Will the U.S. Go to War With Iran? — with Karim Sadjadpour

Summary

The Prof G Pod with Scott Galloway

Episode 385: Will the U.S. Go to War With Iran? — with Karim Sadjadpour

Release Date: February 26, 2026
Guest: Karim Sadjadpour, Senior Fellow at the Carnegie Endowment for International Peace
Theme: U.S.–Iran tensions, the possibility of war, and the prospects for regime change or negotiation

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Overview

In this timely and sobering episode, Scott Galloway hosts Iran expert Karim Sadjadpour for a deep dive into U.S.–Iran relations at a moment of escalating tensions. Against the backdrop of increased American military presence off Iran’s coast and uncertainty over the intentions of both the Trump administration and Iran’s leadership, the discussion explores the likelihood, risks, and potential consequences of military intervention, as well as prospects for diplomatic solutions and regime change in Iran.

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Key Discussion Points & Insights

1. Current State of U.S.–Iran Relations

• Game of Chicken: Sadjadpour frames the current confrontation as “a game of chicken between two individuals: President Trump and Iran's Supreme Leader, Ayatollah Khamenei.” (12:03)
• Iran’s Intransigence: Despite immense economic and military pressure, Iran refuses to compromise, largely due to Khamenei’s hardline ideology centered on resisting America.

2. Trump Administration’s Strategy and Motives

• Galloway questions whether the administration is genuinely seeking a deal or simply posturing for strength:
  “I would have described it as a fait accompli… I think he likes the flex and the macho sheen…” (13:11)
• Sadjadpour responds that a peaceful deal is preferable to Trump if Iran capitulates, but recognizes that odds of a deal are currently low (13:41).

3. Is a “Good Deal” Possible With the Islamic Republic?

• Long-Standing Hostility: Both agree the U.S.–Iran relationship is deeply unnatural, seeing as “there are few nations in the world with whom the United States has more common interests and less reason to quarrel than Iran.” (16:48)
• Regime vs. People: Sadjadpour emphasizes the chasm between a “government that behaves like North Korea” and “society which wants to be like South Korea.” Most Iranians desire change and outside support.

4. Risks and Outcomes of Military Action

• Iran’s Weakness and Risks: Both discuss Iran’s vulnerability, but also how the regime prioritizes survival above all: “They're homicidal, but they're not suicidal.” (22:57)
• U.S. Overconfidence: Previous “rolls of the dice” (Trump’s withdrawal from the nuclear deal, Soleimani’s assassination, Operation Midnight Hammer) did not trigger regional war, potentially emboldening U.S. leadership.
• Downside Dangers: Sadjadpour warns, “Everyone has a plan until you get punched in the mouth” — the region is fraught with unpredictability, and U.S. partners in the Gulf remain ambivalent about supporting direct military action due to fear of blowback (22:57, 30:45).

5. Regional Players’ Perspectives

• Israel: Openly supportive, likely to participate in joint operations with the U.S.
• Gulf States: Profound ambivalence; publicly oppose U.S. strikes due to vulnerability to retaliation, though private advice may differ. They fear a “hit and run” U.S. operation that could leave them exposed (30:45).
• European Allies: Notably less supportive; traditional support (e.g., from the UK) is waning.

6. Diplomatic Off-Ramps and Regime Incentives

• Galloway floats the idea of offering Iranian leaders a safe exit to prevent desperate, destructive escalation (34:31).
• Sadjadpour notes there’s “no overlap in what we're demanding and what they're prepared to offer.” The regime’s isolation and intransigence make such negotiated exits unlikely (35:27).

7. Boots on the Ground and Scenarios for Regime Change

• No Appetite for Invasion: Both left and right, Sadjadpour says, have little support for a ground invasion. However, targeted efforts such as assassinating senior leadership remain possible (39:14).
• Uncertain Aftermath: Whether the regime’s security forces would fracture or double down after such an event is unknowable (39:14).

8. Role of American Values & Soft Power

• Sadjadpour calls for a revival of American soft power and alignment of U.S. policy with the democratic aspirations of the Iranian people, reminiscent of Reagan’s approach to the Soviet Union (42:35).

9. Left/Right Politics and U.S. Domestic Response

• Galloway challenges the American left’s perceived hypocrisy in protesting western-aligned oppression but remaining silent on non-western regimes’ abuses (47:25).
• Sadjadpour notes this “anti-imperialist bias” is perennial on college campuses and the far left, but has little real impact on events in Iran or policy decisions (48:25).

10. Post-Khamenei Scenarios and Prospects for Democracy

• Regime on Borrowed Time: Sadjadpour predicts the Islamic Republic will eventually “crumble under the weight of its own economic malaise and unpopularity,” but cautions that transitions rarely lead directly to democracy (51:43).
• Geopolitical Upside: A nationalist (rather than revolutionary) Iran would transform the region and align with U.S. interests and values.

11. Iranian Society’s Outlook and Diaspora

• Sadjadpour recounts his own near-imprisonment in Iran in 2005 and notes the regime's hostility to its globally successful diaspora (56:52).
• Both host and guest agree that Iran’s youth are “probably the most secular society now in the Middle east” and deeply drawn to western values and capitalism (60:55).
• Hope for the Future: Sadjadpour: “Iran is probably the best example where American values and interests intersect. We’ve underestimated the draw of our soft power” (60:55–63:44).

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Notable Quotes & Key Moments

• On the deep government–society divide in Iran:
  "There's no country in the world with a greater gap between the aspirations of its government and the aspirations of its people than Iran."
  — Karim Sadjadpour [16:48]

• On military risk:
  “Everyone has a plan until you get punched in the mouth.”
  — Quoted by both Scott Galloway and Karim Sadjadpour [20:17], referencing Mike Tyson

• On regime survival instinct:
  “They're homicidal, but they're not suicidal.”
  — Karim Sadjadpour [22:57]

• On the Gulf’s progress:
  “In 1979, Iran and the United Arab Emirates went to the same elevator and Iran pushed down and United Arab Emirates pushed up… The gap between these two countries is really enormous.”
  — Karim Sadjadpour [30:45]

• On Iran’s revolutionary intransigence:
  “...the mindset of the Supreme Leader is that if we give in to this pressure, it's not going to save us, it's going to invite even more pressure.”
  — Karim Sadjadpour [35:27]

• On American influence:
  “We prevailed [in the Cold War] because our values prevailed and think we should muster that same kind of energy vis a vis Iran now.”
  — Karim Sadjadpour [60:55–63:44]

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Timestamps for Key Segments

• State of U.S.–Iran Tensions: 11:29–13:41
• Possibility of a Deal vs. Military Action: 13:41–14:56
• Regime Survival and Iranian Public Sentiment: 16:48–20:17
• Risks of U.S. Military Action & Historical Overconfidence: 20:17–26:35
• Regional Perspectives & “Hit and Run” Concerns: 30:45–34:31
• Diplomatic Off-Ramps and Regime Change Scenarios: 34:31–39:14
• Boots on the Ground Discussion: 39:14–42:21
• Role of U.S. Soft Power: 42:30–45:54
• Left Wing Attitudes & Moral Consistency: 47:25–51:09
• Iran’s Future and Authoritarian Transitions: 51:43–56:49
• Sadjadpour’s Personal Experience in Iran: 56:52–58:39
• Iran’s Secular, Pro-Western Youth: 60:01–63:44

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Conclusion

The conversation concludes with both Galloway and Sadjadpour expressing cautious hope for Iran’s future—one driven not by military intervention or diplomacy alone, but by the “soft power” of American values resonating with a young, secular, and increasingly pro-Western Iranian society. The coming years in Iran, Sadjadpour suggests, will be pivotal not only for the Iranian people but for the broader geopolitics of the Middle East.

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For those wanting a reasoned, balanced update on the U.S.–Iran standoff, this episode is an indispensable listen, offering essential context, clear-eyed risk analysis, and a candid acknowledgment of both the limits and potential of U.S. power and values on the world stage.

Transcript

[Robin Arzon]

When things get hard, how do you talk to yourself? I'm Robin Arson, VP of Fitness Programming and head instructor at Peloton, and this week on my new podcast Project Swagger, I'm sharing my strategies for how to build better self talk. It's time to work on befriending yourself. Follow Project Swagger wherever you get your podcasts.

[Scott Galloway]

For a lot of Americans, credit card debt feels like a fact of life.

[Robin Arzon]

I think it's just important for people

[Podcast Host (The Vergecast or Explain It To Me)]

to understand how credit can work for

[Robin Arzon]

you or against you.

[Scott Galloway]

Why that little piece of plastic has so much power. That's this week on Explain It To Me. Find new episodes Sundays wherever you get your podcasts.

[Podcast Host (The Vergecast or Explain It To Me)]

You don't normally tune into a late night TV show expecting a rigorous debate about free speech, but somehow this is the world we live in. This week on the Vergecast, we're talking about how FCC Commissioner Brendan Carr has turned his agency into the Speech Police and why it's falling to people like Stephen Colbert and Jimmy Kimmel to fight back. That plus the gadgets we are and maybe aren't getting from Apple and others this year. And the latest in the chatbot force on the Vergecast. Wherever you get Podcasts.

[Scott Galloway]

Episode 385385 is the area code covering Salt Lake City, Utah. 1985 the Breakfast Club premiered What? What do a pregnant teen and the fetus have in common? They're both thinking, shit, my mom's gonna kill me.

[Podcast Host (Today Explained)]

Go, go go.

[Scott Galloway]

Welcome to the 385th episode of the Prop Tube Pod. What's happening? It's almost the end of February, which means we've completed, or nearly completed a month of Resist and Uns. The idea was over the course of

[Narrator/Commentator]

a month, to try and put a dent in big tech subscription growth and

[Scott Galloway]

send a signal to the markets and

[Narrator/Commentator]

to the President, believing that the only time the President checks back from irrational and sometimes depraved policies is when the bond market or the stock market declines. So we pulled together a list at Resist and Unsubscribe of what we call ground zero, that is companies, big tech companies mostly, that are very sensitive to subscription growth or lack thereof. And then what we call blast zone, and that is companies directly enabling ice. And the belief was that this was the string we could pull where 40% of the S&P is just 10 companies. And these companies are highly sensitive to any sort of check back in growth. The two objectives were 1 signal and 2 incentives. Signal trying to educate the American public that they have this weapon hiding in plain sight and that weapon is the most radical act in, in a capitalist society and that is non participation. The second was incentives. And that is have big tech executives ranging from Tim Cook to Jeff Bezos to Sam Altman check back and realize that it's just not a one way street. That if they enable, if they are sycophants, if they quite frankly just continue to ignore the depravity and the anti capitalist activities of this administration, that it'll be good for their shareholders and to send a strong signal that results in an incentive where they think twice before showing up at premieres or talking about supporting the president publicly when they're texting people, including myself, on how much they hate themselves. Well, we hate you too. That's not helping a lot. And also to recognize overpaying for documentaries or providing data that directly violate our rights to privacy and constitutional rights that there is a dual incentive. And that is it not only is good for shareholders to kiss up to the president, but could also be bad for shareholders. So let's review signal. We had over 22 million views of our social media posts. We were everywhere. By the end of February, we'll have approximately 2 million unique visits to the site. To give you a sense of how difficult that is, if you were to launch an e commerce site or a content site and try and drive 2 million unique visits, and you asked for a budget to try and inspire 2 million visits to a site that no one had heard of before, it would cost you somewhere between four and a half and $8 million. And that's sort of the first tactical learning. And that is we have a very strong social footprint that we've been working on for the better part of a decade and a half here at Profg Media, whether it was videos we did at L2, whether it was me doing a follower strategy after night feedings with my first son 15 years ago to build a Twitter following. We have consistently invested in social media. And while I think it's ripping at the fabric of our society, there's just no getting around it. Social media is now the means of driving traffic and influence across almost everything. And if I look at the different media vehicles, the traditional media did in fact play a role. And I have a lot of contacts there. And if you're sick of seeing my face, I get it. I have been everywhere from CNN to NPR to Ms. Now to name your media outlet, I've probably been on it. What we found is the traditional media creates a halo. But what has really moved the needle was some surprising things. An article posted to their website npr.org, an NPR article really moved the needle. A virality of celebrities posting When Chelsea Handler posted a video a reel of the thing she was unsubscribing for, it got over 120,000 likes and probably between 1 and 2 million views. And we spiked visits to the site by about 6 or 7,000. And if you do the math and that is conversion to actual unsubs number of unsubs revenue that has been lost by big tech times the multiple she alone probably took a million to $2 million out of the market cap. So traditional media not as effective. Podcasts very effective. But the virality of individuals posting on their own social media is probably number one. We got some mentions from elected representatives. Representative AOC and Kinzinger both mentioned it. Some senators mentioned did that drive traffic? We didn't see a blip. In sum, it looks as if new media continues, especially social media, continues to draft off of and suck oxygen from traditional media. What do we do moving forward? We are faced with some options to partner with other resistance efforts to keep going, maintain the current strategy to zero in our one or more companies. We seriously considered zeroing in on one or maybe two companies. The problem is one of the things we like about this movement is that we're not being arbiters of what you should or should not subscribe to when you resubscribe. This was meant to be a one month effort and so we are not going to actively promote the site, but we are going to leave it up and we're also going to highlight some other great efforts such as first off, quidgpt, the team behind quidgpt, argues that historically the most effective boycotts have two things in common. They're narrow and they're easy. If you're a one action kind of person, we encourage you to cancel ChatGPT from OpenAI. ChatGPT is Trump's biggest tech donor and a facilitator of ICE. Enough said. Also, there's good substitutes. The free version trading at a 40 times multiple of revenue. Just one cancel, one unsubscribe from the paid version of ChatGPT likely hits this firm's enterprise value of around $10,000. Second, the impact calculator. It takes our high level thesis and drills down into specifics showing the estimated financial impact of our individual consumer decisions. If you want to know the exact impact your action has on a company, it's worth exploring. And then, just as we wrap up here, the final objective was a more personal one and that is I have a tremendous amount of anxiety around what I see as happening in our country. I think many of the things that I have benefited so much from competition, rule of law, civil rights, a general respect or a camaraderie amongst citizens, a respect for immigrants, I think those things are directly under attack. And when I reverse engineer all of my success to the things that aren't my fault, a lot of those things are in fact under attack now. And I'm sick of just barking from the cheap seats on podcasts or getting angry or being profane or speaking to you and expressing my indignance, my actions behind a keyboard, if you will, need to foot to my actions in the real world. And also I find that action absorbs anxiety. And it felt really good to do something with other people. And I'm gonna continue to do those things. We're gonna have an event in Minneapolis in nine or ten days highlighting the brave work of the good men and women in Minneapolis. And one of the reasons I'm moving back to the US is I want to play a role in 26 and in 28. So what I would ask of all

[Scott Galloway]

of you is the following.

[Narrator/Commentator]

If, like me, you have benefited a great deal from some of the wonderful attributes of what is makes our America American, of what makes our America America, then I would ask, what are you actually doing outside of your keyboard? Are you planning to register people to vote?

[Scott Galloway]

Are you raising money for candidates?

[Narrator/Commentator]

Are you yourself making signs and going to protests? What exactly are you doing? And ask yourself finally, do you have a debt? If you're of my generation, have you enjoyed unprecedented prosperity with the lowest taxes in history and an all volunteer army where you've never been drafted, never really asked to commit? In sum, I have a debt and I recognize that. And I would ask all of you to ask yourself, do you have a debt? Are you standing on the shoulders of other Americans from past generations that have sacrificed such that we could have such extraordinary prosperity and such extraordinary freedoms? America has faced darker times before. Civil wars, world wars, civil rights battles, plagues. But Americans have always equaled to the moment. This is our moment. So do you have a debt? And are you equal to this moment? We very much appreciate your support and your participation in resist and unsubscribe.

[Scott Galloway]

Okay, enough of that. Moving on. In today's episode, we speak with Kareem Sajapur, a senior fellow at the Carnegie Endowment for International Peace specializing in Iran and US Foreign policy. We discuss with Karim the current state of play regarding U. S. Iran tensions, odds of strikes, and what a successful nuclear deal would actually require. And just a note, this conversation is being recorded on Monday, February 23rd. So if headlines change, you know, forgive us. So with that, here's our conversation with Kareem Sajapur. Kareem, where does this podcast find you?

[Kareem Sajapur]

I'm in snowy Washington, D.C. scout.

[Scott Galloway]

Oh, Snowmageddon. Is, is it as bad as ever? Is this a bomb cyclone? Is it as bad as everyone was predicting?

[Kareem Sajapur]

It's not as bad as New York City. I think the worst is probably behind

[Scott Galloway]

us in D.C. let's bust right into it. I can't imagine. You must be the most requested person in cable news right now. We're in the midst of escalating tensions between Iran and the US As Donald Trump builds up US Forces off Iran's coast for possible military action against the regime. Give us from your vantage the state of play right now.

[Kareem Sajapur]

So I think, Scott, this is we're in a game of chicken right now between two individuals. That's President Trump and Iran's supreme leader, Ayatollah Khamenei. I think President Trump thought he could essentially recreate the strategy that seemingly worked in Venezuela, which is to subject Venezuela to enormous economic and military pressure as a prelude to decapitating that regime and forcing about its capitulation or compromise. And in the case of Iran, this is the largest military buildup in the Middle east that the United States has had since the 2003 invasion of Iraq. Iran is obviously under enormous economic pressure and Trump's top advisers have actually expressed confusion as to why Iran hasn't yet compromised. And I think that has to do a lot with the will of Iran's 86 year old dictator, Ayatollah Khamenei, who's one big idea over the last few decades has been resistance against America.

[Scott Galloway]

So it's interesting you call it a game of chicken and anyone who's listening to defer your children, but I would have described it as a fait accompli, that effectively I don't think Trump wants them to back down or come to a nuclear deal. I think he likes the flex and the macho sheen of that military operation in Venezuela. In my senses, it's a go that we are going to engage in a military operation there. But you think that this is chess and that there's opportunity for a deal.

[Kareem Sajapur]

So I think in President Trump's heart, he would prefer to have a peaceful revolution to this matter, if he can get a deal from Iran, major concessions from Iran without having to go to war. I Think that's a preferable option for him. And every conflict, especially one of this nature, entails potentially enormous risks. Right? Iran is a more powerful country than Venezuela. It has thousands of short range missiles which it's threatened to use against US bases in the Persian Gulf. It's threatened to go after oil installations to spike the price of oil. Even individuals adjacent to Iran's Revolutionary Guards have threatened to destroy places like Dubai. So this isn't a totally risk free proposition for President Trump. And I think if he could get a deal without having to fire a single shot, that would be the preferable outcome. Now, I agree with you that in my view, the likelihood of a deal at this moment appears not very high. And for that reason, I think the likelihood that the United States takes military action is much higher.

[Scott Galloway]

So let's think about this. It feels like the amount of military hardware that's been floating towards or shipping towards the region, transport the region. The thing that struck me was just the number of refueling planes that we're basically going to have this constant gas station in the sky that they are looking at putting in place the infrastructure and resources to have a sustained campaign against Iran. If we come to a deal. What is your view? Is there a good deal that leaves the Islamic Republic in power? Because my sense is that as long as this regime is in power, there's going to be instability in the Middle East. There's going to be a regime that has been pretty oppressive and that. I see an upside here. And this is Pollyanna. I went to ucla. It sounds cliche to say some of my best friends from Iran. And I've always thought Iranians that I met in the United States felt more American to me than Americans. A love of education, a love of commerce and capitalism. Fam. I thought there's gotta be a DNA or my sense of Iran. An appreciation for science, great universities, incredible history, incredible culture. Iran could be a fantastic American ally. And I have this vision where we unlock through some sort of new regime in Iran that ends up being a great ally for the United States and there's just less chaos and less funding of terrorism and that anything that leaves the Islamic Republic in place is, over the medium and the long term, a bad deal for the US Give me your thoughts on whether or not there is a future where we leave the Islamic Republic in power. That is a better alternative.

[Kareem Sajapur]

Scott, I wholeheartedly agree that this is a malicious regime with virtually no redeeming qualities. I've often said there's no country in the world with a greater gap between the aspirations of its government and the aspirations of its people than Iran. Right. You have a government that behaves like North Korea, society which wants to be like South Korea. And, you know, this gap, in my view, is not sustainable. And it's also irreconcilable after what Iran did to its own people last month, which is, according to some estimates, it killed as many as 30,000 people in the course of 48 hours. So I totally agree with you there. And I also agree with you that the state of U S. Iran relations today is a very unnatural state. I always quote Henry Kissinger who said, there are few nations in the world with whom the United States has more common interests and less reason to quarrel than Iran. But what we've seen since the 1979 revolution is that Iran hasn't behaved like a nation state following the national interests and economic interests of its people. It's behaved as a revolutionary cause. And in my view, that is not sustainable. The question is whether the United States has the ability with military force to totally change that reality. And, you know, the last two decades of American history in the Middle east doesn't lend an enormous amount of confidence. We invested a great deal of blood and treasure in Afghanistan and Iraq, and we weren't able to dictate the outcomes that we wanted. So I believe, ultimately, Scott, Iran's future is going to be decided by its people. Now, I should say that this is based purely on what I observe anecdotally. I don't think there's any scientific polling on this, but seems to me an overwhelming majority of people inside Iran who oppose the regime, and I would say it's probably around 80%, if not more of society would like to see outside help. They actually would like to see President Trump make good on his promise. President Trump promised on more than eight occasions that if Iran kills protesters that the United States would intervene, it would have the backing that America would have Iran's back, the backing of Iranian people. And that changed people's risk calculations when they took to the streets because they thought the United States is going to support us. And that support hasn't come. And I think that's why overwhelmingly people in Iran want to see that support. But, you know, one thing I'm always mindful of, Scott, you mentioned, you know, your days in the UC system. I'm a University of Michigan guy, and every year during March Madness, I fill out two brackets, one with Michigan winning it all and one with what I think might see happen. And here it's, you know, we have to be mindful not to conflate our, our hopes and emotions and analysis that I think everyone would love to see, would love to see a magic bullet that just eliminates this regime and empowers an Iranian democracy which once again becomes friends with the United States, as it should be. There's not a lot of great examples from history that there's such a clean operation that exists.

[Scott Galloway]

That's fair. We have a long and storied history of just, of just, quite frankly, of just fucking up when it comes to the Middle East. Do you think that the Islamic Republic could survive a sustained military attack? I mean, it's easy to plan. What did Mike Tyson say? Everyone has a strategy until you get punched in the face, I would imagine. And I'm curious what you think that we're coordinating with Israelis, with the Mossad, to have a series of targeted assassinations similar to what happened before they took out the air defenses. But one of the reasons I'm a fan of military action is I feel this is a unique moment in time where Iran or the Islamic Republic is on its heels, its air defenses have been taken out, its proxies. I mean, one of the things that strikes me is just how damaging and dangerous this regime is, is that now that it's on its heels and Russia's distracted in Ukraine, it feels to me like it's been fairly peaceful in the region. The Suez Canal has not had a bunch of attacks. Hezbollah is not firing missiles into Israel. Right. It feels like, okay, why is that? Basically, the Islamic Republic has had its hands cut off, its air defenses are down. It feels like this is a unique moment in time to go in and kind of we're at the five of the 10 yard line. I think the Iranian people have shown extraordinary sacrifice and committed here. And we're going to get to the 10 yard line and then give them a chance to stabilize, survive, rearm, and we're going to hope for their better angels to show up. It just feels like it's worth the risk. So the risk we go in, we start a, do you believe we're coordinating with Israel on this? And two, you think the Islamic Republic could in fact survive military action? Sustained military action from the US I guess the question is, at some point do we have to put boots on the ground and what is potentially so, and they fire missiles at other western affiliated entities or allies? It feels to me like the asymmetry is way to the upside here. But again, I'm naive and I want to acknowledge every time we've made that calculation. We have underestimated the potential downsides here. But what do you see as the real. Give me a scenario of the real downside here. If you're arguing for letting the Islamic Republic stay in place.

[Kareem Sajapur]

Well, I happen to agree with your instinct, Scott, that Iran is perhaps weaker than it's ever been. It's essentially a government which is in between two fires and internal fire and an external fire. It's probably one of the loneliest countries in the world. It has very, very few allies. And if we try to get inside the head of President Trump and you look at his 10 year history with Iran, well, on three major occasions, he's rolled the dice. In 2018, he left Obama's nuclear deal with Iran. In 2020, he assassinated Iran's top military commander, Qasem Soleimani. And then last summer was Operation Midnight hammer, he dropped 14 bunker busters on Iran. Now, on every single one of those decisions, people predicted that it would trigger World War Three or at the minimum, a major regional war. That didn't happen in any of those occasions. And I think President Trump feels that he was vindicated each time. And now when Iran doesn't even control its own airspace, as you alluded to, their regional proxies have been decimated. I think he feels very confident that if he rolls the dice again, Iran is a paper tiger. And ultimately it's a regime whose paramount goal is to stay in power. They're homicidal, but they're not suicidal. And so for that reason, their willingness and ability to respond in a major way against the United States is not likely to happen because they know if they were to unleash massive amounts of missile fire against America in the region or against our allies, that it could trigger a massive U.S. response. And I agree with what you said, Scott, that 100% the United States is going to be coordinating this with Israel. But I also agree with the quote you mentioned. Lawrence Friedman wrote the definitive book on strategy. And that book, which is about 700 pages, starts with that sentence from Mike Tyson that everyone has a plan until you get punched in the mouth. And we don't know how Iran is going to respond this time to a potential US Attack. It may be that they exercise restraint and they're going to hunker down like a hedgehog because they want to stay in power. Or it may be that their lesson from the previous conflicts was that by not really retaliating in a meaningful way, they projected weakness and they didn't exact any cost from the United States. And it's now a moment to stand up to this American bully. We don't know that, and so I want to emphasize that it is a risk. And if you're President Trump, you perhaps like your odds because American military power has prevailed in the past and the United States is several thousand miles away from Iran. But if you're sitting not that far from Iran and the United Arab Emirates or Saudi Arabia, you have much greater ambivalence about what Iran is capable of doing and whether the United States will maintain that massive military presence to protect against them.

[Scott Galloway]

We'll be right back after a quick break.

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[Podcast Host (Today Explained)]

In the wake of the release of millions of documents related to the Jeffrey Epstein case, the rich and famous are finally feeling some pain. But even with corporate resignations here and with former Prince Andrew being arrested in the uk, the question remains, how did Jeffrey Epstein remain a thriving member of the elite for decades when everyone seemed to know what he was up to?

[Robin Arzon]

I don't think you could be friends with Jeffrey Epstein, whose MO was obviously having sex with young girls, even as Trump said, on the younger side, and not know his mo.

[Podcast Host (Today Explained)]

Untangling the Epstein conspiracy. That's this week on Today explained every weekday and now on Saturdays.

[Scott Galloway]

So let's talk about that because it feels like my understanding is Israel and Jordan are firmly in the ally camp. Who will, who will provide infrastructure? And what's strange is the allies we used to rely on, including the uk, have basically said we're not going to provide you with infrastructure, support, landing rights at Diego Garcia, which is really unusual. That we might have some Gulf nations who are more supportive of the US's military actions and some G7, which I think speaks to just crazy head up your ass geopolitical strategy, the us. But different talk shows run us through the region. In your mind, what do you think the various players in the Middle east are saying to the President? Do they endorse the strategy or are they trying to coordinate and help? Are they bereft and just saying he's going to do this, but we want some sort of security guarantees, or are they trying to talk him out of it? Go across the biggest players and what you think their view is on a potential strike on Iran?

[Kareem Sajapur]

Well, we can start with Israel by saying that Israel is both, you know, publicly supportive of its strikes. They're privately encouraging the president and they will very likely be part of any US operation against Iran. And then if we move to our partners in the Persian Gulf countries like the United Arab Emirates, Saudi Arabia, Qatar, as I said there, there's much more profound AMBIVALENCE publicly, they're going to oppose a US Strike. And they publicly said they're not going to allow the United States to use their airspace to attack Iran because they don't want to be complicit in any operation because they fear the Islamic Republic of Iran. Iran has attacked them in the past. They've used their regional proxies, like the Houthis in Yemen, who are still a menace, to attack those countries. And one of the lessons I learned, Scott, I did a Fulbright in Beirut about over 20 years ago, and my big takeaway from that year is that it takes decades, if not centuries to build things, and it takes weeks to destroy them. And those countries, I take my hat off to them, in particular the United Arab Emirates. I tell people in 1979, Iran and the United Arab Emirates went to the same elevator and Iran pushed down and United Arab Emirates pushed up. And the gap between these two countries is really enormous. When you think about Iran is more than 20 times the size of UAE. Iran has the human resources, the natural resources, the history to be a G20 power, but it's none of those things. It's a global pariah. And the United Arab Emirates, which was really a backwater five decades ago, has emerged as this global hub for transport, for technology, for geopolitics. And they have a lot to lose here because they know that Iran could come by in a week or so, unleashing its missiles, rockets and drones and destroying what has taken them many decades to build. And for that reason, none of those countries in the Gulf are going to publicly support US Military action against Iran. I think privately, the advice they give is probably a little different. But one of the things I would argue that they are all worried about is what they call a hit and run attack. They're worried that President Trump could attack Iran, and then a week or two later, his attentions are diverted back to whether it's Venezuela or Taiwan or another issue. And they're left naked and vulnerable. And they don't have the luxury of being many thousands of miles away from Iran. Now, you mentioned earlier, and people can look online at this map of this incredible American buildup right now in the Middle East. If you talk to people at the Pentagon, they will tell you that most of that buildup is for defensive purposes. It's not that we're going to unleash all of that firepower against Iran. That buildup is there in great part to protect our allies, protect our bases against Iranian retaliation. But the reality is that those forces aren't going to be able to remain in the Middle east forever. And there's no guarantee that any US Military action will topple the regime in Iran. And so that is a risk that I think President Trump and vast majority of Iranians are prepared to live with. They're prepared to roll the dice. In that way, those Gulf countries have a lot more to lose.

[Scott Galloway]

What was it Sun Tzu said? Unless you want to slaughter everybody, you always want to give your enemy an out? And have you heard of. Or what's the state of. Is there a situation where we say to the leaders of the Islamic Republic, you've murdered tens of thousands of people, but get out now, get on a plane to Russia similar to what we did or what they did in Rwanda. They said they had a name from the genocide. Re we're going to exonerate you or come up. In other words, give them incentives so they don't fight to the death and start launching drones against Dubai and just last gasps of desperation.

[Narrator/Commentator]

A.

[Scott Galloway]

Do you think that's a possibility? Is there a scenario where we say to the leadership, and I would think the one level down, all right, here's a potential exit plan for you, such that we don't, you know, a cornered animal is frightening, right, dods?

[Kareem Sajapur]

I mean, there's actually a Persian expression that corroborates that, which is, if you have a wild cat trapped in a room, you need to leave a door open to allow it to go out. And again, I actually do think that President Trump and his top advisors on this issue, if they could push a button, they would like to see diplomatic outcome. They would like us not to have to go to war. The challenge at the moment is I don't see a Venn diagram in which American demands and Iranian concessions currently intersect. Because what we're demanding from Iran, not to get too technical, but we want, we're demanding that they don't enrich any uranium, something that they insist on. And we're also demanding that they significantly curtail their missile program, they cease their support for these destructive regional proxies like Hezbollah and the Houthis, and that they treat their population better. What the Iranians have said is, we will only speak to you about our nuclear program. None of those other things are on the table, and we refuse outright to agree to zero enrichment. So at the moment, there is no overlap and what we're demanding and what they're prepared to offer. And again, I go back to the person of Ayatollah Khamenei, 86 years old, his only big idea over the last decades has been resistance. He's long believed that if you capitulate or you compromise as a result of pressure, that's not going to ultimately prolong your shelf life. That's going to convey and project weakness to your adversary and they're going to take a step forward. And so I think at his age, at the moment, he seems prepared to die a martyr more than he is to die a capitulator. The other challenge we have, Scott, is that in contrast to the government that existed in Iran before the revolution, the Shah's government, in which most of the governments and military's elite had studied in America or Europe and spoke foreign languages and potentially had foreign passports and can remake their lives in Los Angeles and London. These guys, as I said, they're probably one of the most isolated, friendless regimes in the world and there's not a lot of places they can go to for plan B. And so for that reason, what we've seen from them internally is they're prepared to kill tens of thousands of their own people rather than seed power and vis a vis external adversaries. The mindset of the Supreme Leader is that if we give in to this pressure, it's not going to save us, it's going to invite even more pressure.

[Scott Galloway]

I mean, no one wants to talk about boots on the ground. Do you think that right now a military strike just involves. My understanding is it's very hard to execute a regime change from the air, that there has to be either special ops and also I think the Islamic Republic has the benefit of believing this is probably coming. Do you think, what do you think it feels like? At least the prediction markets are saying before the end of March, there's about a 60% or 2/3 likelihood that there's going to be some sort of military action. But there's a difference between, quite frankly, bombing from the air, where their air defenses have been mostly wiped out, and putting boots on the ground. And a lot of military professionals will say you can wreak havoc, but you can't foment change from the air. What do you think are the chances of some sort of boots on the ground strategy?

[Kareem Sajapur]

I think the likelihood of boots on the ground is very slim. I don't see any support within the Democratic Party for that, nor do I really see it among Republicans. I think even people like Vice President Vance would probably profoundly oppose that. I think you have a lot of people in the MAGA base who even oppose air power against Iran and the threat of getting pulled into another Middle Eastern War. So I think the likelihood of boots on the ground is very low. But one possibility, which I've spoken to a lot of people, both within the United States and Israel, is that if the United States does decide to take military action, there's a decent likelihood that we will try to take out Iran's supreme leader, Ayatollah Khamenei. And he goes underground in these moments of crisis, perhaps 150ft underground in a bunker. But that didn't protect the leader of Hezbollah, Hassan Nasrallah. The Israelis bombed his bunker. And. And what's interesting is he died from suffocation. He didn't die because the bombs dropped on his head and killed him. His body was intact, but he died from suffocation. And so that is certainly a possibility. And the reality, Scott, is that no one can predict what comes the day after that. And the big question for the future of the Islamic Republic of Iran is, is the cohesion of its security forces. Up until now, we've seen enormous popular protests, enormous popular discontent. But the regime's security forces, the Revolutionary Guards, the Basij militia, who collectively probably number in the hundreds of thousands. Revolutionary guards are probably 150,000 men. Basiej perhaps double that. We haven't seen yet signs of splinters or fissures amongst them. And the question is, if the United States decides and carries out an assassination against Iran's supreme leader, what happens to the cohesion of those forces? Do they rally together and do they believe it's either kill or be killed and hunker down and survive to kill another day? Or is Khamenei the glue that holds them together and they eventually disband? And the honest answer to that is that we don't know. And we don't know, Scott, because I don't think they know. We oftentimes underestimate the extent to which when people are put in these crisis situations, you oftentimes don't know how you're going to react. Every person is making mental calculations, and this is a gamble, and it could go in multiple directions. And again, I think President Trump feels probably pretty good about his odds. I think the Iranian people would welcome that gamble from the United States. But other countries in the region are concerned about the blowback against them.

[Scott Galloway]

We talked about bunker busters. So Trump calls the military operation where we went after the nuclear sites a resounding success.

[Kareem Sajapur]

Was it, in your view, you're talking about last summer?

[Narrator/Commentator]

Yeah.

[Kareem Sajapur]

Yeah. So it depends what your metric is. I mean, President Trump had said that he had obliterated Iran's nuclear program. And it was end of story. You know, the program was done for now he's saying that we need to get a nuclear deal with him. And his envoy, Steve Witkoff, recently said that Iran is perhaps weeks away from weapons grade uranium, which it's not really clear that I think they don't actually have a great grasp of the issues that they are tasked with negotiating. So, you know, oftentimes their language is a little bit money. But there is a tension there because, you know, he declared success, the program was obliterated. And now the question is, well, why are we negotiating wanting to negotiate with Iran over its nuclear program if we already obliterated it? And here my view is that what's lacking here is one of the strategy that Ronald Reagan applied to the Soviet Union, which is if you go back and read Reagan's speeches, the language was quite simple. He believed that one of the most powerful forces in the world was the desire of human beings to live freely, to live under free societies. And he aligned American power and American foreign policy with that goal of Russians to live under freedom. And he stood with those freedom seekers in Russia, those dissidents. And we had a whole kind of institution, multiple institutions in the United States, places like Voice of America, Radio Free Europe, National Endowment for Democracy, which stood for those aspirations and those goals and help those democratic and freedom movements. And that doesn't really exist at the moment. Those institutions have really atrophied. And I don't think President Trump, he issued these warnings against Iran, not to kill protesters. But living in Washington, I can see that there aren't a lot of people right now, whether in the State department or other NGOs that are empowered to be thinking about how do we advance the cause of change in Iran, how do we potentially help Iran's opposition? And you're ultimately correct, Scott, what you said earlier, that it's my view that the US Iran Cold War, which has now persisted for 47 years, it's not going to be ended by American negotiators or even American bombs. It's going to be ended when you have a government in Iran that reflects the country's national interests of wanting to advance its own prosperity and security. And we can destroy a lot with military power, as we've seen in a lot of other places. But I think those institutions that help kind of solidify the day after and the day after the day after in those countries, those institutions have atrophied in the United States.

[Scott Galloway]

We'll be right back.

[Narrator/Commentator]

What are the Main takeaways of the foreign policy section from Donald Trump's State of the Union address. I do think they've made a decision to elevate domestic issues. As we head towards the midterms, we'll see if that sticks because he keeps getting drawn back to the foreign policy issues. I'm John Finer. And I'm Jake Sullivan and we're the hosts of the Long Game, a weekly national security podcast. This week we'll react to President Trump's State of the Union address, the situation with Iran, and the eruption of violence involving cartels in Mexico. The episode's out now, so search for and follow the Long Game wherever you get your podcasts.

[Robin Arzon]

This week on Net Worth and Chill, I'm joined by her first 100K, aka Tori Dunlop, a fellow personal finance creator who's changing how an entire generation thinks about money. Tori's journey is a masterclass in turning personal finance wins into a platform that empowers millions. She opens up about the real strategy behind hitting that six figure milestone without the typical privileged blind advice, and how she's redefining what it means to be a wealthy woman in 2026. We're diving deep into investment strategies for real people with real budgets and why financial feminism isn't just a buzzword, it's a movement. Get ready for an unfiltered conversation about money, entrepreneurship, and what it really takes to build both personal wealth and a business empire. Listen wherever you get your podcasts or watch on YouTube.com YourRich BFF

[Scott Galloway]

we're back with more from Kareem what are your thoughts around why when there's certain conflicts it inflames elements of the left. And yet there seems to be. I mean, quite frankly, I'm dancing around the book I see the left or the far left as being not anti war but anti west that I find that there's such a hypocrisy of what eclebn refers to a moral color code that when the oppressors are seen as brown, we call it culture and when the oppressors are seen as western or white, we call it genocide. I'm curious on your thoughts around the lack of protest or concern around these 30,000 people who in my opinion have been murdered by state sponsored terror and the lack of what I'll call a a protest movement in the United States.

[Kareem Sajapur]

You know, I'm always reminded of that old quote attributed to Winston Churchill who said I'm paraphrasing here perhaps, but if you're 18 and not a leftist, you have no heart. And if you're 50 and still leftist, you have no brain, which is that there's long been this tendency among young people to want to stand up against imperialism. And you know how that's manifested is to oppose governments, the conduct of governments that are allied with the United States and those governments who are opponents of the United States, whether that's the Islamic Republic of Iran or Bashar. I said Syria. In modern times, there's very little criticism when they kill tens of thousands of their own people. And you know, in a previous generation, it was dictators like Stalin and the Soviet Union or Mao who killed millions of their people. And yet I think the anti imperialists were obviously opposed to American power and the conduct of American allies. And that's just something that I've kind of resigned myself to that. That's the reality of, of college campuses in a lot of places. And I guess if someone who represents that point of view were on the call with us now, they would say, well, the issue is that we don't have any ability to influence how Iran or Assad's Syria or Putin's Russia conducts themselves because they're U.S. adversaries, but we do have influence over how our allies conduct themselves. That would be their counter argument. But I've just kind of, to be honest, Scott, for me that's just a lot of noise. It doesn't really at the moment have any impact on what the United States is going to choose to do. And I don't think it profoundly impacts popular opinion inside Iran. The college campuses inside Iran are overwhelmingly hoping for some kind of U.S. intervention. And yes, there's a great deal of resentment towards those on the left who have shown sympathy for the Islamic Republic. But I don't think that noise is really that meaningful or impactful. It gets a lot of attention on social media, but it doesn't really move the needle one way or the other in my view, when it comes to the policy choices people are going to make.

[Narrator/Commentator]

It just strikes me that if you

[Scott Galloway]

were to go back two or three years and say that Iran had basically been emasculated and that the clear superpower in the region appears to be Israel, just how much things have changed? Do you have any thoughts? I mean, you're called on at the highest levels to provide advice. And I imagine people are constantly asking you to speculate. Have you game theoried out where you think the Middle east is and how the different centers of power will likely change over the next several years?

[Kareem Sajapur]

So there is an essay I wrote in Foreign affairs that came out last fall. It's called entitled the Autumn of the Ayatollahs, about scenarios for post Khamenei Iran. And it is my view that this is a regime on borrowed time. Whether or not the United States chooses to take military action, this is a regime which I think it's like the last years of the Soviet Union. It'll eventually crumble under the weight of its own economic malaise and unpopularity. One of the things I tell people, Scott, is that this is a regime which is a theocracy. It rules from a moral pedestal and it's elbow deep in corruption and repression. And that is especially insulting to people because, you know, if you find out your rabbi or priest or imam is stealing from you, that's much more offensive than your local grocer stealing from you. And so this is a population which is really outraged and that's palpable. And this status quo is not sustainable in Iran. The question is, what happens in the years to come? And one of the statistics that has jumped out at me in my research is that From World War II to the present, only around one in five authoritarian transitions lead to democracy. More than 80% of the time, it leads to another form of authoritarian regime. So, as I said, I would love to be able to say I see Iran transitioning to Norway or Denmark. The statistical odds aren't great for that. But that doesn't mean that change inside Iran won't be an improvement for the Iranian people and for the United States, because ultimately this is a government which has been acting against its own national interests. In my view, the national interests of its people, meaning the economic prosperity and security of its people. And so even if you see this regime replaced with a government whose ethos is not death to America and death to Israel, but long live Iran, that is a geopolitical game changer. The Middle east, in my view, is not going to change so long as this regime remains in power in Iran. Just as long as Germany was ruled by radicals, Europe was not going to change. And the impact will be felt beyond just Iran. The impact will be felt on global energy markets. You know, Iran should be an energy superpower. It's got the second largest reserves of natural gas, the third largest reserves of oil, and it's punching way below its weight because of its isolation and economic sanctions. So that would be geoeconomic game changer. Then all of the mischief that Iran is up to in places like, you know, supporting essentially all American adversaries throughout the world, whether that's governments in Venezuela and North Korea supporting Putin's war against Ukraine. None of that, in my view, is a reflection of Iran's national interests. And so I do think there is great upside if we see a transition in Iran from revolutionary government to nationalist government. But what we also know from history, Scott, is that the popular will doesn't always prevail after dictatorships collapse. I'll give you a couple examples of that. In 1990, when people were protesting against the Soviet Union, probably no one said that we want to be ruled by a mid ranking KGB agent. But that's exactly what happened when Vladimir Putin came to power several years later and he's been ruling Russia for more than two decades. In Egypt in 2011, where people were protesting the government of Hosni Mubarak, probably no one's preferred outcome was to be ruled by another military general. And that's the outcome that prevailed in the form of the General Sisi, who's been ruling Egypt with an iron fist over the last decade. So unfortunately, this is something I'm mindful of in my work, is hoping for the best and always looking what are ways in which we can advance US national interests? What tools advance US national interests? And I think Iran is a very good example of a place in which American values and American interests intersect. Meaning if we did have a representative democracy in Iran, that would be fantastic for the people of Iran, it would be fantastic for US national interests. And I think we should try to work towards that outcome at the same time recognizing that we don't unfortunately have the power to push a button and dictate our ideal outcomes.

[Scott Galloway]

Karim, when was the last time you were in Iran?

[Kareem Sajapur]

The last time I was in Iran was 2005 and I was nearly imprisoned. I had been based in Tehran. I was based there with an organization called the International Crisis Group. I was in my 20s and they had taken away my passport and prohibited me from leaving the country for several months. I was subject to interrogation and there was a moment when I was trying to leave when a couple hours, I thought I was about to be taken to prison and fortunately I was allowed to leave. And I was later warned by Iranian officials that if I go back I would be arrested upon arrival at the airport. And so I heeded that warning and I haven't been back. But many of my close friends didn't heed that warning and some of them were taken hostage in Iran for many years. And so, you know, Scott, you alluded to it at the beginning. Iran has one of the most successful diasporas in the entire world. Captains of American industry, people like Dara Khosrowshahi, the CEO of Uber. These are people who are very proud of their heritage and they would love to contribute to positive change in Iran. But you have a regime which essentially views its diaspora as adversaries. And rather than enlisting their support, hostage taking has become a business for this regime. And so for the foreseeable future, certainly as long as this regime is in power, I'm not going to be visiting Iran.

[Scott Galloway]

And again, this might be Pollyanna. And we'll wrap up in a segment generosity or time. I was in Mykonos a couple summers ago and we went to one of those super high end restaurants where everyone ends up dancing on tables and young people are spending thousands of dollars and signaling and all the rest. And there were a lot of kids from the Gulf and I'm making stereotypes here, but they all spending a ton of money, all incredibly respectful. I got the sense they were basically told by their parents, here's a credit card with no limit, just don't embarrass us. That's the vibe I got. And there were some negative comments from people about all these golf kids are so gluttony. This is a sign of hope. These are kids from the region who are capitalists. They want some of the accoutrements of Western society. This is a positive that they want to be part of. Whether you find it obnoxious or douchey, whatever, it's better than them going hard right or becoming religious fundamentalists who hate the West. Am I being Pollyanna in that there is an emerging younger generation in Iran that wants to look west and is more capitalist and wants to enjoy, I won't even say the freedoms, because in the Gulf we don't usually end up with democracies and it's unlikely we'll end up with a democracy here.

[Narrator/Commentator]

I heed the point.

[Scott Galloway]

But is there an emerging generation of people in Iran that quite frankly want to look west, want to take advantage of some of the capitalist accoutrements, that want to take advantage of the incredible resources and economy that Iran could start producing? And is that an unrealistic vision of what could happen here?

[Narrator/Commentator]

Because I'll go back, I'll finish where I started.

[Scott Galloway]

You mentioned some people. One of my mentors when I was at San Francisco, a guy named Hamid Mogandham who came over during the revolution, CEO of Prologis, probably the biggest Reid in the world. And I can go on. My friends in the fraternity, David Aseel, Carrie Asseel, they all just Literally struck me as being more American than Americans. Is there an emerging generation of people who really would embrace the capitalist Western mentality?

[Kareem Sajapur]

100%. Scott. This is probably the most secular society now in the Middle east. And that's what 47 years of theocracy. That's the legacy it's left for Iran that you have a population desperate to separate mosque and state rather than join it. It's the most anti American regime probably in the world. It's probably the most pro American population in the Middle East. So I think everyone in Iran or the vast majority of young people recognize that Iran will never fulfill its enormous potential as a nation so long as their official slogan is Death to America. But I say there's kind of two kinds of actors in the Middle east. To go to your mentioning of the Gulf countries. So you have countries like the UAE and Saudi Arabia and they have forward looking visions. Vision 2030 Vision 2031. The vision of the Islamic Republic of Iran is Vision 1979. It's a backward looking vision. The Gulf visions are appealing to people's aspirations and hopes. The Islamic Republic of Iran is trying to appeal to people's grievances. I call them falcons and vultures. The falcons want to build soaring societies and cities and companies. The vultures are just trying to feed off the misery of others. And that model has been totally proven bankrupt inside Iran. No one wants to live under this model. I would even argue within the regime. The vast majority realize that this is a broken model that's not going to work. And so I am hopeful about Iran's future. I say there's light at the end of the tunnel and the challenge is to create that tunnel and so people can fulfill the enormous aspirations and enormous potential they have as a nation. And so I just want to emphasize, I think that that is also a US national interest. Iran is probably the best example in where American values of whether it's democracy or free markets or liberal societies intersect with American interest. To see a different kind of Iran. And I think we've been underestimating our soft power and our ability to align ourselves with the aspirations of people. And that was in my view, one of the great lessons of the Cold War. We prevailed because our values prevailed and think we should muster that same kind of energy vis a vis Iran now.

[Scott Galloway]

Karim Sajapur is a Senior Fellow at the Carnegie Endowment for International Peace specializing in Iran and US Foreign policy. He joins us from a snowy nation's capital today. Kareem, I love having you on. I find you just so I can see why you're so effective. You're just very reasoned, very rational, have an ability to speak to both sides. I love the fact I can't discern your political lean. I have a special respect for people in this day and age where I'm like, I have no idea what political party this guy belongs to. I think we need more of that in our think tanks or in positions of influence such as yourself. Very much appreciate your time, Karim.

[Kareem Sajapur]

Thank you, Scott. It's very kind of you to say and always great being on with you.

[Scott Galloway]

This episode was produced by Jennifer Sanchez and Laura Geniere. Cammie Reek is our social producer. Bianca Rosario Ramirez is our video editor.

[Kareem Sajapur]

Editor.

[Scott Galloway]

And Drew Burrows is our technical director. Thank you for listening to the Propg pod from Propg Media.