A Note from James:
What is actually going on in Iran?
I have Brandon Webb on the show today. He’s a former Navy SEAL, he’s written a ton of books about the military and life in the military, then he wrote a murder mystery series set in the military, and now he has a parenting book out.
Brandon also runs SOFREP.com, a major military intelligence news site. He came on for a quick episode to answer the big question: what is actually happening in Iran, and what might happen next?
Episode Description:
In this fast-moving topical episode, James talks with former Navy SEAL and SOFREP founder Brandon Webb about Iran, regime instability, the Strait of Hormuz, and how modern military power is being used differently than it was in Iraq and Afghanistan.
Brandon argues that the top levels of Iran’s leadership have been badly disrupted, creating confusion about who is actually in charge and who the U.S. or Israel could negotiate with. From his perspective, that leadership vacuum creates two possible outcomes: either a moderate power center emerges inside the regime, or Iran’s already strained economy worsens and the population rises up again.
The conversation also tackles the biggest fear many listeners may have: whether this turns into another long, grinding U.S. nation-building project. Brandon’s answer is no. He sees this as a different kind of military and intelligence operation—less about occupying territory, more about using special operations, air dominance, intelligence networks, and local opposition pressure.
What makes this episode useful is that it cuts through the broad panic and gives listeners a clear framework: leadership disruption, economic pressure, domestic unrest, proxy networks, energy markets, and the question of whether Iran’s regime can still hold itself together.
What You’ll Learn:
- Why Brandon thinks Iran’s leadership disruption is the key fact driving everything else.
- The two outcomes he sees as most likely: a moderate negotiator emerging or a popular uprising.
- Why he does not think this becomes Iraq-style nation-building.
- How Iran’s proxy network shapes the conflict beyond Iran’s borders.
- Why the Strait of Hormuz threat may matter less than it would have decades ago.
- How Brandon thinks special operations and intelligence support may define the next phase of modern warfare.
Timestamped Chapters:
- [02:00] A Note from James: what is actually happening in Iran?
- [02:33] Brandon’s two most likely outcomes
- [02:35] Leadership disruption inside Iran
- [03:28] The Strait of Hormuz as Iran’s “ace” card
- [04:00] Why the nuclear issue matters
- [04:51] Economic pressure and oil sales
- [05:08] Why civilians may be hesitant to rise up again
- [05:32] Moderate regime figure or popular uprising?
- [06:00] Why Brandon sees Iran as a long-standing threat
- [06:23] Iran’s proxies in Yemen, Lebanon, and Gaza
- [06:51] Who is actually in charge inside Iran?
- [07:41] What a leadership vacuum might look like
- [08:19] CIA, Mossad, and opposition support
- [09:55] Is this another Iraq?
- [10:14] Brandon’s view of modern military force
- [10:45] Venezuela as a case study
- [11:48] Regime change vs. nation-building
- [12:20] Strait of Hormuz, oil prices, and infrastructure risk
- [12:41] Why Brandon thinks oil disruption may be manageable
- [13:30] Alternative oil flows and pressure on China
- [14:02] James summarizes Brandon’s view
- [14:36] Why Brandon thinks this is not a boots-on-the-ground war
- [15:26] What Afghanistan should have taught the U.S.
- [16:00] Dubai, UAE, and regional risk
- [16:36] Why Iran may have targeted the UAE
- [17:12] Closing thoughts
Additional Resources:
- SOFREP, the military and foreign policy news site Brandon Webb runs as editor-in-chief.
- Brandon Webb’s official website and biography.
- Brandon Webb’s books page.
- Puddle Jumpers, Brandon Webb’s new parenting book.
- Wall Street Journal interview with Brandon Webb about Puddle Jumpers.
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[00:00:01] This isn't your average business podcast and he's not your average host. This is the James Altucher Show.
[00:00:18] What is actually going on in Iran? I have on Brandon Webb, former Navy SEAL, has written a ton of books about military, life in the military, and then he wrote a murder mystery series in the military and he just came out with a parenting book.
[00:00:32] But Brandon Webb runs softrep.com, S-O-F-R-E-P.com. It's a big military intelligence news site and he came on for a quick episode answering what is actually happening in Iran and what will happen. So Brandon, what is going on in Iran?
[00:00:56] Yeah, so I think the two likely outcomes are, yeah, and what I think people don't understand is Israel and the US have totally wiped out the leadership at the top of the regime, right? So you have a lot of confusion, who's in charge, you know, one day it's this person, then Israel freaking whacks them with some type of op. I even heard the Mossad was,
[00:01:26] they had a dentist on payroll that was putting trackers in the IRGC's filling. So it's like crazy, you got to appreciate the ingenuity of the Mossad and the CIA. But there's all this confusion, like who's doing what? And I think that creates a challenging situation when you're trying to negotiate a peace process and what the future of Iran is going to be like.
[00:01:48] And I think what's going to happen is either the regime will put somebody moderate in charge that will have a moderate, serious conversation with the US to make peace, or they're going to continue to kind of throw these tantrums.
[00:02:06] And they've played the only card that they've, their whole ace up the sleeve, you know, for years and years have been the straighter or moose, right? Controlling the flow of oil and energy out of the Gulf. They played that card, right? And even though the world is now experiencing pain, that card's been played. That's it, it's gone. It's been used.
[00:02:26] So either they're going to get somebody moderate in charge that will negotiate a peace process. And I think it's pretty clear that Iran, what they've done to their own citizens and, you know, the rhetoric that they've had towards Israel and the US and the West at large has been, you know, you don't want to put a nuclear weapon in the hands of a regime like that.
[00:02:50] And it's a regime that probably would use a nuclear weapon if they had one. And so either there's going to be a moderate in place or they're going to stretch them out because their economy was already broken and super strained before, you know, the US and Israel declared war. And now it's even worse because their largest resource that was contributing to the economy was the oil, right? And most of it they're selling to the Chinese. That's been totally shut off.
[00:03:20] So I think you could have a situation where the people get emboldened like they were previously before the regime cracked down. Like the reason they're not just like going back out on the streets because people need to understand like they estimates they've killed like tens of thousands of civilians in that recent kind of rising up.
[00:03:39] I mean, anytime you crack down that hard on the civilian population, there's going to be a little bit of nervousness for them to kind of come outside their homes and start acting up again. But I think those two situations are what's going to happen. Either the people rise up and take power and we end up with a brand new regime, which would be great.
[00:04:00] Or we end up with somebody kind of surfacing through the ranks, the kind of mid-tier ranks of the IRGC and having a more adult moderate position, which would, you know, enable Trump's team to kind of negotiate a peace. Look, I'm not a huge fan of Trump, but with Iran, I've always been outspoken of why haven't we dealt with Iran.
[00:04:30] Iran to me was way more of a threat than Iraq was back when we went in the second time in 2002. Always thought Iran has been a long known state sponsor of terror. You see it in their proxies, right? They have the proxies, the Houthis in Yemen, you know, in Lebanon and Gaza. You have, you know, it's clear and it shows up, right, when Israel and the U.S. negotiate this ceasefire.
[00:04:58] And Iran is like, well, that should count in Gaza and Lebanon, too, because they're speaking about their proxies that they have control of. And so it's very clear that Iran has been a bad actor for decades. Given that the whole leadership is wiped out, like, is there a coherent person who can make decisions? Like, who are we negotiating with? Well, that's the thing. I don't know the answer to that.
[00:05:21] But I do know that I would make an educated guess that because of the leadership void, they don't know themselves. I think they're still trying to figure it out. And they're under this massive amounts of pressure. And everyone that pops their head up is like, I'm in charge. He gets whacked by Israel. They're going to take it out. So I think they're dealing with a lot of internal issues. And it just, that's one of those things that just takes time.
[00:05:49] You can imagine if just do the thought experiment of the US government, if we lose, you know, the president, the vice president, you know, call it like the top four or five people in the chain of command. I mean, imagine the political jockeying to kind of like take power that's happening in that situation. And for sure, that's happening inside of Iran right now. So that's why it's taking a while to kind of play out.
[00:06:15] But either someone will come up in a position of power that will be moderate and have that conversation to end it. Or I think eventually the economy will get so bad and the people will rise up again. And in this time, the government won't be able to do anything about it. Because one thing I do know is the CIA and the Mossad are inside Iran preparing for that, like making plans. The IRGC is, I don't want to say it's intact. Like a lot of their leadership's gone, but they're also trained to operate in a fractured way.
[00:06:46] So can the IRGC still suppress the people enough? I don't think so. In this new environment, I think it's going to be a lot harder because, like I said, the CIA, one of the two operational branches of the CIA is the GRS, Global Response Staff, who recruits Special Ops to assist the case officers and developing and meeting spies, kind of like the case officer security. There is no Jason Bourne in that world.
[00:07:14] And then you have Ground Branch. Ground Branch largely is ex-Special Ops guys that facilitate kind of internal opposition. Like you have this uprising that happened previously. Now the Ground Branch is in there making plans for like what's phase two of this look like. So they're going to be well supported, probably well armed, and know that they have the back of Israel and the U.S.
[00:07:41] And in that situation, I don't think, you know, it's going to go so well as it did last time for the IRGC to kind of like really clamp down and start firing in the streets. Because they're going to have, you know, they already shut down the skies over Tehran. So now you have complete air dominance, drones, people on the ground, the CIA and Mossad supporting a potential uprising in the future. It's going to be a very different scenario and play out very differently if that happens in the future.
[00:08:11] So there's three things I'm going to question about. The first is a lot of people say this could be like an Iraq where it's this prolonged situation where we quote unquote nation build. And I'm wondering if this is correct that we're not nation building at all, that we're going to support people uprising, but they're going to have to do it. We can't do it for them. And we're not going to put someone in place. They're going to put someone in place. So I wrote about this, I think, at the beginning of the invasion.
[00:08:36] And what I do appreciate now is how the military is being used. And we look at Venezuela as a case study, right? Like that's a case study and bad actor causing problems in our, and a little bit closer to our backyard, right? And you have a lot of reasons for the U.S. to kind of not want to have Maduro in charge.
[00:09:01] And the military was used how it should have been used in Afghanistan back in 2001. And very strategically, we have far superior technology than most of our adversaries, including maybe China's on par. But we're very skilled at putting this into play where Chinese are still practicing, right? We've been using our defense tech and the whole machine for years and years.
[00:09:31] Like we're very skilled at warfare. But how I saw the military use, I was like, okay, that's how we should be using the military. You go in, you snatch this guy, you bring him to New York, you put him on trial. He's had that indictment on him for years now. And then you're not disrupting the regime. The number two, the woman, you're saying, okay, look, you can keep everything in place, but we expect you to behave like an adult. You want a seat at the table? Behave like an adult.
[00:10:00] And that's largely going the way that Trump and his team said it would go. Like they're like, we don't want regime change. We don't want a nation build. Regime change in the sense that Maduro is out and somebody new is in and she's taken a more moderate stance. And now largely U.S. is like leaving Venezuela alone.
[00:10:19] And I think that's how, you know, fundamentally what the hope is and the plan is in Iran was that somebody moderate will take over or the people will rise up and do whatever they're going to do and wind up with a brand new regime. If this goes on, is there kind of permanent damage to the oil infrastructure in terms of the Strait of Hormuz and the economics of all this?
[00:10:44] Like people are saying, oh, it's already too late and oil is going to be at elevated prices for years and years. And I don't really believe that. But, you know, because I figured if anything, COVID was going to shut down the world in a very extreme way. And it didn't. But I'm with you on that. I actually, maybe this will wake people up to the fact that we need to get off oil in the first place anyway. You know, welcome.
[00:11:09] Like, you know, we shouldn't be on oil when we have all these alternative sources of energy. And it's clear that burning fossil fuels is not great for the environment. So, yeah, I don't care about the Strait of Hormuz. Because I think the fact that 20 years prior, it would have had a much more higher impact.
[00:11:29] But because a lot of the world has sought out and stood up alternative energy sources, the pain is not as severe as it would have been, say, 20, 30 years ago as it is today. But I don't think that I'm with you on that one. I don't think it's a big deal. Are people going to get oil from the U.S. now? Like, are people switching instead of going to the Middle East? Are they going to the Gulf of America and getting oil from Venezuela and the U.S.? I mean, I would suspect that's the case, right?
[00:11:58] Like, we essentially control the flow out of Venezuela now. And, you know, when you look at, you know, the countries affected from the Strait of Hormuz embargo, it's mostly like Asia, China. So we'll see. But they're definitely putting pressure on the economic machine. But we'll see. And like I said, I'm like, I don't have a problem with rising gas prices. People, we should be driving electric cars anyway.
[00:12:25] And so if I were to summarize, your view is it's not going to be protracted. Either the economy completely collapses and the people rise up or a modern regime comes in and is able to negotiate away the nuclear program and consolidate power and maybe be a little more lenient towards the people. And then we'll see what happens. And that there's no permanent infrastructure effects on the world.
[00:12:50] Yeah, and my point I was trying to make earlier was that how we're seeing the military deployed and used is something that was refreshing to me. Because we're not like I don't see Iran as like we're putting boots on the ground and this huge ground presence like we did in Iraq.
[00:13:08] And I think that that is because the old regime that was very conventional in thinking and conventional in strategy on how to deploy the military, those generals and admirals are out. So now you have this very fresh kind of new leadership with inside the military, regardless of Hagsat. That's a whole other conversation. But the way the military is being used now is how it should have been used in Afghanistan.
[00:13:38] Like we should have never stayed 20 years in Afghanistan. That was insane. But you use the special ops teams to get in and out, use technology to your advantage. And exactly how we deployed the military against Venezuela, in and out, and relatively no casualties on the U.S. side. That's how the military should be used in this kind of future of warfare as the world has changed.
[00:14:04] But yeah, the rest of what you said, I think it's how it's going to play out. And I would say my friends in Dubai now believe me because I'm like, why are you spending all this money in Dubai? Like it's kind of risky. And there's this illusion of freedom in the United Arab Emirates. But then the influencer that posts the missile going into the hotel is getting arrested and fined. Like they're cracking down on free speech. And like, yeah, the myth of Dubai has been shattered. Like that's a whole other thing.
[00:14:34] Like the UAE is, I think, in big trouble from them selling this like, you know, Vegas of the Middle East image. Like, you know, nobody wants to live in Dubai and drive their kids to school with missiles shooting overhead. Why is Iran using UAE as a kind of like, hey, we're going to get you if you attack us more? Why is UAE basically singled out? Well, I think that was the case. I mean, my guess would be that they had this, you know, fractured leadership playbook.
[00:15:03] And that they would just fire at everybody, which would happen. And then, you know, the acting president was like, oh, we're sorry, we didn't mean to do that. It's just like you're seeing this kind of old institutionalized plan play out. And then they're like, oh, shit. But I think it was a huge mistake, right? And like they've just made enemies of everybody. Yeah. All right. Well, Brandon Webb, who runs SoftRep, S-O-F-R-E-P.com for military news and intelligence, former SEALs, written a ton of books, been on this podcast a million times.
[00:15:33] Thanks, Brandon. You gave me valuable information. I can live my life at ease now. I'm good. Thanks for having me. For sure. We're coming at you with everything we got. This is the mindset. Free.
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