B (2:54)

Sure.

A (2:55)

And so. So start us off. The first anecdote in your book, which is more than an anecdote, is your father dying?

B (3:02)

Yes, it's one of them. The first one's about, you know, the tech moguls going to visit Trump after saying, after doing all this, we're so tolerant. They just cared about money. And I was making that point. But, you know, let me begin, you know, about entrepreneurism and coming back from, you know, difficult circumstances, as, you know, because I covered you actually way back when.

A (3:24)

Yes. I saw a cameo in.

B (3:25)

Yeah, yeah. And so, you know, you have an understanding of being an entrepreneur. And I would start off by saying, I don't think the media. I think it's in an upheaval, but actually there's all this promising stuff happening that is really interesting, and I've been trying to shed light on it. But I'll start at the beginning. I mean, my dad died when I was 5, and it changed the course of my life just as it would anybody. He was a relatively modest upbringing. His mom was a teacher and his dad was a surveyor, and he went to a school on military scholarships from the military, both college and medical school. And he just gotten out and gotten his first, you know, he had to serve 10 years, essentially 10, 12 years. And he had just gotten out and he died of a cerebral hemorrhage, essentially an aneurysm. And. And we were. Our lives were changed. That was that 34 years old, which is not very old, but he had three kids. And so he, you know, he just. That was that. And so we. Everything changed from there. My mom remar someone not very nice, and I mean, we grew up. Well, I wouldn't say I had an enormous amount of financial struggle as a young person, but.

A (4:35)

But you talked about that, and you talked about. I think you referred to your stepfather as a villain.

B (4:39)

Yes, he is.

A (4:40)

And yet he's still living around the dinner table. You learned things that seemed to be clearly of use to you.

B (4:47)

Yeah, he was strategic, and he was an entrepreneur himself in, oddly enough, welding, if you can believe it. He. And he created his own company. I mean, very entrepreneurial. We played a lot of games, a lot of strategic Games, risk, backgammon, quite a lot of. I just recently started playing it. I'm quite good. And it's because he was so terrible. But I, you know, he was a take, take no prisoners kind of personality. And so I did learn a lot about strategy and thinking and being on top of things and really understanding it not in the way I would have preferred, but my dad was a very, I would say a softer person by a lot, by dramatic, like a sort of a 180 personality. Very encouraging. And so I got a little of that in the beginning of my life, and then not so much. So it was tough. It was tough.

A (5:36)

And you described being in school. There was an incident where you were pulled into the principal's office because apparently you refused to do the work again.

B (5:45)

Yes, I was young. I was second grade. I wasn't pulled in, but I left class. I walked out of class. I said, I know this, and please stop boring me with this. You know, for the early part of my life, they actually thought I was a genius. One of those, you know, one of those kids. And then everybody caught up. I read early. I did math early, read tons. Read was a real reader. And then literally, I could see my math abilities decline as we got into algebra. Like, oh, not a genius, not a genius.

A (6:16)

But already in second grade.

B (6:18)

Yeah.

A (6:18)

You were the kind of person who would walk out of class because you were born, which I just want to say, like, this is a. What I would describe on Wall street. You describe it as a high beta.

B (6:28)

High beta, is that the word you.

A (6:29)

Use, which is very risky, but also capable of extraordinary things as well.

B (6:36)

That's because I really did have a terrible thing happen to me and I was not fine, but I was fine. Like, I think when you have something like that happen to you and you, you survive it, you're sort of like, yeah, whatever. Like, you don't. I think it does inform. I think a lot of people who are entrepreneurial have that quality or just like, you have so much life to live. Do it, do it, do it. You don't, you don't have a lot of reticence of, like, what if, what if? I don't. And I, I wasn't a consider the possibilities person.

A (7:05)

No. And so this is something I really want to explore because I feel like this is actually key to, to so much of your success in the last 20 years. Is this, as you say, like, you decided at one point, I would far rather say what I believed than worry about the consequences. But what you just said. So is that one of the things that you took away from your father.

B (7:26)

Yeah. Oh, absolutely.

A (7:27)

Was that. Wow, the worst thing happened?

B (7:29)

Well, it's just. You recognize. I think very often people don't have a sense of time. And I have a big sense of time. I think about time, like, how much. And I think about what I should devote my time to. Right. Even minutes. I have a joke with my kids. I'm like, TikTok, TikTok. You're taking my time. If they take forever to put on their shoes, kids, I'm like, tickety tock. Kara's. You just took a minute from Kara Swisher. I feel like it's a bank. And there is a. Do you remember there was a movie with Justin Timberlake and I'm blanking time. I don't remember what it was called. Anyway, everybody had time on their hand, on their arm, and then it would go down. You have to buy more time. And rich people had unlimited time. And then when your time ran out, you died. Like, it was really. It was something. It was quite a movie. And I remember I was always attracted to those movies was like, you have this many weekends, this many hours, this many. And it's also random at the same time, which is you don't have control over it. And I think that's a good thing to understand the larger picture at a young age. I think it creates a sense of scarcity. It's. Get a sense of. Do it now. When I am talking to students, I often, they're like, what's your best piece of advice? I said, you're gonna be dead in a hundred years. And that's really my best piece of advice.

A (8:43)

And you come back to that in.

B (8:44)

The book all the time.

A (8:45)

Steve Jobs with his graduation speech, best speech ever, where he said exactly that.

B (8:50)

Yeah.

A (8:50)

He was remembering you're gonna die is the greatest freeing kick in the ass.

B (8:55)

Yeah. And I would recommend everyone listen to and read it. Cause it's beautifully written. Like, let me say it's crafted. I suspect he wrote it. His sister is also. Mona Simpson is a great writer. He had a great writing ability. And unlike a lot of tech people, he was educated. And you know what I mean? Like, he could really turn a phrase and was really good at communication. And he thought about that a lot. Especially when he was. If you recall, he was sick for a little bit. Then he got better. He did, like, gained weight. He looked great. And then he got worse. And so the time that he created the most value, I would say, in his career was during those years of sickness. Or what people would perceive. He was very productive during that period. And I think that was. I think it's because he had a sense of death. Not that he was being, you know, dramatic or anything like that. I just think he had a very fine tuned sense of mortality that unfortunately took him too early, but way too early. But. But in so many ways he really did have respect for time in the way that other. Maybe that's why he was so testy with people. I don't know. They wasted his time, I think.

A (10:05)

So now we get to the first step for you of journalism, which, as you talk about in the book, is at Georgetown. You were gonna transfer. You weren't happy. The editor of the paper said, no, no, no, no, you're not going anywhere.

B (10:17)

One of the editors, Roberta Osteoper.

A (10:19)

Yes. And be a star for me.

B (10:22)

Very attractive to an egomaniac.

A (10:27)

And one of your quotes that jumped right out that I think is actually very important in trying to find one's way in the world. You said something. I love journalism and I was good at it from the get go. And I love the attention and acclaim it brought.

B (10:42)

Yes, I did. Yeah.

A (10:43)

So it seems to me in reading that that right from the get go in journalism, you had the two elements that are very common in any form of career success, which is, A, you were actually relatively really good at this thing from the get go. So you were talented. And B, you loved it.

B (11:04)

That's right. I think, oddly enough, I had a discussion with my oldest son last night. He just finished nyu and we were talking about careers and he's thinking of teaching and he's like, well, I won't make a lot of money. I'm like, well, I think you'll love it. I think you'll be one good at it. Because he's such a kind, and I think he just. I have a sense he'll be good at it. And I was like, you cannot trade that for anything. Like, don't worry about the money. Like, even I was, I'm not gonna subsidize you, but I'll help you because I have made. I have a career where I actually make some money and can help you. But I was like, you have to. Like, you are lucky enough. Not everybody is. Not everybody is lucky enough to get the job they love. Lots of people have to do shitty work that they may not like to make money to make ends meet. But with people of a certain kind, highly educated and stuff like that, they have choices. And I think what happens is a lot of people that have ch. Pretend like they don't have any when they have a myriad. First of all, being in this country, as difficult as it is right now, you get a lot of choices compared to most people in the world. And so I really always thought that if I didn't love it, I would leave it. And that's something that Jobs said. If I find myself unhappy enough days in a row, that stuck with me. I was like, yes, that's right. The other thing is, you have to know what you're good at. Like, I hate to say that, but you have to be, even if you. I loved architecture. I loved it. I did it in high school. I love the T square. People don't remember. Everything's CAD now, but I love my T square. I loved drawing, and I was bad at it. I just knew. I went to Harvard School in the summer. There was, like a design thing that I took in when I was in high school. And they had this thing at their. They're very good architecture school. And everything I designed was ugly. Everything, like. And I knew it. And so I couldn't, as much as I wanted to pursue that career, I just was. You have to be aware of what you're good at and what you're bad at and be dead honest with yourself about it. And that's another thing. People aren't. They aren't. Like, they don't understand their skills very well.

A (13:08)

That's right. And we hear in our society a lot, oh, follow your bliss, figure out what you love, and so forth. And one of the things you're also incredibly outspoken and smart. Co host says all the time. Scott Galloway is, no, you actually have to figure out what you're good at. And it sounds like you did that.

B (13:26)

Yeah, I think it's hard. I think it's hard for people. And, you know, there's all kinds of things that hooks, that hang on, whatever. Like my son, he's like, teaching money. I was like, yeah, but, but, but, but there's a desperate need for male teachers. I just interviewed Richard Reeves. I mean, his son is also a teacher. Just like, I was like, don't butt yourself out of something that you, I suspect, you're going to love. And if you don't love it, leave it. Right. I think that's the difficult part in jobs is a lot of people, they stay way past their due date. Right. And Scott does talk like, you've got to leave. If you have the choice, you must leave and do something else. Sometimes you're forced into it. Most times you're Not. And people just sit there and gripe about people they work with. I kind of hate that. I was like, just go. Just like. Honestly, like, life is way too. And then you get into the life is way too short kind of thing, which is a cliche, but it's actually true.

A (14:17)

And so there's this matching of what you love and your skills, which you seem to have done right away. And then you describe in your book one of the seminal moments of your career, which is you're working on the Georgetown paper in college. The Washington Post publishes a story that you also covered.

B (14:35)

I did.

A (14:36)

And you were outraged.

B (14:37)

Outraged.

A (14:38)

So what happened?

B (14:39)

I went. I took the bus down. I called them first. And I managed to get him, Larry Kramer, who you probably know, he started MarketWatch. And I was like, what in the actual fuck? Like, hey, you know, of course. Like, I'm so naive. I was like, they send the worst person to that. That wasn't a big assignment. It wasn't like they sent Bob Woodward to cover that. And I just was. I was. I loved the Washington Post. And the two disappointments were obviously the Janet Cook thing, which I read the entire report of what happened. She was the one who made up the kid with drug problems. But I love the Washington. Like, I loved it, and I read it every day. And I was just mad at them. Like, I expected more from my newspaper that I loved. And so I went down there, and he invited me. Oh, you really gonna say, that's my face. I'm happy to do it. And so I went. And people don't expect that from a woman. I hate to say that at the time, women are much more reticent, you know, even then, like, it was a much more difficult thing to talk to men like this. And so most women are very. Not most. Many women are solicitous, you know, or try to make. Whatever. People be mad at me for saying, but it's true. And so I went down. I took the bus. I think it was a G2 from Georgetown to 15th street, where the host had this wonderful headquarters with the printing presses in the basement, which was wonderful. They're gone now, but. But I went down and I saw him, and he's like, oh, you think you could do better? I said, I know I could do better. What are you doing? Like, hello? Like, what kind of question is that? And they were hiring stringers, and so they hired one from Georgetown, one from GW because there's a lot of activity on college campuses, and they didn't really have good people to cover Them. And they. And they. It was a smart idea. And so I worked for the District Weekly, which doesn't exist anymore, and just whenever something happened and I would just come up with stories, and I wrote quite a few. I mean, and it helped me get the clips, which was critical then to get into to Columbia and everything. And I got in right after I graduated, so. Which was sort of a waste of time.

A (16:41)

But so, again, I mean, this is an extraordinary moment. And one of the things that, when I was at Business Insider, we had incredible privilege of working with year after year after year of incredibly smart folks coming out of school. Often, journalism sounded cool to them, but. And it was a very sexy thing they were trained to do. But in, I would say, in every group of 10 new interns that we brought in give the same speech, which is, okay, it's time to get to the phone and start talking to people who don't want to talk to you and so forth. What I found just watching was probably 2 in 10 people are actually suited to that in that they like it. Everybody else is very worried about making mistakes. So, anyway, I just want to point out that this other element of you read this story, you are so irritated that you figure out who to call, you effectively yell at them and say anything. All this is very unusual, but also very helpful for what you went on to do.

B (17:40)

Yeah, I think they saw that. Yes. And also, I didn't have the goal of getting a job there. I didn't at all. I just was, like, I was a irritated reader, and I think they perceived that one. I was very persistent. I guess persistence is one of the key attributes of a good reporter. I also could find people, and I didn't mind calling them.

A (18:00)

Yeah. And you have something that either you. Did you learn your way past it, or it was just always.

B (18:05)

No, I was always forthright. Yeah. But I also knew, like, the thing is, people don't call. Right. People don't call or meet people. Like, I remember at the Wall Street Journal, Murdoch had just bought the company, and we, Walt and I immediately invited him to speak at CO All Things D at the time it was called. And that's one thing we did. We're the first people who were like, get out. Let's call him tomorrow. Like, essentially. And one of the things that I was struck by, they made Robert Thompson, who I actually like very much, who was longtime editor, and then he became the CEO of News Cor. All these people were. This is so typical of reporters. They were talking about him. Like, I hear this. I Hear that? So I called him, I said, can we have lunch? I'd like to hear about what you're doing. And he's like, no one's done that. And I go, well, fine. And you know, we ended up having lunch. And I learned a lot about him through that. But nobody at a reporting institution, everyone was like talking about him, but no one had any good information. And that drove me crazy. And I was at a party and they're like, they said something. I said, that's untrue. And they're like, well, how do you know? I go, I had lunch with him. Well, how did you do that? I'm like, I called him like, what do you think I fucking did, you idiot? You know, and you know, and we ended up having quite a good relationship over time because I think he, I suspect he appreciated that I was willing to pick up the phone on call him. Same thing with Rupert and the rest of them.

A (19:27)

And by the way, this is something that you hear in other careers too. Yeah, sales, whatever happens to be people, you know, get in at 8 in the morning before the assistant arrives, just call the person. Maybe they're at their desk early or late or whatever. Yeah, exactly these things. So anyway, so let's jump ahead. I have another question.

B (19:44)

Can I just make. One of the things young people do is face to face meetings. I do tons of just lunches. Like I find people. Remember I had my little camera I used to go around, that was a device in order to meet people. Right. I used to take little videos. So I think that's one thing, like go call them, go meet them, go find where they are. And I'm really good at that. I don't do it as much anymore, but I was really good at it.

A (20:07)

All right, so let's go back. So back to Georgetown. I was very surprised to read that journalism was your second choice.

B (20:15)

Yes, it was.

A (20:15)

As a career.

B (20:16)

Yeah, I would have been good at this military. I would have been fucking. I would have been fired right now among the Trump administration, that's what would happen. Although I wouldn't have been a DEI hire. Whatever the fuck their excuses they're making to shit on women and people of color. I wanted to be in the military. My dad was in the military, very attracted to it. I would have been an admiral at this point, I would suspect maybe not a flyer because I have terrible eyes, but I would have been good.

A (20:45)

Okay.

B (20:46)

Or the CIA.

A (20:48)

I don't know much about that career, but it strikes me that what seems to be a fundamental principle of Your life, which is I say what I think actually might be a big hindrance.

B (21:00)

Not so have you met high level generals? And they're very. First of all, they're highly educated. Most, maybe not the new ones, but the ones I have met have been among the smartest people I've ever met. I have to say. They, you know, people at the War College, they're, they are such really blue light as at Blue flame thinkers as Scott uses that. They are blue plane thinkers. That's my.

A (21:22)

Oh no. I experience not questioning that at all. What I'm questioning is the what which again we see again and again in your career and makes you so good at what you're doing now. And I also to jump ahead again. A few months ago you were, you had a plan to buy the Washington Post and maybe you still do and anytime.

B (21:41)

Jeff.

A (21:41)

I know, I know.

B (21:42)

I just talked to my investment banker yesterday.

A (21:44)

Oh, good. So anyway, we talked about that and I. You were kind enough to ask my advice. My advice was don't do it. It's a waste of your time. And by the way, the thing that makes you so good at what you're doing now when you're running an organization like that can for most people be a liability. I mean, I guess there are some people who can be Larry Ellison or what have you. I don't know.

B (22:06)

That one requires like total like balls.

A (22:11)

I don't know. There's a lot of people. And as much as lots of people love what you say, there are going to be people who don't like what you say.

B (22:18)

Correct.

A (22:19)

And often in a leader role. At least I found. And maybe you can maybe.

B (22:24)

Yeah. You know this. I mean you. I ran a much smaller organization than.

A (22:27)

You did for a while. I was both an op ed columnist who loved to stir the pot. You do the CEO and editor in chief. And there came a very clear moment where I think I stepped in it for the third time. And I had a big group of people who I wanted to respect me, were pissed at me for what I had said. And I just, I got to the point where it's, you know, this is, it's not compatible. You do not want the leader to be.

B (22:56)

I wasn't gonna be the CEO, FYI.

A (22:58)

No, that's true.

B (22:59)

I was not. That wouldn't be my job. I wouldn't be. I would be the whatever, the inspiration. I would not do that. I know one of the things I didn't like, as you know, and I ran a much smaller organization than you did, was I didn't like the CEO part of the job at all. I hated the HR part. I didn't like the employee. I liked the employees, but I didn't like dealing. There's all kinds of stuff you have to deal with that has formalized systems. And I definitely didn't like. I didn't excel at it, and I was okay at it, but I didn't like it. And I remember thinking, I gotta sell this company because I really don't want to run it. I just. I have an idea in my head for a book called Staff Zero, which I like it that I don't have an assistant. People are always surprised I don't have an assistant. People that work on my podcast don't work for me. They're managed by other people at Vox. And so I like it that way. But I get your point. I wouldn't have done that there. I think what that needed was a big shakeup. I also saw it, I hate to say it, as an opportunity to be the good guy. They're being so villainous between Will Lewis and Jeff Bezos. It feels like a Bond movie in the making. So there's a real perceptual marketing opportunity there for inspiration and to really start fresh. And that's why I thought it was also sentimental. I love that place.

A (24:19)

Oh, very much so.

B (24:20)

It was very sentimental for me in many ways.

A (24:22)

Yeah. And going back to your original story where you were outraged about how the post.

B (24:27)

I am outraged.

A (24:28)

Yes. Concocted this or done this bad story. You want to fix it. Same same early.

B (24:32)

I also see a huge opportunity. You didn't. I think you thought that, you know, brands die. And I was like, not this one. They're only. I think that was one of our.

A (24:40)

Well, yeah. What I said was they were very kind enough to call me early in the search, and I didn't want to move to Washington, but also, I didn't. I just didn't know what to do. Like, they're in a very tough state.

B (24:51)

They are.

A (24:52)

And you said you had a plan. You're here at some point. That's great. But we don't have to talk about that this time. So let's go back. So why didn't you go into the military?

B (25:01)

I was gay. Because it was. Don't ask, don't. It was. Well, before that, it was, you're not got to be gay. You can't be gay. You have to be hidden. And I didn't. I wasn't a hiding person. I just couldn't do it. And then Clinton came In with the stupid don't ask, don't tell, which is even worse in a way. Well, no, they're all bad. And so I knew people in the military who were hidden. It was. It was excruciating to do. Like people, young people today. It's like you really had to hide, even as a regular person, like, and you. Like, I was talking to someone. You did like, two different bedrooms for your parents, like, or my. You know, like, that's so fucking ridiculous. It's a waste of time and money and everything else. And so you couldn't be the person you were in the military. You had to hide yourself. And I thought that would be problematic. I was already out, so it didn't matter. I wanted to go on the CIA to do analysis because I really enjoy strategic analysis. And, you know, I was very into, like, if this, then that. That kind of stuff. That's how I'm another reason I'm a good reporter. I'm like, okay, what is happening here? Let guess. And there are usually three things, right? You know that as an investment banker, there's scenarios. And so I. I thought I'd have been good at that, like strategic planning and stuff like that. But I was gay, so that was that.

A (26:16)

So that's a. Outrageous. Of course it is reason and so sad. But I will say, I think you're better placed in this.

B (26:25)

No, I would love.

A (26:25)

There are a lot of animals. There are very few people who could do what you owe.

B (26:29)

I just, I think I. I'm very patriotic. In a weird way, people find it strange. I think I. My father's side of the family had a lot of military. One of my great grandfathers was an admiral. Like, there's a great. I have a great. And I do think the left has often, like, given that up to the. It's ridiculous. They are so performative about patriotism. But I really believe in. I believe in the good military. Not all of it. There's all kinds of problems in it. I believe in the goodness of this country and everything else. And I think we abrogate our. Our position when we let them define it because theirs is so ridiculous and sort of like, put a flag on your fucking shirt and that makes you patriot. That doesn't make you anything. That makes you sort of insecure and pathetic if you have to do this performative stuff. You know, I kind of. The only thing I liked about Trump is he hugged the flag. I was like, fine. He's just. He's doing the performative. He's making it so explicit. That it's ridiculous kind of stuff. So I want. I really believed it was an important job for this country. So that.

A (27:31)

But you went into journalism, which is great for journalism. So you applied to Columbia J School and got in. And then in your book, you say you wish you had invested in Apple instead.

B (27:40)

Yeah, don't you wish I had. I've been owning. I'd have. Owning the Washington Post right now. I wish it was a waste of time. That journalism school is a waste of time. I'm sorry. It just is. I mean, there's some very good journalism school. I know a lot of, like the people that do at the Newmark, they're very specialized. But I just felt like I should have either been working or it's a craft, not an art. I guess journalism is a craft, and so you should be doing it. And it was just a lot of money. I should have put in Apple stock. I would have been really rich.

A (28:14)

All right, so here's another moment in your book where I suddenly said, okay, here we have another seminal moment, which is you're employed by the Post. You're on the Hoya at Georgetown. You go to Columbia J School, the best and most prestigious journalism school in the. You apply and everywhere rejects you. Then you interview, it sounds like at the Post again. And you are told in a remarkable comment from the interviewer, you're too confident.

B (28:42)

Too confident. Yeah.

A (28:43)

And what did you say?

B (28:44)

I'm really good, I think. I think, you know, I was like, well, I should be. Cause I'm fantastic. Like, I don't know what to tell you. And I think I said something like. And this guy was great. He was. I actually ended up being friends with him. I was like, someday I'm gonna be so famous and you're gonna be dead. Like, so, like, this is the rolling of, you know, like. And by the way, I really did understand this guy was a functionary. So he didn't. He had hit his ceiling. And so I was always very aware of who actually had the talent. And when I actually. I went to the Post and I was like a newsaid. I did all kinds of scut work, delivered mail. Let me tell you, the most talented. This was a really big observation as a young person. The really talented people were, by and large, lovely. The untalented people were the assholes, like, the ones that weren't going to. It was really. It really did track much more to lesser people like myself at the time. And so I definitely learned a lot by being in a scut position. I love a scut position. I told this to my son. I was like, get a scut job. Like, get coffee. It doesn't matter. You'll learn a lot if you just by watching.

A (29:51)

So one of the things I was struck by in your book is this fearlessness and bravery. And you will say these things that no one will say. And you don't want a job at the Post. You're just going to complain and they give you a job and all this stuff. Was there a moment after you got fired or when you got rejected by all these newspapers after this incredible experience that you had and so forth? Are you ever depressed or down?

B (30:16)

No. It's weird. My wife is. I was like, you know, I don't regret much. I really don't. My wife is. I was like, I'm not very neurotic. And, I mean, I have my issues, of course, but no, I'm really not. It's really. I wait to be sad, and I'm not. I happen to have. It could be genetic. It could be just the way I'm made. But no, rejection is not a bad thing for me. I'm like, okay, fine, you idiot. Like, and I'm not being, like, stupid when I make a mistake, I'm very aware of it. But I don't get. I think you know this, as most really good entrepreneurs do not get bothered by failure at all. And I don't celebrate failure, by the way. Like, a lot of tech people are like, I haven't found. They use that stupid Thomas Edison quote, I haven't failed. I found 10,000 ways that don't work. I'm like, that's failed. Right, Got it. I don't think. I think they, you know, they fetishize everything. Like, failure is a fetish, but I don't. If it didn't work, it didn't work. And then I try something else. And I think that's a really critical element to success, is that you don't. You don't get dragged down by things and people get as you look at you. Like, look at you. Like, I wouldn't imagine you'd have started a journalism thing after what happened to you. And then. And then you changed this and you went to tv. Like, you're not. Like, you're not dragged down by the shackles of expectations. And I think that's critically important.

A (31:36)

That's right. But I think that at least for me and in my 20s, it was actually the worst period for me.

B (31:42)

Why is that?

A (31:43)

Well, I'd gone to good school, graduated in very good standing, but Then I got into the real world and I had a lot of weird ideas about how things should be and I shouldn't have to do the scut work for too long. For example, I have this great education. Anyway, I needed to be humbled and I was. And that's the moment that I don't see in your book.

B (32:05)

No.

A (32:06)

Okay, that's great.

B (32:07)

I know some of the critics were like, does she ever not like herself? I'm like, no, No, I do not. Try try. Literally, it's a joke in my family. It' like I. And it makes people, and I have to say, especially men, uncomfortable, though sometimes women like I often. The other day I was with Mel Robbins. She was a guest during Scot Free August. And she goes, you know, that interview was really good. And I go, yes, it was. And she's like, whoa. And I'm like, what? And she goes, well, you just said it. And I said, if it wasn't good, I'd say, no, I didn't like it because of this, but it was good. It was, it was like pound for pound, that was a great interview. And she's like, wow, that's the best answer. I'm like, why? It's factual. And so some people find it funny. She did find it funny. But others are like, don't be so like, I don't say I'm good at basketball. I'm not like, if I play, I'm like, that sucked. But I also don't care that I suck at that. So you're about to make a trade based on a friend's text, but which you do you listen to, is it, we could buy a house in Tulum, get optioning those options, we could lose everything. Or let's do a little research, get your head in the trade and make the investment decision that's right for you. Learn more@finra.org TradeSmart this episode is brought to you by State Farm. Checking off the boxes on your to do list is a great feeling. And when it comes to checking off coverage, a State Farm agent can help you choose an option that's right for you. Whether you prefer talking in person, on the phone or using the award winning app, it's nice knowing you have help finding coverage that best fits your needs. Like a good neighbor, State Farm is there. Running a business comes with a lot of what ifs, but luckily there's a simple answer to them. Shopify. It's the commerce platform behind millions of businesses including Thrive Cosmetics and Momofuku. And it'll help you with Everything you need, from website design and marketing to boosting sales and expanding operations, Shopify can get the job done and make your dream a reality. Turn those what ifs into sign up for your $1 per month trial@shopify.com specialoffer.

A (34:31)

Alright, so I wanted to talk about the McLaughlin Group, which was one of your jobs before at the Post where he asked you to make toast because that's what all the staffers did and you refused. And yet he didn't ask you again because he would have had to fire you.

B (34:43)

I said, you can fire me and then I'll call the Washington Post and tell them. I was like, I was very much blackmailing. I was like, fine, here's what's going. This is a strategic thing. I'm like, okay, you fire me for not making toes. I call the reporter at the Washington Post and tell them you fire and it's FA and I'll put my name on it. Like, go right the fuck ahead. Like. Cause it's sort of a game of chicken. We did the same thing with the Journal when they were trying to pretend they fired Walt. And I, like, it was fucking ridiculous. Like, I have the emails like, what are you doing? Or in any. In anything. I'm like, go ahead, you know, go for it. You know.

A (35:21)

All right, so it's easy now that you're on top of the world to look back, oh, I didn't care about this, I didn't care about that and so forth.

B (35:28)

But.

A (35:28)

But I remember those early years in any profession, like, it is tenuous. And you did say so. There was one moment it was tenuous.

B (35:37)

Henry, for Mr. White Guy who's educated. Where'd you go to Harvard? Again, no.

A (35:40)

Everything.

B (35:41)

It's not tenuous.

A (35:42)

No. Which is remarkable, your attitude there. Because what I would say, yes, I had all of the advantages and still managed to blow it. Why exactly so. But. So go back. So there was one moment where John McLaughlin, who you've called an awful human, awful glad he's. You had this excuse to get toast. I mean, remarkable thing to say again, I am. But you, you went on the record in a story and you said, yeah, it was professionally stupid. But I had to say it like it was.

B (36:12)

Was it professionally stupid?

A (36:14)

I don't think this is my question exactly is what were the ramifications? Because I have to say, as I read your career, what's remarkable about it is there seem to be very few agreed ramifications for your extraordinary outspokenness.

B (36:28)

Yes, there isn't yet. I'm waiting. I'M waiting for like a car to pull up and I get taken and I'm have to call Liam Neeson that, you know, I. One time I was in New York and a car made a 180 and I'm like, today's the day I'm finally gonna pay for all my mouthiness. And it was a fan, it was a fire guy who was riding Uber or whatever and he just liked Scott and I and wanted a picture. But yes, there aren't ramifications. There haven't been because I've been very calculated. I also am not a jerk about it. You know, I don't have to have a flourish on the way out. I don't have to. I'm quite polite. I think if you go around to people, I don't think you'll find a lot of people. I'm not a screamer. I don't demand things. I work harder than other people and so I don't. I mean, lots of people might not like me, but I think you'd be hard pressed. Even someone like Marc Andreessen, someone who I had a real break with, right, would say I'm don't do the work.

A (37:22)

So I don't know. Three or four months ago I wrote a story on Substack about AI and all these AI experiments and suddenly my phone explodes. And I think one of the explosions is you saying, oh, you're getting roasted on Blue Sky. And I didn't even have an account on Blue Sky. I barely even heard of it. I go in there and woo, I am getting roast.

B (37:44)

You get roasted no matter what.

A (37:46)

So. And which I have gotten used to to some extent.

B (37:49)

What do you care?

A (37:50)

But I was talking to. Well, here's the thing. I said, Carrie, you know, you stir the pot all the time, people are yelling about you. And your quote, I'll quote it right back to you, is I don't give a fuck.

B (38:01)

Yeah, I don't.

A (38:02)

And I was talking to a friend of mine who's outside the industry yesterday and I said, I'm interviewing Kara Switzerland. Oh, Kara Switcher. I know. Caris Wishart. Love Caris. Busting on all those tech guys doesn't give a fuck about anything. It's great.

B (38:13)

I was like, kill me. That's great.

A (38:15)

Okay, so here's the thing. I will confess that I have learned through trial and just doing things, you're gonna be criticized again and again and again. If you ever wanna say anything interesting, you ever wanna do anything interesting. But I have never given zero fucks.

B (38:32)

But you wrote It. So you didn't give zero fucks. Cause you wrote it in the first place.

A (38:36)

But I feel it. I don't like it, the criticism.

B (38:39)

Why'd you write it?

A (38:40)

And I have met people like you who seem to actually not care at all.

B (38:45)

Yeah.

A (38:46)

And so has that always been that way?

B (38:47)

Yes.

A (38:47)

You just don't.

B (38:48)

Well, look, I walked out of second grade. Yes. No, I don't care what the second grade teacher thought of me. Cause I was correct. Cause I was accurate. Let me tell you. You wrote that piece, didn't you?

A (38:56)

I did.

B (38:57)

It didn't stop. You did not. Also didn't pull any punches. There's lots of sentences you could have added to that piece. Right. But you didn't. So you don't give a fuck. You just. You actually went that far to write it. So why do you care? Why did you write it if you cared about the implications?

A (39:14)

Well, for me, in life, I often learn through stating a view and then hearing a lot of smart people talk about it. And I will modify the view. Often I learn from that process.

B (39:27)

Sure. I do too. Yeah.

A (39:29)

So. Okay, so you do.

B (39:30)

Oh, if someone, like, pivots all about that, modifying views. Cause he says something and I'm like, huh, I hadn't thought about that. Or. That's interesting. Like, that. That's different than. You don't. Like all the, like, ridiculous people. I mean, I'm not a Trump person, but people in their basements telling you what they think of you. Like, what do you care? The noise on, you know, you know, toxic Twitter or whiny Blue Sky. What do you care? What do you care? I get it all the time.

A (39:59)

All right, I will. I. I will work on. I will work on that for me. All right, let's move on to tech. So I.

B (40:04)

You already don't care. Just take the next step.

A (40:07)

Henry, there is another nice little detail as we move on to tech and all the tech bros and so forth you describe so vividly. So Jeff Bezos offered to be your sperm donor?

B (40:18)

No, he didn't. No, he. Yes, he did. No, he didn't. He was asking me about it. He didn't offer it. There was no offering or exchange at the time. Many lesbians were not having kids like this. So it was kind of an unusual thing. And so. So he had a lot of questions. He was a very, you know, Jeff, he's very curious, Curious man. He's very intense. It was like, you know, he's, you know, he gives off a real, like, jittery kind of energy. Very similar To Wall street people, right? And he's super smart, by the way. Jeff Bezos is among the smartest in general people. High iq, people in tech and. Well, I don't know what he's doing now, but whatever. So he was. We were at this party, and I was. I was trying to get pregnant, and he wanted to hear about. About what it was. Cause it was interesting at the time. Now it's sort of, who cares? And so I was explaining it to him, and he goes, well, you do sperm from people you don't know or people like people you know. And I said, yeah, how do you think I'm gonna do it? I'm not gonna go to a bar and pick something up that's kind of weird. And we were in the talking bit. He goes, whoa, would you use sperm like mine? He wasn't offering it to me. He just said, just like someone like me. Like someone you know like. And I was like, well, not you. You're too short and unattractive, I would say. And so. And he. That's what he did. He did his laugh. And someone heard it and didn't hear what I was. It was a hypothetical offer. It was not an offer. Like, is that how it goes? You ask someone, you know, whether it's a friend or someone you know from business? And I was like, well, not you, but, yeah, I guess Mark Cuban, I'd pick over you, for example. But I didn't either. I didn't like, that was too far. And I was making a joke about it, and then some stupid person and recounted it to the New York Post. And then it got in the Post. They were coming after Jeff Bezos at the time. They had some reason to attack him. And so they just used it. And me and the Wall street and.

A (42:14)

Steve Jobs also asked you about that.

B (42:15)

Yes, very much so. He was, you know, adopt. He was adopted. And his parents, he. They had put him up for adoption. And. And so he was very interested in the topic at the time. And so again, he wasn't being, like, weird and prurient. He just. At the time, not many lesbians were having. People weren't doing this, essentially, and maybe straight people were, but nobody talked about it. And so I was willing to talk about it like, okay, here's the. Here's the situation. And one of the things that he talked to me about was, don't. Your. Your birth parent doesn't matter. That was important to. For him to say because he, of course, had his own experience with his own father, which. Who. He didn't like I think he was probably betrayed by them in some way. Felt like. Cause they went back, they had another kid and didn't go back and get em. And who knows, I don't know, you know, I'm not a therapist, so. But he was very interested in who your parents are and what they mean to you. And I thought that was very touching. And then he hugged me. He's not a hugger. He hugged me after that. But you know, that was a lovely, really lovely moment.

A (43:18)

And you talk a lot about Steve in the book for our obvious reasons. Yeah. So that comes clear. And so let's start to fast forward to today. I mean your book is about this 30 to 40 year rise of technology. And it was very meaningful to me because I was only a few years behind you and seeing everything as it happened. So I was getting a real flashback through all that period. And you get into the details of how in the 1990s, early 1990s, yeah, tech was this weird thing on the west coast, some big companies, but software or what have you. And it just blew up the media industry completely. These big moguls toppled and are now and so forth. And now the world is run by tech. So lots of questions about that. But let's go to Steve for a second which is how do you think Steve would have handled the current moment with President Trump and the administration?

B (44:15)

I wouldn't have been horrified. I don't think he would have been acquiescent by any means. It's interesting. I know Lorene and Reid. I think Reid's terrific. I've interviewed him, the sun, he's doing all this really interesting work around biotech and stuff like that. What a nice young man he is, I have to say. I think. And you could see Lorene backing the Atlantic. You know, she's not outspoken, but she's obviously against this and has done a lot of stuff around immigration and empathy and things like that. I think he would have been horrified by this. I don't. I think he stuck. But he was an interesting guy. Cause here was someone, for example, he kept trying to get Rupert Myrtle Murdoch to be more liberal. Like he would sit with him and like he wasn't someone that was like a liberal on high, like being disdainful. He engaged with people he disagreed with and he did that with Murdoch. He developed a real relationship with Murdoch, who had great regard for Steve by the way. And so, you know, Steve wasn't like compared someone was like, oh, Steve was a jerk. I'm like compared to today. He's a fucking Santa Claus. Like, give me a break. He was difficult in many ways and people had criticism of him about his parenting in some cases. Although I have to say, listen, there's issues everyone has with their kids, so you have to sort of sort them out. Including with Elon and his daughter, who I think he's behaving terribly to. But he was, I think he had just certain values that stuck. I don't think he shifted values based on it. And one of them was saying what you think, think taking risks, calculated risks, being very clear down to silly things. Like, do you remember when he took some of the things that you put dongles in on the side he took? Which one did he take? The usb? Not the usb. He took something out the side where you'd put a card in, whatever, and he took it out and everyone was all mad. They're like, oh, how could you do remember that? It was like a big five fucking alarm fire with all those stupid tech writers. How could, hey, like, oh come on, it's his. And it was like his fucking product. He's like, I didn't like it. And we were like, well, why'd you take it out? He goes, I don't like it. And people are critical. He goes, I don't care. Like, fine, they don't have to use my product. I'm making the product I want to make. And so I really appreciated that about him. I think he, today he, I absolutely think he would have been disgusted by the. He never liked Facebook. Trust me. He said it to me many times. He thought it was just grotesque the way they used information for, you know, the way they, they were so sneaky about their stealing of information. I think he didn't have much respect for Zuckerberg, I suspect, I think he would have been horrified by Elon at this, the new Elon.

A (47:02)

But so, so I, what I. When I hear about the attack on Apple, for example, it's world class organization that has built this extraordinary global supply chain and the Trump administration has taken a direct shot at that, squeezing it, basically. Yeah, hey, put it on a ship, bring it back to Texas. Which is impossible.

B (47:21)

Yes.

A (47:22)

And so this is a crown jewel of the company that Tim Cook, the new CEO, has built. And so I look at that job of you're a CEO of this massive organization and sure you have your own views and, and so forth, but you also have a job which shareholders are his shareholders, employees, everything else. And when the administration is taking such a direct shot at you, you gotta give them a gold statue it's always this dance of. Right, exactly. The statue for which I think Tim.

B (47:52)

Is very comfortable giving the statue, too. I don't think he. I think whatever it takes for shareholders, he'll do. That's always been his mo. I think he's quite liberal. I suspect probably not that liberal because he's an older gay man. So you're gonna have a bit of conservatism. If you know older gay men. They are. Many of them are. But I think he's doing whatever it takes for Apple, and that's what he'll do. And there's not gonna be. Interestingly, I made that case. I was like, he's gonna do it for shareholders. Don't get mad at him. This is what he's doing. It's grotesque, certainly, but he can't go, I cannot. I shall not do this. He can't do that. And someone very close to that company actually made a counterargument. I said, well, he's doing what's good for shareholders. And this person said, is it good for shareholders to live in a bribery state? Apple's a global company that's across the world. World. And they have to do certain unnatural acts in many countries. Right. There's always some corruption. They don't pay bribes. I'm not alleging that at all. But you have to behave in kind of these banana republic situations. So now this person's arguing it's bad for shareholders of this country to have to be in a banana republic and pay the vig. And I was like, huh? I had not thought of it that way. You're absolutely right. Right now, Apple has to operate in this country like it's a corrupt, fascist regime or authoritarian regime. And that does suck for shareholders of Apple.

A (49:17)

Eventually, possibly.

B (49:19)

Yeah.

A (49:20)

We don't. We don't know the future.

B (49:22)

This is not the rule of law. Scott has argued this. Now that the rule of law is gone, like, that's what's made our stock market great. That's what's made. We are giving away our crown jewels of propriety. And. And you don't have to stand up and say, I am against you. But then, like, this is bad for business. This is bad for business.

A (49:39)

Right. And companies also do have to make compromises if they want to be global companies. Any company operating in China is making compromises. And this is something that has been a big topic of debate within Silicon Valley, certainly the Google debate around this and so forth. So I think it's a difficult question, and I don't. But I was very struck in your book. Book, the admiration for Steve. And Steve probably would have handled it differently. I don't know that he would have said, that's it. Like, I, Apple, I, I will sacrifice Apple.

B (50:11)

No, I think he would have met with Trump and he had such a force of personality. He might have, you know, Trump would have adored him and he would have, you know, Trump might have changed. Right. I think, but I don't think he would. He was not someone who kowtowed in any way. And I think, I can't imagine him giving Trump a gold statue. Just, he couldn't have done it. He would have sent Tim to do it maybe, or whoever.

A (50:36)

But which would have really drawn.

B (50:37)

I think he would have had a different way of thinking. Like, okay, this is not good for Apple in some fashion. So I don't know. I don't know. I just was, I had been on your side and I was like, you know, that person's kind of right. Like, we're creating a less good system in this country for our finances. Cleanest companies like Apple, like, we're causing them to commit unnatural acts for no good reason except to get no tariff that shouldn't have been there in the first place. Like, that's where it's bad. But there is no pushing back with this, with this guy.

A (51:08)

No. And I think that one of the things we're all seeing in real time is the limit of everyone's power. We have to operate in the system.

B (51:17)

And so there is one power, mortality. And this too shall pass is my feeling on this one.

A (51:24)

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B (51:26)

Was, was.

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A (52:54)

So one of the things that happened, like the opening scene of your book, is the big meeting in 2016 of all the tech leaders with President Trump, or soon to be President Trump, including Tim Cook and Peter and everybody. Everybody. And that sounds so quaint compared to what's happening.

B (53:09)

Agreed.

A (53:10)

And in this election, we had a big swing in Silicon Valley, which is formally Democratic stronghold, to very vocal support.

B (53:18)

Some of them, I don't think it's as. I don't think it's as deep as you think.

A (53:24)

It's certainly a solid faction.

B (53:27)

Let me say Mark Andreessen was always a jerk. So was basically, they were always selfish pricks. And this just gives them the opportunity to show us their selfish prickishness without all the performative nonsense they did before. Sorry.

A (53:40)

So one of the elements of it, which is always surprising to me and you talk about a lot in your book, is this sense of grievance or victimhood. And you talk about Mark Zuckerberg learning, you know, as soon as you get beyond a certain size as a company, people stop celebrating your genius and praising your product, and they start to criticize you. It was very confusing. But that is a stage that we all go through.

B (54:04)

They never get out of it.

A (54:05)

It's a startling stage. Why am I suddenly being criticized? And as you say, you know, I gave the world Facebook. Why don't they love me?

B (54:12)

Because you gave the world Facebook.

A (54:15)

But so where does this victimhood. I mean, given the fact that we are now dealing with a relatively small number of people who have more power than almost anybody in the world and unfathomable wealth, how can you still maintain a victim mentality?

B (54:33)

You know, Nick Clegg just talked about it, trying very hard to pretzel himself. Not to insult Zuckerberg, but that's precisely who he was talking about. I have talked about this, you know, this weird victimization thing. While they have. I'm like, literally, only people with a gun to the head of everyone else would call themselves a victim. Like, it's it's really just. That's an observation I'm making. I'm like, whoa, wow, the victim mentality massive with these people. I don't understand it. I mean, I do wanna. Since I have so many children, like it's not my fault, you know, but it is. It's a lack of history, it's a lack of education, it's a lack of parenting. It's a lack. You could look at a lot of things, but they really do have. I think it comes down to they're so powerful and everyone around them agrees with them. And they slowly eliminate the people who don't. Who are giving them good feedback. And only the adults are willing to engage among Mark Cuban, Reid Hoffman, Evan Spiegel. And I started off on a very ugly foot. Trust me, he was really mad at me. But we had lunch and he's evolved. And so the ones that evolve, evolve. The others surround themselves with people and the expression I use who lick them up and down all day. And therefore they just. They're like. They're aggrieved and it's so fascinating. I think someone will study it someday and. And you know, again, I'm not the only. Like Nick Clyde used to push against this when I would say this all the time. And now that's his little talking point on his book tour. By the way, he won't come talk to me, FYI, like, you'll get him. No, I won't actually, because he's a chicken shit. Nick, you're a chicken shit. And you should come on if you're. Don't mouth stuff I've said for decade and then not come on my show, like. Cause literally that's something I've talked about. I just don't understand their victimization, you know, they're perpetually damaged people. Like Andreessen's a good example. He had a very difficult. Something happen with his parents that he doesn't talk to them. He's just. He's always been mad about something. Like, I've never met more people who are so rich and so unhappy. Like unhappy as people and that I don't get. And their happiness is. The happiness they have is mean happiness. Like someone got fucked, I fucked someone. Oh, I beat them. Oh, that like dunking is their favorite thing and it's pathetic. They're pathetic is what they are.

A (56:59)

So as you talk about this group of people that you've gotten to know and watched and so forth, it often seems like, and correct me if I'm wrong, that you think the main motivation that very few people are willing to admit is money.

B (57:13)

Money.

A (57:13)

It's just getting more and more greedy, what have you. So I would respectfully suggest that there also is something in a. What you just described the filter bubble. I'm amazed as I watch different billionaires venture onto Twitter, for example, and start speaking their mind and thousands of people cheer and say, oh, it's great to finally have you speaking that. When you are surrounded by people telling you you're a genius all the time. Yes. That becomes to be something that you think. I also think there's something in what Mark Zuckerberg said in a speech that you quoted where you do to be willing to be misunderstood or have people mad at you for a while or learn to do an experiment.

B (57:54)

Yes, I get that. Me too. I'm like that. But he's not Leonardo fucking da Vinci. I'm sorry.

A (57:58)

No, that's true.

B (57:59)

I bet he's not a whiner.

A (58:01)

Then. The last thing I would say, which I think is actually a driver for a lot of this, and specifically focused on a moment with Travis Kalanick, the former CEO of Uber, where tech is a winner take all. Business. Business media is not. There can be many, many media companies and voices that do well and so forth. Tech, it pretty much usually evolves to the winner, a couple of others who are hanging on, and everybody else is toast. And so if you're gonna compete, you gotta compete to win. And it is all. Everything is on the table. It is certainly the. The wealth that you have, the paper wealth, all of your employees, jobs, all of your investment winning.

B (58:42)

Like, is that the right way to win? Is there a stone soup way of winning that everybody wins? Like, they can't even conceive of different ways of winning. And that shows me a lack of creativity, a lack of imagination, a lack of any kind of wisdom. And so they can't imagine it being better for everybody versus just themselves. And that's why ultimately they're not. It's not a winner. It's. It doesn't have to be a winner take all. It can be a diff. The way you conduct yourself can be different where it takes into account many more things. I just find some of them so small. I find them to be small people. Like, I don't think of Leonardo Devar da Vinci as a small person. I guess I'm not a historian, but Thomas Edison was supposed to be a real asshole and I believe it. Like, when you read those books about him, you kind of want to have a more Ben Franklin attitude to entrepreneurship. I guess he was about a lot more than just his inventions. Right. He had a bigger idea. And I think the problem is these people have been so badly educated and so in a filter bubble. I don't think it's just money. There's a million billionaires I know who couldn't be lovelier, couldn't be more interesting and try really hard. And I don't mean some of them are conservative, some of them are liberal. Like you know, I don't really care about that. I just think they, they're leaving so much opportunity on the table by being so small minded, you know, Like I just feel like there's much more they can do if they were just a little bit bigger and they just have small shriveled souls and so they can't for some reason can't do it.

A (60:24)

And so even if you accept that it's winner take all, I think, what I think I hear you saying is you can compete differently. Yes, you can be more decent.

B (60:34)

You must. In this world you must still be tough. Right? How can you sit by and watch what's happening with ice and not say something when you're in a position of wealth and like I don't know how you can do it. People are losing their jobs. I mean like you know, and people who can't afford to don't have choices like they do. I just like I always say, you know, you know, I use that this expression a lot. You're so poor, all you have is money. Like you're so poor. You're so like you don't have a bigger. If you really care about history and you care about your legacy and where things are going, is this the story you want to of your life? I just don't, I. Where you don't take response. It's just, it's not a. I mean I hate to be gender but it's not. Men don't behave like this. Good men don't, bad men do or tiny men or small men. And I think they have an opportunity. Like you know, whatever you think of Bill Gates, I think he's gotten better in certain ways that I find admirable. Like what he was doing and not everything he does is great. The Epstein stuff is troubling but one of the things that he has sort of improved himself. Right. I mean he is. I ran into him the other recently and he was like what in the fuck is wrong with these people? He said you were kind of used to be like that. So. So you'd know better than Me like, you were kind of a small minded person. And the minute he started working with government, the minute he went around the world, the minute he saw things and opened his worldview, he did a lot more good and he had so much fucking money. Or Warren Buffett, or like there's so many good examples of really good entrepreneurial people who have a different way, right? Not perfect. I could point to 10 things Warren Buffett has done that's problematic, but I can point to 300 that he's done. That's great, right?

A (62:21)

So what is the solution to this? Because I would say that part of what's happened in the last 10 years is that very vocal factions and powerful factions have made it okay to act incredibly selfishly to the point where it's actually, you know, it's stupid if you don't. It makes me smart.

B (62:40)

Right?

A (62:41)

And that's very infectious. And it's bleeding out. And certainly it is in the tech industry. Made it okay. Okay to act like that.

B (62:49)

It is, but it's not okay. You're still, you know, I ran into someone here. There's two things. One is, I think it's going to be over relatively sooner than you think. Other people do not. They think we're headed for this. I don't. I just don't. I just think I believe in the American experiment in a way other people don't. Maybe I'm more patriotic. I ran into someone that was working for the Trump people from technology at a party. Like, I was like, oh, that person, I didn't like him this first place, so. And now I can't even hide it. Cause I don't want anything from them. Cause I'm not a beat reporter, so I don't even want information. So I don't even have any time for them, like, like whatsoever. And they're like, looks like we won, Kara. Like, that's what they said, Looks like we won, Kara. Like trying to dunk on me. Looks like you, you know, we won, like that kind of thing. And I was like, you know what you did, but you're still an asshole. And I said, you'll always be an asshole and you're gonna die an asshole. And he was like, he didn't get it over. He just, he knew it. Like, he knew what I was telling him was the truth. I wasn't trying to be a dream jerk. I'm like, you're still. It doesn't matter how much you win, you're still an asshole. So. Okay, Are you proud of that? Is your mama proud of that kind of thing. And I was like, you're just really pathetic and in me D what's it called when you take away their penis? Just remove their penis from their body. I was like, okay, I'm still not gonna go out with you. I'm still not having a drink. I don't like you. Like, like they were so disturbed by it. They were like, well, we want. I'm like, yeah, you're still an asshole. Nobody likes you. And by the way, nobody liked you before. But you know what I mean, like just here to tell you. And I think I wasn't telling an untruth. I think I was telling a truth. And that was interesting. That's one thing. Two is when you behave like this, you, you, you, you tarnish a possibly good legacy. When you don't learn and evolve and you don't spin forward and you're always taking from people. Ultimately I'm not a religious person. I wish I was. But there is a price you will pay at some point that there will be a price. And maybe you don't know it now, but you just don't. We just don't know the end of the story. And that's why it seems so grim because we don't know the end of the story.

A (64:56)

But you seem optimistic.

B (64:57)

I am.

A (64:58)

That there is a self corrective mechanism. Virtue is its own reward.

B (65:02)

You have to not. Virtue is its own reward. Virtue is good for business. It is. I've done really well being pretty decent to people. I think that ultimately you have to take the long view of every single thing of history. Right. And every time when I think about autocrats, when I think about everything. There's been so much pain and destruction in this world. But I'm a student of history. I spent a lot of time that was one of my majors was history. You know, I went to the foreign service school. I pay a lot of attention to patterns. Every autocrat ends up dead and all hole that's where they end up. Or, or if you're Nixon out looking at the ocean by yourself, right. Every one of them ends up dead in a hole always. Like even in the worst thing. And they do so much enormous damage before that. And that is true because they have shriveled terrible souls. But I just don't think ultimately that's why I've been doing a lot of like here's how media is working well like stop with the fucking doom scrolling media people. Like stop it. Let's talk about what works and let's get on that. So I just don't have time for these terrible people. I think is where I've always been and I'm still there. And I just don't think history is on their side. I just don't ultimately.

A (66:18)

Two last questions. So on the media, optimism, not all media. We talked a lot about your incredible rise. What's your advice when you speak to young people and they'll say, how do I make it in journalism? How do I make it in anything? Given that now all of our jobs are gonna be replaced apparently in 20 minutes they are.

B (66:37)

That's not true then you lack imagination, you lack entrepreneurship. I think you know, I talked to Katie Drummond. I did a thing with Katie Drummond, Dave Jorgensen and Oliver Darcy. All of them doing different things, right. Look, Katie's just running a big organization, but boy, is she killing it, right? She has a point of view. She's doing, she's making good stuff. Like I always, when I say to young people, they're like, how do we win? I go make good stuff. You make bad stuff, you lose. I don't know what else to say. Reporting, reporting, reporting. Learn to write and learn to express yourself. Whatever it's video, audio, whatever it happens to be. And take a fucking risk. Don't like write about people and insult them for like tear people down and then don't take risks yourself. Like and, and if you do that, if you make something people, it's like cooking. If you make a good steak, people are going to eat it. They are, they are, they are, they are. Always. Every time, time you're not going to be. There's no lights under bushels here. There really aren't. They just aren't. You know that and you, and you can tell the people who are going to do it and when you fail, it's fine. Like really, you know, pick your head up and look at these poor. Like, like I, I have a guy who's, who's doing, just did some nice landscaping in my house and he can't come by because his whole staff is hidden in their homes. Like, pick your head up and stop complaining. Like when those people can't get to work and they live hand to mouth. Like I just can't. I don't want to hear it from those from educated media. I just don't, I don't have the time or the inclination. So I mostly reporting what I would say then.

A (68:09)

Last question. Lots of people today are looking back and saying, oh, it's the AI bubble. It's just like dot coms too. And this consensus has emerged. That is, I think, an echo of what we all learned with the dot coms, which is, here's what's happening, happening. It's this crazy bubble. All this money is going to be burned, it's all going to crash, and then a few winners are going to grow into this great golden age. So that's the consensus. Is that your consensus? What do you think's going to happen?

B (68:36)

You know, look back to your history. I think $400Amazon price was pretty accurate as it turned out. I think you have to take the longer view. Like, yes, I think probably what you're saying. I think there'll be a lot of messiness along the way. I did an interesting interview with Steve Ratner the other day, who himself is sometimes a controversial fig, and I think he was right that there should have been no technology change that hasn't caused enormous pain, but also hasn't ultimately resulted in a more. We just don't know. If you and I were looking at like the Internet in 1996, 7, we wouldn't have thought of Uber, we wouldn't have thought of cell phones, we wouldn't have thought of like any Airbnb. What the fuck? It's not that hard a thing to think of. We just don't know. And that's, I think, kind of cool. And one of the things that would be great in this country is that we have the rule of law and not like a tin horizon, horn hand bruised, dictator type wannabe. That's not how great business is made. Our country is made because we take risks and we believe in the rule of law and people can try things. And if not, we're just like a shitty version of China who's had hundreds of years to perfect its shitty government, essentially.

A (69:46)

And so, yes, although China is doing things actually very intelligently in a way that we are not. That's right. And I would say way. It's seeing the bubble again.

B (69:54)

That's why I say a shitty version of China.

A (69:57)

Exactly.

B (69:57)

Maybe Romania, Great Turkey, nice food, but otherwise not the most exciting place to do business.

A (70:06)

But as I hear about the rhetoric about the bubble and people are being so stupid and all this money is going to be wasted. The amazing thing about this, and we've seen it since canals and all the different canals.

B (70:17)

This is just a big train.

A (70:19)

Exactly. It's just a big R and D lab.

B (70:21)

Yep.

A (70:21)

And if you've ever done any kind of R and D, you know that most of the money is going to be wasted. And then a couple of experiments will Work and so forth.

B (70:28)

And then untold wealth.

A (70:29)

Yes. This process is actually incredibly valuable and normal. It's not stupid. It doesn't have to be a morality play and people don't know. And I would say that's one of the big takeaways that I had about the dot com bubble afterwards is I also expected this pattern. I wrote about that in 1998. Here's what's gonna happen. There's gonna be a big crash. The winners will go on. What I didn't realize is how many, what percentage of that original class of companies were going nuts on were toast. The only survivor from that era is Amazon. And so looking at it now with the thousand new AI companies and the incredible valuations and so forth, that's what I think about. It's like first of all, we don't know whether it's 1996 or 1999. That's the question.

B (71:14)

I honestly don't care if black student loses people money. Good. That's their business is to lose and gain money. Right. I don't care. No.

A (71:21)

And they'll be fine. They're diversified and so forth. But that's the other takeaway is it may be that this first crop gets wiped out.

B (71:29)

They will get wiped out completely. You know that, right? You know, so that they're gonna get.

A (71:34)

Anyway, it is such a pleasure to be.

B (71:36)

Thank you, Henry. And congratulations on your next chapter as a podcaster. You look good in those headphones.

A (71:42)

I'm learning from you.

B (71:43)

You'll be fine. But you should like I like the idea of listen solutions. Really. There's always a solution. And if, if not just lie down and die. Like I don't know what to tell you. Like yes, right now I live in Washington. There's all these fucking ICE agents. They're stupid fucking masks and by the way, a bunch of cowards to do that. It. This sucks. That's correct. Now what are we going to do about it? That's the whole now what are we going to do about it? Should be the mantra for everybody. Like stop fucking whining. Get your stand up and help people. Help other people stand up and do something about it. You know, and they don't. Just cause they're winning now doesn't mean they'll win later.

A (72:22)

And what should people do?

B (72:23)

Just whatever, whatever, whatever. I hear the funniest things. I don't care. And people, of course. The other day I heard a bunch of white ladies is putting a Mexican flag on their cars in California. And then ICE stops them. And then it wastes their time. And I was like, well, put your Karen Ness to good use. And then they yap or tip them so they like. Four hours of yapping with a irritating white lady takes away from grabbing someone. Stop insulting that. It's good. Like it's good. I love it. I'm gonna put a Mexican flag on my car cause I'm a really irritating white lady. So like, I don't know, whatever. Figure something out. You're American. You can figure it out. Anyway, I gotta go.

A (73:04)

Thank you.

B (73:05)

Love you.

A (73:07)

Solutions is produced by Megan Kun Main. Jim Mackle is our video editor. Our theme music is by Trackademics. Nishat Kurwa is Vox Media's executive producer of podcasts. Thanks for listening to Solutions from the Vox Media podcast network. I'm your host, Henry Blodgett. We'll see you soon.