🎧🍌 Inside the All-In Podcast: Lessons from Elon, Trump, Oprah, Travis Kalanick with Jason Calacanis
Origins of the show, setting the record straight on being Uber's "3rd or 4th investor", joining Sequoia's first scout program, what people underestimate about Elon, and going inside the Twitter buyout
My guest this week on The Peel is Jason Calacanis, host of the All-In Podcast. We get into the origins of the show, how they decide what to talk about each week, and if Jason thinks it helped swing the 2024 US election.
He also shares lessons from starting seven media companies over the past three decades, what he’s learned from studying the world’s best interviewers (Oprah, Charlie Rose, Howard Stern), joining Sequoia’s very first scout program, how that led to him being the “3rd or 4th investor in Uber”, his investing strategy today at LAUNCH, what people underestimate about Elon (“he’s an expert at building factories”), and what it was like hanging around the office during the Twitter buyout in 2022.
I think this might be the first time I’ve had the host of another podcast on the show? Let me know what you think and if I should have more, or stick to founders and investors.
If you want short bites of the show in your social feeds, follow on Twitter, TikTok, and Instagram.
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Timestamps to jump in:
3:34 Interviewing lessons from Oprah, Charlie Rose
6:48 How to ask good questions
12:20 Jason’s favorite upcoming podcasters
17:57 Starting 7 media companies
22:50 How he’d start a new media company today
27:56 In-person experiences, “Bang Bang” in Japan
32:44 Vinyl bars, smartphones, mental health
38:41 Origin of the All-In Podcast
42:58 All-In’s influence on the 2024 Election
46:58 Why All-In got so political
52:35 Media lessons from Trump
55:01 Joining Sequoia’s very first scout program
57:55 Jason’s VC investing strategy
1:03:55 How Launch competes with other accelerators
1:08:46 Fundraising is a numbers game
1:13:06 Investing in Uber and Robinhood Seed rounds
1:18:31 Origin of “3rd or 4th investor in Uber” meme
1:20:57 How Jason got the first Model S
1:26:19 What people underestimate about Elon
1:27:37 Inside the Twitter takeover
1:31:44 Career advice for young people
1:35:22 Jason’s experience taking GLP-1’s
1:40:05 How All-in picks topics each week
Referenced:
Find Jason on X / Twitter and LinkedIn
Related Episodes
👉 Stream on YouTube, Spotify, and Apple
Transcript
Find transcripts of all prior episodes here.
Turner Novak:
Jason, welcome to the show.
Jason Calacanis:
Good to be here. Big fan.
Turner Novak:
Well, thank you. That actually means a lot coming from you. A lot of people will say that, but that actually does mean a lot.
Jason Calacanis:
No, I mean, I think you’re good talking into a microphone and you’re funny on Twitter and you don’t take yourself seriously and you’re apparently figuring it out and you’re pretty smart. So all those things combined makes for a good podcaster.
Turner Novak:
A good recipe, yeah.
Jason Calacanis:
Yeah.
Turner Novak:
Still working on it though. It’s so interesting, I feel like, maybe you’ve gone through the same thing where you think you’ve made it so far or whatever, you look back, the you from five years ago, would be like, “Wow, I can’t believe I’ve accomplished all this.” But then you still feel like there’s so much more to go, or there’s other people that are so further ahead of you. I don’t know, have you ever felt that?
Jason Calacanis:
Yeah, what you’re alluding to is the comparison game. And when you compare yourself and you start doing that, always stop yourself. Everybody’s on their own journey and it is the road to suffering. Once you start comparing yourself to Tim Ferriss or Lex Fridman or Joe Rogan or All-In podcasts, there’s always somebody who’s going to be better, richer, faster, stronger, whatever. None of it matters in the end. Everything is ephemeral and everything turns to dust anyway, so just enjoy the ride. Doesn’t mean you don’t want to get better at what you do, but man, comparison is the thief of joy.
Turner Novak:
Well, so on that note, actually, our mutual friend, Austin Petersmith, founder of Howie, which we’re both co-investors in, he used to work for you probably 10, 15 years ago. I can’t remember the dates, but one of the stories he told me about you is that you guys would be on a trip somewhere, he’d be in the car, you’d jump in the Uber and you would be watching an interview of somebody, maybe one of the greats, one of the professional interviewers. So who are some of the best interviewers of all time in your opinion?
Jason Calacanis:
Yeah, there’s a short list. Morley Safer from 60 Minutes was a full contact interviewer and he stayed calm, but he interviewed really spicy folks, despots and dictators, pop culture, whatever. He was actually pretty laid back and could ask a question that was ... He could throw a fastball that you wouldn’t know it was a fastball, it would just seem like a regular old question. Oprah, Howard Stern, Charlie Rose, those were probably the big three that I did study and they have different techniques. Oprah was kind of like the friend who would just purse her lips and, “Yeah, that must have been hard.” Try to get you to cry kind of thing. Just kind of be there with you in the moment.
Turner Novak:
Show some emotion or something, get you to feel a little bit.
Jason Calacanis:
She was a master at that, getting you feel something and she could use not asking a question or a, “Hmm,” really powerfully. Charlie Rose was the best at the, let me do a stream of consciousness question about when you were making Pulp Fiction. Did you know the audience would be able to follow along with the way you did time displacement and then he’d smack his hand on the counter.
Turner Novak:
What was the point of doing that?
Jason Calacanis:
I think he was in his mind forming the question and bringing the audience along with his percolating on it, which I’m doing right now, and by doing that and taking his time about how the question was formed, he was giving the subject time to think about his question and he was giving them multiple angles of where to go.
So the rambling question that Charlie Rose always does, it gives the subject like two or three different directions to go. He’s talking about Pulp Fiction, “Did you know it was going to be as big of a hit? Was the audience confused and is that your favorite film of yours? And he’d embed like three or four different ways to go, but he was also very good at listening. Howard too, so Howard and Charlie Rose also would be listening deeply to the answers to the question. And this is the thing that I always brought to my interviews, which is the next best question is embedded in the previous answer. And so when people make a list of questions, sometimes they’re not listening to the answer because they’re getting nervous.
“Okay, this question’s coming to an end. I need to get the next one queued up. Where am I going to go next?” Just take a breath, take a beat, listen to the answer, and then double click on something in the answer. What that does is it creates a synchronicity with the audience because the audience doesn’t have the piece of paper with your next question on it, they have, but the answer that they’re just listening to, so they’re in the moment. Most interviewers are not in the moment. So being over prepared or being a slave to your question list means you could miss a really great follow-up opportunity. So I’m always looking for that follow-up opportunity.
Turner Novak:
So a mistake would be, let’s say next question on my list is you move to Austin or something, just jump into a completely unrelated topic when someone might actually say... Someone might be curious, then maybe why do you think people mess that up? Why do they jump to the next question and stick to the list and not put themselves in the audience perspective?
Jason Calacanis:
I think they’re probably a slave to the work they put into it and they never thought about the audience. And so I’m always thinking about the audience. I’m always thinking, did they understand what they just heard? So sometimes you’ll hear me on All-In say,” Can you unpack that? “Or I’ll just explain GDP or some acronym comes up, I’ll explain what it is one more time or what the difference is between different GDP readings. A very boring example.
But when I meet people and they say, “Oh my God, I love the podcast.” “Oh, tell me more, what specifically?” And they say, “Oh, I found it very confusing, but sometimes you stop and you have people explain things and I always appreciate that.” So I get that a lot. And sometimes people can be like, “Well, I don’t need to explain that.” Or, they could just look it up.
Sure, you could pause the podcast and look it up. And then people who are in the know, yeah, they might be annoyed by taking the time to slow down, but sometimes slowing down is speeding up in some ways because the person really goes back to first principles and says, “Okay, yeah, here’s how inflation works. Here’s why inflation goes up. It could be you’re printing too much money and it could be there’s too many people competing for a smaller set of goods and lobsters went from being not in demand and they were considered insects of the oceans and then when they were overfished, there were fewer of them and then they became more coveted because they were more rare.” You can kind of explain inflation in a very easy way. It helps the discussion, right? It helps everybody get to that sort of systems thinking, which a lot of VCs become obsessed with because all we have since we’re not building is thinking.
So you just come up with more and more ways to think in a crisper fashion, in a more thoughtful fashion, in a more effective fashion. And that’s why you hear them talk about survivorship bias or this bias or this cognitive belief all the time, it’s because it’s all we have. You’re just trying to make sense of a decision you made 10 years ago. “How did I make that decision? That was such a good decision.” Or, “Why did I make the wrong decision to invest in Google? Oh man, I should have invested in Google.” People just sit there and ring their hands over and over again.
That’s why when you’re in the moment, it’s good to think about your thinking. It’s good to do that metacognition process. Okay, am I in a bad mood right now? Did I get in a fight with my spouse? Am I arguing with a friend? Did my stocks go down? Am I upset about something I read in the press? Okay. Yeah, all those things could be impacting my decision making. Let me meditate, take a walk, go for a rock, smoke a joint, whatever it is, whatever your bag is. Let me slow myself down and think about my decision. Can I make a better decision? And that’s really an interesting ... It overlaps both with the podcasting and the investing.
Turner Novak:
Yeah, for sure. Actually, one really interesting piece of advice I got from ... Oh man, I forget his name, but it’s the guy who started Planet Money, NPR’s big financial podcast. He kind of hit on the same point of when a guest says something interesting, sometimes you can just rehash what they said back to them just to kind of ... It’s almost like saying something again in a book or in a piece of writing for the audience. So they really hammer home the point. So I mean, in practice it would be like, I feel like the biggest thing that you hit on there was you actually listen to the person talk and you’re kind of reflecting on it. And so it’s something I definitely try to practice. It’s like you have your list, I have like 20 things I want to talk to you about, but I’m like restraining right now listening to you and trying to figure out which one we go to next.
Jason Calacanis:
There might not be a great next question based on what I just said. I may have just put a period at the end of the sentence, not a comma or an ellipsis.
Turner Novak:
Well, thanks everyone for listening. This is a great episode.
Jason Calacanis:
Yeah, there you go.
Turner Novak:
We’ll see you in the next one.
Jason Calacanis:
Well, period to this question. Sometimes there is a period. It’s like, “Yeah, and I did that and it was fun.” The energy is better spent on the next question. So that’s the art of it, sometimes there’s a science, sometimes there’s an art, sometimes it’s alchemy. It’s a little bit of alchemy.
Turner Novak:
Are there any up and coming kind of podcasters, interviewers, question askers, researcher type people? I mean, we’re kind of bucketing into everything we’ve just been talking about that you think are on the rise, people should pay more attention to. They’re going to be the next Charlie Rose, the next Oprah.
Jason Calacanis:
I think the space is so saturated right now it’s hard to distinguish much because everybody’s become pretty good at asking questions, to be honest. When I started 15 years ago doing a podcast, I was one of the first podcasts when it was on iPods. There was nobody doing it, so my interview with Travis would be one of one or with David Sacks was one of one. There was no other interview. You could listen to that one or not listen. So now you know, gosh, the thing I find hilarious is podcasters interviewing podcasters. It’s just like a giant podcasting-
Turner Novak:
The Spider-Man meme.
Jason Calacanis:
... circle jerk. It’s just like, what are we doing here? I heard you... It’s interviews about interviews about interviews and debating-
Turner Novak:
We’re literally talking about podcasting strategy and interviewing strategies of two podcasters talking to each other.
Jason Calacanis:
Which is actually like, it’s kind of the moment. I like non-consensus, spicy people. I like people who are a bit fringe. I like people who are difficult, challenging. So like my podcasting tastes go to people like Bret Easton Ellis or who’s the author, he has a Patreon that’s paid, but he’s like a gay author in Los Angeles who wrote American Psycho who was banished and banned for writing that book in his 20s. And now he just talks about his takes on pop culture, getting old and it resonates deeply. So the Bret Easton Ellis Podcast for 10 bucks a month for me is like just art and perfection.
And it’s just him. He’s being himself. He’s struggling with his age. He’s struggling with woke media. He’s struggling with his friends having Trumped Derangement Syndrome and trying to figure out like, “Well, why is everybody obsessed with this? And why can’t anybody finish a novel?” And the end of the novel and the end of the empire, the end of cinema and people not going to theaters and the movie’s not being good anymore when he spent his whole life in a world where people wrote great books and it was meaningful to write a magazine article, a profile of somebody. And then, Red Scare and they do a-
Turner Novak:
Red Scare? Is this a podcast?
Jason Calacanis:
The podcast, yeah. Dasha and Anna, they basically are two ... They’re part of the Dirt Bag Left, I guess, is what they called it originally.
Turner Novak:
Wait, is that you adding Dirt Bag or they actually call themselves the Dirt Bag Left?
Jason Calacanis:
They actually called themselves the Dirt Bag Left. Yeah.
Turner Novak:
Okay.
Jason Calacanis:
They hang out in Dimes Square, which is like a square down in Chinatown on the Lower East Side. But they remind me of the people I hung out with in New York in the 90s where they’re kind of like in their own little New York elite bubble, building their own little media empire, doing their own thing. And yeah, Dasha just got banned because she had Nick Fuentes on the pod, which I thought was pretty hilarious.
Yeah, I like Preet Bharara who does Stay Tuned with Preet, he talks... And he’s got a paid one, cafe.com. So I like the paid ones, I guess. All three of those are paid. I pay for all three of those. I think the people who are like on the fringes who are not doing advertising, who are just pay to hear me talking to a microphone are like super fascinating people, super fascinating.
Turner Novak:
Because it’s kind of a bold take because ... Oh, I’m saying just to have a paid podcast because the typical model is free. Why would someone start a paid podcast? Is there advantage, disadvantage?
Jason Calacanis:
I think they probably want to express themselves, but they don’t need for it to be big or giant and they want it to pay their rent and it allows them to focus on it in a very deep way. Yeah, I’ve started watching the Adam Friedland Show. I think he’s like pretty low key funny, Adam Friedland. I don’t know if you know him. He’s like a standup and yeah, he does-
Turner Novak:
I recognize the face.
Jason Calacanis:
He’s awkward. His timing’s weird. He gets emotional during the pod, but he’s authentic. I think all of the people I’m talking about are authentic human beings on planet earth who are not trying to do a podcast. I think they’re all trying to express themselves first and then be part of the podcasting diaspora second. They’re not trying to be part of podcasting. They’re just pursuing something artistic for themselves. And that’s kind of what I did. I didn’t get into podcasting because I wanted to be part of podcasting. There was no podcasting back then. I just wanted to interview my friends and talk about startups because I was passionate about it at, the end. It wasn’t a complicated formula. It’s, my friends were building cool shit and I’d talk to them about what they’re building.
Turner Novak:
And you have started ... I actually didn’t count, but you’ve probably started three, four, five, six, I guess seven, depending on how you classify these media companies over the years. Do you know the exact number?
Jason Calacanis:
I don’t know the number, but I have a reflection on it, which is I’ve always looked at new mediums coming out as a playground and I just assume they’re going to work. And if they don’t work, who cares? It’s worth going into the sandbox and playing a little bit and seeing what it is. So my first media property, Silicon Alley Reporter, and slightly before that Cyber Surfer were zines, Z-I-N-E-S, zines, which were self-printed magazines. You would print a photocopy of them. And I love that because it was very punk rock. You didn’t need permission. You just wrote some words, took some pictures, laid it out, printed it, and then photocopied it, and then you handed it to your friends or they bought it off of a select newsstands kind of situation.
Turner Novak:
So what year was this?
Jason Calacanis:
That was ‘95. Yeah.
Turner Novak:
‘95. How do you start that? I mean, you got to print things?
Jason Calacanis:
I went to literally a photocopy store with a printout that I’d done on my laser printer and said, “Make me a thousand photocopies of this.” And then I brought them to a party and on the back page it said, “Subscribe for 100 bucks to 10 issues a year.” And then hundreds of people ripped the back page off and sent me 100 bucks and all of a sudden I was making tens of thousands of dollars in subscriptions and it was enough for me to not have to work for anybody else. Boom, I was in business. And then I started selling ads and then in under 10 years it became a 300-page glossy with, I think we hit 12 million in revenue in the top year off my credit card. So it was a pretty crazy run.
And then Weblogs, Inc. We had the number one blog in the world, Engadget, shout out Peter Rojas and Ryan Block both did a tremendous job on that for me. And they were really the talent of it, I was kind of the CEO in that model, but I put it together, Brian Alvey did build the infrastructure and had really great editorial senses as well. So it was a team effort for sure. But Engadget became the number one blog in the world. Steve Jobs read it. It had massive cultural impact. And then yeah, This Week In Startups and All-In. Yeah, those are all major ones that made major impact, in between it, Mahalo, Inside, things that hit a little bit, didn’t hit, missed. But I don’t even really over index on the things that miss. You just focus on what’s next, right?
Turner Novak:
I had actually forgotten about Mahalo until I was ... I went to your Wikipedia page and it was just like Reddit. It was like, anything else interesting we should try to hit on. And I was like, “Oh, I totally forgot about that.” But after, I was like, “I kind of remember it now.”
Jason Calacanis:
Proving my point, nobody remembers your failures, so why over index on them? I mean, if you look at Perplexity today and how they do comprehensive search results, it literally is what the vision of Mahalo was, which was instead of 10 blue links, what if there were images, answers, content? My idea was take the Wikipedia software, which was called Wiki or Open Wiki, whatever it was, and then I just started building pages like, “Here’s an iPod page, it’s better than Google’s page for search results, so start there for navigation.” So Yahoo was waning, Google had searches for everything. And I was like, “Well, what if we use the power of the crowd to build search result pages,” which were called SERPs? It was a really good idea. It got to 10 million in revenue and then Google decided to de-index us because frankly, we were competitive and they’re pretty sharp elbowed and they stopped letting our pages get indexed basically and we went from 10 million in revenue down to like 500K in revenue.
The great irony of it is they were our partner. So we were making the money through their ads, but I think they were just like, “Yeah, these websites are giving people answers and we don’t want them to grow anymore because if they grow, then people won’t do searches. So therefore we’re going to cut eHow and How-To and the How-To Wiki and Mahalo. Anybody trying to give answers like this, we want to put those in the one box, which is that little box that gives you the answer at the top. I mean, this all seems like very insignificant in the face of AI being able to answer every question and steal everybody’s content all at once.
Turner Novak:
Yeah, you would have been screwed either way. It just happened earlier versus today.
Jason Calacanis:
I mean, yeah, content creators are getting screwed big time and it’s going to take, I think the New York Times and the music industry holding the line, Reddit, Quora, whoever’s being indexed without getting paid needs to really hold the line and insist on getting paid to be indexed.
Turner Novak:
So if you were starting a new kind of media property or starting to create content today, and you talked about how you like playing around with this stuff, what do you think is just an interesting kind of vector to enter the arena on or start competing on just considering where we’re at and where the world’s probably going in the next couple years?
Jason Calacanis:
I think video is very interesting, obviously. Audio still remains interesting for people. This short form video to long form is, I think, an opportunity. So catching people on short form videos and then pulling them into longer form discussions, I think that format’s going to ... I don’t really see anybody doing it, but I have been thinking about it a lot.
Turner Novak:
So can you give me an example of that? Because you guys kind of already do that with All-In, don’t you?
Jason Calacanis:
Yeah. I mean, we make shorts out of a podcast and everybody does that, and that can pull you into the podcast. In fact, a lot of those went viral and then people found out about the podcast. But I think there’s something to living in the short format and then stringing them together. And you’re seeing that in Asia already with vertical soap operas and I’m not sure what the category is called.
Turner Novak:
They’re like short dramas or something like that?
Jason Calacanis:
Yeah, vertical dramas. I guess micro dramas, mini dramas. These are all what they’re being called. And they’re made for your phone. They give you just a little bit of content, and they’re kind of corny right now. They’re kind of like novellas or like romance novels. And a lot of times great content starts with a genre. So genre pictures can be elevated, like Aliens is a horror, sci-fi genre. It’s like actually a cross genre picture, but it actually asks a lot of important questions about where do we come from, which are revealed slowly over time in the series with Prometheus, et cetera, but it’s a horror genre. Terminator is like a science fiction genre that asks a lot of important questions about AI. Think about how prescient that was. Blade Runner, a genre film. So anyway, these are genre films. They tend to work in romance and I think they’re targeting like middle-aged women, older women in Asia right now. But I think somebody like Tarantino could master this. There’s a Tarantino of vertical short storytelling. We just haven’t seen them yet.
And so I always like, when I see these things, I just assume, what if it works? What if it works a hundred times as well? What if there’s an artistic version of it? What if there’s an award-winning version of it? So what’s the award-winning version of shorts? What does that look like? We already know what the award-winning version of a podcast looks like, we know what the award-winning version of blogs look like. There were certainly some very influential ones that moved markets or we’ll see an award-winning Substack at some point, will win a Pulitzer type thing or an email newsletter will win a Pulitzer. Maybe they have already, I don’t know, for original reporting or something to that effect. So I’m always looking at it and I just assume, what if it works? I also think there’s going to be something that with this IP, the Star Wars, Marvel IP, somebody will figure out a way to build new IP in new spaces.
I think it might happen in VR or AR where somebody will create the next Star Wars, and an experience like that that will have legs and create a classic world building is what they call it. So Lord of the Rings or a Star Wars franchise coming out of not books and movies, but imagine it comes out of AR or VR where you’re walking around the world and experiencing Han Solo or Chewbacca or Gollum or ...
Turner Novak:
But these are like entirely new characters, right?
Jason Calacanis:
New characters, yeah.
Turner Novak:
It’s not Lord of the Rings. It’s not Star Wars.
Jason Calacanis:
No, not reusing IP. Somebody’s going to make new IP that works in this format. Some might say this KPop Vampire Hunters might be an example of this.
Turner Novak:
My daughters love that show.
Jason Calacanis:
Yeah. Yeah. So you can go to sing alongs with it. So they figured out how to get them to go to movie theaters. Once a week they have a sing along of that Netflix streaming movie in movie theaters, and you can go and participate, which also would lead the mind to think people are online too much. They’ve got brain rot. How do they get rid of the brain rot and being online and self-isolating? Oh, they go to a movie there and do a single long. That is the most gay, fun thing you could do. When I lived in New York, we would go to the village, straight guys, straight couples, whatever. And you’d go to the village just to go have the joyous experience of sitting with a drag queen who was playing piano, singing Broadway show tunes. And it was cool back then because there was no delineation between gay, straight community in Manhattan.
It was just, “Oh yeah, there’s a cool thing going down at the Roxy. It’s roller skating disco night.” It would be like 70% gay, 30% straight. Or if you went down to these sing-along bars in the West Village, they were, I don’t know, 50/50, but you could go sing show tunes. It was a fun thing to do at 2:00 AM after you’d been out drinking or whatever, working late. And I think this K-pop realized people love singing together. Karaoke is like the thing people do in China and Korea and Asia. That is the social thing, is getting a room and singing. Sometimes they do it alone. Sometimes people go and they rent a room alone to practice singing.
Turner Novak:
Interesting.
Jason Calacanis:
It’s pretty fun.
Turner Novak:
Yeah. I mean, you think of just the power of just singing and music dancing. TikTok, probably the biggest recent emerged new platform, it started as this lip-syncing dancing app, like through away like-
Jason Calacanis:
Everybody can do it.
Turner Novak:
Yeah. It’s one of those things.
Jason Calacanis:
We’re all doing that in our cars anyway. We’re lip-syncing to our favorite song.
Turner Novak:
I was singing on the way here. What was I singing?
Jason Calacanis:
You were?
Turner Novak:
I think I was singing Ed Sheeran.
Jason Calacanis:
<< You put 100 on the lane, see, dah, dah, dah >>
Turner Novak:
I actually, I do like-
Jason Calacanis:
Taylor Swift song is going crazy.
Turner Novak:
I do like Taylor Swift. It’s a guilty pleasure. Part of it is just having two daughters who like, they like that stuff so you got to lean into it.
Jason Calacanis:
I have three daughters, so you can’t avoid it. I really wanted to go to the Eras tour. I feel like an idiot that I missed that because it felt like a real cultural phenomenon. Somehow I missed it. Yeah.
Turner Novak:
Yeah. I mean, I’m assuming they ... I think she’ll do another one. She can’t not. You’ve seen the numbers. She made a billion dollars or whatever. She probably made less in profit, but like the headline numbers, she made a shit-ton of money.
Jason Calacanis:
I think she made two billion and maybe netted a billion for herself, but even still, hundreds of millions of dollars, hundreds of millions of dollars. It is very interesting that short viral clips on YouTube result in ticket sales. So I, living in Austin now, got to see ACL the last two years, Austin City Limits, a music festival, like a Coachella, but in Austin. And I got to see Chappell Roan, Doce, Sabrina Carpenter. And seeing them is a very weird experience because you hear their songs as the soundtrack to other people’s videos constantly on the socials.
And then you see them in person and you’re like, “Oh, I know snippets of their songs. I don’t even know full tracks.” Which for me as a Gen Xer, which just feel free to call me Boomer, anybody above 35 is a Boomer at this point. But as a Gen Xer, we had the album, right? And the album was ... the CD was sacrosanct. You bought the Brothers in Arms CD and you played. You bought the Pink Floyd, Dark Side of the Moon, Wish You Were Here. And you played the album, you experienced the album. Sometimes there was a 12-minute track, Telegraph Road or whatever it was.
Turner Novak:
You listened all the way through, right? You didn’t pick songs. It’s like-
Jason Calacanis:
And you would listen generally to the entirety of the album, was how it was supposed to be consumed. It would be like listening to tracks from multiple albums, would be like going to three different restaurants and having an appetizer, an entree and a dessert at three different restaurants, which by the way, is what I do in Japan. We call it Bang Bang. We can talk about that another time, but it’s one of my favorite pursuits, is the Bang Bang.
Turner Novak:
Always the Bang Bang in Japan.
Jason Calacanis:
There’s Bang Bang in Japan. There’s a clip for social. Yeah, this could go viral.
No, Bang Bang is something I saw these foodies do, like chefs. Instead of going to one restaurant, you go to two. So you make two reservations. You got your 7:00, you get your 9:00. You get like three or four dishes at each. So instead of everybody ordering three dishes each at one restaurant, you have four people 12. You order six at one restaurant, six at the next. Or maybe you go seven, eight. You taste a lot of stuff, but you get to have the experience of like two different dinners, two different appetizers, whatever.
So in Japan, I hit 7.5, I think eight. I think we hit eight bangs in one day, two breakfasts, two lunches, two dinners, and then an assortment of other stops along the way, including going to a vinyl bar. Speaking about interesting pursuits, there’s a new thing there, vinyl bars where you go and you listen to music. And I have a friend, Amanda, who likes talk more than I do, if you can imagine.
Turner Novak:
I don’t think it’s possible.
Jason Calacanis:
It’s not possible. So I found my foil. So Amanda’s loud and we’re in this vinyl bar. And the Japanese guy had to come up to her three times and she’s like, “No, please enjoy the music quietly. Please enjoy the music quietly.” Because there’s other people at the table. So you’re drinking like this great Japanese scotch and their whiskey and they’ve got a vinyl there. And it was really interesting. You take a marble from a bowl and they have marbles by decade and they have marbles by genre, and you can put the marbles together.
I want some rock and roll from the ‘70s, or I want some pop or jazz from the ‘50s. I want pop from the 2000s. And you put your marbles into a rack and the DJ gets the marbles. They look at them and then they go into a wall of vinyl and they pick a track.
Turner Novak:
Interesting.
Jason Calacanis:
It was a really fun, cool experience.
Turner Novak:
So is it a mashup, like pieces of the song or is it like one song after each other?
Jason Calacanis:
They play one song after another.
Turner Novak:
Interesting.
Jason Calacanis:
You get to pick a track. So when you get there, there’s 10 marbles, so you get 10 songs ahead of you or six. Maybe there were three or four marbles ahead of us when we got there. We put in a couple of marbles. It was at six or seven. And they have giant speakers there, like these unbelievable, giant, classic sought after speakers and these Macintosh amps from the different company than Apple, Macintosh. They have these giant musical amps there with the tubes in them to make that really beautiful, rich sound. So you have the rich vinyl with the rich pre-amp or the amp and the rich speakers. Yeah, I’m getting into this audio file stuff. It’s really cool.
Turner Novak:
Can you feel the vibration of the music in the seats and the floor and stuff is like one of those places?
Jason Calacanis:
Yeah. You feel it much differently than you would. And I think it’s because, again, back to this like isolation versus experience economy that we’re going through. I’ve never said it like that, but I think it pretty much encapsulates the high and low. The low being like I’m isolated, I got AirPods in. The high being, I went to ACL and was with 100,000 people when Sabrina Carpenter, Chapel Rome were at the peak of their popularity, or I went to this bar and sat there with other people instead of sitting at home and listening to a really good music system and had a really good whiskey and had a really like ... the vibes were immaculate, right? So I think that’s a big part of the future, is getting people out of their isolation and get them into more shared experiences. I’m actually hearing young people are leaving their phones at home.
They have a smartphone, but they also have a flip phone and they’ll move their SIM card and then go out with their flip phone and then with a camera. So they’re buying used old point-at-you cameras so that they can be more present with their friends. And I had dinner with Chamath and Friedberg at the F1 this weekend. We’re sitting there out with a couple of our other friends. Phil Home Youth came in, Jason Koon, other poker players. And we were eating at this really cool Korean steakhouse cote, C-O-T-E, at the Venetian. And it’s a shared thing where you’re doing the Korean barbecue, but with really prime cuts of meat. And I just said, “Stack your phones”, put my phone down. Everybody stacked their phones, six phones sitting on top of each other. And we didn’t touch our phones for dinner. We just talked.
We were present, right? I think all this mental health problems are coming from the smartphone. I could see the introduction of screens and people’s unhappiness correlates perfectly, sadly. And so instead of taking a bunch of pills to make you feel better about your screen use, maybe use your screen less and go experience stuff more.
Turner Novak:
It reminds me a little bit about cigarettes, how it’s probably like for decades we both knew and didn’t know that they were bad for you, right? We knew, but also-
Jason Calacanis:
It was an ambiguity.
Turner Novak:
And then we find out like, hey, these give you cancer, and they like objectively are not good.
Jason Calacanis:
They’re terrible.
Turner Novak:
It’s 50 years later.
Jason Calacanis:
They’re not helping your asthma or clearing the phlegm from your throat.
Remember the ‘70s and ‘80s, people were like, “Yeah, no, no, I just need to clear air out. I just have a cigarette.” You’re like, “What?”
Turner Novak:
You just smoke for an hour. That’s not good for you.
Jason Calacanis:
There’s a great movie, The Insider with Russell Crowe. I don’t even seen Michael Mann.
Turner Novak:
No.
Jason Calacanis:
Oh my God. I mean, I just need to, with you guys under 45 years old, I just need to tell you what to watch. Go watch The Insiders, 1999, Michael Mann. You should see anything by Michael Mann, by the way. Just go Michael Mann or Ridley Scott and just watch everything that Riley Scott, Michael Mann have ever made and then report back. But The Insider is the story of the 60 Minutes interviews, we want to talk about like when journalism was at its height, and the CBS producer Lowell Bergman’s struggled to get this on air with this guy, Jeffrey Wigand, and Jeffrey Wigand is played by Russell Crowe famously. Yeah. It’s awesome.
Turner Novak:
Yeah. I’m reading the IMDB. The description is, “A research chemist comes under personal and professional attack when he decides to appear in a 60 minutes expose on Big Tobacco.” Sounds like that could be good.
Jason Calacanis:
Not a box office success, but nominated for seven Academy Awards.
Turner Novak:
Really? Yeah.
Jason Calacanis:
It’s an incredible film.
Turner Novak:
I want to actually switch topics a little bit just because you mentioned Chamath and Friedberg. And I want to talk to you about all in a little bit. I think that’s probably why people clicked on this one and wanted to listen. Can you just take me back to ... I can’t remember when you guys started it, but what was that moment of deciding to do it?
Jason Calacanis:
It was during COVID. Chamoth was leaving CNBC and he called me on the phone and he’s like, “I want to do a podcast with you.” I was like, “Yeah, come on This Week in Startups anytime.” He’s like, “No, I want to do a new podcast, just me and you talking and whatever.” And COVID had just hit and they were just starting to shut things down. And we couldn’t see each other at the poker game. We played in a weekly poker game and we were like, “Hey, we should talk about COVID.” And David Sacks was famously posting himself with all the protective gear as a joke on social media.
Turner Novak:
Really? I forgot about that.
Jason Calacanis:
Yeah. Which was like, of course the Republican lunatics give him a hard time about that photo, when that was absolutely the right thing to do if we didn’t know this was going to be like ...
Turner Novak:
Yeah.
Jason Calacanis:
I mean, the original reports, and they were true, were the people who first got infected, a lot of them died because it was at its peak. COVID was at its peak deadliness, lethality, and then all of these diseases get less lethals. And one of the things we learned and discussed on the pod is over time these things atrophy in some way. And I’m not a scientist, so I can’t tell you, but that is a trend that thankfully happens with them. And we also didn’t know how to deal with it. So people were in hospitals getting put on respirators. Maybe they shouldn’t have been put on respirators. And then Friedberg was at our poker game and was friends with the group and he knew about science. So we were going to talk about COVID. We pulled him on.
Turner Novak:
There you go. Get the expert.
Jason Calacanis:
The four of us had chemistry that was undeniable. And I just based the format on The McLaughlin Group, which was an old Sunday morning show. But the guy, John McLaughlin, as the moderator, was always a little bit full contact. He was a little bit pissed off. He was talking like a New Yorker, an East Coaster like I do, and he’d give the guys a hard time, “Wrong. I think it’s the wrong answer.” He would force him to answer the question. “Oh, you didn’t answer the question.” He’d push him a little bit, prod him a little bit. And then I added to it just breaking chops a little bit because I’m from Brooklyn, that’s what we do. We roast each other a bit.
In the poker game, we roast each other. So that vibe, I think, just resonated with people. And we had a captured audience at the time, but looking back on it, I think. I look back on guests I’ve had on the pod or at events for firesides or keynotes, and there is this four quadrant box, like how knowledgeable you are, how much experience you have, lived experience, knowledge, et cetera. And then how concerned you are with other people’s opinions or not concerned with other people’s opinions of you, how freewheeling you are.
Turner Novak:
This is two scales of very expert, very concerned or not concerned.
Jason Calacanis:
Yeah. Well, if you made four quadrants, you’d have people on the bottom who didn’t have a lot to say and a lot of knowledge. Well, they shouldn’t be on a podcast. What’s the point? You don’t have much to share, go back to life and get some shit done. So then you’re in the top two quadrants and you have in the top right, top left, people who have a lot of knowledge, but they’re scared to say it. They’re scared to tell the truth. And then you have the other one, truth tellers who also have a lot of knowledge. And so if you look at the four of us, I think decent amount of knowledge, we’re all in approximately 50 years old. So we’ve been through a bunch of cycles, been through wars. We also have FU money and don’t care what other people think about us.
Maybe Friedberg, I would say, used to care. I think in the beginning he was a little more guarded and then he became less guarded. And now he’s like, he’s totally masked off. He’s like, “Socialism, let them take socialism in New York and burn it to the ground. People need to learn that socialism is garbage. I’m glad it’s happening.” I was like, “Whoa, Friedberg, what’s in your coffee suddenly?” But you have four people like that. And then there’s always this palace intrigue of how Sacks wound up at the White House, how JD Vance wound up at the White House. What role did the podcast play in helping Trump get elected? A lot of people think the pod and Elon making big donations were two of ... And maybe those two things are simultaneously happening. So I think people probably over index on the influence of the pod.
They think the pod got the president elected. I would say the number one reason Trump got elected a second time is because they put somebody in cognitive decline against him and then replaced him with a DEI candidate, like back to back bad decisions. Let the people pick their candidate, have a primary. That’s the lesson. Subverting democracy means you get a captured candidate, whether it’s Biden in cognitive decline or Kamala who was picked as a DEI candidate, whether she is or not, they literally picked her. Biden said, “I’m going to pick a Black woman as my vice president.” So now you’ve basically labeled her as that. So she has no credibility. She’s obviously not great on podcasts, which would have been good for her. And then-
Turner Novak:
I was going back to look at our-
Jason Calacanis:
They anointed her.
Turner Novak:
I was looking at our DMs and I was like, “Oh, you guys got Trump on the podcast. That’s a big land. Do you think you’ll get ... “ I think it was Biden or Kamala and you’re like, “No, we’re not going to get them. They don’t do unscripted podcasts.”
Jason Calacanis:
We invited them countless times, publicly, privately, back channels, et cetera. Chamath has said on the podcast, he was a major donor to the Democratic Party. So they literally let Chamath leave the party. They let Elon leave the party, Joe Rogan. These were all lifelong Democrats. Some of them donated money to the parties, some of them supported it. And you don’t go on Joe Rogan. You can’t figure that out. As the presidential candidate, part of it is understanding how to win. I don’t think Trump won this election as much as they gifted it to him.
If they had put any serious candidates out against him, it had been Shapiro and Pritzker or Newsome and AOC, I think it would have been really close. I’m not saying he wouldn’t have won, he might have, but it would have been close. I mean, they just gifted the ... I mean, how do you not even have a primary in August? I was like, “Just do a six-week primary, a four-week primary. It’d be exciting. It’d be box office for TV. Start with like eight people in a debate, go to four, go to six, go to four, go to two, and then pick.” It would be the most exciting summer programming ever. And I told people in the Democratic Party who were significant players in the Democratic Party what to do, not that they’re listening to Jason Calacanis, but that would have been box office. And now subsequently it’s come out that that’s what Obama wanted to do and other people wanted to do. They wanted to do what I called the speed run primary, and they didn’t do it.
Turner Novak:
Because that would have been an insane momentum.
Jason Calacanis:
Yes.
Turner Novak:
You go in and then you have it. I feel like the one risk is if the wrong person wins and the momentum dies or something. I don’t know if you know what I’m saying.
Jason Calacanis:
How would the momentum die more than having Joe Biden not be able to complete a coherent thought in a debate followed by Kamala Harris cackling like a fool and not being willing to talk to anybody unless you brought her white support, vice president. Remember she brought her vice president to the first CNN interview and you’re like, “What?”
Turner Novak:
I don’t remember that.
Jason Calacanis:
But why can’t you just go on CNN yourself? And why does everything have to be staged and massaged? And you went on Call Her Daddy, but allegedly it’s scripted or less free will ... Call Her Daddy is the podcast Kamala’s doing. Really? Who’s running these campaigns? It was a disaster. But I hate politics. I hate talking about it every week, but it is what it is.
Turner Novak:
You hate it.
Jason Calacanis:
Yeah, I’m not a fan of politics. I don’t like politicians. I don’t like politics generally. I much prefer we were doing tech and markets and science and media. But listen, I’m but one of four players on that stage, and the audience really wants us to check in on politics. So sometimes it’s uncomfortable. I’m a moderate, independent. They paint me as a lunatic Democrat who listens to MSNBC. I think that’s probably a debate technique. I’ve voted Republican one in three times and Democrat two or three times in my life, just statistically. And just all my beliefs are more about ... I mean, I’ve been pegged as libertarian more than anything. I’m a pull yourself up by your bootstraps, less government guy. But I think for people who are MAGA, it’s easier to try to paint somebody and just do the name-calling and make them, “Oh, you’re just a libtard. Oh, you’re just ... “ It’s like, “Have you been paying attention to my tweets or where I live or the fact that I wear a gun on my hip?”
I carry a pistol when I live in Texas. I’m obviously not ... I could be living in Mamdani’s, New York or Karen Bass’ Los Angeles. I’m not.
Turner Novak:
So why do you guys lean so much into politics if you don’t like it? Because I feel like you’ve definitely gotten-
Jason Calacanis:
Well, I think the other guys love it. I think the audience expects it at this point. I’ve been trying to keep it more balanced, but I think it’s really just the rule of Trump. Trump takes all the oxygen out of the room. He has every time he’s president. And even when he’s not president, the guy’s a master of taking over the conversation. If we tried to have a discussion today and you were like, “What’s in the news?” It’s Trump and Ukraine, Trump and Venezuela, Trump and Mamdani. Which one of the seven different flooding the zone Trump items would you like to talk about today? The Comey and Comey’s case getting dismissed with the law fare. I mean, he takes up every space. I mean, AI, cryptocurrency, these are our natural topics. Who’s having the biggest impact on AI and cryptocurrency? Trump. He’s literally setting the table for our industry’s top issues.
So in some ways it’s good that he wants to be in the mix in everything, but it can also be exhausting to like ... And also Trump says a lot of things, and then he says things and then he doesn’t mean them or he forgets he said them. So I have rules of Trump. One of them is wait three days before you react to anything he says, because he might never mention it again. He might take the opposite opinion. You don’t know. So he’s like, “I’m putting 150% tariffs.” And then he’s like, “Well, okay, we’re not.” If you react in real time, you’re just going to be constantly spinning. So wait 72 hours, and then also understand if things are ... The other rule of Trump is when things are not popular and he misses, he quickly changes course. He quickly course corrects.
So remember when the stock market crashed in the spring because he was doing the tariff stuff was too chaotic and then he’s like, “You know what? We don’t really have to focus on 150 countries. We just have to focus on the top five or 10, and we’re going to take our time on those.” And he basically just walked back the tariffs completely and all of a sudden the stock market came right back and people were like, “Okay.” He wants to be popular more than anything, I think. And so you just have to learn, okay, it’s going to be another three years of, if he doesn’t get any attention today for his projects, he’s just going to say something crazier and crazier. I think he said yesterday or two days ago, I was in transit that he was going to try these Democrats for sedition, and they were going to be put to death.
I was like, “Okay.” 72 hours later, has he confirmed that he’s going to try to put people to death for having a different opinion than he does? Maybe. I don’t know. I doubt it. I doubt he’ll say it again.
Turner Novak:
Yeah. So I guess the interesting, probably the biggest takeaway is just he just throws stuff out there to flood the zone and stay top of mind, and you got to be able to understand if it’s actually real, it’s probably something he’s going to hit on multiple times.
Jason Calacanis:
Yes. If he’s actually got something going on with Ukraine and a peace process or the Middle East and a peace process, you’ll figure it out if he’s talking about it every day for three weeks in a row and there’s other people in the administration and the other side’s talking about it. So like for example, Ukraine, he demanded they accept a peace thing. They’re accepting it. Okay, now if Putin says he’s interested, okay, maybe you could start paying attention to it. But he said like 50 times in the last two years that Ukraine would be like peace day one. It’s going to be like we’re going to settle it on day one of his administration. Obviously it’s not going to happen. So I think he’s unique in all the world of politics and unique in media as well. It’s like the it girl is the it girl forever. He just constantly takes over every media cycle. It’s wild.
Turner Novak:
We’re going to try to tie this back tech and startups. If you were trying to take that mindset as a founder, what are lessons you think you can learn? Are there ways to kind of insert yourself in a way that is like the correct way to do it, if that makes sense?
Jason Calacanis:
There’s a different playbook going on right now on Twitter, which is like launch videos and a shit poster and replying, being a reply guy, being a thread guy. So there are versions of this. I think Trump is unique in the world. I would not try to base your startup’s marketing strategy of Trump as an 80-year-old guy who’s been in the media spotlight since the ‘80s. He’s playing a different game, having been like the focus of attention for 50 years.
I think what works is talking about your customers a lot, celebrating your wins, showing your product, explaining your product, making these launch videos seems to get a little bit of attention, back to video being the new currency. Appearing on podcasts is always good. If you’re Keith Rabois and you say a bunch of spicy things, but you build great companies, I think does anybody remember any individual spicy thing or do they just remember Keith Rabois successful? They just remember Keith Rabois successful entertaining.
So if I’m starting a company, do I want successful Keith Rabois involved? Yes. Boom. Oh, I’m doing a startup. It’s an early stage startup. Oh, Jason does this week in startups and All-In, maybe he can help my startup. Great. Maybe if it’s early enough, I’ll apply to Founder University or Launch Accelerator. Boom. That’s all I need, just to be in top of mind when you’re looking for a partner. So I think being top of mind when people are looking for scheduling software or an assistant, Howie’s done a good job of that. They’ve shared vibes that hopefully people will get into. Yeah.
Turner Novak:
It’s an incredible product too.
Jason Calacanis:
Product works. I am at the point where I have Athena assistants right now and I’m going to put my Athena assistants on Howie. So I’m going to have like a two-level chaotic system.
Turner Novak:
So when did you first get into angel investing? Do you remember your very first angel investment?
Jason Calacanis:
Yeah, so I was advising my friends on how to raise money, which venture capitalists to raise from, because I had just raised from Hollow and was doing stuff and had sold the company. So people would come to me like, “Oh, you sold the company to AOL. How’d you do it? Oh, you raised money. How’d you do it from Sequoia?” And so it was interesting because I had introduced Sequoia and had sent them emails to Michael Moritz, Doug Leone, and Roelof. “Hey, Elon’s raising money for Tesla. Hey, Mark Pincus is doing Zynga. Hey, my friend Ev Williams is doing Twitter.” And all three of those, they didn’t wind up doing the early rounds of... And then at some point Roelof called me and was like, “Hey, I’m going to do the scouts program. I want you to be the first scout. The concept is pretty simple. You go invest money, we split the carry fifty-fifty and you put 25, 50K checks into stuff. It’s just a way for us to meet more founders and it probably wouldn’t amount to much.” And obviously-
Turner Novak:
Was this their first kind of iteration of the scout program?
Jason Calacanis:
It was the first iteration of anybody’s scout program. It was like they created the category. Now everybody’s got one. So yeah, they created the concept of a scout. The first class was like eight of us. I think Brian Sugar, myself, a guy from Meebo, Seth Sternberg.
Turner Novak:
Well, so this may be a dumb question, but I feel like people probably want me to ask, why wouldn’t Sequoia just write the checks themselves? Why do they need you as a scout? Why don’t they just-
Jason Calacanis:
I think they wanted to expand the reach of their network and not miss anything. I think probably after missing Facebook, Twitter and some things, they started to feel like maybe we’re missing stuff. And if a New York VC, Fred Wilson could win the Twitter deal, maybe we need to have more boots on the ground. So I think it was an experiment and it worked. Yeah, Seth Sternberg was from Meebo. And there was this little kid who looked like he was in high school who was one of the first scouts, Sam Altman. He did Stripe-
Turner Novak:
Wow. I’ve heard of that guy before.
Jason Calacanis:
... as scout investment. I did Uber, DataStax, Thumbtack, a couple other companies. It was pretty funny. And that turned out to be the highest multiple fund they’ve ever done is what I’m told.
Turner Novak:
Really? They’re scout funds. That’s the first-
Jason Calacanis:
I don’t know if it’s a dollar on dollar. It’s obviously not the most dollars they’ve ever made, but I think on a multiple basis it performs spectacularly because it was a tiny fund and I think it was the GPs of Sequoia’s money because they did it as an experiment. Now it’s formalized. They have hundreds of them. I think Andreessen Horowitz has copied it. Everybody’s copied it because it’s just a great way to empower other people to make quick decisions with small checks, increased surface area. My belief in venture is that there’s opportunities at the late stage and the early stage, but in the middle, it’s incredibly competitive and incredibly... The valuations are incredibly overvalued in the middle and that makes portfolios really hard when you’re doing series A, series B portfolios. It’s really hard to make those work. Series A, B, C is so crowded. Now, if you’re doing very late stage and you’ve got two year window, three year window before the investment is realized and you can double your money in three years, okay, great. You got a 25% IRR, fantastic.
So that means the opportunities in the early stage, but in the early stage, you have 80% of the companies go to zero, like seed investments, like 80% go to zero, maybe 80% pull through or 60% pull through to the next round of investing. So you have to have a lot of surface area. You have to have a lot of bets and you don’t know which one’s going to hit. And then you have to have a strategy maybe to double down and you also have to have a strategy to liquidate early because many companies get to 500 million, stall out and become word zero, or they get to a billion or two and they stall out and they become word zero. Because the C rounds, the D rounds are so competitive, there’s so much money in the ecosystem that they overvalue them in those rounds. And that would be actually the best time to start taking chips off the table.
The strategy’s changed completely. There were a fraction of the number of companies being launched 12 years ago, 14 years ago when I started doing this. Now there’s a lot more companies launched. Very few of them get to decacorn status. It’s incredibly rare to hit a decacorn. I hit two really, well, two centurions, I guess, Uber and Robinhood. And I invested in both of those at their angel round, like really hard to do. And that was two of my first hundred investments. Now I do a hundred investments a year. We’ll probably hit 150 next year or so. When we do our fifth fund, we’ll probably be 150 a year pace. And we expect 80 or 90% of them to not make it to series B, let’s say. So we want to be high volume, small checks, accelerator like Techstars and Y Combinator or Founder University where we’ll give people if they wanted their first 25K check at a million dollar valuation when they just have an idea. So that was one of the experiments I ran.
About half the people applying for funding and we get like 20,000 applications a year. We got like five, four or 500 applications a week for funding. We sort through those, we meet with the top 100. We put it all into a database. We categorize it. I’ve got 22 people doing this. It’s like a big data project.
Turner Novak:
How many people did you say?
Jason Calacanis:
We have 22 people in the company that includes the media business and then 12 people on the investment team. So I have people doing four or five meetings a day, 20 meetings a week on the frontline and then some go to the second meeting. So it’s high volume in terms of applications, high volume in terms of the number of applications, meetings, and second meetings, and then extremely low on a percentage basis. So we’re investing in one in 150 or one in 200 people who apply for funding, but we found out half of the companies applying were not really even incorporated or didn’t finish their product yet. We were getting them in year zero, in other words.
So we started a Founder University. It’s a 12-week course, founded a university and people come there, we just teach them all the blocking and tackling stuff. Across 12 weeks, they come twice a week, one for like a talk by a notable speaker. And then on Thursdays, they have a pod of 20 companies and they kind of all share what they’re working on, what’s working, what’s not. Anyway, we invest in 10% of those companies that come. So 350 teams came to this latest one, our 11th in the United States. So we’ll invest in 30 of those maybe, and we’ll do it primarily through a 25K check at a million dollar valuation. So each week when they check in and tell us what they got accomplished, we just say, “Would you like the 25K check or would you like to come to our accelerator or both?” And like two out of three people click both or either one or both.
So most people would like amount of money and then we didn’t realize it, but like 40, 50% of people just want a 25K check to incorporate, like call it the friends and family check to make it real. And so I think we’ve written 150 of those so far. And then we have the right to put a little bit of money like 100K or 250K in the next two rounds. So we have a little super pro rata, like very modest. Then we get to do a little bit more investing as it goes if it pops and it’s working.
Turner Novak:
What does that mean? What are the stats you can share, but besides just that it’s working?
Jason Calacanis:
So I think about 60% of the companies wind up raising another round of funding at a higher valuation in the first year after going to one of our programs. So 60% pull through on those really nascent companies is pretty good. And so that to me is like the earliest sign of success. And we don’t want it to be more than 50 or 60% for Founder University because we want to bet on crazy ideas and experiments. It’s only 25K. So if we do a hundred of them and we lose $2.5 million or we do 200 of them and lose $5 million in a $45 million fund, that’s okay. We consider that the experimental budget. We get to feel out the entrepreneurs. Do they make progress every week? Are they good at hiring? Do they pivot well? And then we can pick off the ones we think are going to be really good and try to build an ownership in the company of seven, eight, excuse me, nine, 10%.
Turner Novak:
So then why do you think someone would pick launch versus they could do YC, they could do Neo. I feel like a16z has speedrun. There’s-
Jason Calacanis:
speedrun, we’ve had about five of our companies go to speedrun. So they kind of come to us first. I would say Founder University comes before all those programs. speedrun comes after all of them. And then why come to YC versus Techstars versus ours? Well, you have to get into one of them, first of all, and they all have less than a 1% acceptance rate. So I would suggest applying to all three if I’m giving my best advice, Neo, Antler, Techstars, YC, Launch Accelerator, apply to all five. I think they’re all really good programs. And what they do is because they only accept 1%, it sends a signal to the market of seed funds. Okay, somebody’s done some vetting system here and they’ve done some polishing.
Turner Novak:
They’re in the top 1%. Yeah.
Jason Calacanis:
And I think we’re probably wrong in picking the top 1%, but I don’t think we’re wrong in picking the top 10%. So I would say, Y Combinator launch everybody... We probably do pick the top 10%, not perfectly, but it’s actually 1%, which means it’s highly imperfect. In other words, somebody who was number five or 10 on the list is probably equally as good as numbers one, two, three, four, five. And we’re imperfect in picking that. So apply to all of them. And if you get into two or three, just whoever’s track record you like and vibe with the most. YC’s obviously a large program, the most recognized program. There’s a weird anti-Y Combinator kind of vibes on X with young people and founders. I don’t know. Maybe it’s like whenever you become establishment, you’re not punk rock anymore. So therefore, okay, that’s the natural course of things.
Turner Novak:
Yeah. I think there might be a common thread of like maybe people are a little bit upset they didn’t get in and there’s like some resentment and they’ve tried a couple times and they just... You think you’re better than someone who did get in and you’re kind of like, “YC sucks.” I feel like there might be a thread in that.
Jason Calacanis:
Definitely that, for sure. We have everybody who meets with us rate us on how we did as a firm. So those 100 meetings, we send them after we’ve made our decision from my email account. So if they found his reply to it, I get it. We just say, “Hey, you met with this person at this date, would you rate us? How likely would you be to refer a friend to launch and then tell us why?” And then I have two Slack rooms, one for eights and betters and one for seven and below. If it’s seven or below or six or below, like I read every single one of those and it’s almost universally the same thing, like you didn’t get it, you didn’t understand what we were pitching you. So then I wrote language for the team that does the first calls, which was, “Can I repeat back your vision to you so I make sure I didn’t miss anything?”
And once we started doing that, the ratings got much better because it required then us to really repeat back to the founder, “Okay, so you’re making an AI agent that you CC on an email message with another person to book a meeting and then it uses AI and human in the loop to book the meeting and you charge $30 a month for $360 a year and it’s as good as a $75,000 a year assistant at that one job function. Do I understand Howie correctly?” Like, “Basically you do. However, what you didn’t mention is we’re going to expand it to these three other categories. So we’re going to be help people book their travel, we’re going to help them book their whatever, hotels and check their accounting for subscriptions that are run out.”
“Okay, great. Yeah. So what I said plus these three things, okay.” And when we did that, everybody’s scores went up, including my own because I get scored. And I think people get very disappointed if a high profile investor says no, they take it very personal as opposed to just looking at the statistics like, okay, one in 150 and we get really great companies applying. So if a third of those are really great companies, you have to beat out 20 exceptional companies, how would you ever expect me to get that right? Even if I’ve got a good track record, I can’t bat a thousand. It’s just totally unrealistic.
But at least if people feel heard and then we follow up with them and then we do a little thing where we follow up with them and tell them, “Oh, by the way, we have all these free credits for this weekend startups. If you want them, you can get them here at getstartupcredits.com.” We’ll get them some startup credits at the end to... How can we be helpful, the famous like, let me know if I can be helpful any other way, but giving you my money and my reputation, which is what everybody wants. But if you’re a founder, just understand it’s a numbers game. You don’t need a hundred out of a hundred people to invest in your company. You need three out of a hundred, two out of a hundred, and then you just meet with another hundred and you get two of those. And every time, if you get product market fit and you have a chart, it gets better, you’ll get there eventually. But most founders are like, they do 20 meetings and they’re like, “Venture capitalists are idiots.” And it’s like, it’s the hard job. I’ve done those.
Turner Novak:
We kind of are idiots, some of us though.
Jason Calacanis:
Or the task is impossible because you are making an investment on incomplete information. Like poker, you can call somebody’s bluff and look like a genius or you can call what you think is a bluff and they have the stone-cold nuts and you lose your entire chip stacking and look like an idiot because they were so confident and you unpacked it and were like, they’re so confident I think they’re bluffing. We have partial information, folks. We don’t know what’s going to happen in the world. We don’t know that AI is going to displace this whole category of startups. We don’t know if some new technology is going to replace the old one and there’s going to be a platform switch. There’s so many unknowns that you’re just trying to make intelligent bets as best you can and then intelligently pair your positions as best you can so as to hit two and a half times the amount of money that was given to you so you can keep doing the pursuit known as venture capital. That’s it.
And once you realize that as a founder, okay, these guys are just terrified human beings just like me, they just have to hit two and a half percent and they could have a 5X fund, a 10X fund, and then a 2X fund or a 1.5X fund, and then everybody thinks they’re a loser and they think they’re losers. And it’s like, there’s randomness. You got to look at the whole career and say, oh yeah, funds one and two, great. Fund three, that was a dud, fund four, that’s looking promising. Okay, I’ll do fund five. It’s hard. What we do is hard.
Turner Novak:
Yeah. It sounds like the biggest takeaway for founders is you just got to have a massive pipeline. It’s just a volume game.
Jason Calacanis:
100%.
Turner Novak:
Don’t give up with those first 20 people. You got to talk to 100, 200, maybe it’ll take 1,000. If you’ve got a good product and-
Jason Calacanis:
I’d say low hundreds is what I see up until series A, yeah. And if you get traction, then it increases massively. So there is a theory to just focus on your traction and get modest traction. And then the seed funds are like, oh, this really impressive team has 300,000 in annual revenue and this team has none. I think I can make a safer bet here. I’ll go with the one that already put 300,000 on the board. And that’s what I see C funds do all the time. They’re like, okay, three people pursuing the same thing. One of them has more revenue and more growth. I’ll go with that one.
Turner Novak:
Yeah, that’s the thing to remember is just everyone’s trying to make money. Just make the investors believe they’ll make money by giving, make more money by giving it to you.
Jason Calacanis:
And if you pick a sky-high valuation, like I’ll have sometimes founders coming out of our programs, they want to raise at a 20 million valuation, they have no revenue, they haven’t launched the product. And I’m like, “You can go for it. It could happen, but you might be up against somebody with a million in revenue that’s growing 50% a year, 100% a year, and they figured out more than you have. And maybe they’ll get those investors dollars and they’ve got a $12 million cap on their notes.”
Turner Novak:
That would be low. Million bucks doubling in a month? I don’t know about 12 million.
Jason Calacanis:
No, no, no. I was saying they’re growing 50% a year, not a month. It’s an imperfect... Like, oh, they’re showing some traction, they’re figuring it out. Some people might bet on that company. And so different investors have different philosophies of which team to invest in. And some people are not valuation sensitive. And I think that’s why the entire category is underwater right now, is that the valuations at the early stages just make it impossible for these funds to perform unless they hit a decacorn and hitting a decacorn is really hard. Most VCs will never do it.
Turner Novak:
Yeah. Well, you said you’ve hit two already. Centurions?
Jason Calacanis:
Yeah.
Turner Novak:
So those are Uber and Robinhood. Going back, was Uber, it was like five million-
Jason Calacanis:
Four and half.
Turner Novak:
... pre-money, post money. Four and a half million?
Jason Calacanis:
Four and half, yeah. I think Robinhood was 15. It was expensive. Both of those were pre-launch, so got lucky.
Turner Novak:
So how did those come about? I think the Uber one, he pitched at an angel event, if I remember right.
Jason Calacanis:
He came to my angel forum, yeah. I used to host a party for 10 angel investors in two or three cities where they would take pitches from five companies. We served burgers and beers and you just pitched, you took questions and then people would give you a commitment on the spot.
Turner Novak:
And did you charge people to attend those?
Jason Calacanis:
Nope. It was free. I invite only. So Naval, myself, Chris Sacca, Cyan Banister would do it in San Francisco, myself, Matt Coffin would do it in LA. I had some folks doing it in New York. I kind of just was off. There was a company called Keiretsu Forum that was charging $5,000 to pitch supposedly angel investors. You were actually pitching accountants.
Turner Novak:
Like quote, unquote. Yeah.
Jason Calacanis:
Quote unquote. And I just said, I’m going to destroy this company. And I went on a holy jihad. I said, I’m going to go on a jihad to destroy the Keiretsu Forum. Here I am 15 years later and I’m still on that same jihad. Don’t pay to pitch your startup to investors. That makes no logical sense. But yeah, Travis famously pitched there and of the 21 people myself and first round and Cyan invested. Rest is history. Yeah. So you get lucky sometimes. Most people thought it was a dumb idea.
Turner Novak:
So what was the common pushback at the time thinking it was a dumb idea?
Jason Calacanis:
It was in the real world. It was a real world startup where you had to deal with drivers and accidents and refunds and nobody wanted to do anything in the real world. The only person, only entrepreneur really doing anything in the real world was Bezos shipping books and Elon doing cars and rocket ships. Everything was like, just make it software. Just make it software, make it a marketplace, asset light. And so, one high profile VC who shall remain nameless was like, “I’ll invest in Uber, if you convince Travis to make an enterprise software and you sell the software to the cab companies.”
And I was like, “Well, the cab companies are the problem. We’re eliminating the cab companies. We’re making them go away because they don’t provide enough value and they take 50%, 60% of the economics. But if you get rid of them, we take 25% of the economics, then the price can go down and the drivers can make more and the drivers can have flexibility, yada, yada.” But no, they wanted it to be the other way. They wanted to sell software to cab companies. And I was like, “Yeah, I’ll get right on that. Let me go waste Travis’s time with a terrible idea.” I never told Travis.
Turner Novak:
I’m sure he got suggested that all the time though.
Jason Calacanis:
Robinhood got laughed at as well. “How are you going to make money? Oh, what’s the business? “We’re going to get millennials to trade stocks.” It’s like millennials who are on their parents’ Netflix accounts.
Turner Novak:
They don’t have money. Yeah.
Jason Calacanis:
“They don’t have money. They don’t care about the future. You’re going to get them. How are you going to do it?” “We’re going to make it free.” “Oh, you can make it free and get a bunch of people who don’t do this behavior.” It’s like the Canva pitch. It’s Photoshop for people who don’t know how to use Photoshop. And it’s like, “Okay, what are they using right now?” It’s like, “They’re not. They don’t make invitations and they don’t do cards and stuff like that. They just don’t do graphic design. We’re going to get them to do graphic design.” It’s like, “So you’re going to get people who don’t do graphic design to pay you for graphic design software.” I was like, “Yes, that’s the opportunity.” And some people are like, “I don’t understand the TAM. The TAM is zero.” It’s like, “Yes, the TAM is zero. We’re going to manifest a TAM.” That’s what Robinhood did. They manifested that TAM.
Turner Novak:
So what did you see? What was the reason you invested if the TAM was...
Jason Calacanis:
I just said to myself, what if it works? Which is what I always say to myself, what if it works? Just like I do when we talk this conversation about media, what if podcasting works? I’ll be there first, I’ll figure it out first. What if they get there first and people start trading stocks, even they’re just trading one or two of them. Eventually they’ll be 35-year olds and they’ll know what 401(k) is or they’ll have a kid and they’ll want to get a 529 started or they’ll want to do a Roth or they’ll want to start putting a certain amount of money into index funds every month or maybe they’ll want tax strategies. What if it works and you have 10 million people? It’s like, okay, it worked and they have 30 or 40 million people.
Turner Novak:
Now they’re doing mortgages and-
Jason Calacanis:
What if they want a credit card?
Turner Novak:
Can you get gold delivered to you or something or physical cash delivered to you?
Jason Calacanis:
Everything. And there was his vision from the beginning. And I said to him, I said, “Well, what if it works?” And he’s like, “Exactly.” And it did. Airbnb is the same kind of thing. What if people will rent their houses out when they’re not using them or rooms in their houses or ADUs? It’s like, well, that’s a crazy stupid idea. You’re going to have a serial killer stay at your house or at your apartment when you’re not there? What if they trashed? It’s like, yeah, that’s a possibility. We have insurance. What if it works? It’s like, it works. Pretty amazing company.
Turner Novak:
So one thing I’ve actually been super curious, I don’t know the answer to this. There’s sort of this joke that you were the third or fourth investor in Uber.
Jason Calacanis:
Sure.
Turner Novak:
Why is there this discrepancy of which one you work?
Jason Calacanis:
Okay. Because I was talking to Travis at some point, I was like, “I want to be the first investor.” And he was like, “Oh, I think you’re the third or fourth.” I was like, “Well, okay. Somebody else got there.” So anyway, they asked me, at CNBC or something, they said, “We hear you’re the first investor in Uber.” And I was like, “I think I’m the third or fourth.” So then it just became a bit of a meme where I just, when I wrote my book Angel, it was like, “Hey, here’s a book about angel investing and this incredible story of investing in Robinhood and investing in Uber and these other companies, and here’s how I did it.” And so during the press tour, somebody put, I think in the notes for people like, “Oh yeah, he was the third or fourth investor.” And they put he’s the third investor in Uber and I put-
Turner Novak:
So everyone would bring it up?
Jason Calacanis:
So I kept putting or fourth in there because I thought it sounded more interesting for doing third or fourth. But then VC Braggs, which is my favorite account, and I’m super engaged with VC Braggs. Sometimes I’ll tweet stuff and then I put @VCBraggs in the reply where I call out myself because I thought it was hilarious because they were going after Prof G-
Turner Novak:
They made a YouTube video about it.
Jason Calacanis:
Yes, and they did a YouTube video about me being the third or fourth. I was the first person to retweet it. I was like, “This is great.”
Turner Novak:
I thought it was hilarious.
Jason Calacanis:
Then they did one about Prof G and his Macy’s is going to be bigger than Amazon and all these terrible takes. Tesla’s going to zero. This one’s going to zero. Mason’s going to beat to Amazon. And so I just thought these were hilarious, so I retweeted them and then it literally has become a meme and I’m here for it. I’m here for the memes. I think I have a sense of humor.
Turner Novak:
Yeah. Well, and I think when I tweeted a couple hours ago that you were coming on the show, I haven’t read it in the past hour and a half, but five, six, seven people responded, “Ask him about if he was the third or fourth investor.” It’s just a meme that’s like-
Jason Calacanis:
We’ll never know. And we’ll have to do some archeology. We’ll have to get the initial bank statements of whose wire came in. I think wire statements speak, but who knows? Maybe I’m the 30th. I don’t know. Maybe this is all folk law. Who knows?
Turner Novak:
Well, there’s this one story. I think you were the first customer of one of the Tesla cars. I don’t remember which one. You know what I’m talking about?
Jason Calacanis:
Yeah, I have the first Model S. Yeah. Very famous story. I was with Elon having dinner and he was ... And he’s spoken about this, so I’m not speaking out of school, but you know, being friends for a long time, and I was very reticent to even bring him up ever because he’s larger than life. And sometimes people were like, “Oh, you’re riding on his coattails, you’re talking about your friendship, whatever.” But he had talked about this one, so I don’t mind talking about it, which was we went to dinner, I went to Boa, he was feeling down because Tesla was dying. It was out of money. Valley Wag was writing, “There’s two weeks left.” SpaceX had just blown up a rocket-
Turner Novak:
Didn’t they say he had six weeks or something? They said six weeks but-
Jason Calacanis:
It was like six weeks of cash left, whatever. And then there was like-
Turner Novak:
But he technically had two weeks or something like that?
Jason Calacanis:
Yeah. So we went to dinner and I said, “Oh, how’s it going?” He’s like, “It’s terrible. The divorce, SpaceX blew up the rocket.” And I was like, “Is it true you have six weeks left of cash in Tesla?” And he said, “No, that’s not true.” And I said, “Oh, thank God.” He said, “Yeah, it’s two weeks.” I said, “I have a couple of million bucks. You want me to wire you a million bucks or something?” And he’s like, “No, it’s not going to make a difference. That would just be a couple days of payroll, whatever.” I said, “Well, certainly there’s some good news and there’s always something that’s good news, right? There must be something.”
And he took out his Blackberry to date the conversation and he started swiping on the little ball and he was showing me, he said, “Don’t tell anybody, but this is the sedan we’re going to make. It’s going to be Model S.” He actually didn’t have a name for it at the time. We were actually brainstorming names and we’re going through it and I said, “Wow, that’s gorgeous. Looks like this car from the future.” I said, “What is it going to cost?” He said, “50K.” I said, “50K? Wow, if you can make a $50,000 electric car, you’ll change the world.”
And so then I went home, talked to my wife, Jade, and she was like, “How’s Elon doing?” I was like, “It’s disaster. He might be sleeping on our couch in a couple of weeks, this is not good.” And I said, “But I think he’s going to figure out Tesla. I think he’s got this new car he’s going to do. It’s going to be like 50 grand.” She goes, “Oh, I want one.” I said, “Yeah, I want one too.” So I said, “Give me the checkbook.” And I wrote two handwritten checks and I wrote a note, E, that car’s going to change the world. I’ll take two.” And I put two $50,000 checks in it and I FedExed it to his office just to make him feel good and maybe I could pay for one day or two days of payroll.
A month later, he closed some financing. Three months later, the checks cashed. Then I get an email one day, “Hey, your reservation number one, your reservation number 73.” And I forwarded it to him and then I talked to him and I said, “You don’t have to give me number one.” He’s like, “Don’t worry, I got the mules and I got all the whatever. I want you to have number one because you’re the first person to buy it. It means a lot to me for you to have number one.” And I said, “Okay.”
And then they sent it to me and then they had shipped it and they were a public company. So CNBC is coming to my house or different news organizations are like, “Hey, we got to see the car. It’s now out. It’s out. They’ve talked about their shipped cars, we know you have one,” because I’m a loudmouth and I had talked about having number one and the car wasn’t exactly perfectly ready at the time. So I was getting updates on a thumb drive because it didn’t have the radio in it yet to do over the air and-
Turner Novak:
Oh, you have to literally stick in a hard drive?
Jason Calacanis:
Sticking a thumb drive to update the software. So I have a Tesla engineer coming every week or two to update it and I was giving them my notes on it. It was very early as you could suspect. And so I’m giving all these notes of things that need to be fixed, like 10, 20 things, lists and I’m sending it to the team over there. And then I go on CNBC or whatever. People are asking me how it is and I said, “Flawless, this car is going to change the world.” And it did.
Turner Novak:
I’m sure they loved that, that soundbite, the clip of you doing that.
Jason Calacanis:
Yum, yum. I would give them my classic CNBC, “Yum Yum. This car’s going to change the world.” And it did. And it’s sitting in my garage. It’s worth a million bucks now. Somebody offered me a million dollars for it. I’ll never sell it. And I have 16 of the Roadster. So I have two of these. Shout out, Elon.
Turner Novak:
You have 16?
Jason Calacanis:
Yeah, number 16 of the Roadster.
Turner Novak:
Oh, I thought you said you had 16. Like a J Leno style-
Jason Calacanis:
No, not 16 of them. But those are worth a quarter million dollars each, I think, the original Roadsters. A lot of people crash them and they don’t crash very well. It’s like kind of a go-kart. So if you crash it, it’s kind of over for the car, maybe you.
Turner Novak:
Geez.
Jason Calacanis:
So the number of Roadsters is going down precipitously because people love to drive them and I think that one will become worth more eventually because even though the other one’s number one, 16 is ... I think there were like only 4,000 of those made. I don’t know how many Roadsters were actually made. They were pretty bespoke. But yeah, and now the self-driving is 95% of the way there. I think they’re going to figure it out in the next year too.
Turner Novak:
How did you meet Elon initially?
Jason Calacanis:
Elon was roommates with my friend Adeo from New York. They were roommates in college at Penn, I believe, University of Pennsylvania. So yeah, just met him socially and we vibed. We used to hang out in LA, both there. Now we both live in Austin, we hang out in Austin. Just a normal human being who started seven or eight companies that changed the world.
Turner Novak:
Yeah, no big deal. What do you think people underestimate about him?
Jason Calacanis:
He’s a great engineer. I think people forget that. He’s actually a legit engineer who understands the underpinnings of these things. They probably also underestimate the amount of value you get from having built many factories. It turns out building factories is the business of Tesla and SpaceX in many ways. It’s not the thing that comes out of the factory, it’s the thing that makes the thing that comes out of the factory. And there’s probably only three or four people on the planet who know as much about factories as Elon. Might be somebody who works for Tim Cook at Apple, Foxconn, Samsung. There’s a small number of people who understand factories to the level he does.
But on a work ethic basis, he’s the hardest working human being I’ve ever seen. When I was at Twitter with him, he’d be like midnight, 1:00 AM and everybody’s exhausted. And he’s like, “Okay, two more meetings.” And next group comes in, next group comes in. It’s 1:30 in the morning, I’m like, “Bro, we got to get some sleep. We got to start again. We got a 10:00 AM meeting here with the NFL. We need to go to bed.”
He’s like, “Okay, one more meeting.” I was like, “Okay, let’s do one more meeting, but at 2:00 AM we can pack it in and get six hours of sleep and be back here to meet with Roger Goodell. Yeah?” “Yeah. Okay. We’ll meet with Roger Goodell in the morning.” You can’t be late for a meeting with the NFL if you’re Twitter. Yeah. But his work ethic is unbelievable. It’s not human. An inhuman, he’s an alien when it comes to his work ethic, I would say.
Turner Novak:
Is he one of those people that doesn’t need as much sleep, only needs four hours of sleep kind of a thing? Or how do you pull that off?
Jason Calacanis:
Maybe. Maybe, but I think it’s just his drive. I think he probably could use some more sleep, but I think his drive is so high and he wants to win. So it’s just preternatural. Is preternatural the word? Preternatural. There’s a word for inhuman.
Turner Novak:
Beyond what is normal or natural, extraordinary, and often inexplicable by ordinary means.
Jason Calacanis:
Yeah, that’s it.
Turner Novak:
Qualities that are so unusual-
Jason Calacanis:
Preter.
Turner Novak:
Preternatural. Yeah. Qualities are so unusual that they seem impossible.
Jason Calacanis:
Yeah. Preternatural, that’s him. Yeah. That would be what I would say-
Turner Novak:
I’ve never heard that before.
Jason Calacanis:
It’s a good word. Preternatural. There you go.
Turner Novak:
So you mentioned kind of the Twitter acquisition. What was it like when that was going down? I think you kind of worked at the company for a while. What all happened there?
Jason Calacanis:
I mean, it was a little overstated. I was consulting, just helping out, unpaid, just friend, hanging out to make the vibes maybe on the margins, help with some decisions. But yeah, certainly don’t want to overstate it, but I was hanging out with Sacks and everybody, enduring it, Antonio, Gracias, all the people who funded it. And it was, in my opinion, the greatest heist in the history of business that occurred by those previous employees.
A large portion of them were not working and making huge salaries and they were spending money in a public company like drunken sailors. And there was SaaS software, office space that had never been touched that was being paid for. There were people making lunches for 10 people at the office and we averaged out what each lunch cost. It was like each lunch costs $400. It was like going to a Michelin ... You could have sent the staff that did show up for work to a Michelin star restaurant and save money based on the amount of food they were making and the cost of the staff.
So it was like, yeah, just stealing from the public. If you think of it as a public company, I was just aghast at the ... And then there were people who were working hard, but there were people who were not working at all. And it was kind of like the abuse ... There was abuse in that system that I think has never been matched, combined with the COVID, like stay at home kind of work ethic. And I think it really did break people’s brains when he got rid of 85% of the people and the service worked better and the product feature started flowing faster. And I think that’s why there’s less people working at Uber, Meta, Microsoft, Airbnb, Google now than there were four years ago.
I think everybody realized these companies were massively overstaffed and you could do more with less. And the revenue for Google or Uber has grown 20 or whatever percent every year, earnings maybe more, and they keep growing with less people or the same number of people. And then with AI, I think it’s going to become more pronounced. So I think we’re going to be sitting here with these companies ... I think we could be looking at Amazon, Uber, Google, Meta, all having less employees in 2030 than they have now and having massively more earnings. All the growth in the world with less people. That’s the promise of this technology. Automate everything.
Turner Novak:
I agree with you on the promise, but because this is a podcast, I mean, couldn’t that be bad though? We’re talking about job loss, like 85% job loss. Or was Twitter an extreme case?
Jason Calacanis:
For the business we’re in, startups, it’s good because I think young people are going to realize ... I gave a talk last night to a bunch of young people at extern.com, one of our investments that does like externships. And I just named the title of my talk, Nobody’s Coming. Nobody’s coming for you. Help is not on the way. It’s over. You’re on your own. And so start a company, get two or three really talented friends, learn all the skills in the world and start a company and build a product or service because people always love a new product or service in the world, but you’re not going to get a job at one of the big companies. This is not happening.
And that’s quite a change from just six, seven years ago. Pre-COVID, you would graduate college, you’d have an offer from Uber, an offer from Coinbase, an offer from Google. You’d have like three of the seven people you met with would make you a really nice offer and you would be picking between them. And now the people who were working there, who were the managers giving you those offers are now your competition for a job. Holy cow. And that happened quickly.
Now, a lot of people don’t like me talking about this so candidly, but we are going to face the greatest job displacement in the history of humanity is my belief. There’s a chance it doesn’t happen. There’s a chance this technology peters out and doesn’t keep compounding as quick as it is. I think that’s like a 10% chance. I think there’s a 90% chance that this time is different, that instead of having a bunch of job displacement over 40 years, we’re going to have it over four, maybe 10 years, four to 10 years.
I think we’re already seeing it. Companies are like, “Maybe we should stop hiring and just automate this. And oh, if we hire a young person out of school, we’re going to have to train them and they’re going to slow everybody down.”
Turner Novak:
And then they’re going to leave in two years?
Jason Calacanis:
Yeah. “So maybe we just automate it or we find a third party you can outsource it to.” Somebody was dogging me for having two assistants on Athena and I’m like, it’s $3,000 a month per assistant. It’s $72,000 a year for two assistants. I couldn’t hire an assistant for 75K or 100K. And if you did, they would leave in six months or 12 months or 18 months. They don’t want that job. They don’t want to do that work.
It’s just, how can you blame a business person for wanting to outsource to a better solution? With two Athena assistants, I have 80 hours of coverage a week, not 40, and they don’t leave every 12 months. And if they do leave, they get replaced by Athena. It’s their job to replace them. So go to AthenaWow.com, you get a couple of weeks off. There’s my plug. I’m first investor. Jonathan had me ... I was the first investor in Thumbtack and the first investor in Athena.
Turner Novak:
Wow.
Jason Calacanis:
Wow. Athena, wow.
Turner Novak:
There you go. Yeah, Athena. Athena, wow.
Jason Calacanis:
I came up with that because of Christopher Walken. Athena, wow.
Turner Novak:
One of my friends asked you or asked me, he’s like, “You’ve been pretty public about GLP-1s.” He’s been super curious. Can we talk about that really quick?
Jason Calacanis:
Absolutely. GLP-1s have changed my life, perhaps saved my life. I gained two pounds a year for 20 years of being an entrepreneur, been having kids.
Turner Novak:
That’ll accrue over time, yeah.
Jason Calacanis:
Yeah. And I used to be a marathon runner. I was like super svelte.
Turner Novak:
I didn’t know that.
Jason Calacanis:
And then just over time, I didn’t pay attention to it. And I was very ashamed of it and kept trying. And I would go from 213 pounds down to 190, back up to 200. It was just brutal. And I’m five eight and a half, so on a good day. So that’s pretty chunky. And my face was really fat on TV. And I heard Tim Ferriss and Kevin Rose, two good friends of mine, talking about Ozempic four years ago on their Random podcast where they talk about random shit. And they were talking about it and it wasn’t for weight loss, but Kevin Rose was using an off-label to get rid of some visceral fat that he couldn’t get rid of.
And I guess then I went to my doctor and I lobbied them about it. And anyway, this all ends in a commercial because now I am literally a spokesperson for ro.co. So ro.co, I was talking to the founder at an event, he’s like, “It’s really inspiring.” And I was like, “Yeah, you guys are doing GLP-1s now. I’m going to move my GLP over to there because I have to pay for it now because I’m not a fat bastard anymore.”
Anyway, he was like, “Would you consider being a spokesperson for us?” And I was like, “Like Serena Williams?” And he’s like, “Yeah, and Charles Barkley. It’d be like you and those two.” And I was like, “Okay.” So we did a sponsorship deal, so I’m going to be in commercials for ro.co. I’m Jason Calacanis. I was a fat bastard. I’m no longer fat. Look at me on my podcast when I was 213 pounds. Now look at me, a svelte fighting weight of 170. I mean, it’s like a 43 pound difference. It’s crazy.
Turner Novak:
Yeah. And that’s huge at 5’8”. That’s a massive change.
Jason Calacanis:
I mean, I now put on a 35 pound weight vest to walk around my ranch to give myself the feeling. And then I’m like, wow, I was walking around like this every day. Now I know why I was exhausted and I was low energy. It’s because I was wearing a weight vest of 35 pounds 24 hours a day. That’s a lot of fat to have on your body. So I will just tell people, look ... And I didn’t talk about it for the first couple years because I was like, this is experimental, but now I think we’re past the experimental phase. So I just say, “No shame in the GLP game. If you’re thinking about it, go-
Turner Novak:
To ro.com.
Jason Calacanis:
... search it at ro.co.
Turner Novak:
Ro.com/Jason.
Jason Calacanis:
Yeah.
Turner Novak:
Ro.co/jason.
Jason Calacanis:
I don’t actually have a code or anything. Just go to ro.co. It’s all good.
Turner Novak:
I think I hear people talk about the benefits of it. Are there any downsides to it that you experienced?
Jason Calacanis:
I think you can get indigestion, you could belch, fart. It slows down the food in your system. So you will, if you talk to people candidly about it, if you forget that you took it and then you go eat three or four slices of pizza, you might like literally vomit. That happened to me twice where I just ate too much sushi and too much pizza. I forgot that I was on GLPs and I was just starting out with them and I was like figuring out the dosage and all that stuff.
Now it’s pretty well established like what the right dosage is. You just slowly move up and you start to tolerate it and the food goes through your system, just simplifying here, slower, so you feel fuller, quicker, and then you don’t have food noise. So I didn’t realize how often I was thinking about food. I was thinking about food all the time. Now I don’t think about food all the time and which gives me time for my kids, for work, for reading a book, whatever. I’m not like, “I need more food.” So I think that’s like actually one of the big upsides to it as well.
Turner Novak:
Interesting. Okay. Yeah. Well, I don’t know if the sponsorship will be live by the time this episode comes out, but we’ll throw a link in the show notes.
Jason Calacanis:
Oh no, it’s already live. Yeah. Just ro.co is fine.
Turner Novak:
Yeah. Oh, cool.
Jason Calacanis:
All right. Awesome.
Turner Novak:
Well, you tweet a lot, right? People can find you @jason?
Jason Calacanis:
X.com/jason, Instagram.com/jason if you want to see my food picks and yeah, founder.university. Apply if you want to start a company.
Turner Novak:
Launch.com?
Jason Calacanis:
Launch.co. Launch.co.
Turner Novak:
All-In. What’s the All-In?
Jason Calacanis:
Launch.com/apply. Allin.com. I got the domain.
Turner Novak:
Allin.com?
Jason Calacanis:
Took me two years. Yeah, I got it.
Turner Novak:
Wow. Nice.
Jason Calacanis:
It took a while.
Turner Novak:
Yeah.
Jason Calacanis:
That was another hard one. I have begin.com. I got begin.com. That’s what I’m looking for an idea for.
Turner Novak:
I never asked you this. How many people actually listen All-In? What are the stats you guys are public about?
Jason Calacanis:
I think it’s millions a week. Yeah.
Turner Novak:
Millions a week. That’s pretty good.
Jason Calacanis:
I mean, it’s pretty crazy. I cannot believe the nature of the audience either. I think that’s kind of the big low-key secret is that heads of state, CEOs listen to it. That’s why it’s, I think, as influential as it is and why we don’t dumb it down too much to broaden the appeal. We keep it high level. Even when I do try to explain terms, it’s a high level discussion. You got to keep up with it because it’s for people who are running companies, countries, venture firms, running books of capital. So yeah, all that.
Turner Novak:
Yeah. How do you decide what to talk about and who to bring on?
Jason Calacanis:
Yeah, pretty basic. Every week, people just vote on what they want to talk about. So if I want to talk about something, everybody just submits URLs. There’s a producer, Lisa, who’s amazing, and we just give her our picks and then I run through it. And then I sort it by how many people want to talk about the topic. So if three people want to talk about Epstein or two people want to talk about Epstein or one person wants to meet up with Epstein, it’ll move up and down the docket, right? Based on that. We always try to have whatever the consensus top news story in the world is as the number one story because people expect, “Oh, well, if Trump is elected president, we’re going to start with that.”
Turner Novak:
Yeah. So I guess I can see then if Chamath and Sacks and Friedberg all want to hit on a political thing, you reluctantly, even if you don’t want to, you got to throw it in.
Jason Calacanis:
Yeah. I don’t decide on the docket. Everybody just does theirs. Everybody puts in their two cents. And what you will see is if only one person wanted to talk about it, then sometimes you’ll hear me do something critical of Trump, let’s say. And then the three other castmates might have nothing to say because it’s critical of Trump and then it just sort of sits there and then we move on to the next subject. Fair. Balls and strikes.
They’re big boys. They can handle me being critical of Trump, even if they’re in the administration or adjacent to the administration. It’s not the first time that anybody’s been critical of Trump. So we’ve kind of worked that out, I think, pretty nicely. We talked about Epstein on the pod last week as an example.
Turner Novak:
Oh, really? I’ll have to check the one out
Well, cool. Well, this is a lot of fun. Thanks for doing this.
Jason Calacanis:
All right. Cool, brother. I’ll talk to you soon. Really enjoyed it.
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