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Guys, Smart Girl Dime Questions is taping live at the Comedy Cellar in New York City on Monday, April 20th. And you're invited. Our guest is Neil Degrasse Tyson. And the big question is, what do we do if we encounter an alien? And how would we know if it's an alien? And do aliens even exist? If you're in New York, join us. Details are in the show notes or on Instagram or TikTok. We're at Smart Girl Dumb Questions. You can grab your tickets and come meet me there. And while I'm here, let me remind you to please hit follow on this show wherever you are listening to or watching it and share it with all your friends and parents and aliens and everybody. Every little bit helps. Thank you guys so much and I hope to see you on Monday, April 20th at the Cellar. Does Elon live rent free in your head still?
B
No.
A
He pays you rent because I know he lives in your head.
B
No, it's simply not true.
A
Does Silicon Valley run the country now? This is Smart Girl Dumb Questions. I'm Neymar Raza, and today my guest is Dick Costello, the former CEO of Twitter. How happy are you to not have that job anymore?
B
Well, it's been a while. Geologically speaking, it's the distant past.
A
Dick is a Silicon Valley icon. He's best known for running Twitter from 2010 to 2015. You took it public during that time.
B
Correct.
A
You have started companies and you have been in the Valley for three plus decades and even consulted on the show from hbo Silicon Valley.
B
Yes, I was in the writers room for a little bit.
A
Did you enjoy that?
B
It was great fun.
A
I can tell you love giving notes.
B
So I give a lot of notes. There's a lot going on in this room. For example, the black and white Rorschach thing with the tables.
A
Oh, they're design notes.
B
The neon out of the corner of my eye, the chair that's like making me feel like Alex Karp where I have to constantly scoot around.
A
Don't start gy writing.
B
I'm gonna. You have to. You're nodding as if to say, let's move on. Your foot is twitching as if to
A
say, this is my note to the producers that we're gonna cut this. You're gonna see me doing a lot of this. This episode is gonna be shorter than most people have sex. Okay. Feel like a good 8 minute episode. Smart Girl Dumb Questions. Okay, let's just lay it out here. This is a trade. Okay. Dick is a rich, powerful person.
B
Wow.
A
And she has come here to the penniless, powerless world of podcasting to take it over. You have.
B
Do you mean with my own podcast?
A
You're just invading.
B
Don't say rich, powerful person. I'm just a hapless yeoman. You know, I wake up in the morning and, you know, ask my butler to get straw, just like you.
A
Just like me. But you have.
B
You've started a podcast, the creatively named Nick, Dick and Paul show.
A
Because hundreds of millions of dollars were not enough for you, Dick. You also needed some fame.
B
More.
A
Yes, exactly.
B
There's always more.
A
There's not more to be made in this business, let me tell you. Not that much. You lured me here because weeks ago, Dick and I were at dinner. Yes, and you said that you have the archetype of the perfect man for me.
B
We're going right to the archetype.
A
No, we're going to save it for minute 57. This is called. This is called foreshadowing, okay? I'm gonna teach you all the things you need to know for your little Nick, Dick and Paul show. Don't worry. So this is foreshadowing.
B
Great. It's a literary device you brought to the podcasting world.
A
So we've agreed to this trade where you get to flack your podcast on my hit podcast.
B
Excellent use of flack.
A
And you will tell me the secrets of the universe to end up.
B
And the archetype.
A
And the archetype.
B
We will describe the archetype.
A
But thankfully, despite this trade, this is not just a con to my audience. You are, in fact, a genius on many things. Silicon Valley.
B
Wow.
A
So we're going to talk about everything. We're talking about venture capital. What is it? Is it a big Ponzi scheme? Is Silicon Valley, like, running the country now, or is D.C. running Silicon Valley? We don't know what the power structure is. We're talking about whether Twitter is still relevant and whether SpaceX is worth $1.5 trillion.
B
I think it's probably going to be worth more than $1.5 trillion.
A
Yeah, but how much more? We're going to talk about if poor people like us can make money in the public markets anymore. You just capture it all in the private markets before we get there. Okay. Thank you for coming.
B
You're very welcome. Happy to be here. I live just, like, a couple blocks away.
A
I know.
B
Well, very part time to the tax folks listening at home. Hardly ever. I'm almost never here.
A
Thank you for coming and talking publicly about your tax avoidance on the show. So here's my first question for you dick. Do you think it's possible that Elon Musk is an alien and he's just trying to go home?
B
He certainly seems to know a lot about a lot of things that are in advance of them actually happening. So you could say he's from the future? I think some might say he's from the future, yes.
A
You have said that. He's proof that time travel exists. I think you treat it like that.
B
People would say, like, elon is sort of proof that time travel is possible, but I doubt he's an alien.
A
Are you in touch with Elon?
B
Well, define in touch. No. The short answer is no. Define in touch. No matter how you define it. I'm gonna go, no.
A
No, you're not. But have you. But you didn't interact with him? Cause your times at Twitter were.
B
No, we've interacted, but it was when I was like, CEO or, you know, between. After I left, but before he took over. We've. We've bumped into each other things.
A
Do you and Elon follow each other on Twitter?
B
I have a funny story about that.
A
Oh, tell me.
B
The day that I got up in front of the company, announced, like, I'm leaving. Jack is going to take over as CEO. Jack Dorsey, the founder of the product. I got. I got off stage after, you know, saying a few words, and Jack started talking, and I looked at my phone, and it said, elon Musk has unfollowed you on Twitter. Right away, it's like, wow, right away.
A
Did you take that as a sign of your looming insignificance or irrelevance? How did you interpret that?
B
You know, I had a. I had a. I got invited to, like, the Vanity Fair Oscars party once when I was CEO of Twitter, and I didn't go, and my daughter was like, why didn't you go? Like, you got to. That's like, the party. You got to go. And I was like, rose, I'm being invited to this party because I'm the CEO of Twitter, not because I'm Dick Costello. And I want to go to things that I'm being invited to because I'm Dick Costello.
A
Like, the smart girl, dumb questions podcast.
B
Like, this particular podcast, which, even without the role of CEO of Twitter, here I am.
A
Because you have the archetype. Let's be honest. That's the only reason you're here.
B
The only reason I'm here is because I have the archetype. But I didn't want to become bound to the trappings of the role, because then I would be like, nah, I can't quit. I won't be able to go to the Oscar party next year. When I quit, I didn't really care about any of that stuff because I just wasn't tied to it.
A
Well, we're going to come back to Twitter, but first of all, I just want to set the scene of Silicon Valley for a little bit. You arrived there in the. What was it, like, the 90s?
B
You say that like it was a long time ago.
A
It was ages ago, right? Was it the 90s? Yes, it's like. It's. The Netscape IPO is happening.
B
It was before the Netscape IPO, but
A
you were around during that first boom and then you were there for the dot com crash.
B
Yep, I sure was.
A
You were there for the revamp of Silicon Valley after that.
B
The relaunch, if you will. The reinvigoration was there for. And then the 2008. 2009 crash. The famous Sequoia PowerPoint deck. RIP. Good times.
A
I don't know that. What is the famous sequoia?
B
In the 2008, 2009 crash, they issued this deck to their companies and founders. That was like, party's over. But of course, as we now know, in hindsight, lots of the benchmark seminal companies were created and launched at that time. Uber and, you know, on and on and on.
A
We're hearing that there is some construction, by the way, for people listening to the podcast. So if you hear noises while you're watching or listening to this, it's okay. Someone's building a beautiful kitchen above us. It sounds. It's going to be great. We're going to show you in a future episode.
B
Yeah, future episode. We're going to go up there and look around.
A
Exactly. In the next episode.
B
We should do it at the end of this episode.
A
Queer Eyes and a Straight Girl.
B
We wouldn't have to sit in these uncomfortable chairs.
A
Do you want a pillow for your back?
B
No, I don't want a pillow for your bath.
A
Because you've been in Silicon valley since the 90s, so I figure you might need a pillow.
B
I think that's a thing you do when people start to give you notes on the decor, they're like, oh, do you need. Do you need something for your feet?
A
I want people to know, because I've never been this mean to a guest before, that I actually know Dick and I love him very much.
B
Do you need more comfortable shoes? You look uncomfortable.
A
No, no, I'm just uncomfortable because there's, you know, a very rich man creeping into my industry. Who's. Who's found himself in a chair next to me right now and I feel threatened. That's what it is, Dick. But it's okay. I won't need to work once you give me the archetype.
B
I suspect you'll just get married and race off into the sunset or something.
A
Exact trad wife.
B
I don't think that's. I don't think that's what's going to happen.
A
You don't think I can be a trad wife?
B
No, there's zero chance. No, of course not. Trad wife. You can't be trad anything, okay? You've Never had a 9 to 5 job.
A
This is true.
B
Am I. Am I right?
A
That's true.
B
Let me ask you a question. Have you ever gotten up in the morning. Forget about whether we're talking about job or anything. Have you ever gotten up in the morning at like 8 Monday, Tuesday, Wednesday, Thursday, Friday and gone to a specific place those five days in a row?
A
Oh, not just one of those. That, like if I'm filming something. So if I'm filming a film for 21 days of production, I might do that.
B
All right. You've been in movies.
A
I've filmed movies.
B
Oh, you made the movies.
A
I've made movies. Great.
B
I didn't even know that.
A
See, we're all learning something for behind the camera, Dick. So you were there for this dot com bust, the 2008 crash, the whole
B
Covid crash, Up and down, up and down, up and down.
A
Are we in a bubble right now or am I just too poor to understand the math?
B
I think the reality is, and it's. Of course, it's never as simple as yes or no, because probably we're in a bubble on some things and not in a bubble on other things. Like, for example, I think once SpaceX and OpenAI and some of these others go public, some of the traditional SaaS companies that have been beaten up will probably race back upward again as people realize, oh, they're not all in that much trouble anyway. I think that AI is such a monumental shift that. Where there's probably a lot more room to run. The stupid thing people always say is we're in the first inning, which I always hate. Like, no one's ever, like, we're in the seventh inning. It's. Is it always the first inning? Why is it always the first inning? Like, I mean.
A
And what does that mean when they
B
mean, like, it's still. What they mean is like, oh, it's still early. Like you think it's Been going on for a while, but it's still early and there's still plenty of new things to do in AI and it's going to. It's got so much more room to run.
A
What they are saying in that is that there's still so much upside to be had. Is that what they're.
B
That's what they mean?
A
Yeah.
B
Yes. That's generally what they mean. And I think that's probably true. Having said that, a bunch of these things are overvalued.
A
You want to list three industries you think are overvalued?
B
No, not industries. I think some of the companies are overvalued. You know what happens is people miss out on the anthropic and then they're like, oh, I gotta. I missed out on that one. And they get FOMO and they have to go feel like they have to make an investment in the space, so they go to this. The one in fourth place, and whatever that one is, is probably not gonna work out as well.
A
And you have a fun now with two partners.
B
A fund.
A
A fund, Yeah.
B
I felt like you didn't say the D. Okay.
A
I thought. Yeah. And you didn't want anyone to think that you had fun. You want. Very clear.
B
Let's be clear. It's a fund.
A
You have a fund.
B
Yeah.
A
And it's called.
B
It's called O1 Advisors.
A
Oh, 1 Advisors. And it's three operators.
B
Yeah, it's me, Adam Bain, who is my CRO, who was CRO at Twitter when I was there, chief revenue officer. And then when. When I left, he was chief operating officer with Jack. And then our third partner is David Fisher, who was the chief revenue officer at Facebook, slash Metta for 11 years.
A
The term operator, when someone's like, oh, that person's an operator. First of all, can be many things,
B
like, you don't care.
A
In colloquial English, it means like, that person's manipulative. That person's an operator.
B
Yeah, Smooth operator. But in Silicon Valley, to quote Sade.
A
Oh, yeah, smooth operator.
B
Well done.
A
But in Silicon Valley, being an operator is like a very good thing.
B
You know, you ran the company, you ran some division of the company. You've got experience doing it, you've made all the mistakes, you know what to do, what not to do, et cetera, et cetera.
A
And it's very distinguished from a founder or can there be founder operators?
B
There can be founder operators. So Zuckerberg's a founder operator. Both the founder and runs the company. But then lots of founders are like, I don't want to, you know, they get to 30 or 40 people and they're like, I hate managing people. I wanted to build a product. I want to go back into my room and, you know, code the Yahoo founders, for example, Jerry Yang and David
A
Filo or Jack Dorsey of Twitter who like wanted to run it then didn't want to run it then wanted to write it then why to sell it. That want to be. They want to run something else altogether.
B
Right now, for example.
A
Yes. He's. He's in all the. He's in all the feelings. And you guys have like a billion dollars almost in assets under management.
B
Just under. You never want to have a billion.
A
Really? Why
B
you were so earnestly like, wow, that's really. That's an interesting. That's what an insight. You always want to be just under.
A
Yeah.
B
You know, you keep your feet on the ground.
A
Smart girl.
B
Time questions start running around with a billion dollars like everybody's listening to me. Everyone thinks I'm a genius. I don't know.
A
I thought because, you know, you might have some like tax avoidance scheme where you're like have to be in New York for fewer than 100.
B
Part of your giant tax avoidance scheme.
A
Exactly. I thought there was something. Okay, so SpaceX is going to IPO. It's 1.5 trillion is the IPO price.
B
I think it'll probably be more than
A
that when it IPOs.
B
Yeah.
A
Wow. So add IPO. But this is what it's like.
B
Look at Tesla. Like, Elon has got this capacity, I would say unusual capacity and certainly remarkable capacity to his believers are all in. When SpaceX goes public, it'll run up tremendously. I think 1.5 trillion is probably. Probably ends up being much more valuable than that in the first week of trading. Which is a crazy number, by the way. I think we can all agree.
A
Of all time. And just to give a sense, Nvidia is worth 4 trillion in market cap today. Apple is worth what, 3 to 4? Something like that. And now SpaceX, which now has acquired Xai and acquired Twitter. Your little baby X. So now it's like this kind of thing.
B
Conglomerate.
A
Yeah. Matryoshka doll of Elon Musk Enterprises. It's amazing that they won't just swallow up Tesla as well.
B
You never know.
A
Could happen.
B
Could happen. I would think that that's probably something like that on the horizon. Is just a guess.
A
It's just.
B
Yeah, I would think that's not sort of a unique insight. There's a bunch of people have said that.
A
Yeah. But $1.5 trillion is a lot of money.
B
Yeah, it's a lot.
A
It's a lot of money, Dan.
B
It's a lot of money.
A
I know you might not feel it's a lot of money because you have much more money than me, but is a lot of money.
B
People are going to start trying to kidnap me. The way you're talking about it. I mean, spent all my money.
A
Yeah, but you have to go to. Not in New York City, please, because he's only here for 80 days a year or whatever it is.
B
What's far fewer?
A
I feel like we should tax people for every day that they're in the city.
B
We do tax people for every day that they're in the city.
A
No, only for their income.
B
Oh yeah, their income. Well, what else are you going to tax? Their clothing? Like you give me that shirt.
A
No.
B
Hey, you've been walking around for the last week.
A
The interest on their wealth. Well, you just made $84 in this last second that I spoke.
B
There's a whole bunch of reasons you don't want to do that, but we can talk about those on another podcast called the Smart Girl. Rich Girl Podcast.
A
In five years. Just give me five years. I'll get there too. But just to give a sense, like, Amazon went public in, in the 90s back in the day for $400 million. It is now worth $2 trillion.
B
By the way, you won't recall this, but I do. There are a bunch of people who are like crazy overvalued at 400 million.
A
Yeah. Oh, yeah, because actually Andrew Ross Sorkin said that there was like, they call it like Amicon or something.
B
Amazon dollar It'll never be profitable. This is crazy. You know, they can never make money. I mean, Bezos, famously, the stock actually then collapsed to the point where I think it was like less than seven, eight dollars a share. And he had to borrow a bunch of money from Warren Buffett to like keep Amazon going.
A
You should have lent him money at that point.
B
I know. Why didn't you come to me? You got to go to the guy who already has all the money.
A
Exactly. So I guess my big question here, my big dumb question is like, can anyone still make money in the public markets? Because when companies like Amazon went public at 400 million, now they're worth 2 trillion. Lots of people made money. Ordinary investors, which is still a small percentage of the population writ large. Google also went public in the early aughts, somewhere around $30 billion shy of $30 billion, now worth $3 trillion. So we're talking about, like, companies going up 3000x, 100x, that's how much these companies have multiplied over time. Or 4000x. I think I'm not doing the math right. Is it possible that SpaceX will be worth 100 times its IPO price or 3 to 4,000 times its IPO price?
B
Probably not.
A
So this is my concern.
B
But look, if you had bought Nvidia five years ago or even four years ago, just pre ChatGPT, post OpenAI, but pre ChatGPT, you would have made an extraordinary amount of money if you invested in Nvidia at the time. And it had been a public company for a long, long time.
A
But it seems like a lot of the value now is captured in the private markets and the secondaries and everything. There's so much fun right now.
B
It's actually captured in the private markets for an interesting reason. The most likely reason that companies don't go public until they feel like, you know, I mean, look at Stripe. $150 billion company. It's been around since the, you know, 2006, 2007, and is extraordinarily valuable and still private.
A
You know, they offered me a job in 2014, and then they offered me a job again in 2015.
B
Should we change the name of this podcast at Dumb Girl? Smart Questions, or.
A
I mean, just keep it Double Dumb. I think it's fine. The Double Dumb podcast. You're saying there's a good reason why the money is being captured in private, in private markets. And what is that good reason?
B
There was a time, and that's actually when I was running Twitter, where once you had more than 500 shareholders, you needed to. You had to start filing quarterly earnings reports with the sec. So you didn't want to ever get to more than 500 shareholders. And so if you had, like, an employee wanting to sell stock, you had to sort of route it to someone like Ron Conway to, like, please buy all the stock that these employers are trying to sell. Because if I get more than 500 shareholders, I basically have to go public. And so what would happen is once you had a certain number of shareholders, you're like, well, we got to start filing quarterly earnings anyway. We might as well be a public company.
A
So, because that's what a public company is. It's a company that files quarterly earnings. There's so much more to that.
B
You have to. You have to report your earnings publicly every court, and maybe soon not because they may get rid of that, which seems crazy, but that's another, another thing altogether. But once you have to file quarterly earnings publicly and do all the work. Like, well, we might as well allow our employees and the management and board and everyone to get liquidity. So, anyway, long story short was could only have up to 500 shareholders before you basically had to be a public company. And the SEC got rid of that rule early 2010s and. Which is why companies now are like, great, we can just stay private forever and we can have 9,000 shareholders and we don't care.
A
But you took Twitter public in 2013. Yes, after that was changed.
B
The short answer is yes, after that was changed. But the longer answer is we were sort of already in process.
A
And you think if that hadn't been the case of this regulation Twitter, if
B
I went back and could do it all over again, I would have kept Twitter private for a lot longer.
A
Okay.
B
Yeah.
A
Thankfully, Elon is fulfilling your wishes. Is venture capital like a bit of a Ponzi scheme?
B
A Ponzi scheme?
A
Yeah. I asked that and then I realized that I don't really know a Ponzi scheme. What is a Ponzi scheme?
B
A Ponzi scheme is they'll let people left holding the bag when the music stops, lose all the money. What ends up happening is you've got a bunch of people at the top who are getting kicked backs from everybody below. Also why it's called a pyramid scheme. And then the people at the very, very bottom are just the ones left holding the bag when the business goes.
A
I think a Ponzi scheme is like tying the value to something in the present to someone in the future that doesn't currently have that.
B
I think we should spend the next half hour trying to define Ponzi scheme.
A
We should probably, like, look it up. But I think it's more. It'll be funnier if we do this whole podcast than have to issue a fact check.
B
Yeah. Yeah. The interesting thing is when I just described a pyramid scheme, it may not actually be the same thing.
A
I don't think it's the same. I'm actually going to look at it because I believe a pyramid scheme, which is multilevel marketing, is different to a Ponzi scheme.
B
I was defining an MLM business.
A
You are so a Ponzi scheme. I will. I will ask Chat Daddy and he will tell me.
B
Are you. I knew you were a Claude girl.
A
I'm actually Gemini. A Ponzi scheme is a fraudulent investment operation where returns are paid to existing investors from funds contributed by new investors.
B
There you go. Like, what's like. Sorry, like Madoff, Bernie Madoff.
A
Yes. Rather than from the profit earned.
B
Yeah. So he's. He's taking investments from new people into the Bernie Madoff fund, and he's using that to drive returns, early investors. And of course, you end up running out at some point, you run out of new money, and the people who are the latest money lose all their money.
A
Yeah. So is that your business?
B
That's more of a Ponzi?
A
Is that what you do?
B
No, that's not what venture capital is, People.
A
Venture capital has this rap because there are a lot of people left holding the bag on certain companies. That IPO during that, that boom that you described. The kind of post 2008 company boom where everything was a tech company. Like, you might do laundry, you might rent clothes from your closet, but it's a tech company and it's going to get a software B2B type of valuation. Like, there are companies whose market cap is now less than the total amount of venture capital that they have. Companies like Rent the Runway, et cetera.
B
That always. That happens all the time, though. That's happened throughout, like, I mean, 2001 with pets.com and, you know, you name it, WebMD and all these companies that raised tons and tons of money and ended up being valued at less than the money they raised. That happens constantly.
A
Silicon Valley is full of these discerning investors on Sandhill Road, like through the series A, B, C, choose your bra size. Like, shouldn't they figure it out that these companies are not worth that much and stop investing in them?
B
Both things can be true. They can be worth that much at the time and then worth nothing at all. I mean, look at things like AI is going to disrupt companies that are worth an extraordinary amount of money right now, and then in a year or two from now might be worthless.
A
But that's not what happened with a lot of these companies. A lot of these companies were overvalued because they were sure. Applied tech industry multiple. Yeah, has that.
B
That happens all the time, though. I mean, like you. You get easy to say in hindsight. I don't know. SBF put 500 million anthropic early on. And people were like, well, that was crazy. Like, probably would have returned the Sam Beckman fried to all of his investors 90 times over by now.
A
Now it's worth like 300, 400, $380
B
billion in their last race. I'm really going to do the Alex Karp thing here because I think we
A
should get you a pillow.
B
No, I don't want a pillow. I feel like Pillow is, is giving up. If I get a pillow, I feel like that's defeat. And you'll be like, I knew you needed a pillow. And then you'll constantly be asking like, is that pillow helping out your lower back issues?
A
But I think that a lot of people right now around the country are mad at people like you.
B
Let's not say like me. Let's not go with me.
A
Why?
B
Let's go with others.
A
Okay. With other, they are mad with other
B
people who are like, no, it's fine, you can use, you can go ahead. Make me the, make me the voodoo doll.
A
There is a sense, and we're talking now about an AI revolution and people in, you know, I've, I've heard various investors and founders say to me, oh yeah, it's going to be a K shaped economy. Describe for people what a K shaped economy is and try not to fuck it up like the Ponzi scheme thing.
B
A K shaped economy, generally speaking means in the past, if, you know, we were all in the same boat, if there was a recession, we all suffered, the wealthy suffered, the working class suffered, etc. If things went well, we all benefit. You know, rising tide raises all ships. K shaped economy is AI will make companies more productive because they will need fewer workers. So the shareholders, people who own stock will gain wealth while the working class or, and, or white collar folks who don't own as much stock and now lose their jobs will become more impoverished. And I think that's probably true.
A
Okay, so no middle class effectively is what it's saying in the shape of our economy.
B
I wouldn't say zero middle class. I would say the, the wealth gap gets more dramatic. More K like than, more K like than you. Like than whatever. Yeah. Meaning there becomes a divergence between the wealthy or getting more wealthy because companies are more productive and spinning off more profits and people who don't own stock and aren't shareholders or who are increasingly jobless with fewer opportunities, that's of course very bad.
A
Yes, you're saying this so matter of factly, but it is very bad.
B
It's very, very bad.
A
Very scary.
B
Profound implications for our society that we're not doing anything about right now. Which is worse than the implications, initial implications of the K shaped economy are the implications for not doing anything about it.
A
See, now they're gonna not like people that are dissimilar to you because now people like you. Because you think there should be some kind of band aid to deal with this.
B
Well, I don't, I don't look and so people go will immediately say like, oh, you can't have universal basic income. There's tons and tons of possible solutions to this. But the fact that we're not even talking about it and that there's almost seems to be zero policy discussion around it. And instead it's, you know, we have to have more liberal, I don't know, crypto markets and whatever markets is sort of like, well, that's probably gonna cause problems down the line. Not doing anything or thinking about this right now.
A
It's particularly surprising because Silicon Valley has never had more access to Washington. And they have said that they wanna run it like a business.
B
Yeah.
A
And they have all talked about, and some of them have even piloted UBI initiatives like, like Sam Altman in Oakland. But even with.
B
We're not, except that they're not running it like a business because our, you would never run a company the way we're running the government now at the craziest deficits we've ever had. I mean, it's actually funny when you're on boards of companies and they, they start using debt to finance the company's operation, board members and investors are like, whoa, don't take on too much debt. Let's be clear, we're not running the government like a business right now. Even though a lot of the Silicon Valley people who are currently involved in the administration would like to say they are. We're running extraordinary deficits.
A
So what does it reveal to you that a bunch of very alarm raising Silicon Valley humans are now in Washington D.C. people like AI crypto czar David Sachs, the Elon Musk who was running Doge for a minute. Emil Michael is the under Secretary of, at the Pentagon at the Department of War and previously was a chief business officer of Uber. So you have these people from the valley in Washington D.C. and yet there is very little prophylactic or other planning happening for the case economy.
B
Excellent use of the word prophylactic by the way. That was great. You have a remarkable vocabulary. Thank you.
A
English is my second language.
B
Well, there you go.
A
Slightly racist that you felt the need to point out that. My English is good, Dick.
B
But I didn't know that English was your second language when I said it. No, no, it was just a random compliment.
A
Thank you. So what does it reveal to you about these people who for so long lamented that this, this country wasn't being run right and if only they could be there. And now they're there. How are they doing? Give them a grade.
B
Give Silicon Valley a grade for its Involvement in Washington. Like f. It's also, it's super self serving. It's on. It's unfortunate because there are lots of policy discussions and discourse to be happening. And instead I feel like, I mean all you need to do is go on Twitter and you just see people yelling at each other. Specifically some of the people you mentioning yelling at each other like, okay, look, but there's discourse and a conversation to be had around all of these topics, but it ends up just being performative, yelling at other people because they're on the wrong side of the trade, if you will.
A
So who's like running the ship right now? Who's the daddy? Is it Trump? Is it Elon?
B
Who's the daddy of what ship?
A
Like this Silicon Valley Washington situation shift that's happening right now. I don't think who's benefiting more?
B
I mean, who's benefiting more are people who are investing in the companies for which, well, regulatory policy is being, you know, the, the floodgates are opening. But crypto, obviously, the prediction markets, you know, obviously with the CFTC grant basically granting them very liberal license to do, one would have to look at and say is sports betting, which DraftKings and FanDuel are jumping up, around, up and down about. Because those guys had to be like, wait a minute, we had to go state by state by state and get approval to do sports betting across the country. And these guys are just go to the cftc, which is a federal authority and have been granted free rein to do whatever they want. So I think the people who are benefiting are, are the precisely the folks from Silicon Valley who've gone to Washington on our getting Washington to give them free rein to do whatever they want. And of course the defense companies as well. You've got, you know, everything from these Silicon Valley investors who poured money into the new primary defense contractors like Andrew and Saronic and others.
A
Okay, let's do a little lightning round on all things Silicon Valley and then I want to come back to this question of like who's in charge? Okay. A Fuck Mary kill. Ready?
B
Okay.
A
AI Edition OpenAI Anthropic Google DeepMind.
B
Marry Google DeepMind. Have intercourse with Anthropic and kill OpenAI.
A
Okay. Okay. Another fuckmara kill Twitter threads or Blue sky.
B
I love all God's children. Naima, come on, you know this Kill threads. Oh, you're gonna marry Twitter?
A
You're gonna marry Twitter?
B
No, no, I'm not. No, I feel like that would be too like sappy but you're not gonna marry Blue Sky.
A
That's so sad.
B
I don't know. That's why I paused on the last one. I would just do. Can we do like. Let's just do an all kill round. Let's do the Pete Hegseth round. Fuck kill.
A
No, we're gonna come back to this because, like, actually, it's like Twitter is always dying, but totally unkillable somehow. And we're gonna get back to it.
B
Okay. The year I took over Twitter. This is a true story. 2010, we had been on the COVID of two magazines. A magazine was a thing that you held in your hands, like a webpage, but physical. And it described current events that you bought at a store. So Twitter was on the COVID of two business magazines in 2010, one of which it was hanging itself and one in which it was exploding.
A
It was like a little bird with.
B
Yeah. So I went up to Gabriel Stricker and I was like, goal for 2011. No dead birds on the national magazine covers. Low bar. But it's always been that way with Twitter. Like. Oh, it's. It's not. And it's.
A
And then you iPublic for $14 billion and $36 billion.
B
But who's.
A
I think you took it public for like 14 and it grew it to 37 billion. I'll give you an extra billion.
B
Anyway, it's always been the way of it with Twitter. It's still relevant. I mean, investors and VCs and founders are on it all the time.
A
Yeah. And we'll come back to this, but let's keep going with this lightning round. Is the metaverse over yet? Because I would like it to be.
B
The metaverse is over.
A
It's over.
B
It's over.
A
Meta had made a big play into the metaverse.
B
They changed the name of the company.
A
Yes.
B
And then they probably want to change the name of the company to Facebook AI or something. AI or whatever. Well, they've pivoted entirely. I think they've thrown out much of the investment in the metaverse.
A
Okay.
B
Discarded maybe, is the better word.
A
Yes. Another Fuck Marik Hill, Sam Altman, Dara Amaday and Elon Musk. As business leaders. As business leaders. As business leaders. So it will make a pg. So it's like, who would you want to co found a company with that's marrying. Who would you want to advise? That's. That's the.
B
And who would you want is the. I would advise Dario. I think Elon is going to be build. Whatever he builds will be the next great thing.
A
You're going to marry Him.
B
Yeah.
A
Okay.
B
I think. Look, for all his. You know.
A
So you're gonna kill Sam Altman or not?
B
You have fire, given me three things, and then you're like, wait, you're gonna kill Sam Altman like you. There's only. There's only one thing left.
A
Okay.
B
Tell me about Elon, Mary, and get advisor shares. It's kill.
A
Okay.
B
You can only do. You got to pick one. That's the whole point of fmk.
A
Yes, but explain this, because you don't like Elon.
B
What are you saying that for? I just think that he's like.
A
He unfollowed you on Twitter. No one likes anyone who unfollowed them on social media.
B
Plenty of people who unfollow me on social media. I think he's, like, a crazy guy. He's obviously, like, different than lots and lots of people. I don't dislike him. I just think he's, like, crazy.
A
But you still. You respect him.
B
Yeah. He's like, look what he's done. It's. I mean, this guy's running, like, five companies with, including, you know, Neural Link and Hyperloop. And it's. I mean, I was running one company. I was working like, 90 hours a week. I would wake up at 2 in the morning and want to, like, smash my head together. Like, oh, my God, are we gonna, like, like, solve this problem? I don't. And then he sleeps like him. And, you know, Max from a firm, they sleep like, four hours. Three. Four hours a night. I need, like. I sleep, like, nine hours a night.
A
We glorify these qualities. You think they're.
B
Oh, I don't glorify qualities.
A
To glorify them. No, I think society as a culture.
B
Yeah, that's fair. Yeah, yeah, yeah. Like, this is amazing. He's up at. He sleeps in the office and blah, blah, blah, blah, blah. Yeah. Like, this is my problem, by the way. I happen to like Walter Isaacson, but this is my problem with his books, like the Musk biography, the Jobs biography. These guys are not the myth. You know, their books are written. They gloss over all the troubling aspects of the personalities. And then people. I mean, I remember this is a great story trying to get Jeff Bezos to join the board of Twitter in 2011. And he's like, I don't know, man. I don't really let my people join boards, but it's. It's an interesting enough conversation that we'll do it. It. And Jack and I meet with Jeff, and we start talking about strategy. And Jack says, well, Steve, Steve. Steve Jobs, who is live at the time in 2011. Steve believes the most important part about strategy is saying no. You have to say no to most things. And it's the job of the CEO to be, like, the editor in chief. And Jeff looks at him and goes, oh, yeah, well, I like to do everything. Big laugh. My team has to talk me out of stuff all the time. And he just goes, you know what? There's lots of ways to be successful. Let's, like, you can't read these books and think, okay, I gotta go do that, because that's the Elon way, or the Bezos or the Steve Jobs way, because these books are myths. And then people end up buying into it, and, you know, I should only sleep three or four hours. Like, this is 1 1,000th of the person's personality. And there are lots and lots of other things that you don't understand.
A
So it's simplistic.
B
Yeah, I think it's simplistic. But then people, like, laud it. And so people try to copy it and, like, okay, if I want to be one of the best. And they try to go, you're not gonna be successful trying to.
A
Yeah, they put on a black turtleneck and show it in the blood World of Theranos, for example.
B
They literally put on the outfit of the person and think, like, I'm gonna go. And you're getting. You know, the book is giving you 1/100th of the story.
A
So you helped write some of the story in Silicon Valley, the TV show.
B
Yeah, I was more in the room for, like, would this really happen? You know, But. But, yeah, I would pitch ideas and they would go, yeah, my favorite was Alec Berg, the showrunner of Silicon Valley. I would pitch it. I would gain the confidence to pitch, and Alec would go, yeah. Or alternatively, he was like, oh, he's being nice to me. That's nice.
A
So this is like, after you leave Twitter in 2015, you become a consultant to Silicon Valley TV show, which is now. Which is probably in season two or three at that time.
B
It's in season three. And in fact, Mike Judge and Alec Berg go to Richard Plepler, who's running HBO at the time, mentor of mine. Oh, amazing. He's amazing. He's fantastic.
A
He's fantastic.
B
And they say, hey, we want to bring Dick Costello into the writers room to advise. And Plepler's like, you know, damn it, you guys. I hired the writer from Arrested Development. I got you Letterman's head writer. I got you one of the guys from 30 Rock, like, more, more, more. You're like, now we want Dick Costello to come. And Alex like, no, no, no. He wants to just do it for free. And right away, Plepler's like, he is very funny. He's very funny.
A
You are. But you actually. All of your success in entrepreneurship and Oper actually filling a hole in your heart because you were once, like, doing Second City with a bunch of, like, SNL stars, right?
B
Like, I showed up to Second City the same day Steve Carell did. He and I showed up there the same day after college.
A
And then dramatically different pods. You're like Gwyneth Paltrow in Sliding Doors, the two of you, you know?
B
Well, to be fair, he auditioned for SNL a couple times, too, and didn't get it either. He just stuck with it and became extraordinarily successful.
A
Did you audition for snl?
B
Yeah, twice.
A
I didn't get it.
B
You don't know how the story ends. Do you remember seeing me at 30 Rock anywhere? You weren't alive back then during the Carter administration or whenever you auditioned.
A
No, that's true then. It might have been. But there is a sense that people in Silicon Valley feel extremely misunderstood, maligned by modern media.
B
Yeah, I think that's nonsense. Gosh, it may be Oscar Wilde who said this. I'm misattributing it maybe. But there's a great old quote to theater actors in the uk, in London at the time, saying, like, you know, these actors, if the press about them is great, they cut it out. They read every word. They, you know, put it on. Put it on the mirror, in the. Backstage, in the green room. And, you know, if the press about them is bad, they're like, this idiot doesn't know anything. Like, you know what you got? Like, you can't do one and not do the other. Right? And I think that Silicon. There's a lot of that in Silicon Valley. When the press was lauding these people, they weren't saying, like, well, you know, Cara really doesn't know what she's talking about. They were, like, happy to be on the front page of the New York Times. And. And then the moment there's negative press about them, they're like, well, these people are. This is. You know, the mainstream media doesn't know anything about what's really going on. Like, it's just like, hey, man, you gotta be able to take. You gotta be able to take a punch. And also, don't put the Wall Street Journal article in a frame above your desk. If you're then gonna Turn around two weeks later and say, well, these people don't know what's really going on.
A
If Silicon Valley were to be remade today.
B
Yeah, there's actually. There was a WhatsApp thread about this by some of the folks and the writers of Silicon Valley about, like, how would we relaunch this if we were to relaunch it?
A
Is it like the show Audacity, which
B
has just come out in AMC a little bit? That AMC show Audacity is kind of like a more dramatic Silicon Valley. The challenge that was generally agreed upon by the folks in the writers room from Silicon Valley about today was when Conan o' Brien was at the Harvard Lampoon in school, he was like, the one thing we couldn't figure out how to satirize was the National Enquirer. Cause it was already, so far, like, crazy. You're like, how do you satirize the thing that's as far crazy as it can be? And the general consensus was it's gotten beyond the ability to satirize it. How would you satirize some of the things that are happening right now?
A
Has to be like, a drama.
B
Yeah. Like, there's People are like, the person. One of the people is, you know, at Doge at the time, Elan is, you know, deciding what we're going to cut from government while running six companies. While, like, how do you. How do you satirize this stuff?
A
He, for example, was not a character in the original.
B
No. I will tell you a funny story about the characters in Silicon Valley. So there's a VC in the show Silicon Valley named Russ Hanneman, who starts his own tequila company called Tres Comas Tequila for being a billionaire. Three commas.
A
That's Mark Cuban, right? Based on.
B
It's partially based on Mark. I actually adore Mark and think he's great. And it was only partially based on him. But then the funny part about it was I would have a bunch of people coming up to me and going, russ Hanneman's supposed to be me, right? I was like, like, no. Also, you realize he's a horrible human being, right? Like, this is, like a bad guy. He's, like, out to screw Everybody. And the VCs who would come up to me in real life would go, yeah, but I have that art in his. That car, that Lamborghini. I have that car. Like, it's not you. Also, he's supposed to be a bad guy. You don't want it to be you. But they all wanted it to be based on them.
A
It's like that constant seeking fame and glory. But Mark Cuban is not a bad guy.
B
No, Mark Cuban's bad.
A
The bad parts of that guy came from Sean Parker.
B
I don't think that's true either. No, no. The funny thing about. So the group. We would go. The writers would go interview CEOs in Silicon Valley and they would say, like, you know, we. And we thought. They all. They all thought rather that this was the funniest thing ever. They would go interview CEOs, and it could be anything. Could be. Jerry, stop. Jeremy Stoppelman at Yelp. Could be whoever. And they would, you know, it could be. Could be Benioff at Salesforce. And they're like, tell me what the purpose of your company is. And they would say, it doesn't matter what the company was. Yelp is local. Reviews didn't matter what the company was. They would say, we're changing the world. And the writers would go, are you changing the world? Or is this like, you know, where to get a good bagel or wash
A
IO, where to do laundry?
B
Yeah, exactly. Are you sure? I think the DocuSign CEO literally at the time said, well, we're changing the world. And they were like. Or do you just sign things in email now? And that's not like, think of all the. Think of how dramatically we're changing nature. I mean, the lack of self awareness was endlessly funny.
A
It was so comic. I mean, I remember. Cause I was studying in Silicon Valley at the time in Palo Alto, at a small school in Palo Alto called Stanford.
B
At Stanford.
A
At Stanford, Yeah.
B
Did you. Are you one of those people that goes, where'd you go to school? Oh, Palo Alto.
A
No, no, I say Stanford. But there was, at that time, there was like, Silicon Valley had a problem problem. Cause they were like, we're gonna fix the dry cleaning problem. We're gonna fix the parking problem. Everything, everything was a problem, and they're gonna fix it all right. Now I feel like Silicon Valley thinks there's a podcasting problem because they have come in to fix it. All in being the key one.
B
Yeah.
A
Okay, so if you were to make Silicon Valley the TV show again, who are the characters in 2014 that were looming large but were missed in Silicon Valley, the TV show?
B
Oh, wow, that's a great question.
A
Cliffhanger. We'll be right back.
B
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B
You have to say the social media folks, I mean, Evan Spiegel and Jack.
A
Mark Zuckerberg.
B
Zuckerberg. It wasn't really about them yet, you know, it was about startups and Google. Huli is obviously.
A
Who were the characters that were captured in the show?
B
The crazy, you know, the Hooly CEO with his guru. And Peter Gregory is the Peter Thiel character. Okay, Gavin. Gavin, the Hooley CEO, what's his name? Running the accelerator that the boys are a part of. Those characters were captured beautifully. I mean, but who are they? They're amalgamations of CEOs, right? They're a combination of Larry Ellison with his, you know, Zen Kyoto gard in Silicon his home in Silicon Valley that one can see when one flies over, and Marc Benioff and his Buddhist beginner's mind. But also living in Hawaii half the year. But I remember Mark asked me to have I hope this isn't talking out of school. Mark asked me to have lunch with him one day at Boulevard, the French restaurant that's below the old Salesforce offices at the time before there was a tower. And I went to go have lunch with Mark at Boulevard. It's this very nice French restaurant.
A
Yes, and to set the scene a little bit.
B
Marc Benioff is the founder, founder CEO of Salesforce.
A
And Salesforce building is this very phallic building in downtown San Francisco.
B
Didn't exist at the time. This is pre phallic building.
A
Okay, Two phallic characters, no phallic building. Got it. Keep going. French food.
B
I walk in and Mark comes in and he looks like he's just come off a 13 day bender. He's like, hair is a mess. He's wearing this short sleeve Hawaiian shirt that's long. Looks. Looks like he picked up off his floor drop from in his closet and you know, ratty jeans. And he's like, comes in, he's like, hey, how's it going? And I looked at him and I was like, what's the matter with you? He looks and like, what? I'm like, it's a nice fresh restaurant. Like you actually work in this building. Coming in in a short sleeve Hawaiian T shirt.
A
But that's a vibe.
B
I know, but like, it's just. That's what was so funny about Silicon Valley. These people were like caricatures.
A
You know, my dad. Yeah, my dad used to call it like nuv poor. You know, there's like nouveau riche and then there's all these guys. Like I once in the coffee shop on campus of Stanford, a friend and I like bought a guy coffee or offered to buy a guy coffee who would come to our meditation class or something. And he was wearing like a necklace, like some ripped sweatpants. Ended up that he was Adam from Scout. The guy was worth like $7 billion.
B
Yeah.
A
And we were like students buying him coffee because we thought he was homeless.
B
I was behind Pierre Omidar and Sergey Brin at a tech conferen one time and they got to the front of the line for lunch and neither of them had money to buy the sandwich. They're like, do you have 10? They only take cash. Do you have 10? They're both like, no. Do you?
A
Here's what can I pay with PayPal?
B
Yeah, yeah, yeah, yeah. That was kind of what we were all making fun of in the show Silicon Valley.
A
Yes. So now as you look around it, why did you miss the characters that were missed, like the big social media characters? Was it just like a generational thing? I'm not calling you old, but why was it telling the stories of like, like the people who had been Padres like 10, 15 years ago versus the people who were up and coming then, like Mark Zuckerberg? Because Social Network was made during this time. So it wasn't like we didn't know they were big characters.
B
Yeah, but it's the same thing as when the Department of Justice goes after someone for being a monopoly. They're always fighting the last war. Like, that's like you guys are going after Microsoft. Like, this company over here is going to be, you know, what about this company? Are you going. You said now you're going after Google. What about. About this Facebook thing over here? That it's. You're just always sort of the stuff that's about to happen, you just don't really see it yet. And the impact of social media and how both, you know, manipulative it can be and how, like, can force people or send people down these anger holes. I just wasn't. It wasn't. What's going on at the time.
A
Maybe also the material, like, I don't know that Mark Zuckerberg is like, before his glow up was as watchable as he is now. Right. Who do you think has the best Silicon Valley glow up? Is it Mark Zuckerberg? There's a lot of plastic.
B
Plastic surgery going on right now.
A
Really.
B
Which is funny and ironic because, remember, you go cut to 10 years ago, the whole ethos was. Or not. We don't wear fancy clothes. We don't drive fancy cars. We don't care about that stuff. We care more about the life of the mind. You know, it was very Barton Fink. It's all more about the life of the mind, you know, and now it's with the watches and the clothes and the plastic surgery, and it's called looks.
A
Looks Maxing.
B
I know what it's called. Okay. I know what it's called. Who do you think you're talking to here? I know who clavicular is.
A
Okay, good.
B
All right.
A
Yeah.
B
Geez.
A
You're part of the manosphere. You have a podcast now.
B
I'm not part of the manuscript.
A
You're a white guy with a podcast.
B
Don't paint me with the manosphere brush. You know what the problem with the manosphere is? There's this weird.
A
It's too small.
B
No, that's not it.
A
Okay. Okay, good.
B
There's this weird sense that, like, to be a badass, you have to be like, you know, ignore things like introspection, Mark. Now, Andreessen has this. That I. I would like to have this discussion with him, actually, because he can't possibly believe it's true, and I'll tell you why. But he's on to this. He's on this. Like, introspection is I mean, I'm summarizing, but introspection was only created 400 years ago, and it's created by these mamby pamby egalitarians who are losers.
A
Yes. And this is Marc Andreessen behind Andreessen Horowitz massive venture capital fund. He recently went viral for saying this on a podcast.
B
You don't have any levels of introspection? Yes. Zero. As little as possible.
A
Why?
B
Move forward, go. Yeah, I don't know. I just. I've found people who dwell in the
A
past, get stuck in the past.
B
Go back 400 years ago. It never. It never would have occurred to anybody to be introspective. Also, like Hinduism, some of the precursors and the dharma to all of Buddhism, the Stoics, Marcus Aurelius and the rest. Yeah, many who are St. Augustine, all of Buddhism. Like, those are all a lot more than 400 years ago. And also Mark regularly references Marcus Aurelius, who might have written the most introspective piece, meditations of all time, on things like the Joe Rogan podcast. So I don't know what. But there's this manosphere sense that, like, you know, that the oracle of Delphi doesn't say know thyself, but instead says, you crushed it, dude. Like, it says know thyself. Like, and self. Self awareness is a remarkable and powerful force. And I just, I don't get where all this stuff is coming from.
A
There's also like, I mean, you. You referenced it a little earlier when you said, oh, a lot of founders are different, or Elon is different. There is like this sense of neuro. I want to be sensitive of how to talk about it.
B
No, please.
A
You don't want to talk about it?
B
No, I do want to talk about.
A
You know, we talk a lot about neurodivergence in our world, and it seems like, as the kids call it, a touch of the tism is what the kind of viral language is around us. And it seems like there's more of that in this particular geography, industry, culture around SEL combine.
B
I mean, the race to define oneself as neurodivergent right now is remarkable.
A
Should I enter the race? Am I behind?
B
What's your neurodivergence?
A
I don't have one, I don't think.
B
I mean, I said to my friend the other day, friend of mine the other day, I said, it's like there's a neurodivergency, this urgent sense to be neurodivergent, and people getting on stage and climbing over themselves to quickly announce how many, like, you know, atypical, idiosyncratic traits
A
they have because it drives up their valuations, it drives up their promise as founders. Right.
B
Also, so it's just not true. Like, there are plenty of perfectly normal, well adjusted kids with good parents who weren't abused, who are great CEOs and founders. There just are.
A
I mean, part of that is like a secular issue, not specific to Silicon Valley, where I do think we're like, kind of in a trauma porn era of our lives. Everything has to be everybody's like, you know, what's your trauma? How's your trauma? Be vulnerable? That's, that's a broader cultural phenomenon. The neurodivergence as a leading indicator of success is a Silicon Valley phenomenon. But is it inaccurate?
B
No, it's total. I mean, no, it's not accurate, but of course it's not accurate. There are lots of ways to be successful, and there are lots of backgrounds from which successful people can come. You don't have to be in a race to tell everybody you've been dyslexic since you were two in order to be successful. But. But it's constant now. I think there's a general over diagnosis of most of these things in American society. There's this weird sense that the reason that more American children are diagnosed as autistic is for whatever medical reason, the reason is, is over diagnosis. And also, you get to like, lo and behold, you get to spend more time taking tests if you're diagnosed with one of these things. And so, so of course, people in very, very wealthy neighborhoods in America are like, I'm gonna get my kid diagnosed as having xyz. So they get to take more time on this test.
A
There's a. Definitely a return to diagnosis. I'm so curious, who's in your phone book? Who is like, the most, like, fuck you person in your phone book? How do you mean, like, contact that you have? Like, what's a cell phone?
B
I know what a contact. I know what you meant by phone book. I know what you meant by that part. Like, you're like, you know, a contact.
A
It's like a yellow page, but it's digital.
B
I know what, I know what, what the phone book is. I meant by. What do you mean by who's the most fuck you person?
A
You're like, what's the craziest cell phone number you have in your phone?
B
The craziest cell phone number?
A
Yeah.
B
Wow. I probably have Kanye's number in my phone from back when I was CEO of Twitter and he would call about things.
A
Should we call him?
B
No, we definitely should not.
A
Who are the people you regularly trade texts with in Silicon Valley that you think would be good characters for a future Silicon Valley?
B
That's a great question. Gosh. You know Susan Wojcicki? I used to from YouTube. And she passed away, of course. She's like, so. She was so great. Susan was one of the best, like operators. Going back to the operator term. She was such a great leader. She was so calm again, like, there you go. Like normal, calm, smart person who was just an ass kicker executive. And like always just super blunt. Like, that doesn't seem right. You'd be like, like, yeah, you're right. Doesn't seem right.
A
I'm more curious about who you think would be good characters this day and age.
B
Who do you have in Silicon Valley
A
that you text with? And you're like, ugh, I wish we were still making the show. Because I could put this in the show. There must be moments like that.
B
I'll tell you who's. I'll put it this way. There are very few other funny CEOs. Very few. Which I think is a problem because I think sense of humor is an incredible ability to connect the dots. People with a sense of humor are people who can. Are systems thinkers generally. And currently has a great sense of humor. Aaron Levy's remarkably funny. The CEO of Box.
A
Oh, yes.
B
I think he might be the only other person I can think of besides yourself. Yeah. With a tremendous sense of humor.
A
I love it. Marc Benioff.
B
Mark doesn't have a great sense of humor.
A
Mark Cuban has a good sense of humor.
B
Mark Cuban has a great sense of humor.
A
Great sense of humor.
B
Mark Cuban has a great sense. I'm going to tell you a funny Marc Benioff story which he will be mad about if he sees this and probably will say, it's not true. I'm at a CEO dinner. This is years ago now. And Mark is hosting it. Benioff off. And he invites the lead designer from Apple at the time, who you. We will leave the name out because it be his relevant story. And Mark says, I've got a two guests to dinner tonight. There's like 12 of us around the table. Two guests to dinner tonight. You know, Janet and my good friend Joanie. I've. And I, I hear, I hear him say that. I'm like, I think he's. And then Mark and, and, and he sits over there and nods at Mark and then he proceeds to sit. Mark say during the dinner, you know, and Joni and I have known each other for, for blah, blah, blah years. And I'm starting and I'm going like, oh, man. I think I introduced myself earlier and said, it's so great to meet you, Johnny. And I'm like sitting there like, I'm such an idiot. I should have like asked beforehand how you pronounce his name. Yeah. Because then he's sitting there and like says it 10 or 12 more times. So right after dinner, literally the moment it stops, I go, I march over to him like, I'm so sorry. Like, I know I said Johnny when I introduced myself. I should have like asked around or asked him. And I'm talk. And he just goes, it is Johnny. I was like, why do you, why do you say. Why do you say anything? He's like, well, I couldn't. Like, by the time I was going to, he'd already said it for like the third time. And that's like that, that right there is what the show Silicon Valley was all about. Like, is anyone, is anyone going to crazy? Meanwhile, I'm sitting there going, God, I'm so stupid.
A
Yes. Because it's that constant security. That reminds me also of when Elon, who I've been calling Elon, you call him Elon. When Elon showed up at Andrew Ross Sorkin Ste book and said, my good friend Jonathan.
B
And Jonathan, like, the only reason I'm here is because you are a friend. Like, what was my speaking fee? You're not making any. First of all, I'm Andrew. But yeah, sorry. It's okay. Yeah, yeah, that was, that was, that was there for all of us to see.
A
Okay. Would the all in boys be characters on the new Silco?
B
Oh, yeah, of course. For sure, for sure. This is precisely what we're talking about. About, you know, I know all those guys. But like the, the talk in your own book constantly Chamath referenced the size of his little Chamath.
A
Oh really?
B
Apparently not so little Chamath. How long in Twitter he started talking about it.
A
How big is it?
B
I don't know. He referred to it by like, you
A
read it and you don't remember the number?
B
No, he referred to it as like. He said, like, it's legendary in Silicon Valley. It's referred to, it's for people call it the blah, blah, blah. And I was like, like, good Lord, that's so disturbing. Okay, like, what are you doing? Like, what are you doing?
A
Give me one word for each of the all in guys. Because you know them. Chamath Palapathya.
B
I'M not bad at word association because everything's more complicated than one word.
A
It's fine.
B
It's like a self promotional sort of
A
like what's the one word for David Freeberg?
B
Understated.
A
Okay. And David Sachs?
B
Overstated.
A
Okay. And now Jason Calcanis.
B
Jason is Jason. He's like, I don't know what even. How do you refer to Jason? Like, I don't know. He's like always been the same dude since Silicon Alley in New York back in the 90s, pre Earth, during magazine era, during the pre Cambrian era of the 90s. He's like this always been the same guy. Jason.
A
I feel like for millennial Silicon Valley people, they used to listen to all in and now they don't. There's been this kind of rejection of all in from the Val. I think it's true.
B
I think it's. I don't think it's just All In. I think it's this politic. Politicization of everything.
A
Yes.
B
Like, it's just like tiresome.
A
It is exhausting. I think everything in America has become political. Dating has become political. Everything what you eat is political. You know, and then you have to have like, you have the only thing that's not political.
B
You have to have a. You have to have like some politicized hot take. Like, it's just tiresome. Yeah, it just is.
A
But it wasn't like Silicon Valley was apolitical. I mean it actually it was apolitical. Like in 2010 it felt apolitical. In 2016 it felt left blue. And 2022 it felt red.
B
It was more. It was better when it was apolitical. It was just better. Like now it just feels like totally self dealing. It just does. Like I'm going to talk my own book and cloak it in. Well, the reason we have to do this for America is like not doing it for America. You're doing it because you're a huge investor in these three companies and like if they deregulate all these things and then. And then shut the door behind you. Wait, once we're making all this money, then we should regulate it and prevent. It's just, it's these guys talk in their own book. I will say this about it and I'll leave it at that. Almost every one of these guys that I know says something differently behind closed doors than they do in public about the political state of affairs in the country.
A
I don't want you to leave it at that. Give me a specific example. Without naming a person, without naming the
B
person they all just say one thing and then in public say something else.
A
But pick for example, what do they say?
B
For example, like the current administration, they feel one way about behind closed doors and think X, Y, Z is crazy and then publicly are like, well, it's the right path forward show. Yeah, they're it's performative in service to their portfolio and not what they really believe.
A
So you think the red pilling of Silicon Valley is just politically expedient? Being buddies with who's in power versus there's a real change in their perspective,
B
I think over time. I think the one, I think the one real change in their perspective is that the left became too participation trophy for them. Like there's like, let's stop giving participation trophies to everybody in America. Like we don't have to do, you know, woke this and woke that and, and everything else. I do think there was a sense in Silicon Valley that like, okay, like enough is enough. Can we go back to like a meritocracy which is, which is I think reasonable and fair. And the left does tend to but like overcorrect for things most of America doesn't care about. It just doesn't.
A
I feel in the people I know in my generation of Silicon Valley founders, et cetera, there were kind of three reasons that they really started to sympathize with the right and those three reasons. And they went from.
B
You've thought about this a lot more than I have, I can tell.
A
But the three reasons I think are. Lina Khan.
B
Yes.
A
The kind of like the pushback against mergers and acquisitions in the Valley. Some of them felt targeted, some of them felt, I mean, I'm not putting a valence on any of this. I just want to say what they
B
have reported to me, she's actually a bad human being. I think Lina Khan.
A
I don't think that's the case.
B
Yeah, I do. Okay, we can have a discussion about this later.
A
Okay. The second is the pandemic, which is like this idea that Elon had as well. It's like people need to work, we need to get back to it. The economy needs to keep moving. And the free speech, speech connection that came out of the pandemic, the Great Barrington Declaration, we've had Jay on the show, et cetera. And the third is like this DEI participation thing that you're talking about. These are the three. And so when Elon Musk came in and bought Twitter and he was like, here's a kitchen sink and let me fire half of you. And he was able to do what he wanted. There was a lot of like, okay, but here's like someone big getting bigger, putting people to hard work and grinding them and firing them when there's bloat or complaints. And they saw that as a kind of hero moment and.
B
And permission to do the same.
A
Yes. Is that fair?
B
Totally fair. For people who don't know, by the way, I mean, you know, Lina Khan sort of along with the UK version of the Margaret Best. Yeah. Went, you know, prevented Adobe from acquiring Figma for $20 billion a number of years ago. Obviously now on this weird argument that you have to convert contort yourself into a pretzel to believe that it would have made Adobe a monopoly, I'm like, I'm sure the people Adobe would be were like, we would love to be a monopoly and wouldn't have, of course, and rejected the acquisition.
A
But it wasn't a tech specific lens. Like, I mean there were also the Penguin Random House, Simon Schuster, there were
B
a lot of them.
A
And there was a sense that like the big have gotten big. And that was a sentiment of the American public, by the way. That was part of the Biden administration. And it's still like even now, I think it's not like that has changed like the Trump administration also for sure now.
B
For sure now it's the sentiment of the American public, I think. But I don't think it was was at the time the American public wasn't like, no way Adobe should be able to buy Figma. Like no, zero. People thought that literally zero dude with
A
sign had that sign.
B
Yeah.
A
There was also this narrative that like Washington was running Silicon Valley, that there was, you know, this has been, I think, largely investigated through the Twitter files, largely disproven. But the sense that the social media companies were falling in line with Washington,
B
that was not true.
A
When you were running Twitter, did you get calls from the administration saying take the.
B
Yeah, but we didn't do it. So the first time in 2011, I think it was I'm in my Monday morning, like meeting with my direct reports and my assistant comes to the room and goes, a phone call for you. And I was like, I'll call him back. Like, I'm like, what are you doing? We're having our Monday morning meeting. And she goes, it's the White House. And my immediate thought, like, this goes to show you like what a Midwestern born and raised I am. My immediate thought was, I didn't do anything. What are they calling me for? I didn't do anything. I was like, my mind was racing like what did I do? What did I do? And I'm like. And then it was like, ps, how do you know it's the White House? If someone you could just call, does
A
it come up on caller ID and like, hi.
B
Hi. She's like, hey, Dick, it's Valerie Jarrett. Like, the President would love you to come to Washington, D.C. anyway, to make a long story short, there was a bunch of back and forth between Washington and the tech companies about like, hey, we want you to take this account down. Or, hey, we need to know if these. And it was mostly terrorist stuff like ISIS and Al Qaeda at the time. I even had a fatwa against me from ISIS for taking down some ISIS accounts. But we didn't take them down because we were asked to by the authorities.
A
Dress.
B
It was both. It was both. I was wearing a Tom Fortune three buttons down. No, we would get in back and forth with the FBI and the, you know, Department of Justice and the administration about, we want to be able to see these DMS because we think it's a terrorist account. And you're like, okay, you need to provide a, like, valid, you know, a valid order from a court. You can't just, like, start asking us for account names. And so I. There was a sense that everyone was falling in line and doing whatever. What. That was simply not true. We weren't, we weren't just, you know, they couldn't call and get access to people's DMs.
A
And you don't think that changed when you left in Jack Dorsey?
B
Ok, I have no idea, but I doubt it because the legal team was the same and they were very good about, like, you got to have a valid court request for these things. We're not just going to. We're not just going to respond to email requests.
A
But. Okay. On this question of, like, Twitter's continued relevance.
B
Yeah.
A
I did an episode of a show a while back. Is Twitter going to go the way of Yahoo Mail? And it hasn't. I have to say, like, despite people's predictions that it was over and people leaving by voting by feet and whatever, Twitter has remained a place for cultural relevance. When something newsmaking is happening inside Silicon Valley. Inside Silicon Valley, and therefore more broadly, because Silicon Valley is very rich and powerful and controls a lot of things or impacts a lot.
B
If you're in tech, you and, you know, you're a founder or an operator or an investor in tech, you have to at least be on Twitter. You don't have to be tweeting necessarily, but you sure should be on There paying attention to what's going on.
A
You helped build this house. How does it feel to now see it be like a bit of a flamethrower.
B
I mean, you move on from that stuff. You just do. I remember, like, after, right after I left, this person at CNBC was like, how does it feel to be the just referred to as the former CEO of Twitter? I was like, well, my mom doesn't walk around calling me that, so I don't really like. Also, I am the former CEO of Twitter. I quit. I could have stayed in the job and done it if I wanted to. I didn't want to because it was horrible.
A
She calls you a failed SNL star.
B
Yeah, yeah, she calls me. Remember when you could have been somebody and you. And you failed at that.
A
You've done just fine. Your non New York residency demonstrates you've done just fine, Dick. No one's worried about you, especially not your mama. I mean, that's very interesting psychological insight into how you move on from companies. I think some people don't, by the way. They get locked in the chair 100%.
B
It's because they. I mean, I mean, I actually think he's an extraordinary human being. Bob Iger at Disney. But look at Iger. He couldn't let go of being CEO Disney, and came back and was there longer than he was there in the first round. A lot longer than he said he's going to do. I remember I was sitting with Peter Chernin, who was on my board at Twitter and was famously the COO at News Corp for many, many years.
A
Years.
B
Aman made the movies Titanic and others. And he and I were sitting at this cafe in like, in Los Angeles. And Iger came in, you know, Peter made some crack like, bob, what are you doing? You know, you're 70 years old, still running this company. You got a boat here in the harbor you've never been on. And Iger goes, well, you know, Peter, 70 is the new 50. And Chernin goes, that may be true, but 80 is still 80.
A
I love that. That's a good line. Let's do a bit of a lightning round of major news on Twitter.
B
You love the lightning round.
A
I. There have been a number of like, kind of public battles that have been revelatory about Silicon Valley recently.
B
Sure.
A
One of which has been Elon Musk has been sued by investors in Twitter. They say that he misled them, that he was fraudulent in presenting the value of Twitter. Those investors have been successful in proving that they were misled, but not that there was A scheme to defraud them.
B
Yeah.
A
This is interesting because Elon has been kind of Teflon.
B
Yeah. When it came to the company for $45 billion. So congratulations. Right. If you were an investor.
A
Well, they said that they lost money because it could have been worth more.
B
Those people are wrong. I don't care what the decision was, but those people are dead wrong.
A
Another public fight that's played out recently. This is not in the courtroom, but in kind of the newspapers of the world. OpenAI and anthropic, or really anthropic in the Department of War.
B
Sure.
A
But explain the essence of this argument between the AI companies, or really one AI company.
B
Anthropic.
A
Anthropic. And the US Government about holding a line because it relates to what you were saying earlier.
B
Sure. In brief, it's that Dario and Anthropic are like, look, for example, we're not going to allow Anthropic to be used to kill people without a human in the loop. Basically, Anthropic is holding the line on ways in which our product can be used for nefarious purposes or to kill other people.
A
Do you think that's fine?
B
I do, yes, for one specific reason, because I think it's. I think it is specifically appropriate for AI. The argument that the other. That the people on the other side of the equation would make is you don't get to tell companies how to use. Microsoft doesn't get to tell you how to use Excel when you buy Excel. They don't get to say, yeah, but you can't use it for military purposes. Sure. But it's not like something close to AGI.
A
And also, it's not agentic.
B
Yeah. We've also been saying for years, well, one of the things we want to make sure we do when we build AI is keep the guardrails on and make sure it's safe and that it can't go off on its own and start killing people. Well, the moment you can see, say, like, hey, we want to be able to use this thing to harm others without a human in the loop. It's like literally the thing since day one, we've been saying, well, obviously, we won't let AI do that.
A
Okay, interesting. The third of these is, I wish we could spend more time on them. And I'm going to run through them is Elon Musk versus OpenAI. This legal battle, which I think is like four innings of lawsuits, actually. But we're in the discovery phase. We're finding a lot of things, including from OpenAI co founder Greg Bachman's physical diary, which is some of like the greatest like bomb in there, including when they're running a nonprofit, talking about how it might go from being a nonprofit company to a B corp, quickly talking about how he would make a billion dollars.
B
There's a physical diary.
A
I don't.
B
But I don't either. And I don't think you should.
A
What do you think?
B
Now we're seeing why you shouldn't.
A
What do you think it reveals about a very technical online person that he felt the safest place to put his thoughts was a physical diary.
B
He probably like a little key that was like a toy key. Click. No, I think Elon has a point in this argument. Like, it's. I remember remember vividly Sam Altman being on stage at one of the Allen and Company conferences years ago and saying the reason AI has to be open is everyone has to be able to access it. And Larry Page actually saying that's actually a really bad idea because it can then be in the hands of bad people. And here we are. Sam was arguing long ago that it has to be an open, open, nonprofit company and so forth.
A
I think he said the fruits of it should be open, but the profits should not be, or something like that. I'm paraphrasing how we.
B
Oh, the little ways we tangle ourselves into knots. So what I meant was, well, look, the profits can't be for everybody but OpenAI. But the. But not the profits is too long a URL. So we didn't want to get that.
A
Do you think the debate over AI has moved forward from that fight you witnessed in Sun Valley between Sam Altman and Larry?
B
Well, yeah, they're a for profit company now.
A
No, but I meant like that kind of debate.
B
Oh, yeah, it's totally. It's totally moved on. What it's moved on to is we have to do it or the Chinese will beat us. And we can't let the Chinese beat us and therefore insert thing we want to do is justified.
A
Yeah, it's a kind of all thing. The other. The other revelatory thing is these texts between Sam Altman and Elon where Sam says to Elon, you're my hero. It really fucking hurts when you publicly attack OpenAI. Elon responds, I hear you. And it is certainly not my intention to be hurtful, for which I apologize, but the fate of civilization is at stake. Overstatement, understatement. David Friedberg or David Sachs.
B
Overstatement, Overstatement.
A
It's not the fate of civilization, whether
B
OpenAI is a for profit company or a nonprofit company is not the fate of civilization. Okay, AGI. And whether you can like whether you should be able to use AI without humans in the loop to kill people, for example, is probably bordering on the fate of civilization.
A
Last and most probably relevant, the archetype. No, of these recent things, we're gonna get to the archetype, but is this big ruling that has come out of la, which is like big tech's big tobacco moment, where a jury has found that Meta and YouTube were negligent in platform design and operation, that they hooked the user, foster addiction, risk, mental health, and they knew what they were doing to the point of internal emails. Were you surprised by that ruling?
B
I was dismayed by that ruling. And the unfortunate part about that ruling is, look, you can say, you know, whatever you want about the platforms and whether you know or whether and how much horrible, horrible they cause in society, etc. But the beauty of previous law had been that the platforms aren't responsible for the content people put on there.
A
Yeah, that's section 230 is the section
B
230 that tech companies section 230. And the reason that's important is because courts had previous, prior to section 230, if you took down something on the platform on Twitter, let's say it was the grossest thing possible, child porn, and you took it down and then you didn't take down the person who's attacking you in an at reply, then you could sue Twitter and say, see, they, they edit stuff on the platform. They already, obviously they took down that thing, but they didn't take down this. Therefore, you know, they owe me this much money. And section 230 was, look, you can't start saying once you edit one thing, you have to edit everything because it's impossible. So that was the beauty of Section 230. It made the platforms immune from this, this piercing of it by saying like, we're not suing you for editing stuff, we're suing you for your design choices like Infinite scroll that make people addict. Like, okay, now you're just getting back to the platforms are now responsible for the content on their platforms.
A
So you actually look. So you having run one of these companies, Twitter, you don't think there's any merit to the idea that, that these companies are in the business of profiting off of something that's harmful and known to be harmful?
B
No, I didn't say that.
A
I like big tobacco or car companies and seat vaults or.
B
I'm not saying that. I'm not saying that. I'm saying the ruling is opening up a giant can of worms, which people are gonna regret.
A
But what was the other way?
B
Okay, because Facebook and YouTube have infinite resources and can defend themselves from all the future lawsuits and pay, I don't know, whatever. The people won $4 million in New Mexico and let's say lots more in California. Who cares? It's a drop in the bucket to them. But the next possible platform, the next startup that tries to take these people on or come up with some orthogonal approach to a new way of thinking about social media, cannot fight those battles in court. And we'll lose every time. Or we'll do what Snapchat did in this case and settle. Cause they're like, we don't have the money to go, to go fight this. And so they'll just be, they'll never be able to get as big as that. And it entrenches YouTube and Facebook as the leaders.
A
But you've talked about how there's like very little introspection going on with all these stoics in Silicon Valley. Like, where is the needle for accountability in Silicon Valley?
B
I agree that there needs to be more accountability in Silicon Valley.
A
That's why I find you interesting. And now I will flack your podcast, the Nick, Dick and Paul show, because I do think what's interesting is that you're able to, from a nonpartisan, non political lens, say, have this nuanced point of view, which is you think section 230 is philosophically important for the growth of tech and innovation.
B
Correct.
A
You also think that the tech companies have gotten out of hand. So, like, square the circle for me of how do you get greater accountability in this non introspective, victimized world.
B
I don't have a simple answer for. Is certainly the case that all of these platforms cause, you know, obviously tremendous damage to kids and teenagers. And they're not spending time outdoors, they're not spending time with each other and like physical contact with friends. They're afraid to ask out girls in person. Like, all, all of this stuff is due to these platforms.
A
And not just kids. Adults too.
B
Yeah, adults too. And, and, and it's probably largely responsible, along with cable news, for the polarization of opinion in the country. And, and like, I mean, all you need to do is go on one of these platforms and you see the posts that reinforce what you already believe, or you see the posts that incite you to anger because it's the opposite of what you already believe. And you can see by the responses it's like an anger hole. If you go on most of these platforms right now, you end up leaving angry.
A
So will AI help soften that?
B
I actually think so. There's a great article about this just yesterday and in fact an interesting perspective I hadn't thought about. What AI actually is really good at is a reversion to the mean on answers when you ask it for as the sort of stupidest simple example, if you go to ChatGPT or Claude or whatever and say, hey, give me a random number 1 through 10, it will always reply 7. That's not a random number 1 through 10. Why does it always reply with 7? Well because when it goes out and searches the Internet for things like the random number one through ten, the most, most mean result that people type in when they're asked is seven. That's what ChatGPT's reflection. So it's a reflection of the meaning. And as the answers to political questions or medical questions or on and on and on are are are the LLM giving you a reversion to the mean answer. You end up with people being convinced out of their polarized opinions into a more moderate view. So one potential solution to the social media polarization is people rely more on AI for a what's a different way to think about this? And AI pulling people back toward the middle. Yeah, we'll see.
A
We'll see if the data in is good or trash. Right. That's what it's like if there's some bias. Yeah, that's an optimistic outlook.
B
It's an optimistic outlook.
A
Okay, I just want to give you because of this trade that we have for the flack for the archetype, I'm going to give you one minute to talk about your podcast and pitch it to people deck of why they should listen to it.
B
The podcast is trying to provide a non political show that offers discourse about policies in media, technology and you know, space travel, AI, everything of today that are happening in the world today without being politicized. And we try to do it in a as in as much as possible, an informative and lighthearted way.
A
Yeah. What I like about the Nick Dick and Paul show is that it's like a combination. I think there are a lot of outsider me to tech podcast. There's hard fork, there's pivot, there's like the journalist commentary on the thing and there's the insider, the all ins, the darkish and then there's the which I quite like the business case study, the acquired model. I think what you guys have is a combination of inside and outside. Because Nick Bilton brings that journalistic. He wrote the book on Twitter. He wrote for Vanity Fair. He brings some of the pushback. And you guys, you know, you and Paul, this guy Paul supposedly are on the inside. You guys are on the inside. And I think it's interesting. I liked when you guys were breaking down the worst things invented in tech. And Nick Bilton, you know, hard hitting journalist, said postmates or something. Doordash.
B
What the fuck? His worst tech invention ever is doordash. And Paul and I are like, what are you talking about? He's like, well, they charge too much in fees. Like, great. Don't use doordash.
A
Yeah. Nick is no longer. That's why I said former journalist Nick Bilton.
B
By the way, have you ever bought a plane ticket two days before as opposed to three weeks before? The price is different. Surprise, surprise.
A
Okay, Dick, now that I've allowed you to flack your podcast and I've even helped you, helped you boost your podcast.
B
You did. You maybe articulated it better than, than I did.
A
But you'll learn, Dick, once you do a few more podcast episodes, you two will be a hit podcast. One day you two can have all of the success. And one day I too can run away to a state like Utah to avoid taxes. It's just going to happen for both of us. The archetype, Dick.
B
Yes.
A
Don't take a swig of water.
B
Right now, the archetype that I'm being asked about is Naima wants to know. I, I, she was like, I didn't want to know. You volunteer, you see, were like, you know, the Mr. Perfect is not out there. I was like, I have the archetype in my mind for you. The guy. We're ready.
A
Yeah. Take notes.
B
Well, you can just, you'll be able to watch the podcast and hear it.
A
Okay.
B
His mid-40s, he's tall, he's in shape. He's not like, you know, it's not like a gym rat, but he's like, he runs, he bikes, you know, he's in shape. It's not like ripped, but he's in shape. It's fine.
A
Okay.
B
He's totally confident and secure, but he doesn't have to be the star of the show. Like, he's not the middle at the big dinner party. You're the middle at the dinner party. Can't have two middles at the dinner party.
A
Yeah.
B
You know what I'm saying?
A
You're a middle too.
B
I'm a middle too. He's happy to come to the dinner party. He's perfect conversational at dinner party, but he's not. He's not the middle. He's not the star of the show.
A
So you think my problem has been that I've been dating too many alphas?
B
I don't know if you've been dating too many alphas, but he's confident because you're. You're gonna not. If the person's not confident, you're gonna be like, there's no way. Like, I can't do this. This poor schmuck who I'm dragging around town, he's well off, okay? He's successful. He doesn't need, like, money, but he's got a good job. I have him. You're not going to like this part. Are you ready?
A
Is he a salaried employee?
B
Oh, my God.
A
I'm teasing. I'm teasing. Keep going.
B
I have him as a senior vice president at Apple.
A
Oh, God, no. I do not like this. Eddie Q. Are you single right now? Eddie Q. I want to sell you a show. Call me.
B
I knew you weren't going to like that.
A
What?
B
I just think that's what I got in my mind. I don't know.
A
You were so fucking fired from this podcast.
B
If I could have put your words in my mouth just now, what you would say is, he runs his own world famous architecture firm and travels frequently.
A
That's interesting. Do you feel like you're well informed enough to build my archetype on me?
B
I do. Yeah. I do.
A
And the entire archetype is based upon me being a middler in a Larry Davidson.
B
It's not just based on that, but
A
it's largely based on that.
B
I think it's got. It's got a lot of weight. There's a lot of weight there.
A
Did you bring any of these people here today? Are they behind door number one?
B
Because they wouldn't do that because they have a job and they're confident enough not to have to come to a podcast to meet you. Give me another question about the archetype. You must be curious about your future husband.
A
No, I think I'm okay.
B
You are.
A
I think I know enough.
B
He doesn't have to be an SVP at Apple. I'm just kind of saying that's generally what I'm getting.
A
I mean, nothing is wrong with SVP's at Apple.
B
Well, some apparently. This there is. You're horrified that he makes a salary?
A
No, I don't.
B
The Nepo baby.
A
I like a self made man. I like a self Made man.
B
Okay, Self made man and struggling artist are two different things.
A
Who takes a little risk, Dick. I mean, I would love to just kick eject you from the Cal High chair that you complained about just now. But I do ask a final question to everyone on Smart Girl Dumb questions. And that is, of all the things that you have hot takes about, what is the thing that you're dumb about? What is the dumb question you have that you don't know the answer to? To.
B
Oh, the thing that I'm dumb about is. Wow, that's really. That's a really great question. I wish I'd watched the podcast more so that I. All the way to the end so that I knew that.
A
Dick. It's a funny thing. Dick never listens to my podcast or watches it. It's amazing that we're friends.
B
I'm dumb about so many things. I'm really, really dumb about world history. Like, I'll go to a place and be like, oh, man, like, what is this here for? And they'll be like, this is where, like, you know, Attila the Hun crossed the mountains and, you know, sacked Rome. And I'll be like, rome was sacked. The Visigoths were the. Who were the Visigoths?
A
So you think about ancient history the way I think about the 90s.
B
Yeah. They're basically the same.
A
They're the same.
B
Yeah. I travel a lot and I'll go places and. And be like, what was this for?
A
I'm gonna recommend you a book.
B
Okay. I want it.
A
My dad used to read to me out of this book called Glimpses of World History.
B
And I need the glimpses.
A
Jawaharl Nehru, who was obviously one of the fathers of India, modern India. He wrote 6,000 Years of Human history largely from memory, while as a political prisoner, he wrote it to his daughter Indira Gandhi, who would become the prime minister of India. And it also had many inaccuracies. And my dad used to read me
B
these letters, and when I was little, I can't wait. And then it'll be up to you to tell me what the inaccuracies are. You'll be like, oh, that. That one actually didn't happen.
A
Maybe my dad read them to you. I'm going to get dad bod guy call you, read you the letters. Okay.
B
You. Yeah, you'll know him when you meet him.
A
All right. Thank you so much, Dick, for coming to the show. Thanks for having fun. That's it for this episode of Smart Girl. Dumb Questions. I can't even give you an outro because I am now just going to on LinkedIn to find my future husband. He's going to be very LinkedIn. This episode was produced with Desta Wonderad, Melissa Lee Gibson Sanjman Ngam it was edited by the great Darlena Tiem, mixed and engineered by Johnny Simon. I'm your host, Naraza. We'll see you next week for an all new Smart girl. Dumb questions,
B
Sam.
Guest: Dick Costolo (former Twitter CEO)
Host: Nayeema Raza
Date: April 14, 2026
This episode explores the balance of power between Silicon Valley and Washington, the culture and evolution of the tech industry, and the real impacts of AI, venture capital, and public markets on society. Host Nayeema Raza interviews Dick Costolo, ex-CEO of Twitter, with humor and sharp curiosity, tackling issues of tech, wealth, power, and Valley caricature—plus digressions into archetypes of the “perfect man.” The discussion is both a behind-the-scenes look at tech boardrooms and a critical reflection on the new tech elite now running policy in DC.
Timestamps: 00:47 – 02:05, 24:42 – 26:30, 26:30 – 27:02
“Give Silicon Valley a grade for its involvement in Washington. Like F. It’s also, it’s super self-serving.” (26:30)
Timestamps: 03:19 – 13:56, 15:31 – 18:26
“You just capture it all in the private markets before we get there.” (03:38)
“I think [SpaceX] will probably be more than [1.5 trillion] when it IPOs.” (12:42)
Notable insight: Public markets deliver far fewer windfalls now than in the early 2000s.
Timestamps: 09:09 – 09:51, 10:06 – 10:31
“People miss out on the anthropic and then they're like, oh, I gotta. I missed out on that one. ... whatever that one is, is probably not gonna work out as well.” (10:13)
Timestamps: 18:42 – 21:07, 22:13 – 22:29
“That’s not what venture capital is, people.” (20:21)
Timestamps: 22:29 – 24:42
“A K shaped economy is ... the shareholders ... will gain wealth while the working class ... will become more impoverished. And I think that's probably true.” (22:45)
“The profound implications for our society that we're not doing anything about right now—worse than the initial implications of the K-shaped economy.” (23:53)
Timestamps: 41:07 – 48:19, 54:21 – 56:45
“The DocuSign CEO literally at the time said, ‘we're changing the world.’ ... Or do you just sign things in email now?” (40:47)
Timestamps: 48:27 – 53:05
“Self awareness is a remarkable and powerful force. ... the oracle of Delphi doesn’t say ‘you crushed it, dude.’ It says ‘know thyself.’” (49:35)
“There are plenty of perfectly normal, well adjusted kids with good parents who weren’t abused, who are great CEOs and founders. There just are.” (51:35)
Timestamps: 60:05 – 63:33
“Almost every one of these guys that I know says something differently behind closed doors than they do in public about the political state of affairs in the country.” (59:23)
Timestamps: 65:53 – 76:20
“The beauty of Section 230 was ... you can’t start saying once you edit one thing, you have to edit everything because it’s impossible.” (74:07)
Timestamps: 78:01 – 79:26
“One potential solution to the social media polarization is ... AI pulling people back toward the middle.” (79:19)
On tech insider-outsider podcasts:
“Smart Girl Dumb Questions. Okay, let's just lay it out here. This is a trade. Dick is a rich, powerful person. And she's come here to the penniless, powerless world of podcasting to take it over.” (02:05)
On leaving the tech CEO cult:
“I didn’t want to become bound to the trappings of the role, because then I would be like, nah, I can’t quit, I won’t be able to go to the Oscar party next year.” (06:01)
On tech’s new elite and government:
“There’s performative discourse and a conversation to be had ... but it ends up just being performative—yelling at people because they’re on the wrong side of the trade.” (26:30)
On the myth of the “Steve Jobs method”:
“You can’t read these books and think, okay, I gotta go do that, because that’s the Elon way, or the Bezos or the Jobs way ... These books are myths.” (33:33)
On introspection vs. the “crush it” mentality:
“The oracle of Delphi doesn’t say know thyself, but instead says, you crushed it, dude.” (49:35)
On the K-shaped economy:
“...the wealth gap gets more dramatic. More K like than you’d like... that’s of course very bad.” (23:25)
On the staying power of Twitter:
“Twitter is always dying, but totally unkillable somehow.” (29:13)
Costolo’s “perfect man” archetype for Nayeema (81:50 – 83:04):
“I’m really, really dumb about world history. ... And they’ll be like, this is where, like, Attila the Hun crossed the mountains and sacked Rome. And I’ll be like, Rome was sacked?” (85:01)
| Subject | Timestamp | |-----------------------------------------------|---------------| | Silicon Valley’s power & DC | 24:42–27:02 | | Are we in a tech bubble? | 09:09–10:31 | | Public vs. private markets | 15:31–18:26 | | VC as Ponzi scheme | 18:42–20:21 | | K-shaped economy, AI’s societal impacts | 22:29–24:42 | | Tech’s political shift | 59:23–63:33 | | Section 230 / Platform responsibility | 73:42–76:20 | | Silicon Valley as TV satire | 41:07–56:45 | | Fun lightning rounds (FMK, characters) | 28:31–31:08 | | The “perfect man” archetype | 81:44–83:41 | | Dick’s “dumb question” | 84:45–85:32 |
If you want a blend of sharp commentary and candid stories from a Valley legend, plus deep skepticism about tech’s current mythos, this episode will both entertain and inform. And if you’re hunting for the ultimate “SVP at Apple” archetype—there’s advice here too (with tongue firmly in cheek).