There’s a photo going around of Trump golfing at his club in New Jersey — concertina wire coiled across the course behind him, an air-defense battery parked in the background.
When I showed it to Doug, his first reaction was to ask if it was AI. It wasn’t.
“Here we have the most powerful man in the world who must feel like a hunted rat,” he said. “How can you countenance playing golf on something that looks like a war zone?”
This is the same man who recently declared himself more powerful than Caesar, Napoleon, and Genghis Khan — and who days earlier had to be smuggled out of an event in a catering vehicle. Doug called it low comedy. But he also asked the question that stuck with me: who took that photo? Because if you can get that shot with a telephoto lens, you can get it with a scoped rifle.
Doug takes it seriously enough that he’s put money on it. He just made a bet with a friend — roughly $10,000 on the line, the price of rooms and dinner for six at the Inn at Little Washington — that Trump doesn’t finish his term.
Iran says it’s done being a punching bag
The wire and the missile batteries make more sense when you listen to Tehran: they’re done negotiating with a man who publicly insults them, and they intend to bring the war to the US.
Doug takes that at face value. Shoulder-fired anti-aircraft missiles are accurate, available, and small enough to smuggle. “If they just take down a couple of domestic US airliners, it’s going to shut down air traffic totally in the US,” he said. Beyond the pale? In 1988 the USS Vincennes shot down an Iranian airliner on a scheduled flight to Dubai, and the American response amounted to oh, sorry about that.
Those Shahed drones Iran builds by the thousand in underground factories? “They’re basically hobby shop projects,” Doug said — big model airplanes running on simple two-stroke motors. Someone can build them in a garage in New Jersey and hit a target a thousand kilometers away.
“Trump has punched the tar baby,” Doug said. “I think it’s game on.”
The next escalation in Iran is the tripwire — after that, the concertina wire goes up everywhere, not just on the president’s golf course.
The war on energy infrastructure
Meanwhile, somebody just attacked oil facilities in Libya. Who? Nobody knows — Libya is really two countries run by rival governments. Zoom out and there’s a pattern: energy infrastructure is being destroyed everywhere.
Hence Doug remains super bullish on gold and commodities — oil in particular. Not crude itself (”black goo,” useless until refined) but the middle distillates: the kerosene, diesel, and gasoline the world actually runs on.
We pulled up the Crisis Investing portfolio on screen — picks obscured, you have to subscribe. Our average position is up a little over 100%. The best performer is up 700% and still pays a 7% dividend, which is why Doug hesitates to sell it. One coal pick yields 9.5%. As Doug put it, channeling the nuns from grade school: “The dividends are just an outward sign of inward grace.” We’re not buying for the dividends — we’re buying for the upside as war expands demand.
What you won’t find in the portfolio: AI stocks, chip stocks, software. “Those things are bubbles that might take the whole American economy down when they crash,” Doug said.
The actual picks are here:
Scuttlebutt from the fleet
Some of the strangest news of this war is coming from our own ships — which notably won’t go anywhere near the Persian Gulf.
A Navy wife confirmed her husband jumped off the deck of the USS Abraham Lincoln. He spent over an hour in the water, and she says the Navy kept it from her for days. The scuttlebutt says he wasn’t the only one. There’s even a claim, amplified by Iranian channels, of a fight aboard a carrier that left sailors dead. Normally I’d dismiss that outright — but when we spoke with Colonel Macgregor a few days ago, he brought it up on his own. I asked him directly: “You mean a mutiny?” He said yes. We can’t verify it, but hearing it from a man still that connected to the military moves it out of the meme category for me.
Add the “laundry fire” on the Gerald R. Ford months ago that somehow required relocating 600 sailors — a story that vanished without follow-up — and the sailors writing home about being underfed. Doug’s comparison: the late Soviet military, where logistics quietly rotted while the officers lived well. The old Soviet joke was “they pretend to pay us, and we pretend to work.” With inflation eating American wages, that joke is starting to translate.
The same rot shows in the civilian numbers. Around 106 million working-age Americans aren’t working. Nine colleges have shut down so far this year — people are figuring out the value isn’t there, choosing trade schools, apprenticeships, or the path we laid out in The Preparation instead.
The reason for optimism
After all that, you might not expect the episode to end on an up note. It did.
Doug had just watched Elon Musk’s SpaceX presentation and came away impressed — hundreds of thousands of Starlink satellites, phones connecting directly to space, and Musk’s claim that 98% of SpaceX’s future revenue will come from AI, data centers, and robots. Robots arriving roughly next year.
I’ve spent the last three weeks pushing my limits with AI tools to see what one person can build. I’ve shipped four products — published, live — with more in the pipeline. I’ve led software teams in past businesses, but I can’t write a line of code. It didn’t matter. Every constraint I used to plan around as an entrepreneur — budget, headcount, specialized skills — has mostly evaporated in the digital world. A friend with zero woodworking experience just sent me a photo of a front-porch bench he built with AI walking him through it. When robots carry that into the physical world, the productivity gain will be shocking.
The distinction that matters: are you a consumer of this technology, or a creator with it? If you’re a creator, the future is bright. If you’re a consumer, less so.
Because the financial reckoning is still coming. Doug worries the AI buildout itself — the trillions borrowed for data centers — triggers the collapse. I think it’s overdetermined: the $40 trillion national debt that grew $436 billion in July alone, the yen carry trade, a Strait of Hormuz that could close and cut off a fifth of the world’s energy. Pick one. Probably all of them.
So the playbook stays the same. Educate yourself and your kids — that’s what The Preparation is for. And hold real assets: in a market where everything is a bubble, the raw materials the world can’t function without are the only cheap thing left.
Doug’s summary: “It’s a story with a happy ending. But like all stories with a happy ending, there’s some fear and trauma along the way.”
We’re living through the fear-and-trauma chapters. Build your lifeboat.
See you next week.
— Matt
Also in the episode: Doug on the drug-boat strikes, Seymour Hersh and My Lai, and why putting politicians on the coinage was the beginning of the end.
