Welcome Welcome everybody. It's you dead cat episode we are extremely excited about. We have Jason Calacanis, the all in host This Week in Startups angel investor are famous for investing in Uber. I've been ahead of this episode, Katie and I went on Jason's show This Week in Startups in 2016. And I was like, you weren't Jason, you were an extremely early supporter of me as a, as a young tech reporter and cub reporter at the information and Bloomberg I remember exactly and in the the episode with Katie and I were sort of, you know, discussing Facebook's content moderation. So it's amazing, paradoxically, just like how much some of the like, same themes keep coming up. But thank you so much for coming on the show.
Thanks for having me.
Yeah, I mean, there's so much to talk about. Is there anything in
the news? Bob Iger? Yeah. That's a really big one. Oh, this week. FTX. Theron house.
I mean, how do you spell your time these days? I think that's a starting point.
So I Angel invest in, people don't really actually understand the pace at which the investment is going right now I put about 60 million to work a year in about 75 to 100 investments. I have 22 people on the podcasting and investment team that's launched this week in startups all in. So it's a pretty at scale seed fund, but I'm a what's called a solo GP. And we've invested in 350 companies to date. And we have the largest syndicate in the world. It's like an angel investing syndicate called the syndicate.com. So 11,000 members, so when I invest in a company, maybe about half the time, the founder wants additional investment, so we will syndicate it. And then I do podcasting in the mornings with Mollywood for This Week in Startups, and then I have started the company inside.com, a newsletter and social news site that I've been working on does a couple of million a year in revenue. And so that gives me like a little media itch to scratch. And then once in a while I work on some special projects,
and all in its PSA. 21st most popular podcast. It was 14 last week, 14 Last week, I was looking at, you know, one of the lists just now on Apple, but I'm sure there are 50 different it's crazy, to be honest, like, I mean, you're getting recognized on the street at this point now, right? I mean,
I mean, if I was in a Tech City, people might recognize me, you know, like, if I'm in Austin, or New York would have been they would have been anyway, right, because of This Week in Startups. But it would be like once Now, the thing about all in is the tech industry is not that popular. So you wouldn't get to that level without having some other constituents. So finance colleges, like I was skiing with my daughters, and I asked somebody if they were done with their table, and she was like, Oh, my God, Jake. I was like, I'm sorry. Do we know each other? And you know, she said, No, I'm a dentist. I said, Oh, you know, she's like, I listened to your pod every weekend twice. I'm like, Why don't you listen to her twice. And she said, You know, I'm trying to learn and to kind of replace, like, Meet the Press. For me, it's like my Sunday morning show, which paradoxically, is kind of how I impart what I based the format on. Well, that's interesting.
I thought you're gonna say, Jason that I'm a dentist, and we play all in during, you know, over the Speaker's office, brushing your teeth, and you'd forgotten. Yeah, it's like, well, people are getting a feeling they're like, is that Shama?
Exactly? It has crossed over in a way that is completely bizarre college kids big time, like a lot of them, listen to it.
And it's saturated.
make sense to me? Colleges, I was there. Just a lot of colleges have venture capital clubs now and venture investing clubs. So it makes total sense.
Yeah. I mean, and people want to hear us talk about things. We're not experts on like politics and COVID and other topics, which
is that's why people listen to us, actually, to hear us talk about.
It's a little weird, though. Like, people are like, How dare you talk about COVID? And I'm like, aren't you talking about COVID with your friends? And they're like, Yeah, but I don't have a top 100 podcasts that I'm like, Well, you could also listen to the pod, and then realize we're not experts, and then go do your own research. And like know, your experts, like I just told you, we're not experts. And you told me you'd understand we're not experts. So why is it so tweaking that, you know, non experts are having a conversation about a random topic.
So this is like, sort of, but this leads to a tech question that I think you're equipped, well equipped to address, which is how technology has really broken down the barrier between experts and non experts, right, because everybody has equal access to a public platform, or near equal access to a public platform. So what do you you know, walk me through how you see that sort of as the pros and cons As of that destruction of the barrier between expertise and non expert,
yeah, you know, we probably all lived in a bit of a bubble where we just thought, well, we can trust anybody who's an expert, right? Well, I just trust my doctor, and they're gonna give me the right information. And then people learned over time like, well, maybe my doctor doesn't have all the answers. Maybe there's some alternative medicine or maybe yoga practice would help me with my back pain. Maybe I don't need to just do drugs and, you know, take Vicodin or something, right. So people, I think, over the last couple of decades, probably, like you're saying, Katie, because of the internet, have had access to the same information as their doctor. So you're sitting in your doctor, doctor's office doctor says, oh, you should take Vicodin for your back pain. And you look it up and you find an article. It's like, well, this is addictive. You say, Well, isn't it addictive? And doctors like Yeah, but I don't have anything else for you. And then somebody else says, oh, you know, I did hot yoga, it healed my back or I lost 10 pounds. So I think we've started to maybe get back to where we should have always been, which is, the search for truth is elusive. And you should take a multi pronged approach to figuring out what the truth is and what the truth is for you. So your truth might be different than mine. And I'm not a conspiracy theorist here. But, you know, sometimes yesterday's conspiracy theories are tomorrow's Pulitzer Prizes, right? We've all seen this happen. What's an example of that? You
think about, like, Theranos or something?
Yeah, I mean, listen, we all have been journalist for a long time, and we put Theranos on the cover of magazines. I didn't, but I'm sure all the publications worked for a headline in her New York Times. Yeah, I'm sure has put them put her on the cover
with Marc Andreessen.
So didn't Marc Andreessen his wife, right.
ripped it against flame, but Marc Andreessen, Laura wrote it, but yes,
we did. We did publish it. We did
have to take ownership of it. Right. Yeah. So anyway, so there are notes. This one I think, actually with COVID. Under if you read pro publica is piece with Vanity Fair on the Wuhan lab, the lab theory, you were kicked off. Yeah, you wouldn't be kicked off of social media or your podcast would be labeled. And you'd be kicked off Spotify. If you even acknowledged that 18 months ago, and pro publica is going to win, you know, a journalism awards for it if it turns out to be true. And maybe it's not. Maybe the CCP is denying it now. So here we go. Our jobs journal. Wait, yeah, yeah. So you know, when I was a journalist, and I started in the 90s, one of the first journalists I met at the New York Times was a cub reporter named Jason Blair. And he called me on the phone. He said, Oh, you have silicon Our reporter, I'm going my new beat is Silicon Alley, can we meet and I met with him and I was like, This guy's a dope, like, really is dumb. I was awestruck by how stupid he was. And he's like, let me know, like, whatever information you have, so I can write a story, and I'll get you good press. And I'm like, I started, you know, I went to some of the other New York I saw handsaws like, Who is this person? And you know, I kind of eye rolls or whatever. And everybody makes mistakes.
That whole scandal led to the downfall of the then editor of the New York Times, it was actually quite a quite a messy, devastating episode. Champion. Yes. But your your point, Jason, is that you could kind of tell early on meeting this guy that something was amiss with him. And he seemed, even for a journalist fairly dumb.
He, yeah, it just didn't, he didn't seem like the level of a New York Times journalist. And I was listening, I had started my own publication, I wasn't getting published by The New York Times, I just was a hack who started a newsletter called Silicon Alley Reporter, which became a 300 page color glossy. But you know, I was looking at it. And we were really trained hard to like, take our time, make sure we had three sources, you know, we didn't back in those days, you didn't want to have off the record sources, that wasn't kind of allowed. If you inserted any kind of opinion, you would get admonished. And you know, you had time to file and probably, I don't know, one out of three stories was killed, because it wasn't good enough. Now you fast forward because of blogging, which I was part of, and the pace and the competition and the buzz feeds of the world and business insiders of the world. You know, the pace and the filing in which people have to do stuff and the lack of fact checking. I'm talking about like a dedicated fact checking department. All of that is gone with the exception of a small number of publications. And so there's going to be more mistakes. People are filing faster people doing this process journalism thing, which is really lame, and they're relying on unnamed sources. So we think there's
a social media play into that, you know, like, walk us through the role that social media has played there. Yeah.
What do you think is played into it? Good.
I mean, I don't know. I mean, because you had mentioned social media, and you mentioned Business Insider. And so do you think that those are the culprits?
The culprits of what
of this sort of like sped up journalism cycle?
It's definitely competition, right? People are forced to file faster and you're competing, because it's everything's instantly published. It's not like you can wait for the next day and print. So yeah, I mean, the pace has increased, the resources have diminished So it's, there's gonna be we learn when
stuff is wrong, much faster like it's harder to imagine sort of as Stephen glass Jayson Blair, sustaining for as long
as you're on the other side of this, if you're on the other side of it and your subjects of, you know, the press today, having been on both sides, you become acutely aware of the mistakes and the mistakes hit the subjects harder, faster. And so, you know, you look at the New York Times away piece, you know, they demolished that founder felt very biased to me. And so, you know, I think that's where this standoff is happening between the tech industry and certain industries. And the press is,
there's so many went, first of all, where's your allegiance on you? In our district in 2016?
Everyone have their own truth? I don't know how that's a no, no,
no. But like, do you see yourself as a journalist? I mean, you talked about doing random acts of journalism back in 2016. Obviously, at one point, you really saw yourself as a journalist, was a
journalist. But your writers right. Now, I would say most people would say I'm a commentator, but probably an informed one. I mean, and I think that's what's happened is you're having, because of this contentiousness going back and forth, and us my allegiance, my allegiance is only to the truth and fairness and kindness to be honest,
I was No, I
mean, I'm dead serious about that. Like, what if I make a mistake? When I'm doing commentary on a subject? I think deeply about like, Oh, what did I get wrong here? And I try to make up for it. Right? Absolutely. whenever something comes up like Sam banc been freed now, I'm like, a legend. A legend. Let's make sure he's a legend on the pod. And trying to you know, just give a slight benefit of the doubt until the information was that Sure.
I was watching all in. I mean, you guys use data from like an anonymous source that x had on on some companies performance? I'm trying to remember what the
anonymous or is or do we have
decided to make by Yeah, right. You guys get to frame it is inside information? Well, I mean, if you're on the bigger gap again, from No, but you guys can't like disclose. I don't think it was a firsthand
on the I think what you're getting at here is you guys what's happened in the standoff? Right? She had this standoff that's occurred, there's equal, there's both sides could do better, right. And I would say the tech press is far too negative. And now they've put the tech leaders who, you know, listen, we have much more influence now in tech than we ever did. It's impacting everything. And I'm not saying tech companies don't make mistakes far from it. Trust me, I'm an investor. And these companies have to do some of the cleanup work. But now what's happening is people going direct, because they're like, well, we can go direct, right? We don't need the press. So people ask us to do you know, many folks have asked us to profile all in and the boys just decided, no, we'll just keep working on the podcast every week. And we're bigger than any. The towel live tech public. The top five tech podcast isn't as big as all in now. So why would we even need to? I'm only coming on this podcast? Because I'm friends with you. Yeah. Well, no. I mean, you came on my podcast. You know, I obviously appreciate Tom and Katie's careers,
because you're gonna be fun and interesting, not because you're like, This is gonna get me something.
No, it's not gonna get me anything. Yeah. So it's more like it's a fun conversation, actually. Yeah. So I think that's what's gonna be the trend. Since I see you're trying to get in here on the discussion. And Eric, is having a hard time moderating. Tom, I see you want to jump in.
This is why Jason, you're the world's best moderator. Because even when you're not the moderator, exactly how many tips
but I think, Tom, what do you think about sources going direct now? Well, many sources just deciding I'll just go direct, I'll route around. And I won't talk to the press? Well,
you know, I guess this gets into the definition of what the press is. And I think you actually sit in a very interesting place, because you have a journalistic background, right, you've spent a lot of your career building journalistic institutions that adhere to what many people would consider standard journalistic practices. So you're, you're a conveyor of well sourced truth as your reporters, and you've tried to do it. And what I find so interesting about all in which I listened to fairly regularly, and I do think it's a really entertaining podcast, is that you and specifically, David Sachs, do spend a lot of your time talking about this transition away from legacy media to going direct. And you've refused to, you know, participate in any of the profiles written about you, because you see no upside to it, you sort of see it maybe partly as they're being antagonistic to you. Yeah, it'll be a hit piece.
It always is. Right? It's
gonna be a hit piece. You're like, why participate in it, though, right at any way? Why should we even bother talking to the reporter over it? And yet, it seems to me and correct me if I'm wrong here that you guys spend a lot of your time. We believe, very strongly that we as reporters are out to get the tech companies that we want to take these companies down because, at least in the case of you know, you're being a direct media company, it's a competitor to us, that we view you as a threat and so it's in our best interest to sort of position you as a bad thing, because that I don't know helps our business model or That's actually not the reason. Okay. Explain. Explain to me the reason.
No, I mean, we make $0 from all in. Famously, there's no ads, right? So it's not like we look at it as we're competing against the press. I think the press has been so unfair for so long, that there's a level of frustration in dealing with them in the tech industry. And so most people in tech, they won't say it publicly, are just like, why bother? If the press is contacting you, it's a negative story. And if you were to go through the New York Times, and just pull up the last 20 stories, and there has been some back channel of like, hey, the New York Times decided to go negative X number of years ago, on tack and hold truth to power. But you know, this whole, we experience from our side with our portfolio companies. If the press calls, what people say is do not respond. It's going to be negative, and just write your own blog post to your own blog, get the message out directly. The press is only trying to do something negative to get clicks. You you. That's a dialogue here in Santa Clara Valley right
now. Is there a recognition though, that the press isn't just finding these things? It is actually employees within the companies who are calling us with the information like when I mean, I understand what you're saying here? So is there a second part of the conversation that's like, Don't comment, don't work with them. At the same time, you might want to try to figure out what's happening inside your culture, because you pay these people a lot of money, they get a lot of perks. And yet, they're still doing the nuclear option of reaching out to somebody they've never spoken with. It's not like the people who are calling me were my best friends. I've never met any of them. They're still reaching out to people who they've literally never met before, to go to them with this information. So you might also want to get your house in order, there might be an actual legitimate prof course. Yeah, no. Or is it just like the presses? So me? Not because we're these genius reporters all the time, people are coming to us.
Of course, this each situation is different. There could be people leaking information, because there's something horrible that's occurred, like Thera knows, right. And so in that case, it's just, et cetera. And then there are cases where, like, with the New York Times profile of away, I'm not an investor, I don't know the founder, where they're like, Oh, the founder, told everybody in Slack work hard, because this is our busiest season. And then the New York Times makes this bashing story about the away founder, you know, that she gave like a spree to curb speech, like work harder, everybody this is it. And then a bunch of, you know, snowflake employees complain about I can't say, but you're on time, like,
that was an example of employees coming to the times I don't think a way was
a company, it doesn't matter. Your time on the radar of
the time. So it's like, if that is the case that the employees are feeling that way. In addition to being you can be mad at the times, and but how
is it the most important, how was that the important story? And
I'm saying like in where you're having these internal conversations, you can say like, the times might be being unreasonable on this story. At the same time, what is going on that more than one, multiple employees would be so pissed at what you're saying? It's not completely harmless speech, that they would even take that step? It's not like those employees knew that reporter,
Katie, employees today more entitled than they were 20 years ago? Yes or no?
Well, that I don't know. It depends on the industry.
People are more entitled 20 years ago, they
people who work at Starbucks, I would say no people who work in the industry, is that like people
at Starbucks are no more entitled. I don't think so. I've been to a Starbucks.
But you know what I mean? Like, I think that if you if you're looking realistically at work, I don't think you can say that all employees are more entitled. And I don't think you can say all I'm saying
I'd say all Americans are more entitled, How about that. But put that aside, don't here's why I
say that. There's a huge gap. And I think there are a lot of people who don't have a lot of money or opportunity. And I've
never had a lower unemployment is at an all time low, but that there's a quality of life alignment
and low wages. And I sure there are a lot of people who are working multiple part time jobs. And I don't know that I would say that they're all in titled, especially since I don't really walk in there stress or no stress, hammered
Uber for years over driver pay. More and more drive. Hold on, let me finish Katie, driver after driver after driver has now you know, embraced Uber and they're making $36 an hour. It's a perfect example of like the press were all over this new innovative product that it turns out, people voted with their dollars. People voted with their time people want the flat.
I mean, like I don't have any skin in the game ever. And I use Uber I have a lot. I will say a lot. I just had a conversation with a driver. I had to wait 14 minutes for an Uber the other day and I got and I was like, why was the waste so long? And he said, Well, we have all decided we don't want to drive as much because Uber is taking a bigger cut of our salary. And he was sort of showing me what we made. So I was very curious to see what he was going to make on my ride, which was for me $18 He didn't make seemingly that much. I don't know but it's funny that you say he's making $36 an hour.
That's the average as total, Eros said in the last quarter, so you will find employees who have a while it was
totally random. I'm not asking. That's Eric and Tom's John.
I don't want to hold on.
Before we get there, I want to just save one point. Finally on this, the issue is not any one of these individual stories. The issue is that nine out of 10 stories in the New York Times is incredibly negative about tech. Now, when I was coming up, nine out of 10, we're probably pause, you know, pretty positive, positive, and it probably would be, there are positive stories to tell. And there is not balanced right now. Whether it's the tech industries follow up, because things went off the rails at times or wealth inequality, it feels unfair,
I mean, literally, talking in 2016, just to sort of, I mean, we, you made the point, first of all that, like when people get escape velocity, they're only going to speak with people who they're certain are going to use kid gloves. Like there was acknowledgement at the time, sure that the people were shopping for safe places to go, access journalism, you were talking about code, and we were all being pretty gentle. And, you know, we all like Kara. But there was a reality that, like, people knew that they, you know, she, I think you said, They'll ask the hard question, but they won't ask the hard follow up question. You know, there was sort of already then in 2016, there was sort of a sense that, you know, yeah, Tech was very savvy about avoiding sort of difficult questions. And I guess, I think what Katie is getting at is what happened is, the workers got very negative, right? I mean, the, the sort of gap between the management and workers spread due
to the reason we couldn't write a negative story before that was because the workers wouldn't talk.
I mean, or that, that your that your assumption, it could also be that they felt great about the companies they worked at, you know, Google employee 15 years ago, have anything to complain about? Probably not. I honestly think it's gender. I think it's like, a big part of this is generational. Like, I think people just look at work differently today than they did. And when I started in the tech industry, you were signing up for 6070 hour weeks, you were part of like this pirate samurai like, you know, off the grid, kind of, you know, revolutionary squad, and now tech so big, that it's everybody. And so you're gonna have people who maybe don't want to work as hard or they're not necessarily consider themselves pirates or barbarians, or whatever, Steve Jobs and Bill Gates sort of framed it as during the era I came up and and that's fine. I actually don't have a problem with people who want to work nine to five jobs in tech. There's room for that. And there's room for people who want to work 60 hours a week, I have it inside my own companies, you know, some people are work to live and some people live to work. We have a difference as far as I'm concerned. If I'm being honest, yeah. I but I
think we're in agreement here that like a lot of this was a change in attitudes toward work. And there was a time when Yes, people were so happy working at Google, you could call every single employee at the company, you would never get anybody to tell you anything other than positive stuff. And so the stories were positive.
Yeah. But then they tripled their salaries, and gave them more benefits and unlimited vacation. So if there's any reason to be mad at your employer, you know,
well, sure. But that's where it's the entitlement definitely came in, I'm sure.
Do you feel, Tom, that the tech industry went through a period of extreme entitlement?
Oh, absolutely. And I think it's, you know, it's coming home to roost for a lot of these companies right now, because you saw Google, as the prime example of this, you know, setting out these unbelievable perks for all their employees. And as a realizing, as they're trying to get people to come back into the office and find, you know, the same sort of Shawanda work that they may have had a couple of years ago that they don't feel it, you know, they've gotten used to a certain standard of, you know, snacks in the break room, and, you know, days off and resting investing, and all this stuff that came with being, you know, a highly desired worker, that they can't recapture for a lot of the same reasons. But, you know, when I, when I looked at, maybe we can zoom this back, or push this back towards all in, it seems like, there's a politicization of a lot of these companies as well. And I've seen a lot of the communication teams that run these companies, a lot of them came from the politics world. And I think that the coverage of these companies, and Katie can speak to this probably better than anyone here mirrors a lot of the way political operatives communicate, and the reporters themselves kind of view themselves as almost political reporters. And I don't know how often I see, politicians say, oh, man, the coverage of Congress is too negative these days. You know, God, you guys are only writing about the scandals. Why don't you talk about all the good bills that we do? And it's like, Well, okay, sure, first of all, pass a bill. But also, you know, there's just a reality of that with the greater power and almost political valence that these companies have, there's going to need for the press to write about these things in an almost political way. And that itself is going to just skewed more towards the negative. I mean, don't you view some of this is almost a success of the industry that you've been a part of for so long that because these companies are so powerful, they get covered in a way where you question you know, the roots of that Power and the people at the top of these companies 100%
Yeah, I mean, this really all goes back to one company and that that's Facebook, really Zuckerberg, you know, he had a pretty a moral compass, you know, in terms of how to run the business. And, you know, it created massive second and third order effects for society. And I think that was like the turning point, as far as I'm concerned of when like the press, and tech kind of split up and became like, pretty hostile and cantankerous. I think it was that company, and I saw it all kind of go downhill after that.
And you're pretty critical of suck, right?
The worst actor in tech, okay. But other than that, we don't have much of an opinion. No, I mean, put it I'll put it this way. You know, I'm like old school, like, people create products and services. And, you know, there's some love or joy with the Creator, like, say, Evan Spiegel and then to blatantly rip off Evan Spiegel the way he did, over and over and over again, amongst the digerati. You know, the creators of companies, it was just like, is this really where the industry is going? Like Evans, Evan Williams, or Jack would not do that. Kevin Systrom with Instagram would never do that. He did it under duress, obviously, when Zach put a gun to his head and said, you know, copy stories and put it in Instagram. And so it just got rid of kind of this congenial. Like, yeah, sure, we might take inspiration from what you're doing. But we're gonna make it our own. Right. So okay, sure. You know, every phone needs to have a calculator and a flashlight. And you know, there's some basic stuff, but we're not going to just wholesale rip everybody off. And I think that was like, why he was so hated in the industry is that he was just this copying machine. And it was almost like the Borg came into the industry and kind of made it just not fun. Yeah. And it was his relentlessness. If you don't, if you don't remember, he did like a poke app. And then he to do like ephemeral messaging. And he did like four or five swings at the bat, to try to like, take on Snapchat. Oh, I
remember it really? Well, as a matter of fact, I remember the first time they redesigned messenger and it looked exactly like Snapchat. And I took a screenshot of it. This was at f8. And I sent it to Evan, that snap, and I was like, Does this look familiar to you? And I think he just responded with like a rolly eyes. Sigh.
It sounds like a sigh. You know, it's kind of rough when you know, but anyway, putting it aside, you know, I think there's actually a pretty cool path forward. What is, yeah, it's pretty actually straight forward. It's actually happening right now, which is, if the tech industry and journalists who work together can be all be self aware, and listen to each other a little bit, the criticism, you know, that tech will have of the presses, like maybe for every two or three stories where you slam us can, can we get a profile of something new and interesting, that's, you know, maybe not trying to destroy the founder and get them fired, you know, whether they deserve it or not, we can debate but the percentage of coverage the blend feels unfair. And it depends on the publication, of course, but with a company like the New York Times, like they people have just given up talking to
you, we're pretty cynical of like crypto, right. I mean, we have the worst times, yes, sort of bullish and FTPS. And look silly, you know, it feels like when they, we have been in a period where there hasn't been some great new platform, there isn't like, there are a lot of great SAS companies, which I write about all the time, right. But there are these sort of singular platform companies like a Google or an apple that you can point to right now. Or do are there companies you think, really deserve?
Yeah, they're not going to get as many clicks. And what we have to also recognize as journalists is that our industry has now moved into compensation is tied to your follower count, your ability to drive clicks, and your persona. And that didn't exist as much when I was coming up, there was an occasional Walt Mossberg or columnist, etc. You know, people who are critics who had outsized compensation and deals. But now you know, when I went to sell my first book, and doing the second one, now, your podcasts rank and your follower count drive, your advance, or the number of emails, your job in journalism, if you have a quarter million followers or 2500, your compensation will be decidedly different. So there's a, you know, a little bit of a perverse incentive now to be full contact to get those clicks. Here's my
question for you, Jason. Because I think you've outlined a very interesting dynamic that's happened within journalism. And I don't disagree with you to an extent we've seen this move towards sub sex, or generally the
like, how do I relinquish being a journalist so I can just get this feed direct?
Casey, Casey maniac, The New York Times versus stuff, the substack, where he was on
the verge, but I hear what you're saying. Rather, here's my question, just because I think what I don't quite understand in this argument, which is an interesting one, which is that your argument is that the more you focus on your brand, the more it subverts the quality of journalism, right and you need to get the clicks and you're more inclined to read negative stories. Yeah, it's
not 100% Carl, okay.
But do you at all because you're a personality, I mean, I've known about you on the scene for a long time. You're a journalist, you're you know, you
have a million journalists anymore. I'm clearly a commentator, but what's previous? Right. And
but you also were a known quantity. I just feel like I've known your name, you know, within the journalism media world for a long time. Do you not at all feel that you were part of that trend that you further that at all that you Oh, I
further did for sure. I mean, just hiring Peter Rojas to be our partner at weblog zinc and doing gadget was part of that. Yeah. I mean, I'm not saying that. The trend is the trend, Tom, the question is, how does it impact coverage? And how does it impact reporter behavior? How does it impact a journalist behavior in this age? I think what journalists are going to learn over time is they need to be a brand independent of like Taylor Lorenz might be, you know, the canonical example here. You know, if your brand has to get bigger than the publication, and she's about the brand, that's bigger
objections to journalism, I
guess, how sort of get that brand, how you get that brand? How you can get that flywheel going, I think is the issue. I think, actually, the criticism of the Walt era or the Kara Swisher era. So if we're gonna, like, compare the criticisms, errors, and I'm not saying this is my criticism, this is the criticism inside of journalism, and inside of the CEO, sort of suite is back then it was access. So if you had access to Steve Jobs, Kara Swisher and Walt made at least a million or $2 million each during those conferences. Right. So then you have to ask yourself, Okay, would they write the most critical piece or not, they would like to think they would. And then access could be removed. And so and Steve Jobs having done this with directly with Steve Jobs and Engadget, he pulled our access. That was a major financial hit, when he pulled our access to going to the Steve Jobs, keynotes for engagement. That could have been a death blow. And I had to negotiate directly with Steve Jobs to get Engadget back inside the, you know, the Apple keynotes. And so you know, when you're the publisher of the CEO, you can see this up close and personal. I don't think that people had to compromise their coverage back then. But it certainly had to be on the minds of the publishers and the CEOs of coverage. And now it's probably too negative. And it's probably too negative, because that also drives views. I do think paid content does change this a bit. And I think that's part of the endgame here, subjects go direct. The top journalists have paid publications, and the search for truth gets even better for consumers.
But do you think the truth is emerging through direct, like, there's so many different types of articles in journalism, but like, it's very hard, like the FTX scandal, you guys are fairly negative on the media and sort of positive about Twitter accounts, you know, surfacing information, but like, coin desk, you know, really sort of moved the needle in terms of saying that there was something amiss at Alameda research. And I feel like a lot of the narrative through lines, how people understand the stories, even the biology, David Sachs, all these people are extremely negative about the media, tweet out links to stories all the time, I guess, it can just it can be frustrating that people are so negative about the media and then so clearly rely on the media for their worldview, or to know what's happening. Because everything's connected person, the world can't, can't piece everything together themselves without some some reporting.
I think independent journalists and voices is good for journalism. And I think subjects going direct is good for journalism, it gives people more access, and more direct access, I think that's actually a good thing. It's gonna be a little more messy, like you don't just open the New York Times and trust everything and move on with your day, you don't just turn on CNN and accept everything as gospel. Nor should you trust any CEO or powerful person with their own podcast, directly communicating, they all are going to spin it in some direction. But it's like Kurosawa, and Russia, man, there's like your version of the truth. There's mine. And there's the actual truth. There's many versions of truly important.
You were touching on before, which I thought made a lot of sense, like the access journalism piece of it, basically, you know, they wanted you know, like a Steve Jobs. So wanted your audience. So they cared about you being there. And there was sort of a give and take where they could take away access, but you had some leverage, because they needed audience now with go direct, the media companies have less and less leverage. Yep. So they don't have any way. And fitting into an earlier point where, you know, if you're a top person, you want to go somewhere where you know, you're gonna get sort of positive coverage. What incentive does somebody have to actually face hard questions besides you just being sort of a masochist to engage with people? But like most people, you know, like, they have no incentive, they have their own audiences, so they have no reason to face. Yeah, it's hard questioning. What's the solution to that? Do you think that's
the last time anybody here asked a hard question to the CEO? tick tock recently I mean, has anybody been able to ask a hard question to Zuckerberg? You know, he went on Joe Rogan, right? He's going on Lex Friedman. Right? Gonna go for the what shouldn't
people be more upset about that? Like, I feel like there isn't much. You're Not You don't seem very upset that people aren't getting.
I honestly think it's a mess right now. And then sometimes things have to collapse in order for something new to be built. I think that's part of the process is that we're going through, I think this is like the messy middle. And there's something new coming out the other side, the three of you, or the four of us, you're talking is part of that process. I think it's the messy, high of the storm right now.
Putting aside my, you know, now that I can have opinions and putting aside my media concerns, I guess, I do worry that as a fan of the show that you guys don't represent the Democratic Party and sort of left wing point. I'm the only one. Yeah. And you're I mean, donates. You agreed with them that like balancing the budget was your top issue on the most recent episode? I do. Yeah. But I've always thought that we can vote for a Democrat or Biden, and then I
always chin. I always vote for the best candidates. I've voted Republican in my
life shameless partisan, like the guy is. I mean, he'll know. I just I just feel like there's an Shamov is clearly someone who likes to be connected to the Democratic Party, but it doesn't. He doesn't come off as like a true believer.
I mean, I think what it is, is the the Democratic Party is so far left that moderates don't feel at home in the party. And I think that the
Democrats just did well in the midterms, after Sachs was saying that would never happen. Sure. And you guys, you guys, so
I said rain? Pretty. I said it was about I said it would be I predicted it would be about Roe v. Wade, and I torture tax about it. If you remember,
I felt like he got off pretty fast from being sort of the like, red wave proponent here.
I don't know. He was pretty honest that he got it wrong. And he that the Republican Party needs to learn from it. But they won't. They'll never kick Trump out. It's very bizarre. I'm like, if Why don't you just say you'll never vote for Trump? And it's like, well, because he might win the primary. I think he's gonna win the primary. I'll be honest, I wouldn't count Trump out.
How have you surveyed the audience? Like, I mean, it feels I guess if the Reddit. I don't know if you read the Reddit for the island, but I do not.
Yeah, are you? By the way? I'm just laughing on the political angle, because both you and Sachs are pretty outspoken in local politics and the Bay Area and San Francisco. Sure. Is that a thing you're continuing to be involved with? I mean, obviously, you guys were dead set on getting cheese removed as da but are you continuing to involve yourself and in local politics here
have the Donate name, Mayor, Jason dacotah. So I have the domain. And I've had, I mean, I had $2 million offered to me to run for mayor like in campaign donations from David Sachs. No. But but I'm sure he would in a heartbeat. No, what I did in that case was I just did a GoFundMe page. And I wasn't involved in the recall. I just hired a local journalist to cover strictly the cases and the human side. And I only put $500 into what happened to that, by the way, I remember seeing that Gotham by the bay, she wrote a series of articles and those articles were picked up by national news that didn't have the time to, you know, spend 3040 hours chasing down people who had been the victims of crimes and the prosecutor who gave all the violent criminals like a pass. So you know,
but that's as far as you're taking that you're not going to try. I mean, you know, obviously Mike Morris has got his his his local news outlet that he's spending quite a bit of money on. You don't want
that. I you know, I don't I'm not a fan of politicians. I don't like politicians all that much. We're hanging out them. I get invited to all these like, you know, lunches and dinners, and then they tell me the price have to pay to have lunch with, you know, Obama or the lunch with, you know, Hillary or the lunch with DeSantis. And I'm like, No, I'm gonna pay 25 grand to have lunch with one of these people. I barely would want to hang out with
your friends to do that. Right. I mean,
I guess I don't know why it's not my thing. I think I could have more impact investing in companies and raising my kids and go my pockets.
So you're not going to run for mayor. Are you like you like you guys? Like you guys all know the value of floating. Kara? I considered that everybody was running for president. It's a great compliment. Do you think David Sachs really wants to be Secretary of State you guys? He would
definitely be a cabinet. I will guarantee you he'll be a cabinet member at some point for sure. We will be visiting sacks in the White House. We'll do it all in pod from the White House. For our lives are overwhelming.
believe that if what's his name, if Trump could be interviewed by what's his name from Barstool Sports? And I have no doubt that there is it's open season on who would appear on a podcast.
I think he's 100% going to be in there. Yeah.
You don't want to talk about it. But we have to put something we What will you say anything about social media these days? Or you know you're
a huge fan of social media. I use social media all day long days. to it. I think social media Twitter, I find tick Talk completely addicting, and I feel really horrible anytime I use it. I'm sure. An hour goes by. And I'm like, what just happened? Yes. I
deleted it. When I realized I was on tick tock one day for seven hours.
Goodbye. Yeah, it's they've really figured something out. I think it's a real national security risk. I think you have to ban the company or make them?
Well, let's introduce this, even if it shares some security risks, you know, China does not allow Instagram to be used in China. why would why do we have to allow a Chinese social media app to be used in the US?
It does not. Reciprocity matters.
We're talking about tick tock views, you're trying to ease our way into asking a Twitter question.
We asked you about the Twitter,
you can go dead silent.
I'm coming to this from covering not textbook covering the special Counsels Office
scraping the pod. But why did you choose to not? Do you won't say
anything?
What? Sorry? I'm sorry. Like I can't, I'm coming to this from a totally different topic. So Eric, Tom, bear with me. Can you walk me through why you can't because you used to be receptive to all this stuff.
I am a little too close to it. And then people will, of course, reblog, whatever I say. So when I when Travis was, you know, running Uber, people assume that I was a proxy for Travis. In other situations, people assume I'm a proxy for other individuals, or that I'm like an official spokesperson or a back channel or where they call those people who are in politics surrogates. Yeah. So I have chosen that I don't talk about my friends. We were talking about
your sense with. Go ahead, Eric.
Well, we were just saying we were talking about this before the show like there aren't enough. Not with you know, we were saying this, but there are you know, there aren't enough surrogates right now, I think part of the reason the media has become so negative to tie back to the beginning, is because workers are the sources available. You know, Elon, what did he fire, like the whole concept, part of
the Twitter stories are just about what the workers are saying. You guys
will change the subject.
Leave me out of it. Is I'm a huge fan of the Twitter app. Yeah,
I have. Verified, verified. Alright, let's change.
I like Katie's approach, though, as a journalist. Here's here's why Katie is such like Tom and Eric from world. Exactly. But here's why. Katie, you are so much better of a journalist and Tom and Eric put together
I don't just scream at you. For the record. Jason.
I have not been yelling at all. Here. Am I strategies, reporters let people talk and talk and talk until they
see themselves. Breaking your chops if you are an excellent No. Reporter
Carolyn's opinion, Jake. I know that's
not true. Jason, I actually my first time meeting you I kind of cornered you and talking to me. Oh, really? about this at all? Yeah. Because you would just pivoted follow inside.com and PTSD. Yeah, you wouldn't talk to the press at all. And I emailed you saying, I found out what you're doing. If you don't talk to me, I'm gonna I'm gonna write a scoop a
little time. This, this piece is coming out without your participation. So I will say I did that myself.
Yeah. But but for my time in LA, one of the things that I knew the you know, the most about you is that you were an early supporter and friend of Elans. I mean, you you knew him from his days, you were one of the I think so You were you were driving like the pre
I have an early testing, you have an early Tesla, and I have Tesla's a great car, and number 16 of the Roadster. And number one of the Model S serial number 000001 signature.
And I remember you saying in an interview once that, you know, after Elon, you know, he was really down on his luck for a while, you know, maybe post PayPal and before Tesla started doing well, he was broke. Yeah. And he had talked to you about it. So you were kind of there for him at a time that he was at his lowest. So you understand him at, you know, the various states of his success and non success. What do you think we are missing about Elon as the press in terms of writing about him?
I have been lucky enough to have a lot of great friends in tech. And he is one of the great entrepreneurs of our time, and he will figure everything out. That's the beginning and the end of it
with as much as we can say about Elon here.
That's it. I do not speak for Elon. I am not a proxy for Elon. He is on Twitter right now. You can hit you can you can text
me email to come on the show.
Let's talk about Twitter on a different episode. I am curious, like I mean, you've been skeptical of crypto like what what do you make of sort of the FTX unraveling and like how much worse Do you think this is gonna get?
I think that 99% of it is fraud and incompetence. I'm talking about the entire crypto space and one legend. A legend after legend a lead Good, but not looking good. I think 99% of crypto based on the meetings I've had, and there have been hundreds of meetings I've had over the years, I'd say 99% of it is a grift or incompetence, or some combination of grift incompetence and naivete. The technology tool stack that you would call web three is a collection of interesting components of other technologies, whether it's encryption or decentralization, we had decentralized BitTorrent or Nutella, whatever the encryption technologies existed, blockchain technology, all this stuff is like, you know, like interesting components. But other than money store money transfer, most of this stuff does not have a viable customer base. And so almost all the companies I met with, I would ask them to show me the product or talk to me about the customers, they show me a white paper and tell me I was stupid. And you know, when I had them on the podcast, I'd say, hey, had dough Quan on the pod. Hey, explain to me what this Terra Luna doing is he couldn't explain it. I asked him three times to explain it to me. He couldn't explain it. I was like, Well, I don't get it. I guess I'm done. And I'm one of the greatest angel investors of all time and have been in tech for 30 years. So I know I'm not the smartest guy, but I'm definitely not the dumbest guy I should be able to get you live
through like the.com Boom, we have the crypto This is it worse than a no, this is worse.
Credit was much worse, systemically more like my impact or
in the.com era people were true believers. They thought they would figure it out. And the thing got overhyped. In this case, I think people are deliberately buying tokens, flipping them to retail. And I think when the investigations come out, it's going to be a really bad look for a lot of people in the tech industry beyond
crypto or only crypto. Just
crypto is where this is manifesting. There's, you know, when you buy shares in a startup, you're locked up for 10 years, right? Like I buy Uber or I have Robin Hood shares you have maybe some secondary offerings come masa comes in, or Yuri Milner comes in wants to buy some people shares, you know, privately, can happen. It happens one out of 100 times, you know, this was I think, people because I was in some of these meetings, and I was watching people do this, they were lawyer shopping, which is where like, a lawyer doesn't give you the answer you want. So you just go to like the fifth sixth seventh floor, you start going down like lawyers and Cayman Islands, lawyers in Panama. And all of a sudden some lawyer for 1,000,005 tells you Yeah, we can totally set this up in Panama. And whenever you're picking a jurisdiction, and a law firm, based upon the eventual outcome, that you're gonna get sued or arrested, you're doing something that you probably shouldn't be doing. And if you can't do it in Delaware, if you can't do it with a Wilson Sonsini, or whatever law firm Fenwick, auric, you probably shouldn't be doing it. And so I was watching founders getting these like, legal opinions and then setting up these, you know, nonprofits or you know, where they would store the coins, and they would sell the money. And then VCs were buying the coins and then liquidating them in there is no, there's a whole
Law, which is,
oh, do they invest in crypto, they were involved.
Just just a bit I hear
instead of instead of the.com bust, it's more like the junk bond scandals and the penny stock camp scandals of the 80s, where it was like, totally unregulated. People were making the rules, they were shopping for attorneys, it's almost the same exact pattern, and then flipping everything to retail and getting out and then screwing an entire generation of investors. Is that what you just said?
That's what it feels like, to me, for sure that day is like because and find out your analogy. It's yeah, the.com thing was just a bunch of like folks who thought, hey, we will eventually figure this out, you know, and we may not have enough people right now to justify this valuation, but we'll fill it in. It wasn't like, I'm gonna buy a bunch of these tokens, and then I'm going to sell them on something to a bunch of, you know, bag holders in the public. And I'm going to start doing podcasts about how amazing crypto is gonna change the world and use my previous, you know, trust in my brand to go flip these things. Right. And, you know, there are some moments of things being real. I do think like NF TS for ticketing, or for maybe stock photography, or music licensing, where like, I took the stock photograph, I worked for the New York Times, and I agreed with them as a stringer. They get half the rights, I get half the rights. There's no hopes and dreams, you know, those things can be done something Yeah. Dows Dows have some interesting components. I've looked at those. Now. It's not legal. But when you look at securities law, and you decide I'm going to break securities law, because somebody in another jurisdiction told me it's okay, shame on you. It's one thing for Airbnb to be like, you know, I think these laws around what's a hotel and what's me renting a place renting an extra bedroom. I'm going to interpret it this way and there's no consumer harm when there's no consumer harm and you want to bend or evolve the rules for ride sharing, or for you know, Airbnbs that's one thing because you always have the consumers who come in to your defense, defense and say, Listen, I'm making $800 a month selling my extra room who's the government to tell me I can't? It's my room. I'm paying for it. And what don't we have property rights? Same thing with Uber, right? Uber took that strategy in New York Lyft took that strategy. Hey, tell the Mayor de Blasio, that, you know, we shouldn't have a cap on Ubers because of this evil medallion industry. Now you go to, you know, these crypto folks, and it's like, yeah, you need to defend my right to sell some, you know, you know, civilians in Florida, these tokens that are worthless. And it's like, what, this is
like the Wolf of Wall Street?
They don't you think that the same thing can be said about specs? Like, have you guys been hard enough? About like tomorrow about this back craze?
Okay. So in terms of specs, one of the things, so there are a range of specs, and I've had a couple of my companies go public via specs, and it's a little bit frustrating. Because as much as you want to get liquidity for your investors, we had desktop metal, a really cool 3d printing company, very real company with real customers that love their real products. But we had companies staying private for too long, like Uber and Airbnb, and then we started have companies going public too early. If the framing of these companies was to the public, these are highly speculative investments, do not make them more than 5% of your portfolio 2% of your portfolio, whatever, it would have been fine. But the problem was, you had this Robin Hood, you know, Wall Street bats, you know, everybody betting on stocks in a very kind of, you know, aggressive fashion, almost, in some cases gambling as opposed to like, but your mouth was the avatar for for this? Well, some of those companies are very real, you know, the company sees fact, some of them are very real. And then some of them like, you know, Virgin Galactic, or like a speculum you can get I don't have a problem with adults buying a speculative company, or a real company that has, you know, five years worth of revenue or one that doesn't, they just need to be educated properly, you know, and so I think there was almost like, they were too successful as retail investors, the retail investors needed to not run these things up. But that's what happens in the market. Like I think Joby the veto company. I don't have a stake in this a couple my friends invested in it, I want to buy the shares in that company, I've been watching it like to do a J trade. Like, maybe I should buy some of this because it's it's cheaper than it was as a public company. Even BuzzFeed. BuzzFeed is worth 250 million or something crazy. Like BuzzFeed is doing three or 400 million in revenue, but their valuations 250 What? BuzzFeed is a decent media property, why is it worth so little? And that went out by spec? So, yeah, specs, we want to have more, that we want to have more public companies and we want to democratize access to them. Right. But it was probably the bad timing of when this happened when retail was kind of losing their minds, buying everything that was a new issuance, and you know, Trump can defend himself if he wants to. But, you know, I think
it's so fun to talk to him. So you don't you mentioned at the beginning of the podcast, there's obviously so much going on right now, how do you sort through and determine how would you rank the tech stories happening right now in terms of like, broad importance beyond the tech industry, which are the most important, like three stories do you think?
Well, the most important stories is how many people does it take to run Amazon, or Google or Facebook, or another company, or any other company, pick a company, any company into and the truth is, people were hiring for a growth cycle that was two or three years out, that was kind of how Larry and Sergey explained it to me back in the day with Google, they just wanted to get as many many talented people in the building as possible. And then figure out what to do with them later. And everybody copied that playbook. And it was also a blocker strategy. They wanted to have smart people in the building, let them run amok. You know, self organized, we're paying you three or 400 grand a year, but you figure out what you want to do go find to interesting people and run orchid or Google Plus or come up with Google Video, you know, just self organized, who cares? It's you know, we're we have a money printing machine, that strategy permutated all companies whether it's Uber, which hasn't done a riff recently, or Airbnb, which did a bunch of riffs and got to profitability. And Facebook, the mighty Facebook, you know, he finally decided to cut the staff. So I think what we're gonna see is a lot of companies getting a lot smaller and tech, and a lot more focused, and it's going to be a pretty brutal 2023. I predict. That being said, I'm investing more than ever, because now valuations for startup companies where I invest, you know, they've gone back to when I invested in Uber, it was a $5 million company. And, you know, I see companies regularly that that don't have the traction and don't have TK that are asking for 25 million. And I'm like, huh, like, you're no TK. This company doesn't have the promise of Uber. So why is it worth 25 million? I'm never saying that to myself. You But now these valuations have come back down to earth, and then teams are doing more than less so austerity for America, writ large, controlling spending, austerity measures inside of companies. It's going to be 2023. Could be gnarly, let alone a Black Swan.
It's gonna be ugly. Yeah. And then if we have a real recession, all right, well, no,
it's gonna be I think it would be a real recession. What I'm worried about is if some unknown unknown happens, forget about Taiwan, or where Ukraine, Russia, like we know about those. I'm worried. Like, 911. Yes, yes. And 911, God forbid, situation is really like that could send this into a contagion like event, where, you know, you would have a lot of we could go from three or 4% unemployment to 10. And the 10 million jobs we have opened could go to zero. That's what I'm worried about. Right. Now.
Last question here. Jason, just forward here on the media side of things. Yeah. Where do you where do you see that headed? I mean, you mentioned BuzzFeed, let's not even touch them specifically. But like, you know, what's, what's going to happen to, you know, the status of the legacy media companies?
Well, I mean, I did get Molly wood, a career journalist as well to join me for This Week in Startups. So keep that in mind. So I'm pursuing both, you know, I wanted to have somebody who's a great journalist, like Molly be my co anchor on This Week in Startups for a reason she brings like a level of, you know, seriousness and credibility to the pod, you know, which kind of balances out my bombastic nature.
She's a Robin, to your to your Howard, I guess?
What I'm probably more like more like my Mollywood. You know, like my credible finance journalist, like, okay, not to diminish Hollywood. Yeah. Molly's my Hollywood. Yeah, that's it basically made me she's like a super credible, you know, career journalist who worked at the New York Times, CNET, and marketplace, so, but now she's learning how to be an investor too. So it's kind of neat. I would say, I think, you know, the, the independent newsletter and the Kevin Kelly's 1000 true fans, is going to be very alluring to the top journalists. And I think top publications are going to just continue to pursue subscriptions over advertising, so they can spend more on it. I mean, the information is doing a really solid job. Washington Post doing a really solid job, you know, that's put it on pretty stable footing. I think the New York Times with their collection of subscription assets, like the athletic and crosswords, and whatever, wire cutter pretty savvy move, and the more you have subscriptions, the more predictable it is. And the less you're dependent on click baiting strategies, like Business Insider pursues, you know, no, it's not a dig. I mean, but we, when when I say something on all in, you know, or we have a topic, they might drag that out five different stories that are all 300 words. And, you know, they you know, how they
do Sure, yes, to the headlines. It's a whole it's a whole thing. Yeah.
So you can't take the Washington Post, you know, and insider, and Casey and Eric, and, you know, like, there's a lot going on here, it's not one thing, I kind of feel like we're talking about paper, you know, like, you can make a magazine or a newspaper, you can make paper towels, you can make toilet paper, like, paper can do a lot of different things. And, you know, making content can be a lot of different things. Yeah, but I think a small,
best, in the worst, you know, maybe to just ask an appointed way, do you think it's, I mean,
they didn't have a, if the New York Times didn't have super voting shares, I would invest in the New York Times, if they had, they have God control over that company like so you think they just won't run it profitably, or I think they'll run it for the benefit of their sixth, seventh, eighth, ninth 10th generation, not the benefit of the public, or the shareholders, or the employees
very interesting what ValueACT is doing right now, I find it fascinating that they would even bother. But to see them go in as an agitating force, it's just really tough.
I think the best thing the family could do would be to figure out a way to Yeah, I guess this was a, I guess this was Season Two of secession, a way to make this in the public's interest and have like,
in succession, they're trying to sell it to like the Murdochs. You know, to the public. You don't you want them to I believe I'm happy with the the elite family who read the New York Times I think they are you want
to have been around the New York Times forever. Eric, why you want to have men run the New York Times forever, is what you're saying? No,
I mean, they had a female editor at 1.1 Point
they did. Yeah, yeah. You want to keep the patriarchy in charge. Okay. All right. We know where you stand. You want the patriarchy
it's interesting when you're back on your feet, you bring up woke politics. I know you guys hated woke politics. This was fun, guys. I really appreciate Thank you. I really appreciate
it. Thanks, Jason. In Silicon Valley Goodbye Goodbye Goodbye Goodbye Goodbye Goodbye Goodbye
