Jason Calacanis | How Does Angel Investing Work? | Modern Wisdom 154

1. 0:00 – 15:00

   ... it would be…

   1. JCJason Calacanis0:00

      ... it would be like walking up to the, to the betting window and being like, "I, I, yeah, I'm gonna place a bet on this team," and, uh, you, you pick the wrong team-

   2. CWChris Williamson0:09

      Mm-hmm. Mm-hmm.

   3. JCJason Calacanis0:09

      ... than you intended. They give you the slip. Your team loses, you go to rip up the slip and you look that y- "Oh, I made a mistake? Oh, I bet on the other team? Oh, I won?"

   4. CWChris Williamson0:17

      Fun-fucking-tastic.

   5. JCJason Calacanis0:18

      "Oh, okay. Great."

   6. CWChris Williamson0:19

      (laughs)

   7. JCJason Calacanis0:19

      "Fantastic," right? Like, literally, that's the job of an investor. You just don't know which ones are gonna win, so you just basically treat everybody who's in your portfolio amazing. You try to just be as supportive as possible. Um, which is, you know... Again, it's like life is pretty simple. Just find the best people you can, invest in them, support the heck out of them. If it doesn't work out and they did a good job, then bet on them again.

   8. CWChris Williamson0:49

      Jason Calacanis in the building. How are you?

   9. JCJason Calacanis0:54

      What what?

   10. CWChris Williamson0:55

       How you doing? Fantastic.

   11. JCJason Calacanis0:56

       Thanks for having me on the pod.

   12. CWChris Williamson0:57

       You are in the most beautiful studio that I think I've ever seen.

   13. JCJason Calacanis1:02

       Yeah. And you're in your, and you're in your bedroom.

   14. CWChris Williamson1:05

       I am. That is true.

   15. JCJason Calacanis1:05

       With a lighthouse poster.

   16. CWChris Williamson1:07

       With a what? (laughs)

   17. JCJason Calacanis1:09

       With a lighthouse poster behind you. I see it.

   18. CWChris Williamson1:11

       With a lighthouse poster indeed, that is.

   19. JCJason Calacanis1:12

       Yeah.

   20. CWChris Williamson1:13

       But you know, we're all s- we're all starting somewhere.

   21. JCJason Calacanis1:16

       With a wave crashing around it.

   22. CWChris Williamson1:17

       Well, it's very, it's chaos, right? What were we talking about just before we started? There's some chaos going on here.

   23. JCJason Calacanis1:22

       Chaos. Well, wait. W- where is that lighthouse?

   24. CWChris Williamson1:26

       I'm not sure. I'm not sure.

   25. JCJason Calacanis1:26

       Does it have some specific meaning?

   26. CWChris Williamson1:28

       (laughs) No, no, I'm not...

   27. JCJason Calacanis1:29

       What would Freud say about picking a lighthouse on the edge of ex- human existence that's being pummeled by giant waves? What would that say about a man who puts that as the first thing he sees when he wakes up and the last thing he sees when he goes to bed?

   28. CWChris Williamson1:48

       Can you tell that I'm an-

   29. JCJason Calacanis1:48

       You a bit of a loner?

   30. CWChris Williamson1:49

       Can you tell that I'm an only child, Jason?
2. 15:00 – 30:00

   Yes. To begin with,…

   1. JCJason Calacanis15:00

      how to do podcasts." Like, okay, if we get one customer a year or 10 or 100, like, okay, I guess it's a success. It's more than zero. Whereas with a startup like Uber or Calm, you know, you're, you're building something that is more complex, um, and has a smaller chance of success. But if it does succeed, oh my lord, it could change the fabric of society and humanity forever. Uh, and many companies have, like Google, Facebook, Uber, Airbnb. These things are changing society. And in order to do that, it's sort of an Olympic-caliber sport. Um, uh, so that is the difference right now. Y- you know, that's, that's the main difference in the type of companies we invest in. And so, that's where most of the confusion comes in. People wanna start a company that makes, you know, ginger beer or tea, uh, or they're doing a company that has a noble purpose. And it's like, these do not qualify for the one in 1,000 or one in 10,000 chance of an outlier. Therefore, you're not fundable by this industry, and that turns people off sometimes to the industry and, and they don't understand it. Or, if I told you you're gonna start 10 businesses, six are going to zero, the seventh and eighth will return half the amount of money you put into them, the ninth will return two or three times what you put into it, and maybe if you get lucky, the 10th or the 20th or the 30th might return more than 30X. You put in a dollar, you get more than 30X. So it's a type of gambling and risk-taking that is very unique, very confusing from the outside, and even from the inside, um, the people who do this kind of gambling struggle with their own psychology and their own existence. So, it- it's no doubt that it's confounding to everybody.

   2. CWChris Williamson16:50

      Yes. To begin with, are tech stocks where the money goes due to scalability? Is it just a fact that that has the ability to really rock it off?

   3. JCJason Calacanis17:01

      Yeah. So I mean, if you look at public stocks, yeah, I mean, if you invested in Google, Netflix, or Amazon (laughs) you know, at their IPO or any time after the first five years of those companies, you'd be pretty happy today, I think. Uh, Facebook as well. And so, the, the companies are getting much larger today than they ever have, and I think they've become, um, very, um, resilient because they've been adding multiple business lines in a way that previous companies didn't. So, it used to be companies were one-trick ponies. They went public in year six, seven. Now you have companies staying private and going publics in year 10, 11, 12, 13. And they're, they're much larger businesses, they're much stronger businesses. And then once they get public, they get more ambitious. They start doing acquisitions and they become super resilient. So the resiliency of a company like Facebook having bought WhatsApp, Oculus, and Instagram, three huge bets, or Google having bought Android, um, YouTube, much stronger businesses. And then even in the classic businesses like Disney having bought Pixar, Marvel, uh, and Star Wars, you know, those companies now make them so much stronger that they're not reliant on just the Disney IP, you know? Snow White and, and (laughs) Mickey Mouse.

   4. CWChris Williamson18:15

      Mm-hmm. Mm-hmm.

   5. JCJason Calacanis18:15

      Uh, which, you know, those things could fall out of favor, but now they get this new life because they have all the Marvel characters, all the Pixar characters, and all the Star Wars characters and all those worlds to just keep building and building and building. So-... uh, I- I think buying those kind of stocks, um, and I'm not a s- public stock picker, it feels like there's very little downside because the idea that Amazon or Google would go away, uh, any time soon or perhaps even in our lifetime s- does not seem realistic. Um, we did see Yahoo go out of business. So previously when they were one-trick ponies like Yahoo was, uh, or other companies, yeah it might be more ... it might be possible, like, you know, buying eBay or something. That's been a pretty resilient business. But, you know, they- they've got one business really and, you know, that- that does make it, um, difficult.

   6. CWChris Williamson19:07

      I get it. So-

   7. JCJason Calacanis19:08

      Or more challenging.

   8. CWChris Williamson19:09

      ... let's go back to the-

   9. JCJason Calacanis19:10

      But we're investing in private companies.

   10. CWChris Williamson19:12

       ... the private.

   11. JCJason Calacanis19:12

       Yeah.

   12. CWChris Williamson19:12

       Yeah, yeah, let's go back to private. Where do you find these people? Are you walking down the street, you see some guy who's got a t-shirt on that says, "I own a startup." Like what happens?

   13. JCJason Calacanis19:22

       So the way I meet people, um, is, you know, I have a podcast and amongst founders I would be, you know, a celebrity on the scale of Lady Gaga, uh, or Michael Jordan. And then there's everybody else in the world-

   14. CWChris Williamson19:38

       Have you gone out- have you gone out and felt like that, Lady Gaga?

   15. JCJason Calacanis19:40

       Absolutely. Um, I'm wearing a new dress right now.

   16. CWChris Williamson19:42

       (laughs)

   17. JCJason Calacanis19:42

       Um, for those of you listening, it's, uh, getting a little uncomfortable in the second half of the hour. Uh, you know, but outside of the industry I'm a nobody, right? So when I lived in LA and I would go to industry parties, nobody would know who I was, and then when I'm in an industry party, uh, you know, I might get asked to take ten selfies in the tech business. And it really is a popularity contest amongst, uh, investors. Investors have brands and people want to be affiliated with different brands, so you- you might make an analogy of, like, Creative Artists Agency or Endeavor and the different agencies, William Morris Agency, whatever, in Hollywood. You get affiliated with an agency or you got affiliated as a musician with a record label, um, you know, you, uh, then become validated, you become anointed in a way, and it gives other people permission to engage with your startup, or in the case of CAA and agencies or labels, music, tours, whatever, uh, movies. So a lot of what we do here is we anoint people and we fund them and then we tell them where the landmines are and we say, you know, "Uh, let us know if you make it to the other side (laughs) and how we can help."

   18. CWChris Williamson20:53

       (laughs)

   19. JCJason Calacanis20:53

       And you know, it- it's- it really is basically like you're sending, you know, um, these founders into a war zone and you see who makes it to the other side, we see who- who, you know ... The- the good news is, it's not fatal, you know? And so if you fail, and two out of three or three out of four startups fail, depending on, you know, how you measure it, um, might be even greater based on, you know, the number of experiments being run today by founders, you need only start three, four, five companies to have a likelihood of success, right? So that's what I tell people when they- when their first company fails is that like, you know, Travis' third company was Uber, you know, Elon's third, one, two, three, yeah, third or fourth c- third and fourth companies were SpaceX and Tesla, right? So a lot of times people do their best work on that third time up at bat, fourth time up at bat. That actually seems to be a sweet spot, right? You're not, like, as nervous. Y- some people, Bill Gates, Jeff Bezos, Mark Zuckerberg, they hit the home run right out of the park. Uh, that's not common. It's memorable, so there's a survivorship bias to it, the fact that those companies have become big.

   20. CWChris Williamson22:00

       Mm-hmm.

   21. JCJason Calacanis22:00

       Or confirmation bias rather, uh, not survivorship. Or maybe it's both.

   22. CWChris Williamson22:03

       (laughs) It's uncommon-

   23. JCJason Calacanis22:04

       Confirmation.

   24. CWChris Williamson22:04

       ... amongst uncommon situations, right?

   25. JCJason Calacanis22:06

       Yeah. Um, it is very uncommon for somebody on their first company to hit a giant outlier success, but because when it does happen it's so memorable, that it feels more common than it is. Which I believe is the definition of confirmation bias or survivorship bias. Right?

   26. CWChris Williamson22:29

       Survivorship.

   27. JCJason Calacanis22:29

       So survivorship bias is like okay, well these people survived, therefore there was something y- y- y- you- you- the fact that they survived, you- you read something into who will survive the next time, right? The- the problem with that was the- the way they ca- they figured out survivorship bias was they looked at planes in World War II that had actually ... where the bullet holes were when they landed, and they found the bullet holes, you know, were in all these different places, and they were like, "Okay, well, this is what we need to fix," or whatever. And what they didn't realize (laughs) is those are the planes that made it back-

   28. CWChris Williamson23:02

       (laughs)

   29. JCJason Calacanis23:02

       ... got hit in the wing and didn't get hit in the cockpit or the engine. So it turns out the- they weren't including in the sample where the bullets were on the planes that went down because they couldn't recover those planes because they blew up in the sky and crashed.

   30. CWChris Williamson23:16

       (laughs)
3. 30:00 – 45:00

   I like yours. I…

   1. JCJason Calacanis30:00

      (laughs) come next to me, we're gonna fight together. Whatever comes through those doors, we have a better chance of succeeding if we fight together as one." And he gives this big As One speech, you can look it up. Or, there's another great scene in a movie called Black Hawk Down where the snipers say, "Listen, we gotta go in and protect the pilots of that other Black Hawk, uh, drop us in." And they said, "Listen, we- we don't know when we're gonna have reinforcements. So if we're dropping you in, I need you to confirm with me that that's what you want and that you recognize that we don't know when we can get you reinforcements or if we can ever get reinforcements there and we're dropping you into this hostile territory, where it's gonna be the two snipers versus thousands of Somalians who are armed and are surrounding the helicopter." And-... you know, that's a ... I use those metaphors, um, because they ... In each of those cases people are working together, um, a- and they're blocking out things that are not important and they're focused on what is important. A- and that really is what entrepreneurship and leadership is about, that ability to focus in, slow down, take that breath, and say, "Okay, this is a dangerous situation. This is a critically dangerous situation. This is a ... You know, they're going to drop us into this, you know, situation in Somalia and we're not going to get out in all likelihood, but we're gonna take that chance anyway and we're just gonna focus and let our training and our plan execute itself, you know, whatever happens." Now, those are all violent, crazy situations, um, but those are the metaphors I choose. I'm sure somebody else could come up with a, a much more peaceful one, but, God, in my experience, it's a fucking war.

   2. CWChris Williamson31:30

      I like yours. I like your words.

   3. JCJason Calacanis31:32

      Running these companies-

   4. CWChris Williamson31:33

      I like your ones.

   5. JCJason Calacanis31:33

      Running these various companies is a fucking war. It really is. And, and that, and that's just the successful ones, you know? (laughs) The ones that are not successful-

   6. CWChris Williamson31:40

      (laughs)

   7. JCJason Calacanis31:41

      ... you know, it, it's, uh, you know, it's a war and chaos and-

   8. CWChris Williamson31:47

      Whilst fighting the coronavirus.

   9. JCJason Calacanis31:49

      (laughs) While fighting the coronavirus, yeah, exactly. Like, those are ... And those are things that are outside of your control. You know, imagine you're in the hardware business right now, which is hard enough, you're building a hardware startup and you've got shipments coming from China where you're supposed to have your hardware solution, you know, that client's paid for, and now it's, you know, lost in customs or something. Uh, there's a business disruption. Business disruption for A- for Apple with hundreds of billions of dollars in the bank? No problem. Business disruption with somebody with six or 12 months of runway in the bank? Big problem.

   10. CWChris Williamson32:22

       How much of what you've alluded to there, which is your ability to work out the controllables and the uncontrollables, bring a little bit of order to this chaos, how much of that is learned and how much of that is your constitution? And if it's learned, then what elements are? Would you be able to talk about a routine or any of the things that you do which tend to help you with that regard?

   11. JCJason Calacanis32:44

       Well, um, I would say, you know, some folks are the product of their environments, um, and that's their primary driver, and then other folk- folks are very good at adding skills. Um, a- and, you know, I, I think you can probably do both. You know, Tim Ferriss, uh, the seeker as I call him, you know, he seeks out knowledge and he learns it and he advances, um, and learns very quickly. That's kind of his thing, he just adapts and learns new skills very quickly. So it clearly can be done. Uh, but there is, at its core, I do think, you know, uh, some situations that are high pressure that people, uh, grow up in that do define them. And so one theory I heard, I don't know if this is correct or has any basis but it, it certainly is an interesting one to consider, is that a lot of the great founders, uh, who are good in operating in chaos and under stress had a situation where one parent loved them very much and one parent maybe wasn't as available or was actively, uh, cruel or mean. And that person then had to balance and learn to solve this problem every day of their life in their childhood, right?

   12. CWChris Williamson33:56

       That's interesting.

   13. JCJason Calacanis33:57

       Two parents, you know, one who loved them and one who was chaotic or something, and they had to just make sense and navigate that. It does ring true to me. I mean, obviously we see over and over again immigrants really overperform an index, um, you know, in terms of the percentage of them leading very large companies, uh, in their leadership ability. Something about, uh, immigrant parents and, you know, the, the, the work ethic that maybe people see in their parents when they work three jobs and they put in 60, 78 hours a week and they force their kids to study because they say, "I don't want you to have to work 90 hours a week." Um, you know, there, there's something positive about that, which is, you know, why it's a little bit heartbreaking that we have this nationalism where we don't wanna let in the people who are taking the greatest risk in the world, leaving one country to come to another to try to make a better life. It's like, those people are, you know, um, under such incredible duress, um, just doing that, that they become exceptional citizens, I think, by and large, a- and become incredible for those countries that get to receive that gift, right? Like, if you look now in Silicon Valley, um, the number of Indian-Americans, uh, who are leading companies out here is just extraordinary. Um, and we had just a massive influx of Indians, uh, who suffered greatly, you know, in, in their journey here a- and to build a new life here, faced racism, faced, you know, uh, having to work menial jobs to build stuff up, and, an incredible work ethic, an incredible, uh, focus on education. And now Microsoft, Google ... I mean, the, the number of Indian-Americans running companies is just stunning, uh, and amazing. And now we wanna not let them in to the country? It's bonkers, right? I mean, it's very sad for England, it's very sad for America. Just, you know, nationalism.

   14. CWChris Williamson35:44

       How about for you? How about you? Talk, let ... T- talk to me about your constitution. Talk to me about what it is that you're ... Or y-

   15. JCJason Calacanis35:50

       Oh, me.

   16. CWChris Williamson35:50

       Part, part of your practice as well.

   17. JCJason Calacanis35:52

       (sighs) ohh.

   18. CWChris Williamson35:52

       Talk to me about what, what makes-

   19. JCJason Calacanis35:54

       yeah.

   20. CWChris Williamson35:54

       ... what sets you apart.

   21. JCJason Calacanis35:56

       Well, I definitely fall into the category of the, or the archetype of, like, growing up in a difficult situation. Brooklyn in the '70s and '80s. Um, you know, my dad losing his bar when I was 18 years ... 17 years old, uh, and, and just growing up in a bar and, and just seeing chaos all the time, I, I think ... And then practicing martial arts for many years and running marathons, I think I just got a level of discipline and fortitude, um, that ... You know, I think some people, maybe they have a reaction the other way. They become ... You know, they give up or whatever. Um, I, for whatever reason, just grew up a fighter. And I, I mean, I still have that fighter mentality, um, you know, that now ... I'm super aware that the analogies I use, uh, you know, are these war and violent ones. (laughs) Uh, or, you know, or non-violence in the case of the Jedi and Samurai, just violence as a last resort. So, you know, I-I am incredibly hardworking and dedicated and loyal. And maybe, you know, to a fault, um, at times just not letting things go, right? So I have a hard time letting things go, companies failing, you know, businesses failing, projects failing. I, I just have a never say die attitude, which is probably long term not a great idea, uh, for returns. Uh, being able to cut your losses and give up and move on and use that space to do another project is likely the better scenario as an investor and as an individual. Um, but, you know, I, I just don't like giving up. I like to fight until the last, you know, arrow, the last bullet, you know (laughs) . I, I like to fight it to the end.

   22. CWChris Williamson37:37

       Do you think you'll work on that moving forward? Do you think you'll maybe try and, try and, try and develop that a little bit moving forward? Or is it something that you're glad is a, a curse that you have to suffer for the strengths that it gives you?

   23. JCJason Calacanis37:48

       Yeah, I kinda like it. I'll be honest. I kinda like it. I like, you know, being against the odds, uh, you know. Uh, I, I like the feel ... I, I sleep better at night knowing I fought till the end, you know?

   24. CWChris Williamson38:01

       For those that are out there.

   25. JCJason Calacanis38:01

       And I just, I feel like that's my job. Yeah, I mean, when I'm with the founder, I always tell the founder, you know, "What do you want to do? You want to keep fighting or do you wanna, uh, you know, close this chapter of your life and move on to the next one? We will be here either way. If you wanna keep fighting, I'll fight with you. If you wanna shut the company down or sell it for parts to Google or Facebook and spend two or three years there licking your wounds and resting, investing, and collecting a giant salary on the roof of Hooli while drinking cocktails and whatever, fine, let's do it. Um, and then we'll, we'll come back in two or three years and, and kick ass again." Eh, and so I kinda leave it up to the founder. That's the balance I've found. I, my natural, you know, inclination is to fight, fight, fight and never give up, uh, because I've seen so many times that, you know, month 18 or month 30, a founder figures something out and the company goes supernova. And sometimes the idea is just not a great idea, and so you should ... Or the market conditions are just horrible and you're, and you're just fighting against something that you cannot beat. You know, like if you're fighting against, like, you know, a, a tsunami, like (laughs) it's, you can't swim your way out of a tsunami in all likelihood, right? You'd probably want to retreat. So there's, there's a time for retreating. Um, I, it's just not in my nature generally.

   26. CWChris Williamson39:26

       I get it. I get it.

   27. JCJason Calacanis39:26

       Uh, uh, and that, and I think it's, I think it's actually a limiting factor at times for me. I probably should cut my losses on a lot of things and just say, "Yeah, you know, it doesn't look like this business is gonna work out. I wish you luck with it, and we have to focus on the winners."

   28. CWChris Williamson39:42

       (laughs)

   29. JCJason Calacanis39:42

       I just have a very hard time doing that. I know VCs who do it really well, and I'm just amazed that they can just be like, "Yeah, that didn't work. Um, we've committed as much capital as we want. We're gonna get off the board and we wish you luck. Let us know if there's any way we can help." And I'm like, "Wow. Okay."

   30. CWChris Williamson39:57

       Super rational approach.
4. 45:00 – 1:00:00

   Mm-hmm. …

   1. JCJason Calacanis45:00

      like he's, he's really a physicist and engineer who knows how to build stuff. And if you look at what he's building, like he's really good at metal. Like a lot of what he does is like building parts and metal and shaping it so that it can go to space or that electric car can be lighter and go further range. And a lot of the shit he learned at SpaceX went to Tesla and Tesla to SpaceX. Like material science and engineering is what he does.

   2. CWChris Williamson45:27

      Mm-hmm.

   3. JCJason Calacanis45:28

      And people will think like, "Oh, there's a lot more going on here." It's like, is there? Right? Like, he's an e- he's a- he's an engineer and he's a great engineer. And people, you know, look at him more like Steve Jobs or whatever. Steve Jobs wasn't an engineer, right? I thi- I think Steve Jobs was a marketer, right? He knew how... Like a packager, like he really understood how to package and market something to people. Simplify it, maybe. Like maybe he's a, at his core, Steve Jobs was like just a great designer, um, of products, right? Uh, and, you know, a brand builder, right? Like he built a brand and packaged stuff. He's really a packager, now that I think about it. Like he made this package, Apple. It meant something, it evoked something.

   4. CWChris Williamson46:06

      Mm-hmm.

   5. JCJason Calacanis46:06

      It was simple, clean, opening the box-

   6. CWChris Williamson46:09

      Beyond the tech.

   7. JCJason Calacanis46:10

      ... going into the store, using it. All the... Yeah, all the experiences. So y- he's kind of like an experience designer. Um, yeah, at his core he's an experience designer. Actually, that'd probably be the best way to say it. He's an experience designer.

   8. CWChris Williamson46:23

      I'd agree.

   9. JCJason Calacanis46:23

      Because the store is an experiencing, using your phone, using your laptop, opening up your phone, taking it out of the box. It's all an experience. And so yeah, you need to know what you're good at, right? I'm a talker. Like my skill set is talking. That's my superpower, is talking. And, uh, so I do a podcast and then I talk to founders and I run an accelerator where you talk a lot about people's hopes and dreams and tra- and strategies to succeed. So talking is a good one.

   10. CWChris Williamson46:49

       Precision with your speech is something that I think is uh, uh, a very, very under-regarded superpower. It's something that I encourage a lot of the people that are listening to do. If they're not having a conversation with a friend for 30 minutes every week where they're undistracted and they're talking about something that they care about and that they're genuinely engaged in, I find the process of doing a podcast and recording, I find it therapeutic in sharpening and honing in terms of the skill and, and what it then enables me to do outside of that, in a way that I never had before I did this. And I wouldn't-

   11. JCJason Calacanis47:19

       Do you feel more energy when you finish the podcast than when you started?

   12. CWChris Williamson47:25

       Yes.

   13. JCJason Calacanis47:27

       Right. So you're an extrovert, uh, not an introvert. You come out of a discussion like this with more energy, more inspired than you do going into it. And people who are introverted would come out of this and feel exhausted and they would need to take a break and read a book or take a nap or be alone. And so that is really the ener- the energy of those two different t- archetypes of humans, introverts versus extroverts. And knowing that, like some people you interview them and they're just like, "I, I... This was like exhausting for me," right? Um, other people, they, they're like, "Great. Let's do hour two, let's do hour three." You know, they just want to keep talking.

   14. CWChris Williamson48:03

       Mm-hmm.

   15. JCJason Calacanis48:04

       And so, you know, it's, uh, very important for you to understand what your skill set is, what your personality is, what you enjoy and then lean into that, 'cause the truth is when you're starting a company, you can always get other people to fill in. So if you're Elon and you're a great engineer or you're Steve Jobs and you're a great, you know, experience designer, uh, or you're a great talker and, you know, or you're a great sales ex- executive, you can, you can acquire those other skills from other team members. You don't need to have them.

   16. CWChris Williamson48:31

       Mm-hmm.

   17. JCJason Calacanis48:31

       So this idea that there's one type of founder, I get asked that all the time, "How do you pick the founders? What founders succeed most often?" And the founders that succeed most often are the ones who are self possessed and don't give up. Uh, it doesn't matter if they're introvert, extrovert. It doesn't matter if they're sales, marketing, product, developer, engineer, visionary, talker, you know, uh, leader, manager. All those different archetypes succeed all the time. There is no...... commonality, I don't think, other than people who are super self-possessed, uh, and they're very focused, uh, and they don't give up. So, if you're gonna look for traits, introvert, extrovert, you know, what job they did previously and how well they did that job, it's probably not as important as those other softer skills which are actually the harder ones, which is, does this person, uh, really care about this idea? Are they gonna quit? Will they give up, or are they going to, you know, build a plan, get a team, and pursue the goal? And it really is that simple. What's the goal here? What's the plan? And who's going to execute the plan? And man, I can't tell you the number of times, you know, you'll ask that to a founder, and they don't have a plan, and they don't have a goal. And I- I- I tell everybody our goal here when they come work at Launch, our investment company, launch.co, you can see our website. It's just a simple website. Anyway, what we do here at Launch is we invest in companies, and our goal is to be the best investors in Silicon Valley, or the best investors in the world, period. We want to be the best investors in the world, so we just work backwards to, what does that mean? Well, we think it means supporting founders early. That's the tactic we're using, you know. That's the plan. And the plan is to invest in 80, 90, 100 companies a year, and in 10 years have a thousand investments, and invest 10 times as much in the winners as we do in the ones that, uh, fail and go out of business. That's it. That's the plan. Let's execute on it. Podcast's a big part of it. Podcast, we get to put our founders on the podcast, This Week In Startups. We get to put investors on the podcast, angelpodcast.com. We get to meet new founders on the podcast. I met the founder of com.com and invested in the company because he was on the podcast. And, uh, it's a tool. You know, it's a tactic. Uh, it just happens to be a tool and tactic that is in my wheelhouse as the leader of the company, right?

   18. CWChris Williamson50:57

       (laughs)

   19. JCJason Calacanis50:57

       But I make it very clear for people, like, this is why we're here. And you know what? It's a lot of work to work with 100 companies a year, 'cause that means we gotta meet thousands, and we have to sort through 10, over 10,000 to meet with a couple thousand. You know, we're gonna meet with two or three thousand companies this year after having gotten pitched by over 10,000, right? So, just start thinking about those numbers. So, if we meet two, three, four thousand companies in order to get down to a hundred investments, it's a lot of work. It's a lot of work.

   20. CWChris Williamson51:28

       And you're searching for that-

   21. JCJason Calacanis51:28

       One in 50 people-

   22. CWChris Williamson51:29

       ... potential payoff at the end, right? Which is, that asymmetry-

   23. JCJason Calacanis51:32

       And nobody-

   24. CWChris Williamson51:32

       ... is exactly why it's there.

   25. JCJason Calacanis51:35

       And nobody knows. And nobody (laughs) ...

   26. CWChris Williamson51:36

       (laughs)

   27. JCJason Calacanis51:36

       There's the punchline. Nobody knows what's gonna work. So, by the way, we're going to place a large number of bets, meet thou- we're going to place a hundred bets after meeting thousands of people, after sorting through tens of thousands, and we don't actually know-

   28. CWChris Williamson51:51

       And it might not work.

   29. JCJason Calacanis51:51

       ... which one of the hundred every year is gonna be the breakout. And in fact, if we all bet, if the 12 members of the team each picked two companies each, I doubt that we would, even picking 25 of them, I don't think the majority of people would pick the winner. I don't think I thought com.com would be the second-best company in my portfolio. I did think Uber was gonna be, you know, a very successful company. Um, but I thought a billion or two billion dollar company, not a $60 billion company. So, I was off by 60, 30 to 60x.

   30. CWChris Williamson52:24

       (laughs) Quite a bit, yeah.
5. 1:00:00 – 1:14:08

   Just- …

   1. JCJason Calacanis1:00:00

      write about it." They just don't, journalists don't do it anymore because it doesn't, nobody clicks on it. Like you don't get clicks on Twitter for saying, "Jason invested $100,000 in this new company that's gonna try to change housing. Let me tell you about it." Like, that's not gonna get as much as, you know, "Bezos gave away only 10% of his money and he didn't guarantee how he's gonna give it away or over what time period or who he's giving it to." And like, they'll find every reason to criticize him and how he gives away $10 billion.

   2. CWChris Williamson1:00:27

      Just-

   3. JCJason Calacanis1:00:27

      Instead of saying, "Wow, amazing. Who would like to give $10 billion next?"

   4. CWChris Williamson1:00:32

      (laughs)

   5. JCJason Calacanis1:00:32

      "What an amazing gift." Because America's not spending on, you know ... Uh, what countries are spending $10 billion fighting global warming? I don't know.

   6. CWChris Williamson1:00:39

      Yeah.

   7. JCJason Calacanis1:00:39

      But this is a great example. You know, we should be having him on, we should be having Bezos on TV high-fiving him, and instead they're gonna be like, "Oh, well, you have too many drivers driving around causing pollution driving, you know, sprinter vans around," or, "You're killing the environment with cardboard." It's like, okay, yeah, that, there's a story about cardboard and sure, we can write that story, but can we just take a moment to let that sink in that he's decided to put $10 billion of his own money, that's a big number, towards, you know, g- raising awareness for global warming and solving it.

   8. CWChris Williamson1:01:12

      And the crazy thing between those two situations, the first one being you've done a thing, or this is something which is happening, and Bezos putting up $10 billion, is both of those things are news. Like that is news. It's a definition of news. A thing has happened which is potentially newsworthy. It's just that one of them has been spun a lot harder, and been used as this crutch to push what some people would call an agenda. And I think what you've mentioned there about Trump, it's the fact that the, they say the best lies ha- contain elements of truth, right? And that's why you're able to do-

   9. JCJason Calacanis1:01:44

      The devil mixes lies with truth. The devil mixes lies with truth.

   10. CWChris Williamson1:01:49

       There it is.

   11. JCJason Calacanis1:01:49

       The Exorcist.

   12. CWChris Williamson1:01:51

       (laughs)

   13. JCJason Calacanis1:01:51

       William Peter Blatty. It's a really, really great book, if you want to read it, yeah. And Legion, the follow-up. Really good books.

   14. CWChris Williamson1:02:00

       I watched, I watched Legion.

   15. JCJason Calacanis1:02:01

       Yeah.

   16. CWChris Williamson1:02:01

       Is that the one where they're in a, they're in a m- like motel-type, uh, café thing, and then-

   17. JCJason Calacanis1:02:05

       Nursing home.

   18. CWChris Williamson1:02:06

       ... all hell breaks loose?

   19. JCJason Calacanis1:02:07

       Lots of bad things happen. Anyway, the books are better, because the books are really about Catholicism and God, and pain and suffering, and why would a just God allow suffering, and the Devil and evil, so it's really through the lens of Catholicism, you know, a priest trying to come to terms with his own faith. Um, and it just has a little bit of like this horrific edge to it, uh, with murder, and why does murder and pain and suffering exist in the world. Like there's a scene in it where there's a, a group of people who have no ... It's a little graphic, but a group of people who don't have, uh, the ability to feel pain, like there's something wrong with their nervous system so they don't feel pain, so if you were to put a cigarette out on their leg, or if a cigarette fell on their leg and burned them, they wouldn't feel it. And there's just a scene there, as I remember, it was very evocative, of a little girl who was suffering that disease who wanted to look out the window, and she climbed onto a radiator, and the radiator turned on when she was looking out the window and she got burned on her legs, and didn't feel it. Why would God allow that to happen? Right? An- an- and that's actually, you know, why that movie is so powerful, is because even though you- you don't get that from the movie explicitly, it's kind of this undertone, where you're trying to figure out like the nature of evil, and why does evil exist in the world, right? It's like one of those core, you know, uh, mysteries of life, like why, why, why do people do evil things? Like what is the point of it all? Why do people blow things up? Why is there terrorism? Why are there murderers, like serial killers, whatever?

   20. CWChris Williamson1:03:45

       In a world that's got a God in it, it's a difficult, a difficult question to answer.

   21. JCJason Calacanis1:03:49

       Well, we got to God, it only took us an hour. So 01:15:00.

   22. CWChris Williamson1:03:52

       (laughs)

   23. JCJason Calacanis1:03:52

       We got there.

   24. CWChris Williamson1:03:52

       Uh, final question. Final, final question, Jason.

   25. JCJason Calacanis1:03:55

       Yeah.

   26. CWChris Williamson1:03:55

       Do you have any cool tech on your radar at the moment?

   27. JCJason Calacanis1:03:58

       Cool tech on my radar. Um, I am, uh, particularly interested in robotics outside of factories. I think it's a very, um, you know, interesting space that is going to, um, get very big. Um, I'm also very interested in education that is self-paced and occurs, you know, online, uh, or in small groups. Uh, but that is, uh, student-led kind of, you know, um, self-instruc- uh, what do they call it? Um, there's a term for when it's student led, but, um, I, you know, I, I like to look at the areas ... I, I look at markets where technology hasn't had a huge impact, and for me, you know, robotics, people doing like manual labor that sucks is one. And that could be very interesting for humanity. Um, and then another one is housing, and even housing plus robotics is kind of interesting to me, like robots building houses.

   28. CWChris Williamson1:04:59

       Mm.

   29. JCJason Calacanis1:05:00

       Um, education, where the education system is super screwed up in the United States. I'd love to see more and more solutions for, you know, we're seeing these ISAs, uh, income sharing agreements, where people agree to share $30,000 worth of their salary over the next five years in exchange for you teaching them how to be a programmer, or something like that, uh, or there are websites that'll teach you, you know, very niche websites, one to become a dancer, like steezy.co. We invested in S-T-E-E-Z-Y.co. Um, a- and, you know, or brilliant.org, which teaches people math. This idea that they're going to be a vertical site that's just really good at teaching you one thing, uh, is fascinating to me, because people go for these giant educations that cost $50,000 a year, and they put themselves into a quarter million dollars in debt, and then their first job out of school is 40 or 50K, so you know, after taxes, if they're making $40,000, and they're 200 in debt, they got a five to one ratio of, you know, after tax income to their debt load. It's just never going to be paid off, right? Even if they lived with their parents and paid off $20,000 a year and lived off the other $20,000, it would take them 10 years to just get to zero. They'd be 31 years old before they were able to even consider having any kind of a life. It's bizarre. Um, so yeah, I, I just look at those big, broken markets, things that are hard, um, and just try to think as an investor, "God, I can't wait for a founder to take on this one."

   30. CWChris Williamson1:06:34

       Mm.

Episode duration: 1:14:05