Jason Calacanis: Startups, Angel Investing, Capitalism, and Friendship | Lex Fridman Podcast #161

1. 0:00 – 1:51

   Introduction

   1. LFLex Fridman0:00

      The following is a conversation with Jason Calacanis, who's an entrepreneur, investor, author of Angel: How to Invest in Technology Startups, and as many people may know, he's a fun, brilliant, long-time podcast host of This Week In Startups and co-host of the All-In Podcast with Chamath Palihapitiya, David Sacks, and David Friedberg, who all happen to be poker buddies and self-proclaimed besties. The result is always a great listen due to both the love and the heated disagreements. Quick mention of our sponsors: Brave Browser, Linode Linux Virtual Machines, Four Sigmatic Mushroom Coffee, and Rev Speech-to-Text Service. Click the sponsor links to get a discount and to support this podcast. As a side note, let me say that I've been learning a lot about real world finance in the past few months. To give you a bit of context, on the side I've studied trading from an algorithmic trading perspective as a machine learning and game theory problem off and on for a few years in undergrad and grad school. I found the distributed complex system aspect of finance and economics in general fascinating. But now, I find even more fascinating the human side of the whole thing, ideas of greed, power, freedom, and truth. WallStreetBets, Robinhood, and the whole beautiful mess around this topic allows us to have great conversations about human nature and the systems that underlie the rise and fall of civilizations. If you enjoy this thing, subscribe on YouTube, review it on Apple Podcasts, follow on Spotify, support on Patreon, connect with me on Twitter @lexfridman. And now, here's my conversation with Jason Calacanis.

2. 1:51 – 12:58

   WallStreetBets and Robinhood

   1. LFLex Fridman1:51

      I have a million things to talk to you about-

   2. JCJason Calacanis1:53

      Yeah.

   3. LFLex Fridman1:53

      ... but we do happen to be living through what I would think of as a historic event in, in terms of its impact, in terms of like almost philosophically thinking about the role of people and how they can fight power with this whole WallStreetBets and GameStop situation.

   4. JCJason Calacanis2:13

      Yeah.

   5. LFLex Fridman2:13

      I was wondering, you've covered in your, uh, amazing All-In Podcast, you guys have been having fascinating battles over this whole situation.

   6. JCJason Calacanis2:22

      (laughs)

   7. LFLex Fridman2:22

      I was wondering if you could tell maybe from your perspective, as it's unrolling, uh, the, the saga of WallStreetBets and GameStop, what are some interesting insights-

   8. JCJason Calacanis2:32

      Yeah.

   9. LFLex Fridman2:32

      ... uh, that, uh, you have about this whole set of events?

   10. JCJason Calacanis2:36

       In full disclosure, I was an angel investor in Robinhood before they launched, and when I met the founder Vlad and his partner, you know, they pitched me at a, a, a bar not too far from where we are right now in Palo Alto called Antonio's Nut House.

   11. LFLex Fridman2:51

       (laughs)

   12. JCJason Calacanis2:51

       And my friend Adeo ... It's a (laughs) really good story. My friend Adeo had asked me to speak at his founder's institute, which is kinda like an accelerator for people who are thinking about starting a company.

   13. LFLex Fridman3:01

       Yes.

   14. JCJason Calacanis3:01

       And so I gave a talk and then he said, "Hey, let's go to Antonio's Nut House and, um, we'll meet Elon for a drink." Uh, and so Elon met us for a drink there. And it's the, it's the divest of dive bars.

   15. LFLex Fridman3:11

       Uh-huh. (laughs)

   16. JCJason Calacanis3:12

       Like, you'll take a beer and it-

   17. LFLex Fridman3:14

       I love the image of all of this. You, you hang out with Elon at a-

   18. JCJason Calacanis3:17

       There's, there's dirt on the floor.

   19. LFLex Fridman3:17

       ... at a crappy bar.

   20. JCJason Calacanis3:18

       Yeah. I mean, it is the worst bar in the peninsula. Like, just garbage on the floor and like cheap beer-

   21. LFLex Fridman3:27

       Yeah.

   22. JCJason Calacanis3:27

       ... and warm beer. And like you'll pick up your pint glass, there'll be lipstick on it.

   23. LFLex Fridman3:30

       Yeah.

   24. JCJason Calacanis3:30

       It's just brutal.

   25. LFLex Fridman3:31

       Classy.

   26. JCJason Calacanis3:32

       Not your lipstick. You understand?

   27. LFLex Fridman3:34

       Yes.

   28. JCJason Calacanis3:34

       Somebody else's lipstick.

   29. LFLex Fridman3:35

       Yes. (laughs)

   30. JCJason Calacanis3:35

       And so we're sitting there and Vlad walks up with, um, his partner and he says, "You're Jason Calacanis." And I said, "Tell me about your startup." He said, "How do you know I have a startup?" I said, "You recognize me."
3. 12:58 – 16:09

   How does the WallStreetBets saga end?

   1. JCJason Calacanis12:58

   2. LFLex Fridman12:58

      How does this whole thing end, uh-

   3. JCJason Calacanis13:00

      Probably in tears.

   4. LFLex Fridman13:01

      For who?

   5. JCJason Calacanis13:02

      Yeah. (laughs)

   6. LFLex Fridman13:02

      Who's crying? Is everybody crying? (laughs)

   7. JCJason Calacanis13:04

      Exactly. Who's crying when?

   8. LFLex Fridman13:06

      (laughs)

   9. JCJason Calacanis13:06

      So I think there were some of the hedge funds that were crying initially.

   10. LFLex Fridman13:09

       Yes.

   11. JCJason Calacanis13:09

       Then maybe some of the WallStreetBets people who bought last would be crying. And then eventually, there's, uh, probably another set of hedge funds or even the WallStreetBets mob and, you know, that army. Some of them might have broke ranks and then shorted the stock.

   12. LFLex Fridman13:23

       Yeah.

   13. JCJason Calacanis13:23

       So nobody knows. So everybody has to be aware of what's happening in the game. So if WallStreetBets said, "Hey, let's squeeze these hedge funds 'cause they have too much short interest. Let's all buy the stock." Then some of them might have said, "Okay, you know, it's at three, two or $300, maybe I'll join the short movement now that they've covered." And they could have shorted their... And been, like, double agents. So people have to understand, like, this stuff is gnarly. And it's a, it's a free-for-all. I mean, it is a literal free-for-all.

   14. LFLex Fridman13:49

       There's a kind of morality, like a big statement that WallStreetBets made in terms of, like, the elites can't just push us around. They can't bully around. But at the same time, you know, they're also interested in making money, right?

   15. JCJason Calacanis14:03

       Yeah.

   16. LFLex Fridman14:04

       Is, uh, is, uh, what's your sense? You said that some of the people in WallStreetBets might have broken off and, and shorted the stock.

   17. JCJason Calacanis14:10

       Sure.

   18. LFLex Fridman14:10

       Are they more interested... There was an emergent, like, morality that emerged-

   19. JCJason Calacanis14:15

       Sure.

   20. LFLex Fridman14:15

       ... and, and said, like, "We're not gonna put up with the centralized elites." But is that going to continue? Are they going to fight the power structures that are bad for society or are they going to now, like... I mean, are they ultimately going to introduce more chaos that's going to damage the economy and damage the world? Or are they going to continue being the good guys and fighting the, uh-

   21. JCJason Calacanis14:37

       Yeah.

   22. LFLex Fridman14:37

       ... the, the, the evils that manipulate, uh, the market? What's your sense?

   23. JCJason Calacanis14:42

       You know, it, it really feels like The Dark Knight series of (laughs) films-

   24. LFLex Fridman14:45

       (laughs)

   25. JCJason Calacanis14:45

       ... where, like, some people just wanna see the world burn.

   26. LFLex Fridman14:48

       Yeah.

   27. JCJason Calacanis14:48

       I think there is a contingent of people who just literally want to see chaos.

   28. LFLex Fridman14:52

       Yeah.

   29. JCJason Calacanis14:52

       Like, you know, that contingent on some of these, you know, forums who just wanna create chaos, right?

   30. LFLex Fridman14:58

       Yeah.
4. 16:09 – 21:30

   Capitalism

   1. JCJason Calacanis16:09

      And one of the things that concerns me most about where we're at in society is the sort of socialism, communism. You know, (sighs) entrepreneurship is bad, technology is bad, and polarization of wealth. And, you know, people getting rich is a bad thing. When I grew up, I'm 50 now, but when I was a Gen Xer growing up, we kind of maybe too much idolized Bill Gates and people who are doing interesting things in the world. And we thought capitalism was a force for good. I still believe capitalism is a force for good, because when a group of people builds a product or service that changes the world and it, and it gets globally distributed, whether it's Tesla or SpaceX or Google or Airbnb or Uber or Robinhood, you know, everybody gets to benefit from that product or service having to compete. And if you look at the places where there's no competition, like public education or less, you know, prof- you know, uh, you know, established, uh, you know, colleges and stuff like that.

   2. LFLex Fridman17:03

      Yeah.

   3. JCJason Calacanis17:03

      Less competition for accreditation degrees. Like, things tend to get a little weird, don't they?

   4. LFLex Fridman17:08

      Yeah.

   5. JCJason Calacanis17:08

      Um, and people tend to be protected. And that's not good. You need co- you need competition. Um, doesn't mean that, you know, people shouldn't have global healthcare. It doesn't mean that, you know, we shouldn't have a safety net, but we need to keep capitalism vibrant. Especially because China has now co-opted capitalism and created their own version of capitalism, which is communism with capitalism. It's like this weird operating system. Like, "We still wanna keep communism, so we can take any of your gains at any time-

   6. LFLex Fridman17:35

      Yes.

   7. JCJason Calacanis17:35

      ... but we'd like you to be entrepreneurial."

   8. LFLex Fridman17:37

      Yeah.

   9. JCJason Calacanis17:37

      And then you have somebody like, you know, um, you know, the founder of Alibaba, Jack Ma, who disappears for a couple of weeks.

   10. LFLex Fridman17:45

       Uh, who's that? No. Just kidding. (laughs)

   11. JCJason Calacanis17:46

       (laughs) Yeah, exactly. It's like, "Who's Jack Ma?"

   12. LFLex Fridman17:48

       (laughs)

   13. JCJason Calacanis17:48

       It's like, he kinda disappears for a couple of weeks. Then he comes back and he's really sorry about the things he said, and then he disappears again. And like-

   14. LFLex Fridman17:55

       (laughs) Yes.

   15. JCJason Calacanis17:56

       You know, we have to be very careful. If China wins capitalism-

   16. LFLex Fridman17:59

       Yeah.

   17. JCJason Calacanis18:00

       ... this is gonna be an existential threat for humanity.

   18. LFLex Fridman18:04

       Yeah.

   19. JCJason Calacanis18:05

       The Chinese are no joke. I mean, they are seriously focused, um, and they are picking the winners.

   20. LFLex Fridman18:12

       It's a very weird system, because it is in fact... I don't know what you call it. Like, communism, capitalism is such, uh, overloaded terms. But they do encourage entrepreneurship, but they...... and they do a good job of it.

   21. JCJason Calacanis18:25

       Oh, yes.

   22. LFLex Fridman18:25

       But, but then they're like, they're like the surveillance thing, and they're controlling things in a way.

   23. JCJason Calacanis18:30

       Yeah.

   24. LFLex Fridman18:30

       It's, it's weird because it seems to work really well for them, uh, in the short term.

   25. JCJason Calacanis18:36

       Yes. It's definitely got short-term benefits.

   26. LFLex Fridman18:38

       So the question is like what, (laughs) what, uh, how that gets distorted and then becomes worse and worse and worse. Well, it should potentially, might be. And I, I think on, you know, the, the entrepreneurial spirit, which you have a podcast all centered around-

   27. JCJason Calacanis18:54

       Yeah.

   28. LFLex Fridman18:54

       ... the entrepreneurial spirit i- is, uh, is one of the magical things that makes this country great. I don't know if money is deeply tied into that. I do get bothered by people, y- you know, treating the word billionaire as if it's a bad word.

   29. JCJason Calacanis19:08

       Yeah.

   30. LFLex Fridman19:08

       But in general, like all the hard things, all the difficult things we're going through in this country, it seems like the way out is going to be, uh, making the, uh, the entrepreneur the hero of society, of like letting that young kid with a big dream and the guts to take the big risks-
5. 21:30 – 22:37

   Ideas vs Execution

   1. JCJason Calacanis21:30

      And often I meet people and they're like, "I need a technical co-founder, and I, I, you know, but all I need is a million dollars." And I'm like, "Okay, well, what is your skill?" And they don't have a skill.

   2. LFLex Fridman21:38

      Right.

   3. JCJason Calacanis21:39

      And I'm like, "Well, are you a designer?" "No." "Are you a product manager?" "No." "Are you a developer?" "No." "Are you a sales executive?" "No." "Okay, what are you?" And it's like, "Well, I have an idea." Well, as my friend Sam Harris, I think, uh, your friend as well, says like, "Everybody has like a million ideas an hour."

   4. LFLex Fridman21:55

      (laughs)

   5. JCJason Calacanis21:55

      Like, you don't really get credit for those. Even when you're asleep, your idea is spewing ideas. Like zero credit for your ideas. It's all about execution. And we're s-

   6. LFLex Fridman22:03

      You have to believe that you yourself can be the core of that execution. You yourself can build the thing and every, no matter what your circumstances are. I mean, we could talk about like structural racism and all those kinds of things that push things down.

   7. JCJason Calacanis22:15

      Very valid, yeah.

   8. LFLex Fridman22:15

      But from the individual perspective, when you just like are coaching or giving advice to an individual, you can literally change the world. I mean, WallStreetBets is an indication of that in the financial-

   9. JCJason Calacanis22:24

      Absolutely.

   10. LFLex Fridman22:24

       ... space that you yourself can have, can change the world. That, that's why this country is, is amazing.

   11. JCJason Calacanis22:30

       Still the best country in the world, right?

   12. LFLex Fridman22:31

       Yes.

   13. JCJason Calacanis22:31

       I mean, it still is amazing the opportunity provided to people. All this educational experience is online.

6. 22:37 – 28:05

   Learning to learn

   1. JCJason Calacanis22:37

      And the ability, what I tell young people who are looking for advice, I say, "You know, your, the skill you need to refine is the ability to learn new skills."

   2. LFLex Fridman22:45

      Mm-hmm.

   3. JCJason Calacanis22:46

      Like, if you become good at learning a new skill, a- and Tim Ferriss, uh, a friend of mine has really pioneered this, like he can get to 60% or 70% of like the knowledge in a skill in some incredibly short period of time. Now, I'm not saying he's gonna become a virtuoso drummer or a great basketball player, but Tim and I were on vacation together in like a group vacation in Italy and there was a basketball court.

   4. LFLex Fridman23:09

      Uh-huh.

   5. JCJason Calacanis23:09

      And, uh, I said, "Let's go, let's go shoot some hoops." He's like, "I'd never shoot, shot before." And I was like, "Okay, come on. I'll, I'll teach you."

   6. LFLex Fridman23:15

      (laughs)

   7. JCJason Calacanis23:16

      And Tim is fabulously uncoordinated. People don't know this.

   8. LFLex Fridman23:18

      Yes.

   9. JCJason Calacanis23:18

      Like, he-

   10. LFLex Fridman23:20

       (laughs)

   11. JCJason Calacanis23:20

       ... tried to dribble a basketball and do a layup-

   12. LFLex Fridman23:24

       Yeah.

   13. JCJason Calacanis23:24

       ... and it looked like he had a blindfold on. I mean, you-

   14. LFLex Fridman23:27

       Yeah.

   15. JCJason Calacanis23:27

       ... you've never seen something less elegant than Tim Ferriss doing a layup in basketball.

   16. LFLex Fridman23:31

       Yeah.

   17. JCJason Calacanis23:32

       And then he watched me do it three or four times, and I watched him study me and I, listen, I, I've been playing basketball in Brooklyn since I was a kid. I got a couple moves. And he was just taking notes and taking notes and taking notes. And by the end of a couple of hours of doing this, I could just watch him checking his form and figuring it out.

   18. LFLex Fridman23:49

       Yeah.

   19. JCJason Calacanis23:50

       That's every skill in the world now. And what I tell people is like, I'm like, "Have you, did you watch Game of Thrones?" And they're like, "Yeah." "D' you watch Breaking Bad?" Like, "Yeah." I'm like, "Okay, that's about 400 hours." (laughs)

   20. LFLex Fridman24:01

       Yeah.

   21. JCJason Calacanis24:02

       How about you don't watch the next two and you put that 400 hours into learning how to be a graphic designer, a UX person, a developer, whatever it is, and learn how to add skills?" And that's what I did my whole life. I was a kid from Brooklyn, went to school at night, but I was very quick to get to maybe 50% of the knowledge base of graphic design or being a writer or being a sales executive, whatever it was, a developer even.... and I was just good enough to not have people be able to bullshit me, like when I hired them.

   22. LFLex Fridman24:31

       (laughs)

   23. JCJason Calacanis24:31

       And that was a big unlock. When you know enough that people can't snow you, that's a really good one. And look at yourself, like, you've figured out how to set up an entire podcast. People don't know this, but you don't have a team around you. I have a team of like five, six people working-

   24. LFLex Fridman24:44

       But s-

   25. JCJason Calacanis24:44

       ... on my podcast.

   26. LFLex Fridman24:45

       But see, even knowing enough about to set this up, you would then be able to hire a team.

   27. JCJason Calacanis24:50

       Correct.

   28. LFLex Fridman24:50

       And you'll be able to call them on their bullshit if, if-

   29. JCJason Calacanis24:52

       Yes.

   30. LFLex Fridman24:52

       ... they're not doing a good job. And that's really important. And I don't know that much about this whole thing, but I know enough to be able to then-
7. 28:05 – 34:06

   Risk-aversion

   1. JCJason Calacanis28:05

      their game. And that's what we want, right? And this virus and this pandemic, I think the, the, the great thing that will come out of this horrible experience that we've all had, psychologically, death, learning, just so many bad things occurred, the economy, people losing their jobs, but we also got to see the human spirit with these mRNA vaccines and, and just how if we took out some of the regulation and people were super motivated, we might actually be able to eliminate all, uh, pandemics e- from ever happening again. And before that, Bill Gates was banging his fist and Jeff Skoll was doing the movie Contagion. I mean, for two decades people have been banging their fists, "We have to be prepared for this."

   2. LFLex Fridman28:47

      Yes.

   3. JCJason Calacanis28:47

      And everybody's like, "Yeah, whatever, YOLO."

   4. LFLex Fridman28:49

      (laughs)

   5. JCJason Calacanis28:49

      "It's not gonna happen." And now it's happened, and people are like, "We need to be able to destroy every, you know, pandemic and virus before it happens." And you're, you're... Listen, you know a lot more about science than I do. But these MR- mRNA has been around for a while.

   6. LFLex Fridman29:03

      Mm-hmm.

   7. JCJason Calacanis29:04

      We've just never gotten aggressive about doing it. And then you think about challenge trials. I don't know if you've been following this, but they're doing challenge trials now in the UK this month where they're introducing COVID-

   8. LFLex Fridman29:15

      Mm-hmm.

   9. JCJason Calacanis29:15

      ... into healthy young patients and then giving them the vaccine or, you know-

   10. LFLex Fridman29:19

       Wow.

   11. JCJason Calacanis29:19

       And that is against all-

   12. LFLex Fridman29:22

       Yeah.

   13. JCJason Calacanis29:22

       ... rules and regulations about, you know, do no harm. But then you think about it. We kinda celebrate people jumping outta planes, and we got that one guy, Alex Honnold, who's climbing-

   14. LFLex Fridman29:34

       Yeah.

   15. JCJason Calacanis29:34

       ... up mountains without a rope.

   16. LFLex Fridman29:35

       Yeah.

   17. JCJason Calacanis29:35

       And they give him a North Star-

   18. LFLex Fridman29:36

       Yeah.

   19. JCJason Calacanis29:36

       ... you know, back page ad and a, and a, and a s- a, you know, an endorsement deal.

   20. LFLex Fridman29:41

       Yeah.

   21. JCJason Calacanis29:41

       And we celebrate that. We celebrate people surfing with sharks. We celebrate people doing deep welding. We pay them extra to go 200 feet underground and weld stuff. And people do dangerous stuff all day long. Astronauts-

   22. LFLex Fridman29:56

       Yeah.

   23. JCJason Calacanis29:57

       ... but we won't... Soldiers.

   24. LFLex Fridman29:59

       Yeah.

   25. JCJason Calacanis29:59

       Firefighters. But we won't let people get paid to be- do a challenge trial.

   26. LFLex Fridman30:04

       Yeah, we're weirdly risk averse in certain areas that completely don't make any sense.

   27. JCJason Calacanis30:07

       It doesn't ma-

   28. LFLex Fridman30:08

       Yeah.

   29. JCJason Calacanis30:08

       And this is where the world needs to think. The, we, we could have said these 1,000 people, young people, who we know are n- in all likelihood not going to have a bad outcome, but there's a possibility.

   30. LFLex Fridman30:17

       There's a possibility.
8. 34:06 – 42:33

   Robinhood

   1. LFLex Fridman34:06

      I, I'd love to ask you, because you were an early investor in Robinhood-

   2. JCJason Calacanis34:10

      Yeah.

   3. LFLex Fridman34:10

      ... and you sort of, you're in a very nice place of, uh, being a huge supporter of the sort of WallStreetBets-

   4. JCJason Calacanis34:19

      Yeah.

   5. LFLex Fridman34:20

      ... kind of distributed power of the people, and at the same time, uh, because of y- you being an investor, like, intellectually giving a chance to Robinhood in this kind of chaotic time of conversations-

   6. JCJason Calacanis34:33

      Hmm.

   7. LFLex Fridman34:33

      ... to think about like, "Well, what did they do right? What did they do wrong?"

   8. JCJason Calacanis34:37

      Yeah.

   9. LFLex Fridman34:38

      So you, you have a kind of a balanced view on the whole thing, which is really nice. Is there... We've talked about what Robinhood did right-

   10. JCJason Calacanis34:45

       Yeah.

   11. LFLex Fridman34:45

       ... I think. Can you, uh, sort of steel man, uh, Chamath's argument (laughs) -

   12. JCJason Calacanis34:51

       Uh-

   13. LFLex Fridman34:51

       ... of, uh, what Robinhood did wrong in the last few days?

   14. JCJason Calacanis34:56

       Yeah, I mean, their communication is always the number one issue with these startups, right? And if you, you have to get ahead of any problem, and you have to put all the bad news out immediately. And in the case of Robinhood it seems, based on what, you know, has been in the papers and what Robinhood said publicly, is that they had this kind of liquidity crisis, right? Where they were being, uh, because of these exchanges telling 'em, "You have to put up this amount of money in collateral," and them being pinned at number one in the app store. There were so many people trying to buy five shares of this stock, five shares of this meme stock, that it kinda broke their system. And then the people who clear the trades for them, they said, "You gotta put up a billion dollars, two billion dollars, three billion dollars." Well, you can't do that overnight. And I think that they were in an uncomfortable situation of, like, going on TV and saying, "Uh, we have a liquidity crisis." (laughs) Like, that could be like a run on the bank. Everybody then logs in at the same time to Robinhood and tries to sell every share they own 'cause they're afraid-

   15. LFLex Fridman35:51

       Yeah.

   16. JCJason Calacanis35:51

       ... that the whole thing's gonna collapse, right? So I think there was this kinda like black swan event, and they probably didn't communicate it all that well.

   17. LFLex Fridman35:58

       At the center of that, this, this is really interesting, maybe you can comment on the nature of communication. Uh, Vlad, the CEO-

   18. JCJason Calacanis36:05

       Yeah.

   19. LFLex Fridman36:06

       ... the guy you met at the bar-

   20. JCJason Calacanis36:07

       Yeah, right.

   21. LFLex Fridman36:07

       ... was at the, I think, at the center of the communication, right?

   22. JCJason Calacanis36:10

       Yep.

   23. LFLex Fridman36:10

       So Elon is an example of a guy who also is at the center of the communication for-

   24. JCJason Calacanis36:14

       Sure.

   25. LFLex Fridman36:14

       ... his particular set of companies. And that, you know, on Twitter, seems to be a really powerful way to communicate.

   26. JCJason Calacanis36:20

       Yep.

   27. LFLex Fridman36:20

       And there was something, this is me saying it-

   28. JCJason Calacanis36:22

       Yeah.

   29. LFLex Fridman36:23

       ... there was something about Vlad that sounded like he's hiding stuff. That-

   30. JCJason Calacanis36:29

       I th- yeah.
9. 42:33 – 44:58

   Parler and AWS

   1. LFLex Fridman42:33

      so, and the other more dramatic thing to me is that-

   2. JCJason Calacanis42:35

      That was one month ago.

   3. LFLex Fridman42:36

      That was one month, and the pres- the, the president of the United States got banned-

   4. JCJason Calacanis42:39

      From Twitter.

   5. LFLex Fridman42:40

      ... from every major social network. And, uh, which I think I'm still, uh, deeply troubled by-

   6. JCJason Calacanis42:47

      It's interesting. Yeah.

   7. LFLex Fridman42:47

      ... is Parler being removed from AWS. That changed the way-... I, that changed a lot of things, as- as somebody who's an aspiring entrepreneur, that changed the way I see the world. That little-

   8. JCJason Calacanis42:59

      Yeah.

   9. LFLex Fridman42:59

      ... and maybe I'm being over dramatic but-

   10. JCJason Calacanis43:01

       No, you're not. I think you're paranoid for a reason. You're paranoid for a very good reason, which is as big as these companies can become, they are beholden to the mob. And if the mob says, "Hey this person needs to be canceled," they're going to get canceled because you can't lose your entire audience. You could lose your whole customer base, and you could lose all your employees.

   11. LFLex Fridman43:21

       Yeah.

   12. JCJason Calacanis43:21

       I think what's interesting about your fear about Parler and AWS taking him off is we went from being, like, a social network which is, you know, the software layer, and then we went to, like, the infrastructure layer, you know, and they'll even go after like Cloudflare, which is a CDN provider, right? They're just like a plumbing, you know, it's like sort of like the telephone. So we're, we're basically holding everybody responsible on- on the whole chain of events here and what that's gonna do is, you know, I'm not a huge believer in crypto, but distributed computing, um, where nobody, and decentralized and distributed computing platforms, um, and open standards. Podcasting's an open standard. The web is an open standard. FTP was an open standard. But Twitter and, you know, uh, Facebook are closed. And what's gonna happen is we will see a group of individuals create peer-to-peer networks for social media where nobody can control it, and the same for cloud computing where, you know, there's a- there's a- a crypto project where everybody will... And I invested in a company that tried to do this and, um, got sold and- and didn't work out, but take your hard drive on your computer at home. You give, you know, a terabyte of your 10 terabyte drive over to the cloud, and then everybody else does their terabyte, and then all of a sudden you've got this virtual cloud and anybody can store stuff on it and it's all encrypted and then nobody can stop it. And that could be tweets, it could be videos. And so this idea that, you know, YouTube will be able to tell people- kick people off because they're skeptics of, I don't know, the pandemic or the vaccine or they've, you know... Uh, they'll make things that are more censorship resistant. I think that'll be the reaction

10. 44:58 – 51:32

    Social networks

    1. JCJason Calacanis44:58

       to all of this.

    2. LFLex Fridman44:59

       Well, this is my question for you, going back to that crappy bar and people pitching you. Is- is there... Do- like with Clubhouse, do you see competitors? Do- do you think it's possible that another perhaps more decentralized or another kind of social media will emerge that will take on Twitter and Facebook and might be able to replace them? Like if you look at the whole landscape-

    3. JCJason Calacanis45:20

       Yeah.

    4. LFLex Fridman45:21

       ... uh, with Clubhouse and everything else, do you think some other company might emerge?

    5. JCJason Calacanis45:26

       There'll be 10 versions of Clubhouse. We looked at social networking, we thought Friendster was it. Like Friendster was so good nobody would be able to compete with that. It was growing so quickly. And then MySpace was a juggernaut and they hit 100 million in revenue and 100 million users and it was like well that's game over. And then Facebook and LinkedIn and Snapchat and FriendFeed and countless others, you know? So there's usually 20 people who will win in a category-

    6. LFLex Fridman45:50

       Mm-hmm.

    7. JCJason Calacanis45:50

       ... and 80% of the category will be owned by the top two or three players. Um-

    8. LFLex Fridman45:55

       But will those players change do you think? What's your sense of-

    9. JCJason Calacanis45:58

       Oh yeah, for sure. I mean if we- if Facebook hadn't bought Instagram, it would be a company in decline right now. People would be shorting the stock, right? Facebook peaked and then was sort of heading down, um, and Instagram saved them and WhatsApp saved them. So you know, that's another kind of weird moment in history that they were able to accumulate that much power, uh, consolidate that much power. Instagram should've never sold to them. That should've gone public. They had just raised money from Sequoia and they had raised $50 million at a $500 million valuation and they didn't need to sell, and that was a big mistake to sell. Uh, they should've kept going and they should've take- took on Facebook. And if Instagram was a standalone company right now, it'd be worth 500 million.

    10. LFLex Fridman46:33

        Do you think, uh-

    11. JCJason Calacanis46:33

        500 billion. Yeah.

    12. LFLex Fridman46:35

        Do you think, uh, Facebook might buy Clubhouse, has been, uh-

    13. JCJason Calacanis46:38

        Uh, they'll probably copy it. I mean Zuckerberg has no moral compass or ethics or anything. I mean he's a marauder. I mean-

    14. LFLex Fridman46:45

        (laughs)

    15. JCJason Calacanis46:45

        ... he basically copied Snapchat seven times.

    16. LFLex Fridman46:48

        Yeah.

    17. JCJason Calacanis46:48

        Like he did Poke and he just kept trying and trying and trying. It's part of the reason why the WhatsApp founders and the Instagram founders left is they found Zuckerberg so distasteful in terms of his ability to copy. Like-

    18. LFLex Fridman46:59

        What- what do you think makes, uh, a great leader in that sense? 'Cause okay, so when I look at Zuckerberg, uh-

    19. JCJason Calacanis47:05

        He's a great executor.

    20. LFLex Fridman47:06

        Is he a great execut- I- I-

    21. JCJason Calacanis47:08

        But I don't think he's a great leader.

    22. LFLex Fridman47:09

        I was bullish on, I was excited by Facebook in the very early days.

    23. JCJason Calacanis47:12

        Sure.

    24. LFLex Fridman47:13

        Uh, I thought it was an exciting opportunity to connect people and stuff started going wrong in certain kinds of ways.

    25. JCJason Calacanis47:18

        Yeah.

    26. LFLex Fridman47:18

        And again, maybe it's our human nature but I attribute a lot of that to the leadership.

    27. JCJason Calacanis47:25

        Absolutely.

    28. LFLex Fridman47:26

        And-

    29. JCJason Calacanis47:26

        I mean the guy started it because he was unable to ask girls if they were single and on a date. I mean that was his explicit-

    30. LFLex Fridman47:32

        That could be a good motivator. That could be a good motivator.
11. 51:32 – 56:21

    Leadership

    1. LFLex Fridman51:32

       good at that. I... You've talked to so many great leaders in this world, privately and, and publicly.

    2. JCJason Calacanis51:39

       Yeah.

    3. LFLex Fridman51:39

       What do you think makes a great leader of these tech companies? Is... Uh, do you have an example? Like, is Elon, to you, a great leader? He's also a controversial one, right? There's-

    4. JCJason Calacanis51:49

       Yeah. I mean, he's got a s-

    5. LFLex Fridman51:50

       There's a love and hate.

    6. JCJason Calacanis51:51

       ... sense of humor. Yeah.

    7. LFLex Fridman51:51

       Uh, controversial in the sense that there is... And I know a lot of people who've worked with him, for him, that there's also a love-hate, uh, relationship. The, the hate comes from the fact that they get pushed extremely hard. It's a, it's a very competitive environment, but it's, but it's a positive one because it's an... There's a vision that's underlying. It's similar to the Steve Jobs thing, and it has to do with the, back to our Michael Jordan discussion as well, that there seems to be this, the demons involved and tension and just a- a- a- a-

    8. JCJason Calacanis52:24

       Yeah.

    9. LFLex Fridman52:25

       ... anxiety, all those kinds of things.

    10. JCJason Calacanis52:27

        If you wanna do great things, um, there will be some suffering (laughs) , uh, and-

    11. LFLex Fridman52:33

        (laughs) .

    12. JCJason Calacanis52:33

        ... you know, there'll be some pain, and it's not easy, uh, if you wanna change the world. And then some people have this expectation that it's going to be easy. Um, and what you'll typically find for any great leader who's trying to do something super ambitious... Like, if you wanna be like... If you're a rich guy and you start like a restaurant and you don't care about making money and people have made restaurants before, like you could be high fives and everybody could love you, whatever. But if you wanna change the world, you wanna do something hard driving, there's gonna be sacrifice involved. And so the problem is people are looking at something that is an Olympic caliber sport or a Navy SEALs like effort.

    13. LFLex Fridman53:10

        Yeah.

    14. JCJason Calacanis53:10

        In other words, an effort that requires massive sacrifice. We would not look at somebody who wins a gold medal, like Michael Phelps, and say, "Oh my god. He had to get up at 4:00 AM every day and he had to swim and he had to do an ice bath?"

    15. LFLex Fridman53:22

        Yeah.

    16. JCJason Calacanis53:22

        "Oh my god, that poor guy. He suffered. He was tortured. He..."

    17. LFLex Fridman53:25

        Yeah.

    18. JCJason Calacanis53:25

        "People were super mean to him. They put him in an ice bath." It was like, no, he wanted to be the greatest swimmer of all time and he knew what the sacrifice entailed. And then what happens in work, in business, is that people conflate like, "Oh, well, I- I went to work to make a living, to pay my bills," versus Michael Phelps' approach to getting gold medals, or Michael Jordan, or pick the person, Elon or Jeff Bezos. And when you look at the reviews of like a place like Amazon, there was this incredible story in the New York Times where people were... I don't know if you remember it. This is the worst place you could ever work, Amazon.

    19. LFLex Fridman54:01

        (laughs) Yeah.

    20. JCJason Calacanis54:01

        And they... We talked to 200 people and they all told us, they all described for us in the New York Times a culture of cutthroatness and brutality that has never before been seen.

    21. LFLex Fridman54:11

        Yeah.

    22. JCJason Calacanis54:12

        And then you see all these people who work for Bezos for 24 years, from when they graduated with their MBAs until today-

    23. LFLex Fridman54:18

        Yeah.

    24. JCJason Calacanis54:18

        ... and they've never left the company, and they are ride or die forever. And what you're seeing there is, there's a mismatch of people going to work in an extreme pla- sport, uh, or an extreme endeavor who should not do that. There are people-

    25. LFLex Fridman54:35

        Yes.

    26. JCJason Calacanis54:35

        ... who should go out into the rice fields and pick rice-

    27. LFLex Fridman54:38

        Yeah.

    28. JCJason Calacanis54:39

        ... and then there's another group of people who are samurai-

    29. LFLex Fridman54:42

        Yeah.

    30. JCJason Calacanis54:42

        ... and who wield a sword and who take on missions that are dangerous.
12. 56:21 – 1:04:43

    Work-life balance

    1. LFLex Fridman56:21

       you know, you're not... This is not l- like the work-life balance idea-

    2. JCJason Calacanis56:26

       (laughs)

    3. LFLex Fridman56:26

       ... doesn't even apply to that.

    4. JCJason Calacanis56:27

       Work-life balance. It's ridiculous.

    5. LFLex Fridman56:28

       It's w- well, yeah.

    6. JCJason Calacanis56:29

       It's a ridiculous concept. Like, the idea that there's like work-life balance in a startup is ridiculous. If you're looking for work-life balance, do not go to a startup-

    7. LFLex Fridman56:38

       Yeah.

    8. JCJason Calacanis56:38

       ... or any kind of ambitious company. There is a series of places you can work in the world-

    9. LFLex Fridman56:42

       Yes.

    10. JCJason Calacanis56:43

        ... where you do not need to do anything more than what's put in front of you.

    11. LFLex Fridman56:48

        Yeah.

    12. JCJason Calacanis56:48

        And you just put the round peg in the round hole and the square peg in the square hole- pole, and you go home. And you get your like, you know, you- you get your little, you know, bits, uh, grains of rice and you- you go heat 'em up and eat 'em. That's it. And then there's this other thing which is the extreme pursuit of changing the world and sacrificing. And we have a generation of people, multi-generations of people, who are soft. They're just soft. I mean, what is the big struggle we've had to deal with in America in our lifetimes? Like 9/11 and we- we didn't have the Vietnam War and then we had this like weird Iraq wars and Middle East wars that were f- kind of like a small number of people went and we sent drones. Like, we have not had to sacrifice. Gen Xers, you know, maybe the tail end of boomers experienced the Vietnam War regrettably. But, you know, we've had a couple generations now, three I guess, that just haven't had to suffer.

    13. LFLex Fridman57:40

        Yeah.

    14. JCJason Calacanis57:40

        And so we're soft as Americans. We're soft. And then you look at people in China and we're like, "Oh my God, these poor Chinese people are living in these tiny cramped apartments." Like, they were living in like essentially lean-tos in northern China with no running water or like one spigot of ice cold water for the entire village. Like, they're thrilled to be joining the middle class.

    15. LFLex Fridman58:01

        (laughs) Yeah.

    16. JCJason Calacanis58:02

        Even if it's the bottom of the middle class, right? Uh, they- they've taken hundreds of millions of people in China and moved them into the middle class. And we're like, "Oh my God, these people are suffering." It's like, you know, they're up to $4 an hour, $3 or $4 an hour in the factories there, and they were just two decades ago at, you know, I don't know, uh, it was probably 50 cents an hour, something crazy like that. I- and now they've improved the quality of life there so much, just like America did 200 years ago or 100 years ago, they've improved it so much in China that now they're getting out-priced for factories from Vietnam, Sri Lanka, Pakistan, India. And people are moving... And people in China are moving the factories out of China into other countries.

    17. LFLex Fridman58:42

        (laughs) Yeah.

    18. JCJason Calacanis58:43

        Because the Chinese are now outsourcing (laughs) to Vietnam and other countries. So this is the way of the world, you know? People move up and they get a better lot in life for their families. And just in America, we've gotten soft, and as a generation, w- how do people die in America now? Suicide, obesity, heart attacks, anxiety. I mean, w- we're suffering from things that if you told people 100 years ago that the number... the top ways Americans would die would be overeating and suicide, they'd be like, "What? You're literally killing yourself or eating yourself to death? That's what's happening in America?"

    19. LFLex Fridman59:16

        Yeah. And- and when everybody, not everybody, uh, en masse, there's a large number of people who have become softer and softer. Uh, capitalism creates an environment where there is people that still step up amidst that with a big dream-

    20. JCJason Calacanis59:29

        Yes.

    21. LFLex Fridman59:29

        ... and challenge the conventions-

    22. JCJason Calacanis59:31

        Human spirit. Yeah.

    23. LFLex Fridman59:31

        ... and that human spirit just to rise above that. And Elon is an example of that. Uh, Jeff Bezos an example of that.

    24. JCJason Calacanis59:36

        Countless, countless examples. Yeah.

    25. LFLex Fridman59:37

        Uh, and- and they push, you know, the limits of those, uh, of human beings that are willing to step up.

    26. JCJason Calacanis59:45

        Yeah.

    27. LFLex Fridman59:45

        And, you know, I- I, uh, you know, I think about sort of how to create a company that, um, that amidst all of the softness-

    28. JCJason Calacanis59:53

        Yeah.

    29. LFLex Fridman59:54

        ... still creates a revolution. It's not... It doesn't seem trivial.

    30. JCJason Calacanis59:58

        Mm-mm.
13. 1:04:43 – 1:12:29

    Great leaders lead by example

    1. JCJason Calacanis1:04:43

       I mean.

    2. LFLex Fridman1:04:44

       As you're describing, you've hosted, uh, This Week in Startups for, uh, how many episodes?

    3. JCJason Calacanis1:04:49

       11 years. Almost 1,200 now.

    4. LFLex Fridman1:04:51

       12.

    5. JCJason Calacanis1:04:52

       Yeah.

    6. LFLex Fridman1:04:52

       And so you've talked to some of the great leaders in business in general. Uh, is there a common thing that you see, or, uh-

    7. JCJason Calacanis1:05:01

       Really messed up-

    8. LFLex Fridman1:05:02

       I'ma-

    9. JCJason Calacanis1:05:02

       ... relationship with their parents. Like, just-

    10. LFLex Fridman1:05:04

        Some trauma?

    11. JCJason Calacanis1:05:04

        ... find me a great entrepreneur. I will ... Show me the trauma. (laughs) Their dad was like, "You're not good enough."

    12. LFLex Fridman1:05:10

        In the teena- in the teenage years? Is that, is that truly ... Is there some- (laughs)

    13. JCJason Calacanis1:05:14

        There is definitely something to-

    14. LFLex Fridman1:05:15

        Like, hardship of, at some point in their life kinda thing?

    15. JCJason Calacanis1:05:18

        Yeah, I think so. I mean, and there's definitely something, uh, with immigrant parents. Um, that is a, a bit of a stereotype out here, but I've heard from many investors, like, that's, like, their, "Oh, did y- Are y- Were your parents immigrants and did they beat into you that you have to succeed and you feel the need to succeed because they suffered to get you to this country?"

    16. LFLex Fridman1:05:36

        Yeah.

    17. JCJason Calacanis1:05:36

        Like, there is an archetype there that I h- I ... When I started investing, I heard from a lot of people. It's like, "Yeah, you wanna find those immigrant founders who are coming out of Stanford, 'cause they had to fight to get there, and their parents had to fight," right? So it's, like, two huge fights and there's so much at stake, as opposed to somebody who's fifth generation and, like, had everything handed to them and they were legacy and got into schools for free. But I think in general, the ability to get people to join you on that journey-

    18. LFLex Fridman1:06:01

        Yes.

    19. JCJason Calacanis1:06:01

        ... is so critical. So, you have to be charismatic, and it doesn't mean, like, you're an extrovert. There are introverts who are super charismatic. Uh, and there are soft-spoken people. They don't have to be, like, super vivacious or rambunctious people. Um, they could be just quiet assassins. But you need to be able to get people to come on the journey with you. You have to be that storyteller and you have to have that passion, and then you have to transfer that enthusiasm to investors, the press, to customers, to all the stakeholders. And if you're enthusiastic about it and you're engaged, then it's easier for people to come on that journey. Uh, and that's why people really start to think about, "Well, what is the purpose of what I'm doing?" And it sounds corny, and I, when I first heard that, I was like, "It's kinda corny." But then I read this book by, I forgot his name, Rick something, um, he wrote The Purpose Driven Church.

    20. LFLex Fridman1:06:49

        Mm-hmm.

    21. JCJason Calacanis1:06:50

        And he had spoken at a TED or something and everybody went crazy about it. And he's like, "A church should have one purpose, one single thing they do." And, and, like, his church, which was, like, one of these mega churches in San Diego, just wanted to do education for this specific country and that's all they did, and they just, they benchmarked those. I think it's very important to have a purpose and a mission. Not everything, uh, but ...... you know, a specific purpose of some kind of joy that you wanna put into the world. You want to solve some kind of big, hard problem. And then everybody knows why you're coming to work every day. And then for the founder, when you dread going to work that day, and you don't feel like solving that problem anymore, that's the, that's the tell. And a lot of times I meet young founders, I'm like, "Why are you doing this?" And they're like, "Well, I was looking for an idea, and this is the one I came up with because I think I'll make a lot of money." And it's like, "You're gonna quit." (laughs)

    22. LFLex Fridman1:07:40

        Yeah.

    23. JCJason Calacanis1:07:41

        You're gonna get to month nine or 10 of this, and you're gonna run out of money where, like, your CTO is gonna quit, then your CFO is gonna quit, and you're gonna lose your biggest customer, and you're just gonna say, "This is not worth it." You know? And if, you know, using, you know, Bezos or, um, you know, Elon as examples, they, they just needed to see this... the world change first in very specific ways.

    24. LFLex Fridman1:08:04

        (laughs) Yeah.

    25. JCJason Calacanis1:08:04

        And Steve Jobs, you know, they needed to see a change and... It doesn't matter if they made money or they were losing or winning, they just went to work every day and they had to change it.

    26. LFLex Fridman1:08:12

        It's almost like they didn't have a choice. I mean-

    27. JCJason Calacanis1:08:14

        No choice.

    28. LFLex Fridman1:08:14

        ... Elon makes it sound like it's torture, his whole journey, but he can't help it. He's... (laughs)

    29. JCJason Calacanis1:08:19

        Um, having been a witness to it, um, you know, just as friends for, for that long, uh, I, I have never seen an entrepreneur suffer more than him. And, uh, you know, he's been public about that. Like, "You do not want to be me." (laughs) Um, he has suffered to... for those companies. He has suffered to get them where they are. It has not been easy.

    30. LFLex Fridman1:08:36

        Can you psychoanalyze Elon in that aspect? Like, is there... is it just he can't help it, he must see the change that he, uh, hopes for in the world?

Episode duration: 2:11:09