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Dick Costolo
Partner at 01 Advisors, 01 Advisors

Madman Theory | The Nick, Dick and Paul Show

📅 May 14, 2026 The Nick, Dick and Paul Show 39 MIN 266 VIEWS 238 SEGMENTS · 3 SPEAKERS
🛎 If You're New Subscribe ►    / @nickdickpaul   Madman Theory | The Nick, Dick and Paul Show This week, Nick, Dick, and Paul talk about madman theory and how it's used. They discuss whether or not figures like Donald Trump and Elon Musk use this theory or if they truly believe their actions, if other leaders act like a "mad man", historical figures who've used it such as Richard Nixon, and so much more! ❤️ iHeartRadio » https://bitly.cx/xbngT 📢 APPLE PODCASTS » https://bitly.cx/06Q8 🟢 SPOTIFY » https://bitly.cx/Abgsk ✨ KEEP IN TOUCH WITH : INSTAGRAM »   / nickbilton   »   / costolo...

Questions asked in this interview

12
  1. 1:17Do you want to explain it or Paul's best at doing these things?
  2. 3:47I didn't like you anyway. Doesn't matter like or or?
  3. 5:09... was a piece was it in the Wall Street Journal or the FT where insiders saying he was saying it straight up that I need to pro there was a was it on Easter Sunday I think it was where he put out this profane message on what's it called?
  4. 8:25Was it at the Hilton the same hotel?
  5. 10:11But people were saying like I was looking around thinking like shouldn't security be a little tighter here?
  6. 12:47Why are you looking at me when you ask how far away do you?
  7. 16:34Why does he jump up and down and move around?
  8. 17:20Are they partaking in it or it's just America?
  9. 24:15Am I going to get cancelled?
  10. 27:47And that's part is that like a mad boy theory? Is that boy theory?
  11. 35:52Legitimately smart people running profitable businesses who are like, well, obviously the three Trump assassinations, these staged like what?
  12. 37:10Does AI help turn this back or does it make it worse?
Nick Bilton 0:00 ↗
Welcome to the Nick, Dick, and Paul Show. I am one of your co-hosts, Nick Bilton, a former journalist and screenwriter and documentary filmmaker. And I am not a madman, which will make sense momentarily.
Dick Costolo 0:14 ↗
I'm Dick Costolo, the only remaining surviving former Twitter CEO.
Nick Bilton 0:20 ↗
Not true.
Paul Kadoski 0:21 ↗
The only remaining surviving sane.
Dick Costolo 0:24 ↗
Oh, all right. No, we mustn't do that. That's not fair at all. Um, and currently an investor.
Paul Kadoski 0:31 ↗
I'm Paul Kadoski. I actually invented Bitcoin.
Nick Bilton 0:33 ↗
Yeah, there we go.
Paul Kadoski 0:35 ↗
Did you know that? Yeah.
Nick Bilton 0:36 ↗
I don't know if I mentioned that before.
Dick Costolo 0:37 ↗
That was last episode, folks. Tune in.
Paul Kadoski 0:39 ↗
No, that's perpetual.
Nick Bilton 0:40 ↗
Please tune in last time.
Paul Kadoski 0:41 ↗
Yeah, I invented Bitcoin. And also a venture investor.
Nick Bilton 0:46 ↗
Also a venture investor. So, on today's episode, we're going to be getting a little current. We're going to be talking about the recent assassination attempts and lots of things that are going on in the news, but we're going to begin with something called the Mad Man theory.
Do you want to explain it or Paul's best at doing these things?
Dick Costolo 1:21 ↗
Does he know? He does a good job. He says what it is. Yeah. Yeah.
Paul Kadoski 1:25 ↗
Well, I know some words, but Paul knows bigger words.
Dick Costolo 1:30 ↗
Well, I know a few.
Paul Kadoski 1:32 ↗
Loquacious.
Dick Costolo 1:33 ↗
Loquacious. It's a good word.
Paul Kadoski 1:34 ↗
That's a good one. Personnicity is another.
Nick Bilton 1:37 ↗
I love when Paul uses a word that you and you're like, do I have to pretend I know it or should I look it up or?
Dick Costolo 1:44 ↗
It's a character flaw of mine. I use it just as a test, really.
Paul Kadoski 1:46 ↗
Got it. Yeah, I come in with four or five words preloaded and then you well, so explain the madman theory.
The madman theory goes back to the Nixon administration. He's having a conversation in his office.
Dick Costolo 1:57 ↗
See, he's already got historical context.
Paul Kadoski 2:00 ↗
Sorry, I can prove the historical.
Dick Costolo 2:02 ↗
No, it's good. This is what's interesting about this though is it actually the office was very sparse back then and now it's gold-plated, but that's a whole separate story. Keep going. Keep going.
Paul Kadoski 2:12 ↗
The interior decorations.
Dick Costolo 2:13 ↗
Gold-plated in quotes.
Paul Kadoski 2:16 ↗
That's right. Possibly not. Um, and so he was explaining at the time, his idea, Nixon was explaining his idea to one of his aides that he felt the way to get what he wanted was to make the other side, and in this context it was in Vietnam, was to make them feel like he wasn't predictable, that he was willing to do or say anything. And he was telling his aide that that's what they needed to communicate to these counterparts. I hear's what I think Nixon should do, but he's a madman. He could do anything. I can't predict what he will do. Because the idea behind the madman theory is that if your counterparty thinks you're wildly unpredictable, they're more likely to make concessions to prevent those unpredictable things from happening.
Dick Costolo 2:56 ↗
It makes non-credible threats seem more credible. So, they're more willing to make concessions on things they otherwise wouldn't make concessions on because he's nuts, right? He's a madman.
Paul Kadoski 3:04 ↗
And so, this was the idea. But the key idea is that whether or not Nixon was a madman is an open question. But that giving the appearance of being someone who is a dangerous counterparty who might be willing to say or do anything is fundamental to this idea. And strangely enough like the whole idea of madman theory then got picked up a little bit in the political economics and in government research and government literature. And so this idea does it actually work? Is it a real thing? And it's actually got a little bit of credence behind it. This idea that people will to a degree give concessions if they're uncertain about how rational you actually are as a counterparty. And that's the madman theory.
Nick Bilton 3:47 ↗
Do you think that Nixon was like actually a madman and that made it up to justify his insanity? Like I'm breaking up with you. I didn't like you anyway. Doesn't matter like or or?
Paul Kadoski 3:57 ↗
No, no. He was his was very rational. It was entirely rational where he was saying, 'I don't believe that we can get the concessions we want and get what we want out of Vietnam.' Um, without them feeling like I'm a more dangerous counterparty. If I look entirely predictable, they're going to run out the string. They're just going to keep on negotiating and never actually giving me anything that I want. I need to look crazier. If I want the kinds of things that I claim to want, I need to position. I have to handle this completely differently. And so, no, it was done very rational irrationality. It was rational.
Dick Costolo 4:30 ↗
What has the research shown of the effectiveness of it?
Paul Kadoski 4:32 ↗
So, it's modestly effective. The problem is that over time, if you serially pretend to be mad and present yourself that way and then get the concession you want and then lapse back into sanity, that the gig is up pretty quickly where people realize, okay, this is just a shtick. This is just no different than a, you know, comedy routine that you do. It's not that you're actually mad. You're just pretending it to get the concessions. And so, it's not a there's this idea of finite and infinite games. It's a finite game. You can't play that game forever. You can't keep repeating it and hoping for the same outcome.
Nick Bilton 5:04 ↗
So, is Donald Trump playing that game over and over and over again and now creating?
Paul Kadoski 5:09 ↗
He says he is he literally there was a piece was it in the Wall Street Journal or the FT where insiders saying he was saying it straight up that I need to pro there was a was it on Easter Sunday I think it was where he put out this profane message on what's it called? Truth Social. I was going to say talking social on his social where he was where he said you know praise Allah and there was profanities and it was like all of this crazy stuff on Easter Sunday just seemed completely but it was done according to the journal's piece that was quoting people inside that this was done very rationally to look particularly crazy to get the concessions that he wanted out of the Iranian whatever well I was going to say out of the Iranian administration but that's not even a thing but out of whatever.
Dick Costolo 5:53 ↗
Whatever's left of the Iranian whatever coalitions exist.
Paul Kadoski 5:56 ↗
But the problem is is that it's now completely backfiring for him because or maybe not. But it appears like it is because for example he's threatened, you know, to literally wipe Iran off the face of the planet. He then he said he was going to, you know, bomb this and that and then he didn't. And it's, you know, drop this nuke. He didn't. He, you know, the same with Russia while he was negotiating Ukraine and so on and so forth. I think the traders now have a thing called TACO. Trump Always Chickens Out.
Dick Costolo 6:28 ↗
So is it?
Paul Kadoski 6:30 ↗
But that's the deep problem with the madman theory. This idea that inevitably you either have to do something genuinely mad or people realize that this is actually just a game theory kind of gambit.
Dick Costolo 6:42 ↗
Yeah. Also, nobody executes the madman theory when they feel like they're really winning. Because if you really feel like you're winning, consistency and stability are what you want to project. So it's no coincidence, I guess, that at the present moment you start to hear things come out of China like China will be a reliable force for stability and China is providing the greatest certainty in this uncertain world. Like that's the way you speak if you know we've got the upper hand.
Paul Kadoski 7:14 ↗
Yeah. You don't feel like you have to go to these crazy extremes of pretending I'm a lunatic. Right. And matter of fact, and as you say, you kind of open up the field for other people to say, I don't know what this guy's doing, but I'm reliable.
Dick Costolo 7:26 ↗
Right. Which is a bizarre position to have put China in, for example, as a counterparty. Right.
Paul Kadoski 7:32 ↗
What's interesting is there's also the ancillary result of what happens as because of these actions. So, I mean, Trump is the most assassination attempts of any president, right? It's one after the other. And we saw this happened at the White House Correspondents' Dinner. I actually know some people that were there and the stories I've heard are bananas of just how lax security was.
Dick Costolo 7:58 ↗
Um one thing that I found really fascinating, someone told me this past week was.
Nick Bilton 8:03 ↗
That's surprising because.
Dick Costolo 8:04 ↗
It's very surprising. I was at that thing back when I used to be somebody and the 20th CEO of Twitter got invited to things.
Paul Kadoski 8:15 ↗
Were you really at it?
Dick Costolo 8:16 ↗
Yeah.
Paul Kadoski 8:16 ↗
How many times did you go?
Dick Costolo 8:18 ↗
Once.
Paul Kadoski 8:19 ↗
Did you like it?
Dick Costolo 8:19 ↗
I don't know. Why are you asking these things like it's an interrogation?
Paul Kadoski 8:22 ↗
Well, because I'm very curious.
Dick Costolo 8:24 ↗
Well, yeah, I liked it.
Nick Bilton 8:25 ↗
Was it at the Hilton the same hotel?
Dick Costolo 8:27 ↗
Yeah.
Nick Bilton 8:27 ↗
And that was funny where Reagan got shot, but Yeah.
Dick Costolo 8:30 ↗
Well, they all got shot there. That's where the thing always is. Is it chicken or beef? I don't remember that. That's a good question. It's like it's one of those like 2,600 people.
Paul Kadoski 8:41 ↗
It's one of those chicken or beef.
Nick Bilton 8:42 ↗
Chicken, beef, or fish.
Dick Costolo 8:44 ↗
Did you get the chicken or the beef or the fish?
Paul Kadoski 8:45 ↗
All right.
Nick Bilton 8:46 ↗
I'm curious what you would I never get the fish because I'm always a little worried. I've been sitting out for a while.
Dick Costolo 8:51 ↗
I almost certainly got the chicken.
Paul Kadoski 8:52 ↗
I always get the beef because the chicken might be undercooked. The beef. You're safe. But keep going.
Dick Costolo 8:57 ↗
I was sitting at a table next to George Clooney is really the only thing I remember. And he had literally two people around him preventing women from coming up to introduce themselves to George all the time.
Paul Kadoski 9:10 ↗
Paul and I do that all the time.
Dick Costolo 9:12 ↗
I was like, 'God, I should have done that.'
Paul Kadoski 9:14 ↗
Just like Kadoski has happened.
Dick Costolo 9:17 ↗
This feels so familiar.
Nick Bilton 9:22 ↗
This was when Obama was president then. And was security crazy?
Dick Costolo 9:27 ↗
Yeah, it was crazy. Like of course it was crazy. Like here's the president. We all know the president's going to be here. So it's I was surprised and of course now I mean of course you hear in hindsight security was lax because after the fact that this you know guy sprinted through but it was so lax about it.
Nick Bilton 9:49 ↗
Well there's two things. One is that I have a friend who was there who said that they showed up a little early because they were at a party in the hotel and they came down and the Secret Service was just in their underwear.
Dick Costolo 10:05 ↗
Guns on the floor. Just wait.
Nick Bilton 10:06 ↗
Oh man, hold on. Give us five minutes. Five minutes.
Dick Costolo 10:09 ↗
Secret Service is playing video games.
Nick Bilton 10:11 ↗
They had a hacky sack. No, there was the Secret Service wasn't really there. There was a few milling about. This was like an hour before literally they said before they've got to be there like I'm telling you I heard this from numerous people. The other thing I heard was this sounds like after the fact. This has been reported too. I'm not like breaking news here on the thing. The other thing I heard was well first of all there was the tickets were literally printed out paper. They weren't there was no barcode scanning. And it was like it was literally you showed the ticket and there were people who had forgotten their tickets that were literally just showing on their phone the screenshot of the invitation they had gotten and they were being let in. So someone I spoke to said there's a very you can see I have a text on my phone from someone named Kosh Patel that says come to the Correspondents' Center tonight exclamation point. But people were saying like I was looking around thinking like shouldn't security be a little tighter here? Um and so on.
Dick Costolo 11:09 ↗
Anyway, the other thing was, so this was the part that I found fascinating and this has been reported. It hasn't really been picked up for whatever reason, but Trump afterwards shared on Truth Social the video of the guy running through like a linebacker.
Paul Kadoski 11:24 ↗
I've seen that.
Dick Costolo 11:25 ↗
But you haven't seen the video of them grabbing him. Why? Because he tripped and fell apparently. So, and they haven't shown that because it doesn't look good. So, he comes running through the door was actually open. So, someone I know who's a journalist was just leaving the bathroom and saw the guy running, tripped and fell and then it's unclear who shot who and how and so on, but then they piled on him, but the door was open and had he not tripped and fallen, he would have made it into that room.
Paul Kadoski 11:59 ↗
So, that to me tells you that they weren't necessarily as organized as they should have been. Don't you find that interesting?
Dick Costolo 12:05 ↗
No, it just seems it all seems strange though. Like if you ever have been around a presidential event at all in any form in any place. There's advanced teams. There's snipers on roofs and it's just endless.
Paul Kadoski 12:17 ↗
Endless, right?
Dick Costolo 12:18 ↗
Like blocks away. Starting blocks away.
Paul Kadoski 12:21 ↗
Right. And it's not like this was the Republican convention. It wasn't like he thought he was going to a safe place. This was like journalists, right?
Dick Costolo 12:28 ↗
Yeah.
Paul Kadoski 12:28 ↗
You know, like it must have at the very least it was a neutral place where you needed to spend a lot of time in scrutiny so none of it makes sense to me.
Dick Costolo 12:37 ↗
No, none of it makes sense to me either. And also what also doesn't make sense is that this guy had a shotgun. Because that is the dumbest move ever.
Paul Kadoski 12:47 ↗
No, how far away do you have to be to kill someone with a shotgun? Did he really think he was going to make it? Why are you looking at me when you ask how far away do you?
Dick Costolo 12:56 ↗
You just said it's the dumbest ever shotgun.
Paul Kadoski 12:58 ↗
I mean just.
Dick Costolo 12:59 ↗
Shotguns especially.
Nick Bilton 13:03 ↗
Here's Dick Costolo with a ballistics report.
Dick Costolo 13:07 ↗
We now go live to Dick Costolo with a ballistic.
Paul Kadoski 13:10 ↗
See, I think that's trying to make someone who's doing an irrational act seem like they probably spent more time thinking about it than they did because if you think it through, there was no.
Dick Costolo 13:18 ↗
I mean he did he took an Amtrak 4 days, rented out a hotel room. A lot of people do those things.
Paul Kadoski 13:24 ↗
Yeah. Yeah. Yeah. That doesn't signify.
Dick Costolo 13:27 ↗
Still not still not sanity tells, right?
Paul Kadoski 13:30 ↗
So, no, there's no question that seem but the crazier part for me just seems to be it's surprising that having seen these kinds of events and how much work was that something bizarre about how porous it was. I don't even pretend to understand that.
Dick Costolo 13:47 ↗
I completely agree. I've been to those events at the, you know, I mean the New York Times when presidents showed up and secret and there were literally guys on the Port Authority roof that were, you know, the streams and streams of soldiers and FBI agents and you couldn't you weren't even allowed to get in the elevator.
Nick Bilton 14:06 ↗
Also apparently the code word for saying the president's under attack is just the word blue.
Dick Costolo 14:11 ↗
Blue.
Nick Bilton 14:11 ↗
Simply running into a room and starting to shout primary colors will incur Secret Service crossfire.
Dick Costolo 14:23 ↗
Yeah, which is good to know obviously.
Paul Kadoski 14:25 ↗
Yeah, it's helpful given my tendency in this thing. And that was my favorite little fact that I learned during this was the blue.
Dick Costolo 14:31 ↗
It was blue. All the guys running around yelling blue, blue, blue, blue. Like what is that?
Paul Kadoski 14:35 ↗
I just think though.
Dick Costolo 14:36 ↗
And then shooting at each other.
Paul Kadoski 14:37 ↗
I don't.
Dick Costolo 14:39 ↗
Shot.
Paul Kadoski 14:40 ↗
It's not clear who shot that agent.
Dick Costolo 14:42 ↗
Yeah. Yeah. And his phone protected him.
Paul Kadoski 14:45 ↗
Yeah. I heard the phone took a piece of the bullet.
Dick Costolo 14:48 ↗
Yeah.
Paul Kadoski 14:49 ↗
Probably an iPhone. Those things are so heavy.
Dick Costolo 14:51 ↗
It definitely wasn't an Android.

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APA, MLA, BibTeX
APA

Costolo, D. (2026, May 14). Madman Theory | The Nick, Dick and Paul Show [Interview transcript]. The Nick, Dick and Paul Show. CEOInterviews.AI. https://ceointerviews.ai/interview/2926675/

MLA

Dick Costolo. "Madman Theory | The Nick, Dick and Paul Show." The Nick, Dick and Paul Show, 14 May. 2026. Transcript, CEOInterviews.AI, https://ceointerviews.ai/interview/2926675/.

BibTeX
@misc{costolo2026_2926675,
  author       = {Dick Costolo},
  title        = {Madman Theory | The Nick, Dick and Paul Show},
  howpublished = {Interview transcript, The Nick, Dick and Paul Show. CEOInterviews.AI},
  year         = {2026},
  month        = {may},
  url          = {https://ceointerviews.ai/interview/2926675/},
  note         = {Speaker-attributed transcript with timestamps}
}