Are Insiders Cashing In on Trump’s Iran Talk? | Pivot

Are Insiders Cashing In on Trump’s Iran Talk? | Pivot

PivotMar 27, 20261h 2m

Kara Swisher (host), Scott Galloway (host)

Trump tech advisory council and conflicts of interestKara Swisher’s Ellison comments and media ownership concernsIran war messaging, markets, and insider-trading incentivesPrediction markets regulation (Kalshi/Polymarket) and political tradingFlorida Democratic upsets and anti-Trump local backlashDHS shutdown impacts, TSA pay, and Delta ending VIP treatmentMeta/YouTube liability in social media addiction lawsuitsOpenAI strategy shift: Sora shutdown, IPO positioning, roboticsAmazon AI phone concept and Prime/telco bundling

In this episode of Pivot, featuring Kara Swisher and Scott Galloway, Are Insiders Cashing In on Trump’s Iran Talk? | Pivot explores trump’s tech council, Iran talk, and Big Tech accountability collide They criticize Trump’s proposed tech council as stacked with conflicted Big Tech leaders whose policy recommendations would predictably favor deregulation and self-interest.

Trump’s tech council, Iran talk, and Big Tech accountability collide

They criticize Trump’s proposed tech council as stacked with conflicted Big Tech leaders whose policy recommendations would predictably favor deregulation and self-interest.

They argue Trump’s shifting public statements about Iran and negotiations could enable massive market manipulation, creating ideal conditions for insider trading through rapid oil and equities moves.

They highlight surprising Democratic special-election wins in Florida (including the Mar-a-Lago district) and discuss the DHS/TSA disruption as a political and operational backlash against shutdown brinkmanship.

They frame early jury verdicts against Meta and YouTube as a pivotal legal turning point that strengthens hundreds of pending “social media addiction” cases despite modest damages awarded.

They examine AI/tech business pivots: OpenAI sunsetting the Sora app to refocus amid competitive pressure from Anthropic, skepticism about OpenAI’s hardware push, and Amazon’s rumored return to phones as a Prime-flywheel play.

Key Takeaways

A ‘Big Tech council’ without critics is policy capture, not expertise.

Swisher and Galloway argue that staffing AI advice with executives who profit from weaker rules (chips, data centers, platforms) crowds out independent research, safety voices, and adversarial debate—producing predictable pro-industry outcomes.

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Geopolitical ‘talk’ can become a tradable asset when leaders move markets with unverified claims.

They suggest Trump’s Iran statements can whipsaw oil and equities, and with modern instruments (e. ...

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Prediction markets are colliding with governance and national-security risk.

They note bipartisan moves to restrict certain prediction-market listings and to curb trading by officials/candidates, warning that betting tied to military deployments can incentivize exploitation of sensitive information and even profit from casualties.

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Corruption norms matter—until someone scales the loopholes into a new business model.

Galloway contrasts “small-cap” congressional stock trading with what they portray as larger-scale, norm-breaking behavior, arguing the U. ...

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Democratic candidate quality and local signals may be shifting the 2026 narrative faster than expected.

They treat the Florida flips—especially in a district Trump recently carried strongly—as a leading indicator of backlash, and point to improving recruitment (younger, service-oriented candidates) as a strategic advantage.

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Corporate ‘small’ decisions can become high-impact political pressure when they remove special privileges.

They praise Delta for suspending specialty services for members of Congress, arguing it’s a brand-enhancing way to signal dysfunction and raise the cost of shutdown tactics—while spotlighting harm to TSA workers.

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The first social-media addiction verdicts are ‘end of the beginning’—precedent is the prize.

Even with low damages, they emphasize liability findings and insurer pushback (claims of intentional conduct) could supercharge subsequent lawsuits via discovery and established theories of harm around design patterns like infinite scroll.

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OpenAI’s retrenchment suggests the AI product cycle is entering a focus-and-moat phase.

They interpret Sora’s shutdown as a rational response to weak retention and high cost, intensified by Anthropic’s enterprise momentum; Galloway further predicts OpenAI’s Jony Ive hardware initiative could be quietly euthanized due to “unsolved product physics.”},{

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Notable Quotes

No regulation and buy more of my shit. That’s gonna be their recommendation.

Scott Galloway

This is an insider trader’s… Ivan Boesky could not have dreamt of this situation.

Scott Galloway

They’re making money at your expense and cheating while doing it.

Kara Swisher

This is the end of the beginning.

Scott Galloway

We need the age gate. No one under the age of 18 needs to be on any of these platforms.

Scott Galloway

Questions Answered in This Episode

Which specific Big Tech figures are reportedly on Trump’s tech council, and what concrete conflicts (chips to China, data centers, platform regulation) do you see for each?

They criticize Trump’s proposed tech council as stacked with conflicted Big Tech leaders whose policy recommendations would predictably favor deregulation and self-interest.

Get the full analysis with uListen AI

What market data would you look for to substantiate the claim that Iran headlines are being used for insider trading (timing, instruments, counterparties, futures volume spikes)?

They argue Trump’s shifting public statements about Iran and negotiations could enable massive market manipulation, creating ideal conditions for insider trading through rapid oil and equities moves.

Get the full analysis with uListen AI

How should U.S. law treat ‘prediction markets’ differently from gambling when the underlying events involve national security or military deployments?

They highlight surprising Democratic special-election wins in Florida (including the Mar-a-Lago district) and discuss the DHS/TSA disruption as a political and operational backlash against shutdown brinkmanship.

Get the full analysis with uListen AI

In the Meta/YouTube addiction verdicts, what design features were most central to liability—algorithmic recommendations, infinite scroll, notifications—and why?

They frame early jury verdicts against Meta and YouTube as a pivotal legal turning point that strengthens hundreds of pending “social media addiction” cases despite modest damages awarded.

Get the full analysis with uListen AI

What would an effective ‘age gate’ look like in practice without creating a privacy nightmare (ID checks, device-level controls, carrier verification, liability shifts)?

They examine AI/tech business pivots: OpenAI sunsetting the Sora app to refocus amid competitive pressure from Anthropic, skepticism about OpenAI’s hardware push, and Amazon’s rumored return to phones as a Prime-flywheel play.

Get the full analysis with uListen AI

Transcript Preview

Kara Swisher

You know what, Mark? Just pay the money and fix it. Like, just stop. [upbeat music] Hi, everyone. This is Pivot from New York Magazine and the Vox Media Podcast Network. I'm Kara Swisher.

Scott Galloway

And I'm Scott Galloway.

Kara Swisher

There's so much going on that-

Scott Galloway

Oh, that

Kara Swisher

... that. Listen, President Trump plans to install big tech names like Mark Zuckerberg, Larry Ellison, and Jensen Huang to a technology council to weigh in on AI policies and other issues. W- we were not invited.

Scott Galloway

AI policy, buy more of my shit.

Kara Swisher

Buy more of my shit.

Scott Galloway

US government, buy more of my shit.

Kara Swisher

Give me what I need. You know, it's again, the ref-

Scott Galloway

No regulation and buy more of my shit. That's gonna be their-

Kara Swisher

The ref-

Scott Galloway

... the recommendation

Kara Swisher

... of anybody who has a different alternative view, that these are the only experts. Our invita- I would say, I would say our invitation is lost in, in, or the dog ate our invitation, but he hates dogs, so Trump ate our invitation. I just don't... This list is nobody who has any doubt about it, nobody who has any good research, no one whose interests are not aligned with it, no regulation with, with any kind of reg-

Scott Galloway

And conflicts everywhere.

Kara Swisher

Everywhere. I just, these, these people-

Scott Galloway

Well, you know, Jensen Huang's a big fan of selling g-

Kara Swisher

Yeah

Scott Galloway

... uh, being able to sell his chips into China-

Kara Swisher

China

Scott Galloway

... despite the fact these [laughs] are the chips that-

Kara Swisher

Yeah

Scott Galloway

... you do warnings with and track our Ohio class submarines.

Kara Swisher

And Larry Ellison wants more data centers. And Ma- and you know. I just, this, ugh, God, these people. Like, you'd think if you were a real president, and I think this guy is losing it every single day, and including the polls, which are just, like, look out below. But, um, it, it's really amazing that he doesn't want other inputs, like, that may vary from his rich friends. It's just... I, I find it... It, it's just not good policy not to have people who doubt each other and debate it. I just, I don't understand.

Scott Galloway

Yeah.

Kara Swisher

We're waiting for our invite. Even just you, even you, if he needs the white guys. Yeah.

Scott Galloway

Even you.

Kara Swisher

Well, you'd be good.

Scott Galloway

That's, I love that. Why thank you.

Kara Swisher

[laughs]

Scott Galloway

Even you. I mean-

Kara Swisher

Well, you're the white guy. They're not gonna have me. I'm irritating to all of these people, and so, uh, you know, I'm just saying. I'm just saying.

Scott Galloway

You, uh, uh, uh, speaking of which-

Kara Swisher

Oh, yeah

Scott Galloway

... someone was, someone said, I don't know, on one of these many, many platforms which are just-

Kara Swisher

Mm-hmm

Scott Galloway

... so good for your mental health-

Kara Swisher

Mm-hmm

Scott Galloway

... that Kara was a total shill for big tech.

Kara Swisher

Oh, God.

Scott Galloway

And I, I, [laughs] I wrote, "Do you realize," like, I have been on... When you go on a board and they don't want you-

Kara Swisher

Mm-hmm

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