This Week in Startups - E1000: 1000th Episode Retrospective! Jason & TWiST lifers Lon Harris, Brian Alvey, & Tyler Crowley re-live favorite moments & guests, highlighting innovations in podcasting & tech over the last decade, hitting global trends & what’s in store for the next 1000

Episode Date: November 12, 2019

1:10 Jason intros episode 1000 + Brian Alvey & Lon Harris 3:58 "Money is the Root of All Evil" theme song 5:22 What were the first few episodes of TWiST like? 6:27 What is working with Jason like? 7:49 Tyler joins the show from Thailand and shares his history with TWiST 10:55 Brian gives his experience being the first guest on TWiST 11:59 Historic Clip: Gary Vaynerchuk on E24 18:12 History of podcasting as an industry 26:30 Historic Clip: Travis Kalanick on E180 29:54 What led to podcasting becoming a global phenomenon? 38:54 Historic Clip: Naval Ravikant on E244 42:31 How crazy was Jason in the early days of the show? 46:35 Historic Clip: Dave Goldberg on E251 47:55 Cultural shift in the general understanding of early-stage investing 53:44 Historic Clip: Chris Sacca on E291 58:36 Historic Clip: Chuck Johnson from a deleted episode 1:02:16 Historic Clip: Ed Catmull on E665/6 1:05:07 Jacqui explains how she booked Ed Catmull 1:11:24 Historic Clip: Aileen Lee on E988 1:14:52 Historic Clip: Jimmy Chamberlain on E491 1:21:43 What were "Insights from Tyler"? 1:22:47 Historic Clip: Greatest Insight from Tyler 1:25:51 Historic Clip: Peter Thiel on E525 1:27:27 Was the Peter Thiel/Gawker situation the greatest example of pettiness ever? 1:30:25 Historic Clip: Daniel Ek on E580 1:33:58 How has the perception of TWiST changed since the early days? 1:35:15 Historic Clip: Niklas Zennstrom & Sebastian Siemiatkowski on E583 1:39:57 Historic Clip: Peter Sunde on E765 1:43:23 What will the future of streaming & IP look like? 1:49:32 Historic Clip: Molly Wood on E969 1:51:05 What were the biggest changes from the last decade? 2:05:32 How has Jason changed as an interviewer? 2:09:50 Historic Clip: John Carreyrou on E828 2:11:55 Who should play Elizabeth Holmes in the upcoming movie? 2:13:02 Jason unveils the TWiST 1000 Cake and signs off and thanks everyone

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Welcome to This Weekend Startups. It's been 10 years since I started this podcast. And this is the 1,000th episode of this week in startups. And it's been my great privilege to share this show with you in the stories of founders, entrepreneurs, technology for the last 10 years. And we thought hard about what should we do for the 1,000th episode. It is a milestone. It is something significant, I guess. And I thought to myself, there's nothing I'd rather to do

than bring some of my best friends that I've had over the 10 years who helped me start the podcast, as well as some contributors from the later years, and talk about some great moments we've had on the podcast. It's not often that you do something a thousand times like this. And the show, for me, is like brushing my teeth or having breakfast. It's no effort at all. In fact, it's a joy. I wake up every Monday morning and I look at my schedule.

And the highlight for me professionally is the conversations I'm going to have on this program. And it is truly meaningful when you stop me on the street or send me an email. And like one founder told me, I watched your show all through high school with my friends and college. And now I'm pitching you my startup ends my dream come true. And I just thought to myself, a legacy I never considered. would be that tens of millions of people would watch this podcast, which I did for my own entertainment and for my own desire to talk with interesting people. It never occurred to me at any point in time that this might inspire some of you in my audience to start companies or for you in the audience

to think differently about the world and what the possibilities are for you and your friends. And to me, it's truly meaningful. And when you see me in public, stop and say, hey, Jake, out, and tell me what your favorite episode is. And we thought, Why don't we do that on this podcast this thousand time? We could have asked some big friends to come on the pod and maybe do something, you know, like a great guest. But I said, no, I want to have Tyler back. I don't want to have a great guest. I want to have my Tyler back.

I want to have my Lonnie Donnie back. I want my Lon Harris back. I want my Brian Alvey. No great guests. Just my friends. My friends who actually made this show what it is. The truth is I tell founders all the time. you're going to have to be great at building a team because nobody gets there alone.

And I am the shining example of this. And this show is probably the best example I can think of of nobody getting there alone. Tyler, Brian Alvey, Jackie, Lon, Gina, Brandis. So many people have contributed over so many years. Grant, Luke, Matt, so many people making so many contributions to these thousand episodes. And I'm so looking forward to the next thousand. And who remembers 10 years ago, this theme song? It's what it's all about me.

They said, money is the root of all evil. What? Funny how it feeds my people. We ain't going to live like equals until we get the money, spend the money and defeat you. Yeah. Money is the root of all evil. What? Funny how it feeds my people.

We ain't going to live like equals until we get the money, spend the money. All right. That was like the intro at some point, and we had no money. And we just took a stock-free song because we had been using at the time. We had been using at the time Jay-Z's run this town. Yeah, that Alicia Keys' Jay-Z song. That was before YouTube would take you down. So we just went with some copyrighted music. And it was like, oh, my God, I love the theme music. And I'm like, what is the music? And then everything was New York because I had just moved to L.A. I think that was a big early issue with the theme song was that the shows from Los Angeles, but we'd come again from this song that is all about being in New York. It's very confusing. Very confusing. But we really didn't think that much about it.

And that's Lon Harris, who's with us, who was the original newsreader. Yes. You and I met back in January of 2007. And you were one of the first hires at Mahala, rest in peace, which is now inside. And we still work together on that. Do you remember anything about those first? episodes or the idea to do it. I mean, you had already been doing a show called, I believe, the Calicanus cast.

Right. So when we were in your pool house working on the early days of Mahala, that was when Tyler came in to help you produce the Calicanus cast and keep doing that. So that had been sort of all going on in the background. Right. I'm not 100% sure where originally the idea of like, because, you know, you would just come in some mornings to Mahalo and be like, here's what we're doing. In my perspective, in my perspective, that was what happened. Like, you just came in one morning. We're like, we're turning that room into a podcast studio.

Calicaniscast is going to become this week at startups. And then we'll start a whole bunch of more podcasts and it just sort of grew. And the story grew in the telling. But that's very Jason, though. That's like one Saturday he texts me. And he says, I'm thinking about doing an incubator. And then on Monday, it goes down on the newsletter. We're doing an incubator.

We're hosting, right? Yeah. You just text me this thing. It was the same with the podcast. Yeah. I just happened to be in town. And you're like, oh, yeah. on Sunday come by and we're going to put a microphone on you and talk yeah oh okay sure i think

that might be an infuriating or inspiring quality i have to work with is that i sometimes just start doing crazy stuff but you guys seem to have liked that part of working with me there's there's definitely pluses and minuses to this yeah on the plus side you i've worked at a lot of places where things stagnate because everybody kind of gets here's what i'm doing and here's my job and everybody develops tunnel vision. And then you're a year later and you look back and you're like, this past year we got no closer to our goal because everybody just kept their head down and kept working, working hard, but without thinking about what's coming next or planning.

So it's good to suddenly just have big ideas, then like, make a turn. We're going to do this now. But it can be frustrating. I think the comparison I used with you that I've used other times is it's like being on a train and you're in the front of the train. Yeah. And you're looking out ahead like, want to go right. I want to go left. But those of us at the back of the train are like, oh, we got to figure out how to like make this work. You know, like we're, we're sort of like

it's this delayed effect. So I do sort of feel that way. Like sometimes you can feel like you're being pulled and you don't know where you're going or what you're doing because things could change way up ahead. I tried to do it less and explain more of the reasoning behind it, as opposed to just being unilateral. We're doing this. I'm considering this. Here's why I'm considering it. Does anybody have any feedback on doing this? And Tyler's us from Thailand. Hey, Tyler. Hello, hello, hello. Sahu D. Cup.

What are your first recollections of Calicanus cast and then this week in startups? Because you and I met because you were commenting on my blog and you were a day trader in downtown L.A. 12 or 13 years ago, reading my blog, you're making trades based on it. Strange enough, I was waiting from Thailand at that time when I commented on your blog. and happened to come home for Christmas

and you said you invited me over to the house and then you, similar to, as you were saying, you know, just had this idea, you know, this podcast. And so I remember running the guitar center and getting those microphones that you're talking into today or at least the ones that Lon and Brian are talking into, those exact ones. And in fact, that same mic stand that Brian's using today.

Yeah, the heavy ones later. Yeah. Yeah. And just getting the nuts and bolts of the equipment and putting it down. And we did the, I remember doing the first one in your, right out in front of the pool house. And then calling, getting new guests and the guests kept getting better and better. And the quality kept getting better and better. And then the cool part was like the intro that you just showed where the fans of the show started helping improve the quality of the show by,

giving a better intro and jingles and other elements that uh and that is when it to me realizing that this was going to take on a life of its own yeah and in that first group we i remember we had ron conway ev williams louis a bunch of the web celebrities gary vaynerchuk kevin rose were in the calicanus cast era and then we rebranded to this week in startups because i was like leo is doing this week in tech this other woman denise howell is doing this i believe it's her him this week and legal. We should just make it startups. It'd be a lot easier.

But that why, you remember, I mean, Leo has since come to be cool with it all, but I remember that was a big brouhaha. Oh, yeah. There was a lot of attention about that at the time. Yeah, and it was weird. I apologized to him for later. I was like, I didn't realize I thought it was an homage more than anything,

but I never realized it was a problem, and I'm sorry. And I apologize to him if he felt, you know, had overstepped. Yeah, but I think he realizes that now, but back then there was. were not that many podcasts. So to have two podcasts with any kind of similarity,

I think felt at that time very strange. Now in the age of everybody has a podcast, it seems like, of course you're going to have lots of different things that are overlap or have similarity. And I couldn't get any guests or was hard to get guests. And I was like, who can I get immediately who can't say no? That was you, Brian.

I was like, Brian can't say no. because he's my best friend. So I asked you to come on the first podcast. What do you remember about that? And how did I pitch it to you? Because I can't ever remember. Yeah, it was just like the accelerator, the incubator. It was just like, oh, hey, two days from now or tomorrow, I'm doing this thing.

Try to find a collared shirt, maybe brush your hair. And I had a lot of, I had like Einstein's grandmother hair. Yes. And that was it. We went into some long conference room at the Mahalo place. I don't think they hung some sheets and then we just kind of sat and did our thing that was it and we talked about

whatever mattered back then and you got some feedback from that episode did anybody listen to it? Do you remember? Well so I think we told people that we knew I think somehow it was streamed live like it was out there. Yeah back in the day there was you stream right yeah big live streaming

was a big deal back then there was Justin TV and you stream right two players and Justin became Justin's Twitch now Twitch right yeah he's spun out to Twitch. And we were live streaming. And the audience for live where we get like 100, 200 people would... Yeah, they were

very engaged and they were listening and they were commenting. It was fascinating. But we didn't know what we were doing. Certainly didn't know anything about radio or any of that stuff. But I think one of the first episodes that broke out, Lon, I think you remember this one, was Gary Vaynerchuk, episode 24. Maybe we could play that clip. Jog everybody's memory.

The people that are watching right now don't understand how fucking smart they are. Right. They don't realize they're part of a two to three percent Jedi that understands where the whole world is going. Right. And the opportunity to create a real-life business because we're entrepreneurs from the get-go.

Right. If we told our forefathers, the entrepreneurs of the 60s and 70s that you could build these businesses on this internet thing, zero cost to create the content. Zero cost to distribute. Zero cost to distribute.

And now because of word-of-mouth marketing, like Twitter and Facebook. Zero marketing costs. Zero marketing costs changed everything within the last few years. Zero friction. And I think everybody should be in the content game. Fuck Gourmet magazine.

Whole food should be the content leader. Wow. I mean, people give Gary a lot of, you know, whatever. He's over the top or whatever. But, I mean, talk about calling it 10 years ago. That podcast would be huge. And that distribution and content would be a huge thing. The part that stuck out for me even at that time was he's yelling about, you know,

like everybody should be making content for the internet. Why isn't Whole Foods making content for the internet? If you think about it now, Whole Foods owned by Amazon, Amazon Prime, making a ton of content for the internet. Exactly. He literally called it. He called it. Whole Foods is bought by Amazon.

Amazon bought the streaming service we were likely using at that time. Yeah. My house the world changed. Back then, I had no kids. The iPhone was version one. Twitter was based. We were in between iPhone 1 and 2, we determined. Yeah.

Word of mouth marketing. He didn't even call it social media back. Yeah. The word didn't even exist. That is actually a great point, Tyler. They called it word of mouth marketing because we didn't have the concept of virality, really.

I mean, like, social media as a term existed, but it wasn't, we didn't, we didn't understand, like, at that point, it was just another thing. It was like another, some of these startups are doing this thing called social media. I think Twitter was calling itself micro blogging. Yeah, micro blogging was the term. So it wasn't, like, accepted as, oh, yeah, I mean, if you're making a company, you have a social media department and they mark it for you online. Like, that was not, like, real-time media, like, the idea that it could be in real-time and

Twitter had this brand. of itself as we're a real-time platform. Yeah, that was the mind-blowing part about Twitter was that if you said what you were doing, other people could see what you're doing within seconds. That was the truly mind-blowing thing because it was on SMS.

It was the real-time nature of it. And the bar crawl or the, you know, where we're going next, that's out by Southwest. Somebody would tweet where they were going, and that was the mind-blowing part of Twitter. It was like a scavenger hunt-type game. And, yeah, I mean, you have to think back to 07, 08, 09.

we're not all used to our whole lives being on our phones yet. Like your smartphone, it's still a few years old. People didn't have them. Some people were still on BlackBerry. Some people were still on Nokia's. Right. So the idea, you know, today we sort of take it as, well, yeah, what's exciting about that?

You get a message on your phone and you're right back and it's all in real time, whatever. But like the idea that news and you could make news and find news and virally share it all from your phone is still pretty new and exciting. We've come a long way from what was like instant micro blogging to the death of democracy and and ruining elections. You know, who would have thought 10 years ago that I'm telling you what I had for breakfast on Twitter would lead to what we have now. And the joke used to be that it was so disposable. Like, well, nothing would ever get, you know, like, oh, we stare at tweets all day about what people are eating for lunch. You know, like that was the joke about it.

It was everything was not important. People only post garbage. Nothing. Nobody reads it. Nobody cares. The idea then that we would have a president literally setting national policy on Twitter. Or Arab Spring. Yeah.

Any of those things. It would be mine. You wouldn't believe it. Right. It was considered a goof. And it was considered nobody was watching it. And to that extent, people were very loose about it and would say things that were off the cuff to the point at which discovering what people said in the first half of the Twitter era to find out who said something completely inappropriate, just search for a keyword. Sure.

became like a national sport in the last five years. Right. Yeah. No, that was the era when James Gunn was just writing pedophilia jokes because he wasn't thinking one day I'm going to direct a Disney franchise and people are going to go back and scrutinizing jokes. Yeah.

Crazy to think that that's how far it's come. Yeah. The ultimate hack for being more productive is for you to get better sleep. As a founder, as a team member at a startup, as a venture capital, as a investor, you need sleep because you need to make great decisions, sharp decisions and you need to have your energy and your mojo when you get to the office. Well, if you don't sleep, what happens? We've all been there. The anxiety, you're up all night, and then you start thinking about sleeping, and then you don't sleep because you're getting

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and I put a couple hundred grand in because I love this product so much. And thank you to 8Sleep for supporting the 1,000th episode of this week in startups. And I look forward to the next 1,000. There's a generation of people, this is what I find the most mind-blowing. People don't know that the word podcasting came from the iPod. We were listening to these podcasts primarily on iPods. Exclusively. The software only worked on an iPod.

You had an iPod catcher. It wasn't yet in iTunes. I mean, I suppose there were probably other companies making MP3-type players. that could play. I had one before the iPod. But there was, I looked this up recently. Like Dell, I know had one, you know. Right.

No, I had a big brick one that could hold all that stuff. But it was never a thousand phones in your hand. It was never pitched to you by Steve Jobs to put it in your pocket, right? But I looked this up. The term was, it was either 2005 or 2006, like February. It was first mentioned, first coined. And within a month or two, probably five, oh five, we had an Engadget story about what is podcasting.

And if you look at it, it's hilarious. It's like how to get a podcast. Where do you find them? you download them, how do you listen to them? Stuff that we take for granted, our phones just do today. Right. But there was a whole how-to on it there. And we were very early.

Yeah. You had to get the RSS feed with enclosures. Correct. I had a hand encode the Engadget enclosures. Right. For PT and Peter Rojas and Ryan Block to put those in there. And then they would publish a new feed and have to run out and like re-edit the thing to put the enclosures back in because we weren't ready yet.

And then if you were a consumer, you had to have something in your Mac's system tray. where you'd put the URL in, you'd have to have your iPod plugged in, you'd have to hit the sync button, and then it would make an album with the name of the podcast. So they figured out how to hack the iPod to say, there's an artist known as Jason Calacanus with an album called This Week in Startups with tracks that are numbered. Yeah, and that's what I was going to say is,

I mean, at the beginning, I only knew how to get at podcast through iTunes. I think like most people. When the technology was new, you were sort of relying on. on the player to find the, I didn't even know how to go track them down. And what's interesting is, and this is where Dave Weiner does not get a lot of credit, the person who created this whole movement by adding enclosures to RSS,

the three things you can do that are uncontrolled and unmediated by big companies. The web, email, and podcasts, all based on open standards that are controlled by nobody. and all three of those are the most resilient forms of media and the most important channels to perfect as a founder. And if you're doing Twitter, Facebook, Tumblr, any of these other things, you're just renting space temporarily. But the more you put into that RSS feed, and the more it compounds, the more independent you are.

And that really is, when you think about independent media, it's astounding to me. Email would be the other one. Email, right? That's funny how email is now digesting the function of what RSS was doing because no kids today don't have a clue what RSS is or subscribing to a feed. But yet you subscribe to an email list now through your email. Why did RSS get killed? How did that happen, Brian?

Google built Google Reader. They made it free. Nobody else could build a reader anymore. And then they decided one day, we're not doing this anymore. I was going to say RSS was a vital part of my daily life until Google Reader went away. Google single-handedly went in, killed the other companies who were making money from them,

and then pulled the rug out from under it. A cynical person would say that was a strategy, but do we think that's a strategy? I guess I'm a cynical person. I just assume that was intentional, yeah. Like they literally killed this open... Well, because now what do you have to do?

Google News. They definitely killed it. Yeah, but when they killed it, I mean, there was a lot of people depended on it and a lot of things were going on with... There was quite a bit of an outcry when they decided to pull Google Reader, yeah? There was.

I remember. I was part of it. And it's, in a way, Twitter replaced it. So instead of you starting a blog and having your own URL and then you just have your Twitter feed. And Twitter doesn't support RSS anymore or does it? I don't even remember. But that was a big piece of Twitter. No, I don't think you can't find RSS feeds from things from Twitter, but they're about to let you start following topics.

Which would be great. There's your RSS reader. Which you can do on Instagram now, too. I mean, there are other ways to do all the things that we used to do with RSS feeds. It's just there wasn't really handy. Why did podcasting become such a phenomenon? I mean, listen, we've been at it for over 10 years. Yeah.

11, really. Why do we think this has become such a global renaissance? Because the number of podcasts in the last two years has gone supernova. I mean, I think there's probably so many reasons. It's not one reason. Okay, let's go through them. I was reading, you know, there was that New York Times piece a few months ago about is YouTube radicalizing America's youth and, you know, like how the YouTube algorithm can suck people in. And this article, it's based on a study, they were saying, that's really not what's happened.

It seems that way. But it's really just that YouTube is providing this platform that's low barrier to entry. And anybody can start a channel. And so it is, it is fulfilling a sadly, it's fulfilling a real demand that there were a lot of white. supremacists in America who wanted to get their message out, who didn't have an avenue to get it out, and YouTube has provided them one. And that's just what's happening. It's not anything about YouTube's algorithm specifically that's doing this. And I think you could probably sort of say the same thing for podcasting that not white supremacists, but that there were hundreds of thousands of people who just

wanted to be heard, who just had things to say. Had a voice. Comedians who wanted to make jokes, people who had political opinions, people who had thoughts about how you should eat or exercise or do crafts at home or whatever. And like all of the sudden now there's this technology that lets anyone share what they're thinking with the world. And it's easy to do. You just need a microphone and a laptop or your phone and you can start a podcast. Yeah. What do you think, Tyler? Why has this become such a phenomenon? In the last two years, it's largely because of the common confluence of things like bandwidth finally getting to a point where, you know, downloading a 200 megabyte file is no big deal anymore, which, you know, like a popular.

Yeah, and the mobile getting to a point and the bandwidth and the speeds getting to that point. The production is no longer an issue, as Alana is saying, anyone can more or less do it. But there's also prior to technology becoming what it is today, going back decades ago, it's human nature to join around a storyteller and forming a tribe and this sort of forming tribes around stories and narratives. And this is the function when you look at the podcast kind of menu within Apple and you see all of those different, you know, icons of those different. You're essentially selecting and subscribing to a tribe and a storytelling narrative. And this is something that humans have been doing since the beginning.

Yeah. What do you think, Brian? Why is podcasting? I think AirPods are the last 20% of podcasting. is AirPods made it so delightful to have your headphones in. Previous to that, you couldn't sleep with headphones in because you had the cable tangling. It just was a pain in the neck, and they're so convenient. I think that increased the last 20% of consumption.

You really sleep with your earbuds in? I fall asleep with the AirPods in all the time. I love to go to a bed on a podcast. Something about it, I just put on a podcast. I'd like to listen and fall asleep. No, I just feel like I'd be too physically, like, aware of them. I don't feel like to do it.

And then I just, every morning, have the ritual of trying to find white iPods on white sheets. It's like really like a fun thing. You just flip your sheet up and just see where they went. And try to catch them as they go flying across the room. But that seemed to be a, in the high speed mobile, plus the separate app by Apple was definitely a watershed moment. That day defaulted that, as opposed to having it buried in, ad feed in iTunes. I mean, plus stuff like Spotify now adding them like wherever.

you listen to whatever else you're listening to, there's probably a podcast option as well, man. All right, here's a famous moment on the show. This is episode 180. Let's cut to this. Important episode for me. The business is on-demand town car service. I push a button and in five minutes a car appears, I can see it coming to me.

When it arrives, I get buzzed. On the map, it shows you a car coming to you. A car coming to you on a Google map, basically. And it tells you how many minutes, the driver's name. And my billing information is already in there. And my phone numbers in this, so I can text. the driver. And we put iPhones in all the car so we see the exact route was taken. When you get to your destination, you just walk out of the car. You don't have to pay anything. You don't have to worry about

tipping. It's all included. It's all included. I think this is your billion dollar company. I'm an angel investor. I'm kind of biased. I mean, I agree with you. Yeah. I think it's a billion dollar company. I mean, that's the craziest moment ever. I, me saying to Travis, I think this could be a billion dollar company. We didn't think Uber was a billion dollar company at that point yet. It was only in one city. I will always remember this day because you showed me Uber before you were making this episode. You had it already on your phone like a beta. Yeah.

It wasn't out yet. No. And you were showing it to me. And I was like, this is never going to. This is a stupid idea. Why would I get into a stranger's car? How do I know they're not going to stab me? You got to have women jumping in and out of random people's cars.

I didn't see it at all. I always remember that this is why I'm not an angel investor. Tiley, you remember this because we had had travol. at the Open Angel Forum, and you were there, and you had the opportunity to invest. Yes. Well, you very graciously, after we were leaving the dinner where they pitched, and by the way, I have a very fond memory of the pitch at that dinner where Travis stands are in front of the screen. He connects essentially a phone to a screen, and we watch. They only had one car in the entire system. There was one Uber driver in the entire system.

There were four users and one driver. Yeah. And the driver's driving and you watch them on the map and all of a sudden at the end, the car pulls up right out, you know, five meter, ten meters from the pitch when the pitch ends. And it was this magical like, holy shit moment. And on the way out of dinner, well, actually, right at that moment, he says, we're raising 300,000 out of $5 million valuation. And you, I remember you holding up a piece of paper that said 50K on it. Like I'm committed for 50K. And they cut me down to 25 because that's so many investors from that party who wanted to get out. Right. Well, there was five other people. I was sitting next to Sion Bannister. And she's like, I think I'm doing this.

And then Shervin was there. He was doing it. Chris Akka was there. He was in. Yeah, everyone at that moment at the end of the pitch he had got his 300 essentially right then and there. And we left together as everyone departed and you were like, you want to split this 50K? and I was like, give me a day to think about it. I remember the next day, say, nah.

And then here's my, I empathize with you, Lon, because three months later, there was a tech crunch post about Uber gets a cease and desist from the city of San Francisco. And I remember emailing Jason and being like, ha-ha, who goes your 50K down the drain? Yeah. Yeah, I can't. Suspend disbelief.

Brian, before we left for the break, we were talking a little bit about why technically podcasts became a big deal, AirPods, iPhone, the dedicated app from Apple, all this stuff. What else do you think? So I definitely think there's two pieces to it. There's the technology side, right? Phones got easy to band with everything everybody said, right? You went from that and gadget story from way back when about how friggin' hard it was to find one, to make one, everything, to now anchor, you just push a button and start talking and then it distributes it everywhere. Like, it couldn't be easier. And then, so that's the technology side. But then also,

I think people have seen the sort of the first wave of people who did this and the impact it has to have your voice or Gary Vaynerchuk's voice in my ears talking to me. It's hypnotic for a decade. And I remember when you were talking about who should read your book, do the audio book of Angel. Right. You were with me. And they were fighting with you on this. You were with me in the room? Correct. Yes. We were talking to people where we were. Yeah. So, So we were at Harper Collins, correct, exactly, in New York. So we were talking. Eight people in the room.

Yeah. Yeah. Okay. So they had a large marketing team and you had no use for them. And so you were explaining to them, I'm going to read the book. And they're like, no, you're not going to read the book. We have professional people to do this. We're going to get, they probably named some people.

Yeah, they named the people who did Cheryl's book. Right. They did Ben Horowitz's book. They're professional. The best people. So they told you a couple reasons why you couldn't do it. One was nobody can maintain the same tone for five days and go back and fix mistakes and do things like that over five days and sound the same.

And they don't have the stamina for it. And you're like, I think I can do it, right? Give me a shot. And it's funny because you ended up telling them like, look, I'll just do my own. I'll pay for it, whatever. You pay for yours. And we'll see which one works. But I think what they were missing, which goes back to the podcasting thing,

is your voice is in people's ears twice a week all week long or when they binge for weeks at a time. And having that, like people will hear you somewhere and turn around and go, it's Jason because they know your voice. So you're in their minds. So I think people are seeing the power that people have from podcasting from just that sort of hypnotics part. There's also, I mean, it's listening to it. It's having that voice in your head.

But I also think psychologically there's something about like it's every day. You're in your car. These voices are with you for your commute. Your brain starts to think of these people as friends. And it's the same thing that happens with YouTube where we've seen like if you watch a YouTuber every day, they open their videos by saying like, hey, hello, good to see you. Thanks for watching. And you begin to feel like this person is your buddy. It's just natural psychology.

And it does. It confers a lot of power on the person who's talking to you. I mean, Adam Carolla got into this podcasting game early. Like, he makes films now. He writes books. He's got this very dedicated audience that's hanging on what he says every day.

That's crazy. I've been on his podcast twice, once in the first year of it, then once last year. And here's a guy like, and I mean, I like Adam Carolla, like he used to host the man show.

He was just to stand up. He, And like he was, you know, a morning drive guy in L.A., but it's not the same as when you've got this audience that's just of yours that you're talking to for like an hour a day, every day. It's its own thing. It's also become powerful. Like, I remember my friend Sam Harris, who used to come by the Mahalo office and we had him do a Q&A with Reddit. And instead of typing, he just recorded it. And he said, do you think I should do a podcast?

I said, you're built for podcasting, but just be careful of what's going to take over your life. And sure enough, that's exactly what it's done. I don't know he hasn't published a book since. And I don't think he'll ever publish another book because he's become so good at. It seems like there's a common theme between who's good at podcasting. Tyler, what makes somebody the ideal prototypical podcaster in your mind? I was saying that it's evolved over time a bit. And I would say now the most recent generation of people who have really, you know, become a success of it.

I think there was a real transition at the PewDie Pie era. And I think PewDie Pie had kind of to Lon's point. really got the listeners to feel as bros like he does with his fist-pounding and hey, bros and how you're doing this? And it goes back to my earlier point of he's creating his own tribe. And it's an extension of family, believe it or not. Like people used to, as people still do in Thailand and in Southeast Asia, a lot of the world, function in actual real tribes.

And that has become sort of dissipation. and fragmented as a result of technologies of sorts, but at the same time it's replicating it and we're becoming digital tribes of sorts. So that's again goes back to the human nature element of it. And the ones who do that best, like I think PewDie Pi is paving the way as to how that will look going more forward. But that will become more extreme. I think you'll start to see that element of, you know, this fraternities and sororities of digital groups combining online is what will be be the defining characteristics of successful podcast. Yeah.

Joe Rogan, Ben Shapiro, Sam Harris. And this is the role kind of towards the right. And then on the left, who are... Well, I mean, it makes some sense because just like what I was saying, like, there was a demand. Like, a lot of people justified or not, a lot of people on the right felt like media doesn't represent my views. Mainstream journalists don't represent my views.

And so here's a platform where anybody. can show up and just start talking. So finally, all of these views can start being expressed. I think that's definitely a big part of why, like, the Ben Shapiro's, the Stephen Crowder, even the Alex Joneses, like those kinds of people can find these huge audiences because there aren't as many alternatives. What do you think of the deplatforming of an Alex Jones? Is that something you would worry about or like on a freedom of speech basis that

corporations are making those decisions or great decision, this guy is causing a ton of harm in the world? I'm curious what Lon Harris thinks. Yeah, I mean, am I a little uncomfortable with companies making decisions about who could say what? Sure, it's not a, it's not a perfect system. But I think there are extreme cases where you have to. And that having the person on the platform is creating more conflict and more confusion than eliminating them. And I think that he's a great example.

I think Milo was a great example of someone who, like, I don't think you should do it willy-nilly. you're like, I don't like what that person has to say, but when it's legitimate hate speech. Yeah. Morrow is the most challenging of those because he's so insincere and so manipulative and so cynical in his approach. It's like, I'm a narcissist. I want all the attention. What gets me the most attention? Oh, being a Nazi?

Being vile. Right. Being vile? Great. I'm all in. So if I say feminism is cancer, that gets me more attention. Great. It's almost like a precursor to Trump, which is I need the most attention in the room.

It doesn't matter how I got the attention. It's the attention that matters. Sure. It's just super disturbing. It's the defining philosophy of our era. There's no such thing as bad attention. Right. No bad PR has actually manifested itself, but I don't buy it.

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episode of This Week in Starups. It means a lot to me in the team here. And of course, our listeners. Let's get back to this amazing episode. We had this crazy guy on in episode 244. And I had met this guy because he was your, he used to come to the angel investing stuff we did. And then he said, I'm going to make this like email this platform to do angel investing. And his name was Naval. And here he is on episode 24. And the consumer, uh, investing business brand and reputation is everything. And the way you build a brand reputation these days by serving the entrepreneurial community. It's almost a race to see who can be the most helpful.

Which is the way it should be. Which is the way it should be, shouldn't it? Because, I mean, the value is all in the entrepreneur and the effort they put in 12 hours a day, six, seven days a week, puging in the shower from the anxiety of complete utter failure. I don't like it when VCs say that they build companies. They support the entrepreneurs, but they don't build the companies. You've had bad experiences in your career? I think all of us have.

Who have been around long enough. I really feel like as an investor, if you can't back the founder, until the founder's ready to give it up, then you probably shouldn't be backing that founder. But that's just a personal opinion. Power corrupts. And I think most of the VCs who have really good reputations have built them by being good stewards. This is a really interesting moment because when you watch me in this moment, I'm studying Naval. Because Naval had this like really amazing insight about being founder supportive when the industry was still the venture capitalist controlled everything.

And he had this radical idea, and this is in the 200 range. When the show, I think as a host, I got better at listening and asking shorter questions and got a little more serious about my interview technique. And I used the podcast at that time as a way for me to get information. And I think that was one of the great reasons I became good at angel investing because I just used it as a way to ask people smarter than me, like really probing questions. Yeah, there's a lot of successful podcasts that are built on that, like, I'm going to ask you something and then you come in and educate me about this topic. Like that actually, Jonathan Van Ness from the, from Queer Eye, he's got, I forget what it's called, look it up.

It's like something with JVN. And that's literally it. He just finds people who do something that interests him and he has them sit across from him. And then he's just like, I don't know anything about this. Tell me about it. Yeah, Brian Copperman with the moment as well. Tyler, what did you think? Do you remember meeting Naval back then?

Yeah, of course. But there's something else going on there, which is he's setting a tone and a cultural expectation that is now being shared amongst all of the listeners of the podcast around culturally what is acceptable and non-acceptable. Because that wasn't obvious at that time when he said that, that it should really be about the founder and his platform. The Angelus really gave much more power back to the founders, actually.

right and then similarly to the same point with the launch conference really in its essence that going back to the very early origins of that was really about changing the culture of Silicon Valley away from startups paying to pitch at conferences and that

is thankfully kind of totally gone now that doesn't exist anymore but people take it for granted that your startups aren't supposed to pitch at conferences but that wouldn't be the case if the launch conference hadn't started the point being that this show I think can take a bit of a bow in helping shift, and of all, deserves a lot of credit.

A lot of people do, but the podcasts like this and others really help disseminate the culture of what is acceptable and not and what we're going to tolerate and not and help get those conversations out there in our tribe, so to speak. It is amazing the power of media to change things. We had that famous moment where the Karetsu Forum was charging $5,000 for people to pitch and I got so outraged about it. I said, we're going to start our own Karetsu Forum called Open Angel Forum and we won't charge and I will go on a jihad and murder the Kuretsu form and I held up in AK-47. And I just want to say, I was an insane, I just want to let

people know I was an insane person at that time and nobody listened to me. It was pre the podcast being popular. I was literal nobody in the industry. I was on the periphery. of the industry at best. The fact that Sequoia invested me led people to wonder if Sequoia had lost their minds or if they would have to deal with me ever again. And I was an outsider's outsider at that time, which is hard for people to understand. And it's also been a hard transition for me to go from being the outsider's outsider to now being inside the tent or maybe even some people considering me the establishment because of these things. But Brian, you did the Open Angel Forum in New York for me. Do you remember that time period? Do you remember the

Karetsu forum? Do you remember I do? Demo conference charging $25,000 to be on stage. What was the manic craziness as my friend? Tell me in all honesty, was I out of my mind? You were, you still are. But if you're right enough, it doesn't matter. See? So we're talking before about founders that kind of take their team on a wild ride and are constantly changing what we're going to do. Oh, let's start a podcast. Hey, let's make a, You know, an accelerator. Great. If you look back and they worked out, then there was nothing wrong with it. But if you really jerk people around for 10 years, then that's a bad thing. So we talked about this on episode 500 and 5001. When you interviewed me for the 500th. I think I kind of led with my God, you get credit for creating so many things, but everything you created was a reaction to something else. Oh, you have a hot dog stand? I can do a hot dog stand, but I'm going to do it with, you know, mayonnaise, right? Something. There's always some twist. And that was one of those. Open Angel Forum, which led to, the Uber investment was Which led to me being the Skoia scout.

Correct. That whole thing came because you wanted to kill off. Somebody was doing something wrong and you thought I can take that. I can do that. I can do it better. I can do it better. I can do it better. I can make a better one. I can make a Wikipedia with ads. Right. I can do that. That's what I was going to say. Mahalo was functionally similar because it was

SEO is garbage and it's ruining the web. Like what if we did it this way instead? Yeah. So we brought that up on there and I went through I think 12 cases of, oh, you have dig. I can do landscape, right? Like, everything was a reaction. And you didn't like that question. I didn't, you know, I never thought that I, you know, I guess one does not examine the course of their life all that much when they're in the thick of it. And I think it's an observation I could never

make myself that I was reactionary. And I think I'm at peace with the fact that maybe one of my skills is to iterate on other ideas that are in the world. And I'm okay with it now, because I don't feel like maybe I'm the creativist person to make the new thing in the world that never existed. Maybe I'm a person who looks at themes that are going on there and just does their own spin on them. And your sort of rebuttal on the old episode was like, but there's nothing wrong with that. I made some cool things. Like, yes, you did. You did.

It was a good answer. Yeah. I mean, is anything original, too, is something as you get older, you wonder. I mean, yeah, everybody's company is kind of iterating on all of the other ideas. Same thing in music. I mean, we're talking about even Uber is, it's what if taxis were good. Like, we know what taxis are, but they don't work right. They're bad.

What if we made an app and technology that, like, allowed taxis to work the way they're supposed to? Right. Episode 244 was taped at the same time as episode 251, the same two or three day period. A friend of mind, Greg Sang, who had a company that was like a dating app. I forgot the name of it right now. but he had a space up in that was previously ABC Studios for local TV, and he let me that black studio, and I slick my hair back with a bunch of gel. And I asked a couple of friends I had, because I was living in L.A. at the time,

if they would tape a series of episodes. And episode 251 is one of my favorite of all time. I don't do Angel investing, and I'm sure you have some of this perspective. I mean, I do it. Obviously, I'd like to make some money on it, but I look at it as much as anything as pay it forward. that people helped me. Right. And I think if you've been relatively successful as an entrepreneur,

it's incumbent upon you to help people who are coming up behind you. And so, like, if I look at my angel investments, if, like, overall I break even, I'm happy. And that was my friend Dave Goldberg, who died three years later, you're tragic, we have a heart attack at the age of 47, a year younger than I am four years ago now. And he was the mensch of Menches. Tyler, you remember him.

you remember that episode I'm sure yep and funny you don't think of it now but now that's clearly the black era where all the curtains

were black everywhere yeah we did black everything it was terrible set design yeah you would wear a black jacket your head is floating

yeah but that's another great example of the sort of cultural influence that Dave's beautiful point there of the pay it forward nature of Silicon Valley

and helping that Of course, that's obvious to people in Silicon Valley or maybe even in L.A., but you have a large audience of listeners today throughout Europe and now it's quite a global thing. That wasn't totally obvious because that wasn't the way the things were going down in a lot of markets, so to speak. This pay-it-forward culture is now extended through, you know, a lot of the rest of the world in some places. part due to kind of people hearing Dave's voice sharing that gospel in that way. So what I really like about that is I'll tell people that there are three things, or I used to tell people when they would ask what I do for a living, how do I explain what I

do to my family members? I would say, well, you've seen a social network, right? The Facebook founder is screwing over as co-founders. Like, that's part of my life. That's part of what I do. And my co-founders don't like that when I tell that story. But I explain Shark Tank and this week in startups. And now people don't really remember the social network so much.

But Shark Tank still thriving, this show, still on. And between those two, it helps me explain what I'm doing. And it's funny to look back at what Naval said or what Dave said and these insights that they have. And you think, you know, there was a time before nobody knew the phrase product market fit. Right. And people didn't call this startups and entrepreneurship. Like they called it like I'm starting a company. I'm going to start a magazine.

I'm going to start at this. I'm going to do this thing. But it wasn't startups, startups with a, you know, uppercase S. and now it's just, it's so easy to explain this. There's a big educational shift in those 10 years. Shark Tank is the number one show. They'll always tell you that it's watched by three generations, grandparents, parents, and kids all at the same time. So people know what does it mean to go out on a shiny floor and pitch somebody for money?

What does it mean to do one of these startup conferences? What does it mean to go on this show and talk to people? And you look at these insights these people have and you're like, well, of course we shouldn't crap on founders. Of course we shouldn't take them for a ride. Of course we shouldn't be jerks. But back then, before product market fit, before this, it didn't exist. Yeah, and before Cora and blogs and podcasts, all the secrets of how to do this were hidden in people's brains and in advisors. A couple of Jedi's.

A couple of Jedi's. And there was no text. There was no place to go to understand how to do it. Yeah, I think some of these big, I think it is sort of partly a function of Shark Tank. It's the same, like you hear lawyers and judges lament like the NCIS syndrome. It's like to say, yeah, Shark Tank is like that. Like everybody now watches NCI, so we all think we know about forensics and we're all familiar with these criminology terms.

It's sort of the same thing. And I'm curious if it's just the shark take effect. I think it's just also the reality of people watching as these tech companies take over the world. I mean, Google going from when I was in college, like, oh, there's a new, like, oh, there's a new Lycos. They've got a new Lycos called Google to now legitimately being one of the biggest companies of the world.

Ditto Amazon, dido Facebook. And I think that has really given this whole multiple generations. of Americans now, this idea of like, oh, here's what it is to start a company and here's how companies grow. And like, when I was a kid, you know, big companies have been around for 100 years. Like, who started Chrysler? Like, I don't know. There's always been a Chrysler.

It wasn't part of the, it wasn't part, understanding and unpacking it. Right. And the trajectory of it. It just wasn't common knowledge. And now it's gone to become in common knowledge. Yeah. I mean, when I was 15 or 20, like, there really weren't that many businesses that had started and then become world dominant multinational corporations.

But even Microsoft, the people who found in Microsoft, the first guy who put in 25K, 100K, a million, the first eight employees, the first 13, all the stuff that happened in Google that we know about, that we know about in Facebook, that we know about in all these startups we talk about today, Twitter, it all happened back in Microsoft. There was just no, it wasn't a sport. It wasn't covered like a sport. And so all of the same things happened in Microsoft. We just didn't know those people.

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Just go to brex.com slash twist and you're going to get $250. Amazing. Thank you, Brex. And we had a Google executive who had recently left on episode 291. And this became the first time I let the podcast go as long as it was interesting, which at the time, everybody was telling me to hit certain breaks and to do a certain cap. And there was a lot of pressure on me not to, there's a lot of pressure to end the show and not make it long and that the show was too long. And I said at a certain point, I don't care. I'm doing this because I am interested

in the conversation. I'll go as long as I damn, please. And if you've got to change the tapes or you're tired, you've got to be somewhere tough-ish. We're going as long as I think it's interesting. I don't know if it was that. I remember those conversations. I think there was this idea that people wouldn't like it. Like if you go beyond an hour or 90 minutes, like people wouldn't like it. That's how long shows are. And if we go too long,

people aren't going to like it. They don't want it to be that long. We just didn't like part of the three hour show. Right. And what we now know is like part of what's interesting and cool about podcast is that it doesn't matter. You don't have a time block. You have to fit between these hours.

Just make it as long as it's interesting. Like Pete Holmes will do a three hour episode of you made it weird and it'll be great. I'll listen to the whole thing. But it's no different than how. than Howard Stern. And I know no bigger Howard Stern fan than you who's listened to all this stuff. It was a big influence on me. Right.

You wanted to be the king of all media. Like that was your thing. And he's been doing that since, you know, with the 80s and 90s. He would go four hours, five hours for an episode. Right. He was contracted before. But even that was like, well, Howard's on from 8 to 1130. It was still like a block of time that he had to like fill or not fill.

He had four hours six to 10. Right. And then if the show was really rolling, he told them I'll just go over. And that became so. punk rock that Howard the next host he would just say you'll you'll start your show when I'm done with mine if I'm rolling I'm rolling and here we are rolling with a gentleman name that nobody had heard of named Chris Saka I just rebranded myself I created a thing called the Salinger group it just sounded mnemonic and familiar I had this great site it's not the soundergroup dot com

isn't up anymore but you can go to the internet archive and you know the way back machine it's you'll notice the site says a lot of nothing it has no address or phone number but it says a lot of bullshit because I needed to cover any angles that I was going to go make money on. Yeah, yeah. And I just went out with this business card now, and I just said, we instead of I, and people like, oh yeah, the Salander Group, I heard of you guys, you guys do good work. And so before you know, it, ching, ching, I'm getting wrong up. People are hiring me as a consultant. They're giving me equity in their company. And like, it became a real thing. Yeah, I started, actually building a real business. Fake it to you make it. So the Salinger Group was so successful

that a bunch of my buddies had lost their job during that time when they had gaps in their resume, you know, because it took a year. Yeah, they're like, hey, buddy, Can I say I work to the Saundry Group? I'm like, yeah, sure. Just tell me what your responsibility is work. Yeah, I'll endorse that on. Rise. Yeah.

And it was funny. Everyone kind of fit the Sounder Group to just make, to stay within their career trajectory. Where did you? Oh, you work in the Hong Kong office? Yeah. Can I say I did healthcare consulting? Yeah, sure, buddy. It's all good.

It's hilarious. And we went for hours. And it was really the first time I felt like I was a good host on the show. Because I wasn't sure, like, the first 100 episodes or so. I probably talked too much, interrupted people. people too much, but I felt in that one that I was starting to learn 300 episodes in how to get the Mustangs to run, how to get people to talk. Because somewhere around episode two or 300, I started studying other interviewers deliberately and trying to figure out how they got people

to talk more. And I started doing explicit techniques around asking questions that would open people up. Do you remember that double episode, Tyler? Yeah. And when I'm watching these episodes now, it's awesome to see. And I think it's not a coincidence that a lot of the favorite episodes are in that 200, 300 category, because that's where all this major shifting was starting to happen. Chris, again, another one of those culture, Silicon Valley culture shapers sharing some early insights there. and you did. You yourself realized, okay, this thing is an awesome opportunity here and you wanted to take it more professionally and take it to the next level,

and it wasn't just about a small time thing. And yeah, I remember you changing your own commitment to making the show as strong as it could be. Yeah, I wanted it to be better. But that doesn't mean we always booked great guests. I've only deleted one episode in the history of the pod. One episode. And I never censored anything on the episodes.

Although if somebody said something they regretted, I always gave them the option to edit it in post. But this one individual, Milo Unopoulos, and a bunch of people were making a bunch of waves and they were starting publications and they were pitching themselves as media executives and I had an individual on named Chuck Johnson. I didn't never knew about this.

Well, because I very quickly deleted the episode for a very specific reason. I realized I had platformed a racist piece of shit. Yeah, he's not a good guy. And he had asked me to be on the pod I needed guests. And he was doing something called got news or something, anything news. It was.

It was got news. Was it got news? And anyway, he was in Gawker every two weeks. And I was like, let's get some controversial guests on here. I was going to have Milo Yonoplas on because he was talking. And before they became alt-right crazy, they were kind of just media executives trying to build things. So Milo Unoplas had a blog network. Remember he had copied Weblogs Inc?

And he had hired one of our writers, a couple of our writers. a couple of our writers and he didn't pay him or something there was some big controversy there but you remember Milo from that era? Yeah, I do. And he was writing for the Guardian and he wasn't right wing.

He was just kind of flamboyant and contrarian, almost like Peter Thiel before he went full Trump. There were already some right wing ideas in there but it was not what he later became. It was not what they later became when they became full Nazi. Yes, he had not taken that hard turn yet. Right.

He was just saying any of it. thing for attention. So I have this kid on and I'm realizing during the interview that I've made a mistake and that I've had a racist piece of shit on my own podcast. You can beep the ish. And I'm going, oh, this was a mistake. And I don't want to be in the room with this idiot anymore. So here we go. I mean, here's the problem that we have, right? So we have several problems. Problem number one is people do think you're kind of a racist. Yeah, no doubt. I said to him, like, I kind of think you're a racist at the end of the podcast that I deleted the episode. Because I was like, and I don't remember what number it was, but I was just like, I don't, I don't remember if Jackie was with me at that point.

It was pre-Jackie, I believe. No, no, no, no, I was here. I was here. I was here. Do you remember booking him in Milo and that period of time? What did you think? Did you think I was crazy for booking him? I think a little bit, but I think you were, you had an open mind about what was going to happen in the

the conversation. So it was just trying to get him to understand what he was thinking. But after the fact, we didn't, I think we took, like, we didn't put any sponsors on the show. We kind of released it as a bonus episode. Yeah. And then pulled it later. Because it was like there's nothing of substance that's been said here. Yeah. And the person is doing the white power symbol secretly, you know. Was he doing the, not on the show, but in other places. And I was like, I don't feel like propagating or being associated with this person. So I just thought I'd take it down. Nothing of value really came from the conversation.

That was the thing was boring. Yeah, I mean, he's not a- And stupid. He's not an entrepreneur. And he just emailed me that he's invested in companies made a bunch of money. And he wanted a meeting last week. And he was like, I think he invested in Palmer Luckery's. Oh, good.

You know. Yeah. And Palmer Lucky, I invited on the podcast because he's doing this. I guess military stuff. I thought it was really interesting. And he said, you guys trashed me on the podcast. I was like, I don't remember, but come on the podcast. Probably deserve to be trashed.

I think he had some burner accounts on Reddit, it was the thing with Palmer. And I don't know if it's true or not, but he said it wasn't true. I was like, come on the podcast, we'll talk about it, whatever. But then we had, I think, a great moment. I love this book, Creativity, Inc. And I thought I was very touched,

and people ask me often, what's my favorite episode? and I don't have a favorite episode but Jackie, Miami Award-winning producer, thank you. I told her that, you know, I really want to have them on because the story hit me very deeply and that was Ed Catmull,

who was one of the co-founders of Pixar and here is Ed Catmull. When did you know that this was going to be a great film? Was there like a screening you went to or a moment in time? Because I think when you're in making a piece of art like this, you kind of lose perspective, don't you? You're kind of like inside the belly of the beast

and the belly of the whale. You don't even know where you are anymore. No, I didn't know. I mean, John had a lot of confidence. Steve did, but honestly, for myself, until it opened up, I didn't know. So obviously, I'm reading all the reviews. Is I'm going through review after review, what I found was that at most, the reviewers would use only one or two sentences to refer to the fact that it was made by a computer.

Right. The rest of the review was about the story. Amazing. And when I saw it, I thought, okay, we've done it. We hit it. Complete vindication for you. And then one week later, we went public. The week after the movie comes out, Steve Jobs times the IPO.

That's right. And when we went out to do the road show before the movie came out, we told everybody, this is what our business plan is, this is what we're going to do. But we don't want you to invest in the company until after you see what we've done. So confident. That is such a Steve Jobs move, isn't it? And not only that, this is where the other brilliant thing is, he said at the end of this film. Right. then Michael Eisen would realize he's actually created his worst nightmare.

A competitor. A competitor. Yeah. He funded the greatest competitor. So he will want to renegotiate the deal. Oh. And Steve said, when he renegotiates, I want to come in as an equal partner, which means we have to put up half the money, which means you have to have the money in the bank. Therefore, we have to go public.

Wow. And the thing was, that's what happened. What a master strategy. So for all the, you know, challenging nature of Steve Jobs, he was so above the rim, like, as a player, like just a strategist. He was just so brilliant. It's fascinating to see, like, how he could see the whole chessboard. I mean, he was looking at three chess boards, three matches ahead. That's right.

And he was our partner. Incredible. It was awesome. I mean, it's pretty amazing. Like, he just saw it. And then, so when he comes back to Eisenhower to renegotiate, what's that like? Does everything he say come true? Yeah, everything happened just like Steve said it was going to happen.

We entered into the deal. We got precisely what Steve said was going to happen nine months before. So it laid out perfectly. Jackie, you did that for me. You got him. I did. Tell the story of getting a catmone because this was not easy. Yeah, it took, you know, years.

I mean, just it's, yeah, there's no real science to it. It was just persistence, you know. Is this the right time? Is this the right time? We'd love to have you on. And then he just, he finally. 20 easily. Yeah, 20 emails.

And what I love about this moment is that you could see because he had been, he had had so many interviews about his book and everything else. But this is a moment where he was really excited talking about that time. Yeah. You know? And he's like, it's awesome. Like he, some of the stuff he has obviously said a bunch of times, but this is a moment where he was really remembering.

And just the whole insider baseball with Steve Jobs and everything else. just was just like, he just seemed really happy to be doing the interview. And it was a really long interview. It was a two-part or it was like a three-hour thing. And he just loved every minute of it talking about it. You know, and this is in the era, I'm thinking it was like 500, episode 500 maybe. This is when I felt like I was getting good as an interviewer because I was using a technique there, very specifically when I look at it, where I will say something to the effect of, what was, I can't imagine. What was that like?

I'm actually confounded by it because I am genuinely confounded by it and it gives him permission to actually go back to that moment. I call it like take me to that moment kind of interview technique. What was that moment like when that happened? Could you remember where you were and trying to get into to recreate that moment is I think you've probably seen me use that technique a number of times since. And once in a while somebody you'll see it in their face where they're and I saw it in his face there. He's he's remembering that moment where he says, and you had Steve Jobs, he's like, and he was our partner. You can see that he was like, I played on a team with Steve Jobs,

and it was super, it worked. And he was talking about Toy Story if that wasn't. It's not clear. It's Toy Story and how close they came to Fowling. And people forget now because it's become so, like, computer animation is just animation now. And like there's a whole generation of kids where that's what cartoons look like to them. But at the time, early computer.

animation we did not think of as on the same par with Disney animation. It was blocky and too shiny and it really looked fake. Like what Pixar did with Toy Story coming out, there had never been a computer animated feature film before. Before that, it was literally like, I want my MTV, dire straight with the blocky fingers. And like lawnmower man. Like they remember that horrific lawnmower man. It looks like it was made on a PCX team.

Right. Where it's monstrous. And for them to come and make Toy Story, filled with these charming, lovable characters who have human expressions and people relate to Buzz and Woody. It was like night and day. Like, you can understand why when you're watching that clip

where he's talking about, I want you to see the movie before you invest because it was revelatory when you first saw Toys. Yeah. Another great guest that took us years, Jackie, that you're particularly proud of, is Alien League, which just happened recently. This is episode 988, just 10 episodes ago.

Most recently, yep. How long did it take you to get Aileen? Well, again, years. So we got her to be on stage a few years ago, but as part of the investor discussion. Right. But to have a one-on-one fireside chat because she's very, she's pretty private.

So it's hard to, and she was always very nice, but she kept turning us down for Angel Podcasts for all of the conference, you know, for the last four years. It's incredibly frustrating, isn't it? And finally, but she was always, you know, lovely and gracious about it, but I was just like, God, I don't know. Maybe she just never wants to do this. And that's the greatest producer of the podcast ever.

Is it hard sometimes to book for me because I am an out there personality and people might think I'm a jerk or an aho or cantankerous? There's some people who would just never be on the show because they don't like me. Correct? Yes. How do you deal with, all right? There we go. Thanks for tuning in everybody. I'm self-aware of this.

When people have that expectation, what do you do as producer, Emmy Watering producer, Jackie, to get people through that? Do you have examples without maybe naming the person of somebody who thought I was a jerk, did the podcast, and then actually enjoyed it, or people where they did the podcast, were confirmed there was a jerk, and then hated you for booking them? The latter has not happened as far as I know. You know, I think it's different between men and women, honestly. Like, I think that men will just, they've just decided about you either way.

I think women maybe have heard things earlier or something or just have some perception. In my crazy days. Yeah. And so for them, you know, I'm careful to point out, you know, I'll just slip in, oh, you know, we're hosting this, you know, founding university for women entrepreneurs and we just kind of like managed to slip in all the stuff that we're doing. Right. We care deeply about diversity in the industry on the investment side of the business. Right.

And make sure they understand that piece of it. Like proving that we're good actors or trying at least. Yeah. Yeah. So they, in a subtle way that's not saying, well, you may not know this, but it's just like, oh, here's what else we have going on. We don't broadcast what we're doing in that way for diversity all that month. Yeah. Yeah.

What's the worst reaction you've ever gotten? Did anybody ever say, I hate that guy? I'll never be on the show because you shield me from this. And it's the first time we're ever discussing this. I know. Tell me the worst thing somebody's ever said. Like, I would rather die than be in the room with Jason Collin. No.

No? No, not that. I'm trying to think. Oh, Nick, Nick has. Does Nick have a story? I think that they're not on the podcast, but I've had, I honestly can't remember who was. It was a woman who I asked her to speak in an event.

And she was just really. And I honestly didn't even engage. She was just so obviously it was like whatever she, information I was. so out of date that I just didn't bother trying to correct what her perception was. And I was like, I, okay. Okay. Yeah, so here's another example of an incredibly amazing individual who was very difficult to get. And I just love how she responds to, you say something very obvious about her and her accomplishments, incredibly accomplished person, and she's very humble. And I just love how, And you are talking about diversity and industry, and you're asking basically, you know, is this enough?

And I just love her answer to this. Okay, here we go. Not only you're an activist, you're a pioneer. And I mean that sincerely. Like to come into the industry when you did and do what you did and to stay relentlessly positive about it in the face of it maybe not being a positive experience at all times and power through and set that example and take it's so seriously that your funds succeed and that you succeed because you know what it means to other people. It's not enough that they have women on the team page. But that is a big step that it's not all white dudes. Well, I think, thank you, by the way.

It's a movement, right? Like, this is not going. Everyone in this room can play a positive part in being an example to other industries of how we change the venture-backing ecosystem or industry, how we change companies, how we change cultures, how we change, how people are hired, how they're evaluated, how they're coached or sponsored, how people communicate with each other. Like, everybody here can do it, and we can, it can't be on the shoulders of women to change it.

It can't be on the shoulders of a small group of women. It has to be a movement. If you think about some of the social movements or the social change that's happened in society, like, for example, maybe the change in the attitudes towards gay marriage, right? It was just this mass acceptance and support for something that just is the right thing to do, and it makes a ton of sense. And I think in tech, that's what we have to do. And a lot of industries, it's funny, like after we started All Raise, we became kind of partners with Times Up, which is also a fantastic nonprofit organization, and there's Times of Entertainment and Times of Entertainment and Times Up Medicine and Healthcare, and there's Times Up advertising. And we've met some of the founders of those organizations, and they've told us they're looking to us to build a playbook.

to show their industries that it can be done. Yeah, and it was great about that moment. And you kind of saw a little bit of there with the cut is when I, and I just said that sincerely, Jackie, like, you're a real pioneer, you know, and it must not have been easy and you power it through it. She kind of got very choked up, and I think we cut the camera off of her because we saw her getting a little choked up. And it was a very powerful moment for me because I didn't expect you would get choked up about it.

You worked in VC for 20 years, and that makes you a pioneer as a woman. Like, you were one of the first. women to be at a major firm and be a partner and actually make investment decisions. That makes you a pioneer. And it was a great conversation on that way. I mean, she, Dollar Shave Club is one of her companies and just. Did she coin the term unicorn? She did, yes.

Yeah, she's coined the term unicorn. That's pioneering right there. I mean, on many levels. I mean, it's one of the hard things is to get people to agree to be on the podcast is not easy all the time because sometimes the people who do the most in the world want to talk about at least. You know, they're just doers, and they don't want to take the time to talk about it. I loved, loved the Smashing Pumpkins.

And Jimmy Chamberlain started getting into the internet. And somehow we had Jimmy Chamberlain on the podcast, and you were here for this and you booked it. And you're also a Gen Xer who's a huge fan girl. Yeah, I know. And I also, I picked this because this was going back. Like, Alien was the most recent. Jimmy was probably the first. And this isn't my first year here.

and I love this because I actually I didn't know you very well you were still in L.A. at the time. It was before you had really moved here. And so I was just thinking like who would be cool and I just happened to do research and Jimmy Chamberlain, the Smashing Pumpkins drummer just started as a startup.

He was doing live one, that music, immersive thing. And so I was like, oh, that would be interesting. So I reached out to him and he said yes. And you just like lost your mind. Like it was so great. I was strastruck because I had no idea. I was a large part of my formative years in my 20s.

I mean, that was my favorite band at the time. Yeah, and I had no idea. And I actually didn't even know. I remember I asked you, I was like, is this? This is when I was still asking you. Is this okay to ask this person on? And you're like, yes. But it wasn't until we got into the studio that I realized, oh, my God, you were such a fanboy.

Like, you were so starstruck. I was taken, yeah. And you know what the thing is, in the early days, I was like, Jackie, I'm really busy. I have this, like, daughter now. I'm busy. where you just pick the guess and she's like I want you to pick the guess I said you're the producer pick the guess

and we came to an agreement that you'd pick half and I would pick half and then I said to you the last couple of years I don't want to pick anybody I just want to show up find interesting people and make some mistakes and if it's a mistake and it's a bad guess and it's a dud which happens what

one out of 20 we'll just make it a shorter issue episode now people know if I made you're into a shorty if your episode's a half episode of course you sucked sorry 10 minutes and Sorry about that, Brian. Brian's always been a full episode.

You had a magazine a long time ago, a Silicon Allie Reporter, and I was an art director on it in 98, 99, 2000, somewhere around there. Before I joined, when I joined it, it was a color magazine. You were doing great. Before that, it was a 16-page photocopy who'd walk around with. On your first ever issue of Silicon Aller Reporter, there was a picture of Billy Corgan, smashing pumpkins, playing some concert, second one.

So it was super early on, black and white thing. And it was something where you're like, Oh, I just got some picture of the guy, and I'm just going to, because he's a superstar. I'm going to stick that on the front of my magazine, sell more copies and show that off, right? That was a big thing to you. What I also love about this is that he kept trying to, he was very polite and really interesting, but he kept trying to talk about technology or entrepreneurship or his startup. And you kept pushing him.

I wanted to talk about my role. Sorry. So anyway, this is like two, this is two very funny instances of it. And the first line, he tries it. And then the second time he tries. Okay, so the first clip, you know, not to get overtly spiritual, but you've got to be available. Like, you've got to make yourself available for the download. Like, that's the thing you learn as an artist.

You know, you learn to not take things for granted. You learn to, like, when something, when you get a feeling, you move towards it. And it's like, you know, I hate to just, you know, pivot into my own company. But when I saw the Live One product, there was a resonance around it that you know. Like, one thing, one thing I know is. the perception of that resonance. Yeah. You can feel it.

Yeah. Twitter has it. Right. Right. There's companies out there that have something beyond an identity. They've got a psyche, like a psychic connection. And what is the, is there some foundation to that that you think? Because, you know, is it being young?

Is it being angry? Is it being high? Is it being. Desperate. Desperate. Yeah, exactly. Or is it like the desire to want to be loved? Is it a desire to want to see the audience actually feel something?

What is it that makes those moments, do you know? It's all of that. What is it for you? It's all of that. When you look back on that time, what was it motivating you? It's wanting to compete at the highest level. Ah, competition. It's really having only one answer.

And that's, you know, to be at the top. I mean, even, you know, when Billy and I started the band in 1988, there was only one way to play. It was either go for the top or, go home. So that was about 15 minutes into the show. Now we're 40 minutes into the show. Okay. And we still haven't talked about a story. Go ahead. Go ahead. Okay, here we go. Oh, no. All right. Is this a tech show? It is. But you know what? I'm sorry I'm so enamored with you and I'm so enamored with artists. And so let's talk about your new project.

I literally, I don't have many fan moments. Like I'm not really like a fan boy of anything, but your music is so. I've seen you. A senior show. You're usually pretty pretty. harsh on you. I'm very harsh and everybody. I've seen you pick guys apart. Of course, of course. I'll pick your product apart if you want to in the next final segment. No, I didn't mean that. No, no, no, but I, listen, I just have to be honest with you. Like, your music played a seminal moment in my, I appreciate it. A seminal moment in my maturation in the, in the 90s, in New York, and really when I became a man, when I really started to, you know, just become who I am now. Sure.

The music is very meaningful me, even to this day. And New York at that time was the greatest place. Wasn't it? I mean, New York and the 90s, you know, pre-9-11. Pre-9-11, you felt like anything was possible. Right, and I don't know, you know, where you lived, but I remember going like to the continental divide, the chase bar, like scrap bar, remember? Or, I mean, how about like all of Peter Gation's places? Limelight tunnel, palladium.

Did you ever go to robots, like Save the Robots, electronic music down the Lower Side? No. Yeah. But the Lower East Side used to be amazing. Like, they were just always a great place. Roxy was great. I mean, just everything. Alphabet City with King Touch, Wawa Hut and 7B and.

Seven B, yeah. Of course. 7B. An interesting thing was like, if you went to A, you were going to get attacked, if you went to B, you're going to get mugged on A. You're going to get beat up on B and you're probably going to get killed on C. That was sort of like R. You know, like, if you want to go that way. Yep.

And like, actually the drugs got harder as you went. Oh, yeah. No, it was crazy. Like if you were on A, you were smoking weed. If you were on B, you were getting X or Z, it was heroin. Like, it was just. And now, I don't know. Have you been there?

Oh, it's so heartbreaking. It's like a grocery store. They turned New York. to like this Epcot Center. Anyway, I'm being ridiculous. That was terrible for me. Did he have a startup? What does that guy do now?

Oh, no. I just, I was so fan-boid out. Yeah, well, it's the special focus. When I was in high school, they were like a huge deal. Yeah. I saw them play the K-Rock Wheatie Roast. Wait, Tyler, did your band open for them? You knew them, right?

Sonny's did. I toured on the Infinite Sadness Tour, actually. actually. Actually, I introduced Jimmy's wife. I would now was actually in their wedding. Oh, wow. Who knew? Tyler was in a band. Sure. And then people don't remember this, but one of the devices on the show was Insights by Tyler. Insights from Tyler. Insights from Tyler. Because Tyler would say some things at times that we

had to unpack on. Yeah, Tyler was a big fan of like abstract similes and metaphors that we would then have to sort of. And some of these might not work 10 years later, but the one that sticks with me was, because somebody made a t-shirt of it, it was like having a wheelchair in Disneyland. Right. It was like, it's like when you, in elementary school, when you used to break apart the sentences, they'd be like, now this is the participle and this is the sheriff. I still don't understand that.

Yeah. That's what we would do. And then he said one, it's like buying roses for a nun. Wow. Like buying a dozen roses for a nun. and people didn't and I'd have to repeat them and try to unpack them

it became a whole bit and it became a bit it had a jingle it had jingle so here we go Insights from Tyler and it would just play and it was great then we had the best insight

from Tyler and I think we have the clip so let's play the greatest insight that Tyler ever made in Tyler history we're going to bring it up now Tyler Brace for Impact because this could be career ending

Newer people might like that one. But I think old school-wise, you really have to go with that. But let me see, the winner of the best Tyler Inside is, and of course the interesting thing if I can get this open, is that Tyler wins no matter what. Tyler is definitely the one. I'm pretty sure Tyler's gonna win. You have a speech prepared.

No. All right, there we go. It's like a wheelchair Disney man. I actually got it right. And I actually did not know that, but I knew that this would be it. Congratulations, Tyler. What a professional operator. Very good, Tyler.

What is the collaboration we were? What do you think is going to work, right, Tyler? It's amazing the percentage of these kinds of opportunities that work out. You know what I mean? It's like white guys in hip hop. It's like on a percentage basis, it works out really well. I have no idea what you just said.

That was an incredible thing or a bad thing. No, it's a great thing. It's a great thing. It's like wheelchair is a Disneyland. It's like you're going right to the front of the line. Gotcha. All right. So that's an inside from Tyler.

Inside on Tyler. And we used to show this photo of me and Tyler climbing the Bay Bridge in Sydney because I had gotten a $10,000, did I get like a $5,000 speaking gig, Tyler or something to go to Sydney? No, that was C-bit Australia. That was at least $10,000 at that time. Yeah, C-bit Australia. Tyler used to do my speaking gigs. I said, Tyler, see how much money you can get. They gave $10,000.

And then he's like, and they're going to give me $2,000 to speak. And I was like, great, we couldn't believe it. So Tyler and I and I and Jade, before I had London or any kids, we went there. And one of the things you could do was climb the bridge. Sure. But you had to wear a dorky hat and these dorky sunglass things. And so we're like wearing these jumpsuits and everything. Let's take a picture.

Yes, but here's a funny thing that nobody else knows except for you and me. Yeah. Jade is in that photo. Yeah, Jade was camera shy. She's in the photo. Pull the photo back up. Now you have to ask yourself, where is Jade in this photo? Oh, the

Under the light bulb. So we put, we covered Jade out with the light bulb and said insights and talk because she didn't want to be on the program. I was trying to protect her privacy, but she's in between us. And we were like, let's do the dorkiest thing we can think of a thumbs up on the top of the Bay Bridge. Yeah. But we had such a great time. So many great memories of going to Long Gray and hanging out with Mark Pesci, who then wound up doing this week in Startups, Australia, which is now in its eighth season. Wow.

And that's amazing. And that makes enough money to like pay for the podcast there. We don't make any money ever, but I was just like, you could take it. And so I was hoping that Thailand went to Europe would do this weekend startups Europe, but he's too lazy to do that because he lives in Thailand and he works two days a month. He took the best of my playbook that we developed together. And then he said, how can I do this but have 28 days off a month? J.Cal works 28 days and takes two days off.

He flipped it. We also had this crazy contrarian guy on episode 525. that was another interesting moment for the show. And that guy later got Trump elected. His name was Peter Thiel. And I had known him. He came to the event live. And that was not an easy interview for me.

But he had a good time. And it was pre all the Trump stuff. Let's hear Peter Thiel. You know, people always characterize me as contrarian. I think that's misleading. You know, one plus one equals three. That's a contrarian belief. It's not interesting, untrue, won't get you anywhere.

So it's always important for it to be something unconventional no one's thought of, but that also has either is intellectually true or has some merit in the business context. You know, like seesteading. What's that? That's his idea about he's going to build a platform and go live out in the middle of the ocean. Yeah, that was pretty contrarian. His libertarian Pacific paradise. Yeah.

It's very contrarian. Super contrarian. It's about as contrarian as it gets. I think of him as like, do you ever play those bioshop games? It's like there's like the underwater city that the crazy megalomaniac Andrew Ryan runs. He does his best to make himself into a Bond villain. Yeah, that's right. The truth is actually he just a very considered guy who has weird thoughts that are different than everybody else's and has been rewarded for them in life.

The Trump thing. He shouldn't have, he shouldn't have shut down Gawker. I'd prefer a world where we still have Gawker and Deadspin. You know, it's a Gawker on its best day should exist. Gawker on its worst day should not. And Gawker on its average day was, you know, just mild trolling. Like if you think about their best work, uncovering people who did bad things in the world and who were hypocrites, noble, publishing stolen sex tapes, loathsome. Sure. And outing people who did not want their sexuality.

I'm not defending. I'm not defending everything Gawker ever published, but I don't like the idea of billionaires getting to make decisions about what media should get to exist. But I do respect his long term, I'm going to destroy this company. Oh, oh, it's petty. It's petty in a legendary way. I mean, is there anybody who's ever done, played such a long game? It's an iconic moment in pettiness. That's the story somebody needs to make a movie of is not about Gawker, about Peter T.L.

and Nick Denton, because at the crux of this, and people don't know this, the crux of the entire brouhaha was that Nick Denton was a gay man who was out at the time. And people have to remember, this is over 10 years ago. When being out was not a given, it's still not today, but certainly back then, in business, Tim Cook and Peter Thiel did not want their sexuality known because it would have ended their careers or hampered them. And for Peter, it was acute because he was managing money from the Middle East where being gay is put you in jail and get you murdered. When Nick Denton saw that he wasn't coming out, but he was seeing him at gay parties, he kept asking everybody on his team to out Anderson Cooper and Peter Thiel and Tim Cook.

And they out Peter Thiel. They didn't out Anderson Cooper directly or Tim Cook. They kind of just kept alluding to it. Dancing around it. And Peter, they were messing with his paper. this was his money was from Saudi Arabia in some cases was what I heard

and for Nick you if you were going to be gay you had to be out it was just black and white to him and that was what the whole beef was about the outing of one gay man by another gay man

I like that Netflix documentary about it nobody speak yeah it was pretty well done do you remember that time Tyler because I was still friends with Nick at the time I'm still friends with Nick yeah

Well, yeah, you guys had a really interesting relationship, and I think you solidified around the fact that you both really were the earliest of pioneers in the blogging space and respected each other in that way. But you were also very competitive. Yeah. And like ValleyWag used to go after you. Hard. Probably go hard on me.

But you never tried to shut them down. You were just like, screw those guys. I'm happy to be relevant. Right. You know, I'm happy to be relevant. And then Tyler left and went. and went to Stockholm at some point, and I lost my collaborator, and he created his own conference series, which he was kind enough to let me come and interview people.

And one of the people I interviewed was Daniel Eck. And here is, Daniel Eck, about accidentally becoming an entrepreneur at the age of 14. Thank you for studying then up, Tyler, when I went to Stockholm. So my first company was when I was 14. It was 97. So it was in the movement where everyone needed a homepage. And you had this really big expensive consultancy companies who were charging like $50,000 to make the simplest web page.

I didn't care that much about any of that. And then one day someone came to me and said, hey, can you build a web page? And I'm like, no, I'm not really interested. Well, name your price. And I just said, well, $5,000, just something that sounded absurd. Just for the record, $5,000 for a $1,000. 14-year-old is absurd. Yeah.

So, yeah. So I just said that number, and the person said, fine. Something like, shit. I get to learn how to create web pages. Right. Can't be that hard. Yeah, that was my attitude. And next time, you know, someone came on and said, hey, can you create another web page

because you did this first one really well, and said, no, I don't really want to do it. name your price. It's a $10,000. And then all of a sudden I got $10,000. So this business thing actually came pretty easily to me. Yeah. You know. Yeah.

It really is that simple. You just name the price and keep doubling it. Yeah. Yeah. You built a company eventually out of that? Yeah. I sort of did. But it was like pretty much by accident.

And it's really great because, you know what I find in a lot of these conversations is that nobody ever asks the fact that. founder, how they became a founder, or what they did before. They're just obsessed with whatever is of the moment. Like Spotify is the obvious thing to talk about, but asking, how did you get started? There's always some very interesting story like that, I found, Tyler. Yeah. I feel the same way about events and conferences. For example, you're now in Europe, that event is the Stockholm Tech Fest where that was at. And the origin of that really is like trying to celebrate all of the cool innovation that's going

on in that region. But you've got other big conferences, you know, and that was obviously has a pedigree kind of borne out of launch. The launch festival has its own origin story. There you have slush coming up in a couple weeks, has its own origin stories.

Not only do people have their kind of entrepreneurial origin stories, but so do the products and the events and podcasts all gets coming down to what is the DNA and the genetics of the birth or the conception of this thing often stays with the founder.

Like to you, this podcast is, you know, you constantly are reminded of the origin and the genetic conception of why it happened. A lot of the viewers that come on years, months, months and years later, don't know how things start, but to the founder, it's always born from that, right? So to Daniel, and as he explains in that story, you know, at his core, he was born from this and it will always be that way. And it is special to hear people's origin stories and how they perceive their own thing, which is often just so oftentimes a huge surprise to people who aren't familiar with it.

Brian, what do you think the perception of the podcast is and how has it changed over the years? You now live in Silicon Valley as well. You've been with me for the longest. What do you think about the legacy now that we're sitting here at a thousand episodes? What any legacy will be? What I love is something you mentioned earlier, which is that somebody would listen to this with friends in high school or college, that they would binge on this, that this was their fuel, that this was the thing outside of their day job where they were thinking maybe I have a shot. Maybe I can build a product hunt or something like that and someday get on the show. And then to watch those things happen is phenomenal. You bring up Brian from Product Hunt who was a super fan of the show who used to call in. And then he built Product Hunt and came on the show. the podcast and he told me that and I was like really he's like you don't remember me calling in I'm like

i don't remember last month's guests i can't remember anybody's name i first met him at like a launch event years ago and he was like he could geek out and like he could tell you episode numbers he was like i you said this thing on episode 94 and it's like i don't know how it's it's crazy to me that the show has spawned those level of dedicated fans who can cite chapter and verse like that. Yeah, so there was an interesting question. I talked to Nicholas Zendstrom and Sebastian Simtkowski from Klarna, the investor and then Klarna. And I asked him just about immigration. Sebastian's the founder, CEO of Klarna, which is one of the unicorns. Yeah. And then Nicholas obviously did Skype and a bunch of other stuff and he's a billionaire. But anyway, I ask him a question.

And here's the controversial question. What about immigration here? This is a big issue. We could talk about abortion if we want to talk about something less controversial. How about religion? Religion is not very controversial. Everybody's an atheist. You know.

No, but about immigration? No, immigration is weird and it's, it's, you know, I live in London and I think it's fantastic where I'm an immigrant. No, but what I'm going to say is that London is a fantastic place in terms of It's such a melting pot. You know, it's like you have people from all different cultures, and they're completely, like, integrated. In Sweden, it's, we don't, we have not been very successful with, you know, with that melting pot yet, I think.

But it is, I mean, it is sad. There's an anti-immigration party right now that's almost up to 25% of the vote. Anti-immigration. And I think, I mean, I just, I look at that and I just feel very foreign in my old country. I am an immigrant myself. I mean, my parents were Polish. I'm born in Sweden. some second generation.

But I feel very foreign when I see 25% want to vote on that because to me it's like to me you know I just, I welcome having more people here.

I think it's such a lot of fun and I think all the people that we bring thank you. And the background here was Tyler tells me before we get on stage that the whole country

is dealing with and this is pre-Brexit pre-Trump 2015, but that immigration is becoming a bit of an issue there and I said You can't say that

You can't imagine how big of an issue It was at the time It was a very big issue And still is And still is And still is And I was like Should I bring it up

And bring it up And bring it up as a discussion You know Because he asked me to MC Do a bunch of interviews I was like You know you tell me It's your show

And he said Yeah bring it up Yeah If you watch that clip closely Like the looks on their faces That you brought that up You know It's like

you were just choking on their words. The whole audience literally gasp. If you listen closely, it's hard to hear because they're very, very large. Jackie, you were with me. You have to come. Yeah, and I think also for context, it's hard to remember what it was like in 2015. It was right before this was about a week. Tyler, you remember to probably, this is literally like a week before that picture of the dead toddler who drowned in Syria came up on shore.

That was the seminal moment when that. that issue became a worldwide crisis. And it was like kind of leading up to that moment. It was right before that moment. And so people were not really talking about it that openly, but it was obviously something that was brewing. And so I felt it too. It was like electrifying.

I mean, no one was supposed to be talking about it. And it was just like something you were not supposed to talk about. Tyler, you would probably know a little bit more. I haven't spent a lot of time in Scandinavia. But one of the things that I think there's a. attention there because it's a it's a group of people as a nation that sees themselves as very progressive. They think of themselves as a very liberal nation as a very forward-thinking nation is very progressive. But then where the rubber meets the road, they're confronted with

this harsh reality of, oh, we really are going to be bringing in all of these far. People, a lot of people who live there don't necessarily like that. So I think you get a lot of tension between how Scandinavian countries tend to see themselves and depict themselves and then the reality of actually doing these things. I think there's a term for it for the liberals here. I don't know what they call limousine liberals. Sure. Or like even just that idea in America of a neoliberal. You really, you like this.

You're what I take it to me. And you'd ask 100 people they have 100 definitions. You're comfortable with the status quo. It's about sounding progressive. Got it. Virtue signaling maybe. But when the rubber hits the road, you don't want the methadone clinic or the homeless clinic in your backyard. Exactly.

So Santa Monica, Mill Valley. It's what a lot of progressive Democrats would accuse centrist Democrats are being. It's like you're triangular. you're playing it safe. You're basically a Republican and Democrats clothing. And I think that that's some of the tension that goes along with this in progressive countries. Tyler wants to do the clip of Peter from Pirate Bay. This is somebody who went to jail. Set this up how you got him, Tyler. Yes. Oh, he's become a bit of a buddy now. But the Pirate Bay is from Sweden, which I think a lot of people don't know. But an interesting background is, I think you say this in your

question and I remember we went to dinner the night before and I said here's a great question for Peter which is all of the P2P explosion that happened which was the most popular one of course was Napster but there were several others there was scour.net which was Travis from Uber then you had Kazah which was Nicholas Zendstrom who you just showed a moment ago which became Skype and Daniel Eck blue Believe it or not, which was peak torrent, became Spotify, right? Coincidentally, a lot of Swedes in that mix. So you had the, you know, the P2Ps that shifted into becoming successful, you know, massive companies and unicorns.

And then the Pirate Bay that didn't, and it just stayed. And they went to jail. So it's like you had these founders who became billionaires. But Peter here, you know, had a very different outcome. and ended up in prison. And to see his, I had no idea how he would answer the question, but I absolutely, and I think you did too, I think we both kind of became really impressed with how he handled that whole interview.

Here we go. All right. So you're most famous for being the co-founder or founder of Pirate Bay. We don't really know. We don't know. No, we don't really know. No one really knows who actually founded Pirate Pay. or there's a long line of people who were involved in the peer-to-peer technology space

who've gone on to do pretty interesting things. Daniel Eck had a company. The founder of Kazah went on to do Skype. Let's see. Sean Parker in America did Napser and went on to do Facebook and be the president of Facebook, the first president. Travis did scour, peer-to-peer, and then did... red swoosh and then Uber.

So a big line of that. You also started in peer-to-peer and have done a lot of different projects. But you went to jail for your project. Yeah, because I have morals. Okay. That's the missing link here, like ethics, morals, and then...

Okay, so the other guys didn't. Okay. I don't want to talk crap about people who's not here. Some of them are here. But I think I have a higher goal than most other guys when it comes to these things. So for me, technology is about

what the change and the impact it has on society, not about how much cash I have in my pocket. Got it. So if you look at a guy who I'm very often referred to, being likened to is Kim.com. We have very similar backgrounds. We started with the same computers, same age. We knew each other as kids.

He's a little bit older than me, but just a little bit. But he was more interested in the money part of it. I've always been interested in kind of what it does for other people. Yeah, and he went to jail for his beliefs that people, that copyrights don't exist in the world. That was a weird discussion. Yeah, I would encourage people to go back and watch that interview because he, even at that time, and for those who don't know, and he has sense very, more than anyone I can think of, very accurately predicted where we are today in terms of Facebook and the data and the privacy

and the centralization of power. and what that all means. And he was saying this years ago when people couldn't get their heads around it. Like, well, what would be negative about Facebook in the data and the control? And now I think people are now on the edge of 2020, finally coming around understanding how much power these companies have and et cetera, et cetera, et cetera. And like Gary Vaynerchuk at the beginning of this episode, so acutely kind of laid out how things were going to be 10 years later,

Peter's another one of those that has a really keen look ahead as to where the ball's going. One issue that's just coming up among people who are huge film fans, classic film fans. Matt Zohler-Sights wrote a great piece about this, I think, last week or two weeks ago. So physical media is basically dead. Blu-rays, DVDs, streaming has killed it. And now we're consolidating all of the power in terms of who owns streaming libraries in the hands of a very few companies. but he's Disney, AT&T, Comcast. They choose what they want to have available online at any given time.

I mean, you could think of an example right now. Disney, they own every Disney movie, they own every Fox movie. They're going to put on Disney Plus or Hulu what they want. Not everything. Song of the South, there's a lot of articles now. They're not putting it on Disney Plus for obvious reasons. But that's just one example. This article that I was referencing is talk about how they're not going to release Fox

films from the archive for revival screenings. So if you wanted to screen Fight Club in your town or Alien in your town, Disney might just say no. And there's nothing you can do. And if they're only available on streaming, a whole generation has no access to them because DVDs are no longer going to be sold. There's no more. Nobody has a VHS. There's no more Laserdisc. DVDs and Blu-rays are increasingly becoming oddities and cultural artifacts. People don't have a DVD player, maybe even in their home anymore. Right. If it's not available to stream, if these companies don't decide to put it up on iTunes or Amazon, it's gone.

They can ghost it. It just disappeared. Like, you literally can't find a copy of it. And this happens today. I mean, I will sometimes think of a movie from the 40s or 50s. And I'd be like, oh, I'd like to revisit that old film noir. And it's just, well, it's not, you can't buy it. You can't stream it.

It's just functionally gone. And so 15, 20 years ago, it might have been kind of hard to think of a good argument for why you'd need to pirate something. It's like, you don't need to pirate that movie. Just go pay three or four dollars and go rent it. But we're entering an error where that may not. be an option anymore. Yeah, Disney used to do that where they say, okay, Cinderella only available through December 1st and then it's gone. It goes back in the Disney vault. But if you bought it,

you still had it. They couldn't take it back out of your house. Right. And the thing now is it all goes back out of your house. So my dad a couple weeks ago asked about the Abbey Road 50th anniversary. There's this three disc set. Should I send this to your son who's playing all these things in School of Rock? And I'm like, he'd love it except we'd have to go out to the driveway to our car to get a working CD player to listen to this thing. We don't have CD players. We don't have CD players. anymore. And it's on Spotify, but it might not be next week. Right. Wow. That's where I hurry it on Spotify. But yeah, Spotify could take stuff down. It's up to them. And it disappears forever. And then it's gone into the void. So I think we're just now, 20, 25 years later, starting to

discover some of the value proposition that something like Pirate Bay had, which is anything could be available. There are mechanisms where some enthusiasts could put it up and you can watch it. But we're We're rapidly exiting that that time period. I have a friend who's not me who found on Reddit the tape traders for Howard Stern. Howard Stern's archive has been scrubbed because at the time the things he said were so inappropriate. He was in blackface, whatever. They were, I mean, it was also just think about the expense of hosting all of that content. decades of the Howard Stern Show.

And what was crazy about all this is they wound up as a group doing like this master project to put all of them into a BitTorrent. Wow. Every Stern show. And then they have multiple copies of some because they have the Boston and the New York tape and the DC tape which have different pieces missing. Wow. And so you started thinking about this completest kind of thing. And then some shows, they are not willing to let people now do these shows and these archives. They're not going to let them come out because they're afraid of like some old stuff.

Right. Well, the Seinfeld Puerto Rican Day episode. That's a great example. Has it been ghosted? If you buy the DVD box set with every episode, it's in there. But if you watch it on streaming, streaming platforms. I'm not aware of that episode. There was an episode where the whole episode takes place.

They're stuck in traffic. They're coming back from, I want to say, a Mets game. And they get stuck in traffic because it's the portals. Puerto Rican Day parade. Which is the most out of control of all parades. So the whole episode is it's shot on this fake exterior street and they're getting out of the car and in the car and they're just waiting and they're stuck in traffic. But the reason it got banned was there's one segment where Kramer accidentally lights a Puerto Rican flag on fire with his cigar. And it looks like he's in the street burning the Puerto Rican flag on Puerto Rican Day.

And so people come up to him. Right. It's absurd. What's the problem? It's offensive for him to burn the Puerto Rican flag on television. That's the joke. But that episode has been scrubbed from the airways. It doesn't.

It didn't play in syndication. It doesn't go on. Oh, South Park had the same thing because they had an episode with the super friends on it. Yes. That were all the super friends, including Muhammad. Right. And they actually depicted. Yes, they made a little cartoon because you're not supposed to make an image of Muhammad.

Yeah. Crazy. Yeah. So anyway, that's an example of, you know, there's a real need for something where you can access this stuff, even if these companies decide they don't want you to have it. And, of course, our favorite. Favorite roundtable guest, Molly Wood. I'm wondering why we allow TikTok in the United States.

Yeah. Because it's a Chinese own company. Now, I don't mean to be a conspiracy there is here. What are the chances that the Chinese government is not using that data to study Americans to get some edge? Zero. Zero. In fact, we know from, I think, Bloomberg reporting, that the Chinese government maintains an office in TikTok headquarters. So it would be like literally if the FBI had an office at Instagram.

where they just hoovered up, or the CIA actually, more secretie, where they just hoovered up all the data. Well, in this case, it could just be that they're hoovering up the domestic data, right? The data of the Chinese users of TikTok. It's a completely different product there. Yeah. No, no, they're slurping up the American data. But they're definitely slipping up. And then you have to ask yourself, well, this has access to your microphone and camera. What are the chances they're not listening in and targeting and knowing who an executive is in business and turning on their microphone covertly.

what's so interesting to me is that China is incubating this like parallel tech economy. Behind the Great Firewall, they are growing the only other companies of the same size and power. Yeah, same scale. As Facebook or Amazon or Google. And so that at some point, and Huawei is Apple, like there's like a, there's a parallel for almost everything. And you just sort of wonder what is it like clash of the Titans eventually? Like at some point, this fully forward formed. economy will spring out, assuming that we don't shut it down with national security concerns.

I just realized. And then there will be the battle for our future. Go around the horn. What's the biggest change that's happened in the last 10, 11 years of the podcast? In society and life, what has changed the most? When we look at technology, when we look at the industry, what to you feels the most different about the last decade? And I'll open that up to Jackie as well. For me, I have one which I never thought I would see and I'm wondering what yours are what are yours do you have yours

I have one go ahead Lon I'll do my last I mean I want to say I think it's it's social media and how social media went from where we all kind of throw our thoughts and opinions about what's going on to where we all find out what's going on and it has become the center of life instead of

reflecting what life is about. And to me, that feels like a really huge shift that has changed the way people think, changed the way people examine questions and solve problems and for good and some good for mostly bad. And I think that that's what we're really seeing is, you know, we had sort of thought, I think, in this utopian way at the beginning of the social media era that this is going, it's egalitarian. More voices. Suddenly more voices. If you, have a good idea, it's a total meritocracy, somebody will hear your idea and it'll viral spread.

I think we thought that there would be more, like, that it would be a better system, that it would be more efficient at bringing good observations to the top. That would be dropping down, like how Reddit's supposed to work. We thought everybody was going to upvote all the good stuff and downvote all the bad stuff, and it would be this very useful tool. And instead, what we found is everybody's upvoting everything all the time. It's just noise. And now there's like no truth.

Like literally Brit Hume, a newsman will go on Twitter and be like, we shouldn't impeach the president because these guys think this, these guys think that. You can't know the truth. Forget about it. And like that seems like a reasonable opinion in 2019. We broke the truth. Yeah, we broke the idea that you can ever know anything with any kind of confidence is just gone. And I think that a lot of that is on companies like Facebook and Twitter. Brian, what's changed most?

I think there's something similar to that. I think that's fascinating and that all outrage, you know, everything's on 11 all the time. Oh, yeah. Kind of thing is that didn't happen back then. Yeah, there's no nuance. But you can take this and just take the Facebook thing. The idea that you can build a business, build a company, build a startup, make it big enough and powerful and just so important that it's more powerful in a country or a government is actually, is mind blowing. and then maybe for your listeners, aspirational.

Right. If with great power, it does come great responsibility. Take Uber, right? What they moved into, what they did, they hit a lot of laws. It said, wait, you can't do that. And they said, well, we're going to do it for a while. And everybody voted with, well, yeah, everybody voted with like, no, I need the car to come to my airport to get me. I need the convenience of it.

And it changed. You take the Napster and the streaming stuff, things like that. People voted with, sorry, record labels. I want an MP3 in my pocket, right? And I don't care how it gets there. And the law is all changed and the things all changed. And those things became. So I'm being silly that, you know, hey, hey listeners, you can build a company that can take down governments or be more important or more powerful, more influential in a government.

But at the end of the day, you can actually build something that changes the world. Capitalism entrepreneurship as an operating system creates massive change and it's only gotten more significant. Jackie. What's changed the most in the last? What's changed the most in the last decade? Since the show existed, you know, started in 2009-ish. What's changed the most? What about society and life?

Tyler, if you're ready, we'll go to you while Jackie's thinking. Sure. I can combine both of those points. When the show started, we were in the PC era. It was pre-smartphone era. And you could argue it started with like the launch of Windows 95. And it went until the launch of the iPhone. And then the battle was between Apple and Microsoft, right?

That era. And everyone was building websites, essentially, during that era. And then we went into, you could argue Microsoft won that era. And then we went into round number two. And round number two was the smartphone area for the launch of the iPhone 2007 until very recently. And this battle was between Apple again. Surprisingly, Microsoft was not in this one. And Google, you could say, was the other big one.

And at the early days, it was Blackberry and maybe a hint of Nokia. And I think we can all agree. Google has come out on top. Apple's a strong player still. We're going into the third era now. And this show has lived through all of these now. It'll be interesting to see how the show evolves in this new third era, which is a new platform, post-smart phone of smart homes and smart cities

and smart everything now that you have microphones embedded in every day. device in your home in your office, which is either Alexa or Siri or Google Assistant. And this opens up what leads to my point, which dovetails perfectly with Brian's point, which is tech used to be the playground of the geeks kind of exclusively, right? And it didn't really involve the government in any real way. And then it largely in part due to you, the early innovations were in the realms of media and blogging and the magazines and the record labels. And all of this is where the first friction points were.

And then it moved into FinTech, and then the banks started feeling the friction of tech, and then MedTech. And now with this new era of microphones everywhere and the data of everything and big data and whatnot, now governments themselves are starting to understand the power and the opportunity and business. challenges of tech.

And so you've got China using tech in a way that it's hard to even imagine in terms of how they use it as a control mechanism of a billion people. And China's not the only one. China's the one that actually have to give them some credit. At least they're transparent about the fact that they're using that data in that

way. But so is the U.S. And this is going to become the big issue going forward is how now that government understands the power of tech, which it never seemed to during the PC era or even the smartphone era, and how they want to use that as control. And the U.S. is forcing WhatsApp and WeChat to, I'm sorry, WhatsApp and Facebook and

to expose all of the data in their sovereign territories. Here's just the most recent stories is Sweden, for example, no one really knows this yet, has decided. And Sweden is always a couple of steps ahead of other bigger countries because they can move fast and they're very progressive, is they've realized if for all government interests, we must have our own sovereign cloud and we cannot use third-party clouds

in the same way that the U.S. is being kind of anti-Waway, well, Sweden's saying we need our actual, we have our sovereign land, and we control everything on our physical land, and we have an immigration border around our land, we need our own cloud, and we need to control all the data that happens in that cloud, because we can't let Amazon have all of the,

these services necessarily or the other cloud flyers. And I think you're going to see this become a new mega trend of China has its own cloud. Actually, its own sort of internet. Yeah. And by the way, China's going to start forcing its internet on its partners. Because then that's the internet

they control and the media that they control within that internet. So if Facebook wants to be there, Google wants to be there, you're going to be on our cloud with our authentication. Correct. With our accounts. We control everything. That's right. So either come into our sandbox. Yeah. And it's going to be the battle of multiple intranets, essentially.

Crazy. I mean, I couldn't possibly follow all that. I just feel like it's for more of a gut. And I'm also sort of older than everyone here, I think. So I have a bit of a longer term feeling. And I'm newer to the tech industry. I think things feel like grittier now. So I feel like before there was a bit more,

it was like very fluffy and frothy. And there was like a lot of money. And people were excited. I think people are, I think there's a downturn coming. And I think that, you know, and as you know, we've talked about this before. I'm very worried about climate change and all of these issues. So I feel like there's this sort of urgency and chaos that I haven't experienced before. Yeah.

You know, I kind of remember the 70s, but not much. I was pretty little then. It was very optimistic when we started the show. And now it feels like there's so many big dark clouds out there. I know. And I don't want to be like the down here. but that is how I feel. I think it's a, it could, listen, we might be sitting here in 10 years and the whole half

the planet's underwater and you're going to have the most, you'll have the best clip. Mine was about how everyone's brain has turned to goo. Mine is not totally dope. Mine is more thoughtful than that. To end up mine is, I really think the thing that is the most troubling to me, it's inspiring in one way to Brian's point of just the impact these can have. And obviously a number of people highlighted the negative impacts. the scale of these projects can have.

And to me, one of the troubling things is, when I started the pod, technology was looked at as, in the technology industry, was looked at it as inspirational, aspirational, and humanity positive. And now we're sitting here. And capitalism is looked at as broken. unfair. And with that, people of ink sometimes lump in entrepreneurs and startups. The capitalist system may not be perfect, but we want people to start companies and we want an incentive structure. We want people to believe that capitalism and people fighting it out in the battlefield

of great ideas is an idea that's worth it. And we have to bring more people along. And, you know, if you look at something as very basic as minimum wage as a floor for society or universal basic income, which I have some reservations about. I think the people who are winning so much in this town have to start thinking about just paying some base amount of tax as corporations and being better citizens and not doing it after the fact, but doing it proactively. Like a proactive way of policing yourself. And I think Twitter saying we're not going to participate in ads this time is the perfect example of that happening. Apple saying we're going to make your phones your domain and we're going to not let people track you.

If you use Safari, we're going to remove tracking, and we're going to obscure your credit card number, and we're going to be the company that protects citizens. We're starting to see a group of founders and big companies start to think, and a cynic might say they're doing it because they want to avoid regulation, but I think there's a crisis of conscience happening in Silicon Valley where we're just going to have to get used to an oversized impact in the world, which means oversized premeditation of what the impact of these products is and

what that impact has on people. Yeah. I mean, I think that, you know, the capitalism versus socialism, OK boomer stuff, that's dominating like the Twitter conversation, of course. And you're always going to have, you know, some young people are just, you're, you're more radical when you're younger. It's natural. But I don't really think a lot of Americans are stridently.

anti-capitalist, I think they're reacting to what seems like totally unfettered, unregulated capitalism run amok. And just like you're saying, if we could get a little bit more of a sense of balance where it didn't feel like eight people have all the money and are literally going to use it to go populate Mars while the rest of us drown, I think that you would not have as much of that debate. There's a reason why AOC Bernie and Warren are becoming such significant forces in politics. Right. And I think that it, the wealthy tend to do this very reactionary, like you're with us or you're against us, like socialism is bad and everybody becomes Joseph Stalin overnight. I agree. Keep going. And I think that that is silly. And I think people hear that

and they recognize that that's silly and that a little bit of, you know, sort of like more progressive policies don't automatically turn us into East Berlin. And I, and I think that that's what we need is, is for it to stop being such a crazy binary, and then you won't have the same amount of anger. The startup phenomena, which Silicon Valley used to be considered going back 10 years, was really the mecca, the concentration of power and the be-all-end-all of the culture globally of tech. And that is really, I would take it even kind of thankfully,

that's no longer the case that tech has really become a global thing, and there are startups everywhere, and that's now an accepted thing. And believe it or not, going back to the beginning, it was actually slightly unconventional that Mahalo was able to start in Los Angeles or in Santa Monica and not be a valley-based company. We almost didn't get funded because of it. And we were, yeah, we were already in operation for like a year before you started hearing Silicon Beach come up. Like we were already longtime in Santa Monica before that was a day. And now you've got, not only do you have Tinder and Snap and everybody else and their brother in L.A.

Now, you've got some people in the valley thinking, Ryan from Product Hunt just moved to L.A. You've got a lot of the notable people from the valley thinking to move elsewhere. San Francisco is definitely, and San Francisco not being the destination is definitely a sea change. It was the destination. It was incredible to come here. And now it's become, I think, just hard. Booking the guest, Jackie, and just thinking about, we've been together five years working on this. So you've been here for the second half of the program's existence.

Five and a half. Five and a half. How have, in your perception, and be as candid as you can, how have I changed as a person and or interviewer in your mind? What's improved? What maybe hasn't improved if you were going to rate me as my producer? I think that you are a much better listener than previously. I think you're always good. But in terms of really listening, like being kinder.

Kinder. Yeah. I don't know if you like that or not. Yeah. I see that evolution in you. Yeah. You're more compassionate. I am more compassionate.

I think you have kids. That's what happened. Yeah, I feel like, you know, because you've had the twins. I mean, when I first started, you had London, but you didn't have the twins yet. Right. Like, you just get, like, a little softer. A little softer, yeah. I actually care very deeply about the guest's experience.

I also feel like you've really had a good impact on me. You've been taking the work even more seriously. You can see we started. It was kind of us just goofing off. And then over time, got a little more serious, bigger audience. And now I actually take the work very seriously. And you're bringing your four ammys here and really leveling up the show has made me want to off my game. So I thank you for that in your efforts.

I was going to tell I was going to ask Brian to confirm the fact that London, I think for the people who know you most intimately, it's been interesting to see how London specifically was an interesting turning point. And I'll let Brian riff on that. But the other bit was when the show started, you were more. of an entrepreneur than an investor and now you're more of an investor than an entrepreneur and that's also been an interesting perceptual shift that has happened yeah i was thinking about building things and myself and now i'm always thinking about other people what they're building and how i can weasel my way onto the cap table brian what's your take yeah no um man i was gonna say something completely different and then she got all nice about this feels like you've been here more than five years by the way

It feels like you've been here forever. I can't imagine this without you. So I'm glad you're here. I like Tyler's insight. I like the fact that you were outsider, that you were upstart, that you were entrepreneur, that you were scrappy, and maybe more confrontational in those days. And your approach to things would be more of a confrontational kind of I have to put myself on the map as a podcaster.

Whereas today, you're an OG at this. I mean, it's funny when we did the blog thing, we were outsiders. The bloggers hated. us. They just hated us. And then when you look back, they're like, oh, we were like pioneers in this thing. So now, same thing with the podcast. You look back and I'm like, you were a bit of an upstart. Now you're a pioneer. You're an OG. You've been around for a long time. And you also have shifted to more of that sort of mentorship mode. And I think it shows up in your interviews. Yeah. I try to look at them as, can I make this? I wasn't actually thinking at all for the first

a couple of hundred. I was just like, hey, what's going on, everybody? Let's, I don't know. What do you do? And I try now to think about every interview and say to myself, can I make this the best interview that subject has ever done? Can this be when they go and they look back and their kids want to see an interview with them? And they have a choice between sending a CNBC clip or some other podcast they were on.

They send the clip of the one there with me and say, this was the best interview. It's a good way to look at it. If you look at your conferences, so look at the launch scale when I would host the second stage, I felt a tremendous amount of pressure to make sure, one, the sponsor, you know, loved what we did in their room versus your room. And then also every single guest. So to me, I had to be thinking, sometimes I was actually giving a talk after somebody, which is screwy. But I had to think about if nobody asks them a question, I need to ask them a question that makes them feel when they get in that car and leave that it wasn't a waste of their time to come here. That they got value out of this.

That something happened. The guest experience. Exactly. The guest experience. So if you think of that from the conferences, it's the same thing for the show. Good way to approach it. I had a very meaningful moment on the show. And John Carreau, who is the Pulitzer Prize-winning Wall Street Journal author, I had seen that he had done this story on Theranos, and I had heard from my friends that Theranos wouldn't let them do diligence on their product. So when I heard him, after the first time he ever, wrote the story. I had him on remote. And when I had him on remote, I just had him tell the story, and I never had remote gas because I liked him in the room. But then when he came back on his book

tour, he did publicly say that this was his favorite interview that he did, submission accomplished to my goal of being the best interview that the person did. But he told me during the interview that the first time I had him on after the first Theranos story, as opposed to when the book came out two or three years later, during the first interview, one of the people who gave him a ton of information, had seen his interview with me, said, I saw you on there. You seem like a cool guy and you seem trustworthy. So then he slid into his DMs. And he said that the podcast had helped him break the story wide open through the function of one of the people who saw the first one. And so he started thinking of the power of the podcast to be contributing. But anyway,

here is John Carriou, the bad blood author. I think the fraud where it's much more egregious is the cavalier attitude toward patients and, you know, putting patients in harm's way and gambling with people's lives. They had to restate all of those blood tests, thousands of them. So they voided or corrected almost a million blood test results. What? And my sources tell me the last lab director they had at the company who just left the company a few weeks ago was advocating, voiding, or correcting all the blood test results.

Thereinos ever returned to patients and doctors because the quality control in the lab was so terrible. If he had prevailed upon Elizabeth to do that, that would have been 8 million voided or corrected blood tests. Yeah. It's an incredible moment. And to have him on twice was just amazing. Now they're making a movie. And now they're making a movie about it. Jennifer Lawrence is going to play Elizabeth Holmes in it.

Which is perfect casting because she can play crazy. I mean, she's great. I feel like Elizabeth Holmes looks exactly like Amy Adams. Amy Adams. Like don't you feel like Amy Adams in a blonde wig doing that deep voice would have been perfect? Amy Adams would be great. Here's the thing. I think Jennifer Lawrence has a level of mania manicness and Amy Annan's more controlled.

I just have to hear the voice. It's whoever can get that, well, you take the capsule and then you put in the blood and then you test the blood. It's like somewhere between Kermit the Frog and. And I was going to go as Elizabeth Holmes for Halloween. I went as Penny was. Black Turtle Neck. And I literally went and I got, my wife was going to do my makeup and then I just had this moment. I was like, this photo is going to get out.

Even though I'm going to a party where there's no cameras. And then I just said to Nick, I think we should do an episode where I play Elizabeth Holmes and I interview myself. But I play Elizabeth Holmes and do that as a joke. And I would totally have done that in the first 100 episodes. But I feel like the show is, I'm a little bit more serious about it now. Right. That's the goofy early days. Giffy early days. All right.

So we have the worst, most uninspired cake ever. Here it is. The Twist 100 cake. It literally says... One thousand. Twist 1,000. It's not the 100 episodes of 1,000. And literally they did the least amount of work possible, but there's a best ice cream you could ever have.

In honor of the early days of this podcast. In honor of the absolutely horrific graphics we had. But in all sincerity, it is the great joy of my life to do this podcast and to be along on the journey with y'all. Thank you to everybody who's contributed over the years, the sponsors and partners who made it all possible, the producers and the directors who suffered through my voice and editing for the last decade. Sorry about that. To the tireless producers who begged people to come on the show who maybe didn't like me or the show and came on anyway and then fell in love with it. And to my friends who put a ton of effort into it when there was really no reason to do it other than we were bored and thought it might be.

be an interesting thing to do on a Monday afternoon. Thank you, Tyler Juan. Brian and Jackie for coming on the pod. Thank you to Brandis and Gina, who did a great job in the early days, and everybody else who's contributed along the way. We couldn't have done without you. And to you, the audience, who tune in every week and who stop me on the street sometimes and just tell me their favorite episode, it really does mean the world to me to know that you're listening. and that in some small way the show might inspire you to go out and start a company or to learn something and to the guests who've come on, thank you for your time, and we'll see you all in the next thousand episodes.

Bye-bye.