:00]: “America is for immigrants by immigrants and should be welcoming of immigrants.”

10. The Future of Entrepreneurship and Technological Innovation

Timestamp: 70:34 – 75:08

Calacanis expresses optimism about the future of entrepreneurship, especially with the advent of AI and new technological tools. He encourages young people to pursue their innovative ideas and highlights the importance of building communities around shared passions.

Jason Calacanis [72:31]: “There's a renaissance coming of young people who realize, oh, Elon created a rocket ship company. I can do that.”

11. Personal Anecdotes and Closing Thoughts

Timestamp: 75:08 – End

In wrapping up, Calacanis shares personal interests such as skiing and his love for the Knicks, emphasizing the importance of creating meaningful memories and maintaining a balanced life despite professional engagements.

Jason Calacanis [75:43]: “What are the memories I can create this week with my friends?”

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Key Takeaways:

• Identifying Potential: Calacanis demonstrates a keen ability to recognize and support high-potential individuals and companies early in their development stages.

• Media’s Evolution: The transition from traditional media to blogging and podcasting has democratized content creation, allowing individuals to build communities without gatekeepers.

• Entrepreneurial Resilience: Success in entrepreneurship requires not just innovation but also resilience in the face of frequent failures.

• Socio-Economic Critique: Major urban centers are facing significant challenges due to policy failures, while alternative cities are emerging as new hubs for innovation and quality of life.

• Balanced Immigration: A fair and pragmatic approach to immigration can bolster the economy and address labor shortages, benefiting both immigrants and native-born citizens.

• Future Optimism: Despite current challenges, the entrepreneurial spirit remains strong, fueled by technological advancements and the next generation’s drive to innovate.

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Notable Quotes:

1. "If you can do that for $50,000, you'll change the world."
   — Jason Calacanis [00:30]

2. "Content is really about community."
   — Jason Calacanis [10:48]

3. "Podcasting is about no gatekeeper, nobody telling you what you can say or not."
   — Jason Calacanis [08:06]

4. "We have to cut expenses or raise income."
   — Jason Calacanis [45:31]

5. "America is for immigrants by immigrants and should be welcoming of immigrants."
   — Jason Calacanis [65:00]

6. "There's nothing stopping you. Email me your idea."
   — Jason Calacanis [72:35]

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Conclusion:

In this compelling episode of The Rubin Report, Jason Calacanis offers deep insights into the intersections of entrepreneurship, media evolution, and socio-political issues affecting major urban centers. From his early recognition of Elon Musk’s potential to his critiques of current immigration policies and his optimism for the future of technology and young entrepreneurs, Calacanis provides a multifaceted perspective on navigating and shaping the modern landscape. His blend of personal anecdotes, investment wisdom, and socio-economic analysis makes for an engaging and thought-provoking conversation.

Transcript

[Jason Calacanis]

And so I told Elon, like, when I. 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.

[Joe Rogan]

Oh, God.

[Jason Calacanis]

And he shows me the clay models of the model S and he's flipping through it. You know, on the black brace, he used to have that little track pad thing. And he said, I think I can do it for $50,000. I said, 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.

[Joe Rogan]

That's your mutant power.

[Jason Calacanis]

That' 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, no. What do you mean? This is incredible. She goes, you're crying. I said, I'm crying.

[Joe Rogan]

Wow.

[Jason Calacanis]

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. 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? See asylum here?

[Joe Rogan]

All right, Jason. That's what I'm going to call you, Jason on Twitter. Slx. 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. You 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 ear. It was going to be a very strange.

[Jason Calacanis]

It could have gotten weird real quick, but welcome to Austin.

[Joe Rogan]

Thank you. It's good to be here in Austin.

[Jason Calacanis]

Yeah. You got a lot of friends here, apparently.

[Joe Rogan]

I have done 87 shows today, but.

[Jason Calacanis]

Absolutely.

[Joe Rogan]

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?

[Jason Calacanis]

My. How is my day? I always like to answer this question sincerely.

[Joe Rogan]

Yeah, we'll get to the instance here.

[Jason Calacanis]

We'll get to the instance of later. You know, I said when uber stock hit 88, that I retire, and it hit 88 the other day because it's just a lucky number In Chinese culture and culture and gambling. So I sometimes buy in for $8,800 when I, you know, I've had a casino, $8,888 just for fun.

[Joe Rogan]

It had nothing to do with the DeLorean in 88.

[Jason Calacanis]

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 Jayson Tatum, I guess, ruptured his Achilles minute, but we would have beat him anyway. 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 see a Knicks championship and. And be really rich and not have both of. One of those things has happened and the other hasn't.

[Joe Rogan]

You. Oh, yeah, exact. But you. But there have been moments we were talking. So we'll do a little basketball stuff and how it connects us. And you're also. You were born in Brooklyn too, right?

[Jason Calacanis]

Born in Bay Ridge Brooklyn, which is the last exit of. 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.

[Joe Rogan]

Yeah. So I. I was born in Benson Hurst. 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 at 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, really? And an investor that I guess ended.

[Jason Calacanis]

Up doing politics, got dragged into it.

[Joe Rogan]

And yet it seems to me very clear that both of our love really is basketball. So we're still in the wrong line of work.

[Jason Calacanis]

Absolutely. You and I should be doing commentary. We should just be doing sideline reports. You could be col. I could do the color commentary. You could do the play by play.

[Joe Rogan]

You know, there was an incredible startup years ago, years ago. I don't remember what it was called. It was like simulcaster or something like that. They dropped 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. Do you know the company?

[Jason Calacanis]

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 with soccer, football in the UK and everywhere in Europe where they have Fan TV and this broke out on YouTube and there's one called Knicks Fan TV and I'm friends with CP who runs it and you know like local sports radio used to listen to. So after every game he has 3, 4, 5,000 die hard knick fans who listen to commentary after the game. And maybe five or six years ago when the Knicks were winning 15, 16, 17 games a year, there were a.

[Joe Rogan]

Couple really it was pretty brutal.

[Jason Calacanis]

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 then 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 the audience becoming part of the show.

[Joe Rogan]

Yeah.

[Jason Calacanis]

And for the fans, by the fans is what CP calls Knicks fan tv. And it's become like a little business and it very much reminds me of what you were doing, doing like with your fan base or our fan base here at this week in startups and all in 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, 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 they as their talent will take them.

[Joe Rogan]

Talent, little hard work, little bit of luck. Do you percentage those out like talent, hard work, good luck, connectivity, location?

[Jason Calacanis]

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 got, I saw zines at Tower Records on lower Broadway in Manhattan and there was a little section.

[Joe Rogan]

There that's got to be gone. Oh, that's gone for decades, long gone.

[Jason Calacanis]

But that, you know, place where people would go and look at records and you'd meet people. It's 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 craze. You're in the Frankie Valley section, you might be other.

[Joe Rogan]

There you go. I thought you were going to make a gay joke.

[Jason Calacanis]

It was okay, wasn't a gay joke, it was a, it was a 50s door joke.

[Joe Rogan]

I can, I like those better in.

[Jason Calacanis]

The Frank Sinatra section you might be no, bitty, you never know.

[Joe Rogan]

Exactly.

[Jason Calacanis]

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. And there was one 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 there was only. 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.

[Joe Rogan]

Yeah.

[Jason Calacanis]

They were next to Spy magazine and Esquire and the New Yorker. And I 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 eighteen hundred dollars 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 for Total New York, one of the first Internet websites. And there were probably 200. And I had about three 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.

[Joe Rogan]

You wrote the entire thing.

[Jason Calacanis]

I had a couple of friends write a couple of stories.

[Joe Rogan]

Yeah.

[Jason Calacanis]

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 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 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 had started. There was one called Boing Boing, if you remember that Cheny 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. Oh, that's 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, Bleecker Street. You just take out your guitar and you go, yeah. 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 the studio that we're sitting in, the lights, the cameras, the microphones, the audio software, the lighting, you know, the. You know, these cables I have set all that up.

[Joe Rogan]

You mean all the tons of time? All the stuff's plugged in?

[Jason Calacanis]

All the stuff that's plugged in.

[Joe Rogan]

I don't know what's going on here.

[Jason Calacanis]

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%. 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. 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 year.

[Joe Rogan]

What year was that?

[Jason Calacanis]

2003 or four.

[Joe Rogan]

Yeah. Cause I started a podcast around 2005 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 gonna put it up now. But I didn't even 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 knew I knew I could do this.

[Jason Calacanis]

Yeah, you're good. You're good. You're a good talker.

[Joe Rogan]

Yeah.

[Jason Calacanis]

Podcasting, the name isn't from, like pods of Wells, which people think.

[Joe Rogan]

Right.

[Jason Calacanis]

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.

[Joe Rogan]

Yeah.

[Jason Calacanis]

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.

[Joe Rogan]

It's interesting because timing wise, that's also probably around when Stern was leaving AM radio. Right. He went to Siri coming out, but. So he went the other route. But it still had the same bones of you'll basically.

[Jason Calacanis]

And Adam Carolla gets a lot of credit because he took Adam Carolla took Stern's 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.

[Joe Rogan]

Oh, Green.

[Jason Calacanis]

Yeah, Green.

[Joe Rogan]

Tom Green.

[Jason Calacanis]

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 me as a young adult.

[Joe Rogan]

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.

[Jason Calacanis]

Yeah, I mean, it's. There was something very charming about the early days of it when there was only a hundred people or a thousand people listening, because it was much more freewheeling, you know, and, you know, heavy is the head that wears the crown kind of situation. Like, 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 because I, you know, fame, even the micro fame that we have, I consider, like, podcasting fame.

[Joe Rogan]

Microfam, I don't want any more fame. I always. I'm just like, whatever I have right now is good enough.

[Jason Calacanis]

That's not. Everybody's built for it is what I've learned. I'm kind of built for it because I like people. I'm a super extrovert. When I took the Myers Briggs, which is known as astrology for men.

[Joe Rogan]

Right.

[Jason Calacanis]

I knew you'd like that joke.

[Joe Rogan]

Yeah, yeah, yeah.

[Jason Calacanis]

I was like, entj. Yeah.

[Joe Rogan]

Years must have been off the charts.

[Jason Calacanis]

Well, I was 94% extroverted the first time I took it 20 years ago. And then 10 years ago, I did it at an off site and I was 100% and 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's like, have you taken the test? I was like, yeah, like 10 or 15 years ago. And she goes, oh, it's. It's changed. She goes, I just. I've only seen that one other time, like, 100% extroverted.

[Joe Rogan]

So I love what happened to that guy.

[Jason Calacanis]

I don't know. Donald Trump. Look at you.

[Joe Rogan]

You have more in common with him than you think.

[Jason Calacanis]

Perhaps. Perhaps. And, 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.

[Joe Rogan]

Ye.

[Jason Calacanis]

Uh, Then, you know, you. 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 daily, and there's something about getting to daily, 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.

[Joe Rogan]

Yeah.

[Jason Calacanis]

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, at D Day. Like, it just opens up this incredible emotional experience for people. I find that absolutely pleasant and cool.

[Joe Rogan]

It's incredible.

[Jason Calacanis]

Yeah, it's incredible.

[Joe Rogan]

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. And then. Yeah, yeah, yeah.

[Jason Calacanis]

I have to brace for impact, because people say, you don't remember this, but you had this profound impact on my life. And I'm always like, I hope in a good way.

[Joe Rogan]

Yeah, right.

[Jason Calacanis]

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 and 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, and 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, I did actually, but I never did. Or even worse, I did and you never responded to me.

[Joe Rogan]

Or how often do you get hit up at the airport where they try to pitch you right then and there?

[Jason Calacanis]

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.

[Joe Rogan]

Right.

[Jason Calacanis]

So I would just always tell permission to be candid. And they're like, or would you like me to sugarcoat it?

[Joe Rogan]

And what are the percentages here? How often do you.

[Jason Calacanis]

100%. Do they want me to be candid?

[Joe Rogan]

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.

[Jason Calacanis]

Call about, oh, to have a follow up call. That could be 5% of the time. Yeah, it's like, 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 or things outside of high growth companies like Uber or Robin Hood 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. So the brain chemistry you have to have for this job is like going up to an archery setup and you split the arrow right on your second arrow and they say, give me another hour.

[Joe Rogan]

Yeah, let's keep doing this, I'm going.

[Jason Calacanis]

To do it a third time. Like, that's the odds. One in 200 wind up having these kind of crazy outlier 500x, 5000x, 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 a unit, 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 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.

[Joe Rogan]

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 that I work like? And how often does that happen where it's like you're not sure about the product, but you just love the person?

[Jason Calacanis]

Like, yeah, it's like two really good questions in there.

[Joe Rogan]

I only get three per episode. So this is it, the rest of it.

[Jason Calacanis]

So he used a lot. He was referring 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 gonna crush it. Nobody else sees the sign. I think it's like almost like being a mutant, like in X Men or something.

[Joe Rogan]

That's your mutant power?

[Jason Calacanis]

That's my mutant power is like I don't have some crazy superpower myself other than I can ident the other mutants and I can help the other mutants. So it's kind of like a Professor X, say Professor, Kind of like a cerebral kind of thing. Because the people who do change the world, they, they. They are very difficult people. They're challenging. They. They argue. They're not perfect. They're awkward. You know, sometimes they're on the spectrum. Sometimes people would describe them as 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.

[Joe Rogan]

Even though we grew up at a time where everyone was told, don't get in a car with a stranger.

[Jason Calacanis]

Of course. Yeah.

[Joe Rogan]

Don't get in a car when a stranger with a stranger went from. Get in a car with every stranger.

[Jason Calacanis]

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.

[Joe Rogan]

Yes.

[Jason Calacanis]

Yeah, stewardess at the time. Flight attendant came to me, and, you know, I 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, we don't take tips. And she dropped it in my lap.

[Joe Rogan]

Wow.

[Jason Calacanis]

At which I said, I'm so sorry. I'm from Brooklyn. We tip everybody. It's quite charming. You don't need to tip us. And 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.

[Joe Rogan]

Did you ever see My Blue Heaven with Steve Martin?

[Jason Calacanis]

Yes.

[Joe Rogan]

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.

[Jason Calacanis]

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. But the first part of your question is, like, well, what makes you tick? Right? Like, what makes Johnny run 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. And 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 Bay 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.

[Joe Rogan]

Was famous first. That's the way you said it.

[Jason Calacanis]

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 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. Yeah, refreshing and refreshing. You know, this is online banking in the early 2000s, and it takes, like, you know, a couple seconds minute 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, no. What do you mean? This is incredible. She goes, you're crying? And I said, I'm crying.

[Joe Rogan]

Wow.

[Jason Calacanis]

And I felt my chin, and I was like, oh, my God, I'm crying. She goes, why are you crying? Like, you made 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. So when you and I grew up in the boroughs, there was a term B and T. Yeah.

[Joe Rogan]

Bridge and tunnel.

[Jason Calacanis]

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 and T. They wouldn't let you into a club if you were in Brooklyn. Literally, they would just go back to Long Island. In your case, right, you're in Long Island. Like, that's even worse than being from Brooklyn. That's further out. You just throw your ID back in your lap.

[Joe Rogan]

Exactly.

[Jason Calacanis]

Of course, I got a fake ID for an NYU ID from St. Mark's Place for 10 bucks. 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. And I 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 gonna 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 go to the back of the Fort way, 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 movies, so one person bought a ticket, went in. We just always had an angle. We had an angle. And so that's what got me through the first 20 years. But after that, you're gonna wind up. And I tell this to entrepreneurs. Cause I've seen it happen over and, and once you've made much more money than me, you know, you, you, you, 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 me. 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.

[Joe Rogan]

How did it change you? So you go from not having anything, then 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 not just that you have more.

[Jason Calacanis]

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. Then it 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, 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.

[Joe Rogan]

Yes. And it was like the funnest part of all of this.

[Jason Calacanis]

We, as Elon and I, 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. Like, but we all have to do our chores. This fun stuff like launching rockets or building podcasts. And then there's chores. Yeah, 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. 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?

[Joe Rogan]

There's going to 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.

[Jason Calacanis]

Oh, my God, what was the Worst.

[Joe Rogan]

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, and give those flyers. We call it barking. Barking. That's what it was. And then eventually, you'll love this. 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. Six nights a week. I gave one to. Once the 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 on 49th and Broadway. We took over the downstairs. We turned it into a six night a week, two show a night comedy club, and I split the profits with the other comics.

[Jason Calacanis]

Genius.

[Joe Rogan]

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 money around it.

[Jason Calacanis]

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.

[Joe Rogan]

Yeah.

[Jason Calacanis]

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, like, you can bend rules, 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. 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. When 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.

[Joe Rogan]

You weren't getting attacked.

[Jason Calacanis]

You were 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. 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 enriching, 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 were 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.

[Joe Rogan]

Like, 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.

[Jason Calacanis]

Yeah, you can still step into, 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. Yeah, they really did not, like.

[Joe Rogan]

Yeah, I remember.

[Jason Calacanis]

And they blocked them to this day. And then Vegas was the last city to fall. And London. Yeah, London was a hard one, too, I think, because they had this great tradition with their. Or, you know, cab drivers who knew every nook and cranny of every little back street and had to take these tests. So there were a little resistance.

[Joe Rogan]

So next thing you know, you basically have anyone, not anyone, but someone that passes. Was it a test originally or how.

[Jason Calacanis]

Do people, I think it was, like, have a driver's license, insurance.

[Joe Rogan]

So they didn't necessarily know every in and out of the.

[Jason Calacanis]

I mean, you knew how to use Google Maps, like, good enough.

[Joe Rogan]

That worked out pretty well.

[Jason Calacanis]

I mean, yeah, you didn't have to, like, be good at small talk.

[Joe Rogan]

So. 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 found super interesting over the last couple 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 to be me. And I don't mean that as. Mean that as a pat on my back. But I always thought it was odd. Like, I. I sense that what they really want is a show. Like, they have. 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 greatest life ever. But then they would walk out of my house.

[Jason Calacanis]

Yeah.

[Joe Rogan]

And I'd be like, I'm pretty sure what they really want was to be. To have what I have.

[Jason Calacanis]

Yeah.

[Joe Rogan]

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.

[Jason Calacanis]

Yeah. 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 a hundred people at a party might have heard of what I was doing.

[Joe Rogan]

In your world, you were known. And then that.

[Jason Calacanis]

And I, 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 rocket ships. 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, you guys. And they just walk off. You know, 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.

[Joe Rogan]

What about Paul Allen? I really only know him through because he owned the Blazers and I loved.

[Jason Calacanis]

Clyde the Glide, and he liked to play guitars. And he had, like, a bunch of people come over his house and play Dead shows and stuff like that.

[Joe Rogan]

So, you know, he was definitely. See that. That was like a Bill Walton connection there.

[Jason Calacanis]

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 this, 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 just. I don't need to be here for the 12th release of Windows. I can go do some other stuff. But our industry 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. 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 a 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, 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, great intent with people. And, you know, like, we.

[Joe Rogan]

And you start hating people. That Eureka, you were so excited to reconnect with this person. Next thing you know, you're fighting with them about nonsense.

[Jason Calacanis]

Marriages are getting broken up, people. It's getting contentious. And really, social media, Facebook, 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 co that people could enjoy but, you know, generally made people's lives better to 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, so making this electric car is going to save the planet? And. Yeah. Wow. We're going to go to Mars. Cool. You know, it's just like, very special.

[Joe Rogan]

People that hate him now thought he was the second coming.

[Jason Calacanis]

I mean, it's incredible, I think. Yeah, because. Because 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, and don't bother. I'm. I'm done. Tesla's gonna 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 gonna 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. I was like, whoa, this is like.

[Joe Rogan]

Right before Chris, where's the money from? I don't know how. I don't know the story.

[Jason Calacanis]

Well, we were at Boa, eating a steak, just the two of us, and he was.

[Joe Rogan]

You were at Boa on Sunset?

[Jason Calacanis]

On Sunset.

[Joe Rogan]

It's literally the only thing from LA that I miss. That was my favorite restaurant and it's the only place I go back to.

[Jason Calacanis]

Two of us went there, and 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. I'm feeling kind of blue. I need some company. So I went and had dinner with him and he was like, yeah, it's. It's kind of like, what's going on with the rocket ship company? He's like, yeah, well, we blew two up. I said, well, what happens when's the next launch? 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 million dollars. I'll ship it to you on Monday and you know, whatever, I'll loan it to you. And he's like, don't bother. Not necessary. I said, well, Elon, there's gotta 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. You know, on the black brace he used to have that little track pad thing on the ball. Yeah. And he's flipping through it. And I looked at it, it and it literally was clay models, you know, like little clay. But I'm looking at it, 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 Taurus 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 going to call it the Model S because T is still. Yeah, Ford still has the trademark. We actually looked into that. I was like, yeah, that's a pretty good name. Model S is good, like st. Whatever sedan. And I said, what's it gonna cost? And he said, I think I can do it for $50,000. I said, if you can do that for $50,000, you'll change the fucking world. This company has to survive. And like, he wound up over Christmas in Saint Barts, 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 Elon Musk, great looking car. I'll take two. Love, Jason.

[Joe Rogan]

And when did those get delivered?

[Jason Calacanis]

I sent it to him, I kid you not. He put in his desk row, he didn't cash the checks. Cause he didn't want to take the 100 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 0000001. 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.

[Joe Rogan]

Right. He's probably don't have a number on him.

[Jason Calacanis]

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 G. Sky Dayton, who had supported me.

[Joe Rogan]

And how'd you drop all the way to 73?

[Jason Calacanis]

Well, he had other people who were investors in the company, and he wanted to.

[Joe Rogan]

With the two.

[Jason Calacanis]

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.

[Joe Rogan]

Right.

[Jason Calacanis]

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. So, I mean, that's if the Smithsonian is listening. I got to find somewhere to put it.

[Joe Rogan]

So then that. Well, that story actually perfectly kind of explains the thing that I was asking about, which is this weird thing of, like, so 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 with this, where you guys on all in People now. You guys do conferences, and people just know you from a million things. Or the. I mean, Elon's level is now off the charts.

[Jason Calacanis]

Yeah, he's the most famous person in the world.

[Joe Rogan]

Right? It's not even. It's. You can't cut.

[Jason Calacanis]

Which is, by the way, terrible. I. I mean, people, I think, you know, oh, I want to be Elon Musk. It's like, no, you don't. He can't even go out to dinner. Like, I'm like, let's go to dinner. I got 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, like many of us on all in and other people who have been in around this administration. I'm not part of it, but I'm around it. We identified pretty early on the existential crisis for America is running out of money and this debt load. And thank God 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 we stop government spending, spending, well, that's not good for the economy. Look, 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. Yeah, 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 and you got to do it fast.

[Joe Rogan]

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 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 Doge guys and it's a really eclectic man, mix of what seem like hyper capable people that you need someone like him and there's no one else like him to actually continue the mission properly.

[Jason Calacanis]

I think he can parachute in and inspire people and keep them Focused, it's gonna be on Trump and JD to keep it a priority. And there are people around Trump who I worry about. There are 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 Lutnick and Besant and Elon and Sachs, obviously close friends. 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. Yeah, there's some people I think were 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 know, creating strife in the company country or, 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?

[Joe Rogan]

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 him. Like this is the oligarchy magically appearing. One of the things that I loved from Linda McMahon who took over department to bed, she gets up there and the first day, you know, she's a billionaire, she 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 and as if the Democrats wouldn't have, you know, or didn't do it.

[Jason Calacanis]

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. But 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 could be worried about that. Maybe they're entitled, maybe they're not effective. But you know, 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 a 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 cleanup. And I think you probably agree, and many people in Trump land are like, can we please stop doing those weird things?

[Joe Rogan]

Yeah, well, as I said even before, there's all the, there's stuff on the margins which I'm just willing. I think, actually what I've learned in 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. With which I think is fine. It's just like a, it's, you know, the prism you look through things.

[Jason Calacanis]

The most charitable way to look at it is like, 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. Then, you know, and then 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.

[Joe Rogan]

Yeah.

[Jason Calacanis]

And it's like, no, it's not going to be, obviously, we survived Trump won. We survived Biden one. Well, some survived Trump too, but really it's the opportunity, is there an opportunity here to make government much smaller? I, as I've gotten older, I've started to appreciate this concept of states rights and that there's this incredible feature in how, how this experiment known as America was constructed, which is the states compete with each other.

[Joe Rogan]

Yeah.

[Jason Calacanis]

And if you think California is devolving like I did, and I think you probably did as well, you're giving the.

[Joe Rogan]

Dave Rubin story now.

[Jason Calacanis]

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, we hate capitalism, we hate entrepreneurship. We're going to just let the cities burn. We're going 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? It's like, oh, yeah, there's a bunch of Griff 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 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 peeking under Dinkins, how dangerous it was.

[Joe Rogan]

I remember that.

[Jason Calacanis]

Then you had Bernie Goetz 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 going to school at that time in college at 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. Whatever. I took them on one subway ride. It was chaos.

[Joe Rogan]

Yeah.

[Jason Calacanis]

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 gonna 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. Like, what's going on here? And the cops have given up, and the. The city seems to have given up on any just modicum of policing or stability.

[Joe Rogan]

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 this about this off camera, but we stood in his office, in the corner office, so he can. Has a nice view of the city. And he's literally just. 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 supposed to be.

[Jason Calacanis]

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 move 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.

[Joe Rogan]

No, the snowbirds just stay.

[Jason Calacanis]

Snowbirds were like, yeah, I could just stay here and not deal with, like, the crime in Manhattan and this chaos. 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 and they're not there anymore. And that actually affects services. So people, you have to get sick and tired. But I think it's a ten 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. 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. These are beautiful institutions that I.

[Joe Rogan]

Private fire department. Keep his freaking thing going. It's still standing when.

[Jason Calacanis]

Yeah, I mean, here's a crazy idea. Water.

[Joe Rogan]

Yeah, yeah.

[Jason Calacanis]

Like, and a private Citizen can get 10 fire trucks filled with water and carrying. Bass is in another country, like in. I don't know where she. Ghana. And like, like what. What does that have to do with Los Angeles? Los Angeles has got serious problems.

[Joe Rogan]

Like, and she had been warned about the Santa Ana winds kicking up before she left.

[Jason Calacanis]

It's just complete disgraciad as. As we would say in Brooklyn. And like, it's such. So disgraceful. And I think people have to get sick of it. And you look at Rick Ruso, why didn't they vote for Rick Ruso the last time around? Because he's a rich billionaire white guy.

[Joe Rogan]

Yeah.

[Jason Calacanis]

Let's just call it what it is.

[Joe Rogan]

Yeah.

[Jason Calacanis]

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 Atlas Shrugged? Who do you think built society right?

[Joe Rogan]

Who's left?

[Jason Calacanis]

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.

[Joe Rogan]

Do you think. Do you think that's shifting the psychological part of that?

[Jason Calacanis]

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, it's different. 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. Thank God. 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.

[Joe Rogan]

Yeah.

[Jason Calacanis]

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 forestry, it's called. So he's exactly right. Like, why aren't 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 bones and shipping 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. 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 takes 20 minutes to buy a razor. You need to get a shave. And it's like, is this like some crazy dystopian Gattaca world or something? Like, the answer is yes. Or you're in New York 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.

[Joe Rogan]

Someone literally raped a dead man on the subway. You heard that one about literally. It was an illegal thought. He was just mugging somebody, and a guy turned out to be dead, raped him. I mean, trying to put that together.

[Jason Calacanis]

I mean, it just sounds like something from a horror flick. It doesn't even sound real.

[Joe Rogan]

Yeah.

[Jason Calacanis]

And then somebody was lit on fire. I mean, what.

[Joe Rogan]

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 Elon that first time. 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. Finally, I was starving. It's about 8 o' clock and I'm looking for a restaurant. I was like, anything. But I could not find anything that was.

[Jason Calacanis]

No.

[Joe Rogan]

So I texted Sachs.

[Jason Calacanis]

Yeah.

[Joe Rogan]

And I said, hey, I can't. I went to. What's a fancy steak chain? That's there over there. Not Ruth Chris. Fancier than that. They have one in Malibu on the wall. Water.

[Jason Calacanis]

Yes. That one.

[Joe Rogan]

I'll get in a second. Mastros.

[Jason Calacanis]

Mastros.

[Joe Rogan]

So I go. I see a sign for Mastro. So I'm like, all right, I'll go to Mastros. 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. Sex. 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.

[Jason Calacanis]

Yes.

[Joe Rogan]

And that's what I did.

[Jason Calacanis]

Yes.

[Joe Rogan]

But that, like that feeling that you're just. But yet you see people, I think, are walking around as if this is all normal.

[Jason Calacanis]

There was, like, a contingent in San Francisco, which was very different than Los Angeles. Angeles. There, 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, time frame, 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.

[Joe Rogan]

The vestibule.

[Jason Calacanis]

The vestibule, basically. Thank you. And like, all these, like.

[Joe Rogan]

And they basically.

[Jason Calacanis]

Yoga must, right? Yes. And it was like, well, my dad owned a bar. Like, that's ridiculous. I got to 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. So 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 cause, 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 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 was filled with not just like liberals, but there's actually social media capitalists and communists, like, quite literal, like, who believe that capitalism is bad.

[Joe Rogan]

One of them's running for New York City mayor right now. This guy Zohan or whatever his name is. Yeah.

[Jason Calacanis]

So, you know, I, 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, and you're in our, 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 three or four thousand dollars 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, 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.

[Joe Rogan]

What country are the rich people gonna go to if America doesn't work out?

[Jason Calacanis]

I mean, pick.

[Joe Rogan]

Yeah. At this point, I mean, it's not like many countries are doing.

[Jason Calacanis]

I have, I travel and I can tell you, tell you I. If you go anywhere, there's probably a.

[Joe Rogan]

Secret one that they don't talk.

[Jason Calacanis]

No, I would say, like, you know, like, Peter very publicly got land in New Zealand.

[Joe Rogan]

New Zealand, Right.

[Jason Calacanis]

So New Zealand is easy, like great place to be.

[Joe Rogan]

But they were terrible under Covid.

[Jason Calacanis]

Yeah. I mean, they, sure, they lock things up, but in terms of like, delightful place to live where you can buy some land.

[Joe Rogan]

Sure.

[Jason Calacanis]

And it's isolated. Yeah. If there was a nuclear holocaust, pretty great place to be. I think, like, pick one of the islands far away from everybody else.

[Joe Rogan]

Yeah.

[Jason Calacanis]

But, you know, putting aside like Armageddon and 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, et cetera. Now, if you gave up your US citizenship and some people have. One of the founders, Eduardo Saraven, 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 that that's. 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.

[Joe Rogan]

But I want to see America to get into Japan.

[Jason Calacanis]

No, they. But they will give you a 10 year visa. Like, but they. You can't be a citizen. You'll never be a citizen.

[Joe Rogan]

Like. Right.

[Jason Calacanis]

Literally, like the only way to become a citizen in Japan, from my understanding of, is if you have some heritage, in which case they would love to have you come back because they're in population.

[Joe Rogan]

Pretty racist. Protecting their own culture. How weird.

[Jason Calacanis]

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.

[Joe Rogan]

I guess I was, I was being sarcast.

[Jason Calacanis]

But it is.

[Joe Rogan]

Yeah. But they're entitled to protect Their culture.

[Jason Calacanis]

Sure. Exactly. Putting aside race and like, is citizenship a right to be a citizen of another country? Like, no, 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. Yeah, it's just a number. How many people do you want in each category? High skilled, no skill, and you know, 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 population.

[Joe Rogan]

Well, since you went there. So then what do you want to do with the, let's say 12, 12 to 16 that are here that are illegal?

[Jason Calacanis]

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 this country by far. So you can complain all you want about Biden and opening the border.

[Joe Rogan]

They were all horrible. I mean, I don't know that it was more horrible.

[Jason Calacanis]

Oh, it was literally Republicans position 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 new Wall Street Journal arguing for the virtuousness of like, why wouldn't we let these folks.

[Joe Rogan]

The constant underclass. Yeah, yeah.

[Jason Calacanis]

And 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.

[Joe Rogan]

Right.

[Jason Calacanis]

We have the lowest unemployment of our lifetime.

[Joe Rogan]

And then ironically, you have Democrats now saying, okay, 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?

[Jason Calacanis]

It's a very simple thing. Like 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 going to the root. They're deporting a couple 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 2 million people, primarily people who have felonies or misdemeanors and 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.

[Joe Rogan]

Great grandparents.

[Jason Calacanis]

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 citizen 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.

[Joe Rogan]

I don't want to end on politics.

[Jason Calacanis]

Well, no, but what do you think? Tell me why I'm wrong.

[Joe Rogan]

No, I'm, 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 that. Yeah. Or even, I don't know, you have to pick a cutoff at somewhere. 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. The 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 Paid taxes and you've paid taxes on something. There's something that we can do. I like what you said about that. You know, if you've 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 I.

[Jason Calacanis]

How much it was.

[Joe Rogan]

Well, the cost and just like the cast, the chaos afterwards and the shredding of a portion of our social contract. Even if there are illegal.

[Jason Calacanis]

What's the point?

[Joe Rogan]

Yeah, it's messy. It's Messy.

[Jason Calacanis]

We have 7 million open jobs right now. We have the lowest unemployment of our lifetime. It's 4%. We. The only reason everybody in this country doesn't have a job 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 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 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.

[Joe Rogan]

You know, it's interesting. I think most America open the border. 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 LA 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 a chance for that.

[Jason Calacanis]

Americans commit far more crimes than immigrants. Immigrants almost universally.

[Joe Rogan]

I know they say that. It just. It just doesn't matter.

[Jason Calacanis]

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 nice thing about you and I talking is, like, there's. There is a moderate path forward, you know, and that's what I've tried to do on all in as is 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 I'm kind of living in Texas on a ranch with a. Carry a gun. Yeah, I mean, yeah, yeah. I'm kind of not a. I'm not carrying a gun right now.

[Joe Rogan]

Right, Right.

[Jason Calacanis]

I mean, I mean, I might be. You never know. It's my right.

[Joe Rogan]

No, no. Whatever you want to do anyway, it's fine.

[Jason Calacanis]

I mean, you can carry a gun.

[Joe Rogan]

I'm not ending on immigration, and I'm also not ending on January 6th. So I'll end you. I'll give you just, like, an open one to end, and we will definitely do this again, which is. So. What. What is exciting to you now? Like, what do 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.

[Jason Calacanis]

And I, I. 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 that 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, you know, 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, Robinhood. You created your media empire. You know, there, there, 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. 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, right, I have to create a family wealth system and it's got to trickle down in this country. But we're like, yeah, I don't give my kids, I don't want to ruin my kids life by dumping money on them. They can either work for the family business or they can. Right.

[Joe Rogan]

They usually become a drug addict.

[Jason Calacanis]

Yeah. I mean, everybody knows it's like not a good idea.

[Joe Rogan]

Yeah.

[Jason Calacanis]

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.

[Joe Rogan]

Yeah.

[Jason Calacanis]

What Bill Gates will give away is greater than 90% of the country's given away together.

[Joe Rogan]

His should probably be taken away, but.

[Jason Calacanis]

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.

[Joe Rogan]

Yeah, I actually meant that more just because of his Covid stuff. Yeah, there's probably some others up there too.

[Jason Calacanis]

That's all speculation. But 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 were like, you know what? Yeah, I'm going to go for it. I'm going to make something. I, I, I heard about this company. I can do better. Yeah, 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 calacanis.com for life. Tell me what your idea is. I'm happy to hear it.

[Joe Rogan]

All right, wait. Now the bonus one is, why don't you at least partly own the Knicks?

[Jason Calacanis]

Here's the problem. As my net worth has gone up, the value of NBA franchise has gone up faster. And I honestly.

[Joe Rogan]

You couldn't get the Mavs when Cuban was selling or something or, I mean.

[Jason Calacanis]

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, the Boston Celtics went for $6 billion.

[Joe Rogan]

Is that right? Yeah, I, so is it not worth it to you to own like some tiny percentage just to be like, you know, partly on the Knicks?

[Jason Calacanis]

Like, isn't that good 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.

[Joe Rogan]

Were you just waiting for someone to give you that idea? I mean, it seems right now, I.

[Jason Calacanis]

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

[Joe Rogan]

And you got that right.

[Jason Calacanis]

And I, and I, I got both this year. So, you know, the, 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 every August. I told you, I mean, it's so great. Your August disappear is like such a great thing. And when your kids are a little old, 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. You know that scene from Blade Runner when Rucker Hauer's on the roof and.

[Joe Rogan]

He says, I just watched it again.

[Jason Calacanis]

Like, it's incredible. And he just says, like, you know, all of these memories will be gone. Like cheers 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, 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.

[Joe Rogan]

I'm bored, man.

[Jason Calacanis]

Even I'm going to do it January.

[Joe Rogan]

When's the last time you did three days without a phone? Three days? Two days.