This one starts with a piece of paper that, until recently, would have sounded like satire: a proposed $250 bill with Donald Trump’s face on it.
Doug’s reaction was immediate. “I think it’s shocking, disgusting, and crazy,” he says. “This is what a third world country does, put the current ruler on your money, and it’s never been done in American history.” He goes further than he ever has on the man himself: “I think he’s demented, frankly.”
That sets the tone for a conversation that gets uncomfortable fast — even for the people who once gave Trump the benefit of the doubt. Doug now counts himself a former supporter, someone who “wanted to believe” the happy lies and now sees an “active danger.” The plan to print Trump’s image inside currently issued passports, he says, is “unseemly” — the kind of thing that pushes a hot button for the rest of the world every time a border agent flips to that page.
From there, the stories pile up:
The 51st state. Trump’s post labeling Venezuela the 51st state — retweeted by the White House — gets a blunt verdict from Doug: “It’s actually batshit crazy that something like that would happen. What’s the matter with these people?” He blames a cabinet of “total sycophants” afraid to disagree with the big man, and notes that Tulsi Gabbard’s resignation came “way too late and for the wrong reasons.”
A CIA agent and a steamer trunk of cash. Maybe the most jaw-dropping story of the episode: an FBI raid on a CIA supervisor’s residence turned up 303 kilos of gold — roughly $43 million at today’s prices — plus $20 million in currency and 30 luxury watches. The man had reportedly been rejected by the CIA twice, then padded his résumé with fictional credentials (a military jet pilot, a Navy captain) before being waved through their supposedly rigorous vetting. “It beggars belief,” Doug says. “I wouldn’t believe it if I read it in a novel.” His real question isn’t about the agent — it’s about the supervisors above him, and an agency he calls “literally out of control.”
The Strait of Hormuz — still effectively closed. Matt lays out three concrete facts that cut against the official narrative that the U.S. wants the strait open: the closure was war-gamed years in advance, shipping reopened the moment a ceasefire was declared, and every time traffic started to recover, Washington clamped back down — most recently with Bessent’s secondary sanctions on anyone paying Iran’s transit toll. Somewhere between 1,500 and 1,700 ships are stuck in the Gulf, degrading in salt water, snarling supply chains worldwide. “Until I see evidence that they really want it open,” Matt says, “then I think they want it closed.”
We also take subscriber questions, and the back half is where the investing meat is:
Higher prices are coming. Asked to bet deflation versus inflation over the next twelve months, Doug doesn’t hesitate: “Higher prices.” With the government running a $2 trillion-plus deficit financed by the Fed, he sees only two roads — an all-out credit collapse they’ll try to bail out, or the printing presses running hot. He’s betting on the presses.
Polymarket vs. the stock market. A great philosophical question gets a sharp answer: the market exists to raise capital for productive businesses, but “most so-called investing in the market today isn’t about financing productive enterprises, it’s about gambling.” The line between a Robinhood account and a betting site, Doug argues, is thinner than anyone wants to admit.
What could prove Doug wrong? In a genuinely fun stretch, Doug and Matt steelman the optimistic case against their own worldview: gold becoming un-scarce via asteroid mining or transmutation, AI and robots adding real productivity without gutting the labor force, a real DOGE actually balancing the budget, even — Doug’s perennial favorite — “friendly aliens” landing on the White House roof with a free-energy cornucopia. Non-zero odds on all of it.
The final bubble. Doug thinks the mega data centers are “a gigantic misallocation of capital” and that the trillion-dollar IPOs lining up — SpaceX at $1.8 trillion, with OpenAI and Anthropic behind it — are “bells ringing at the top of the market.” All three, as Matt points out, are money losers. The real upside in robotics, both agree, comes out of China and companies like BYD, not the U.S.
Plus: why oil stocks are the cheapest they’ve been relative to the S&P since 1980 (4% today vs. 30% then) even as oil matters more than ever in the real world, why Doug loves a dividend as “an outward sign of inward grace,” and his honest answer on what car to buy in the age of kill switches and surveillance — spoiler: two 20-year-old Mercedes 550 SLs.
It’s a packed one. Hit play below.
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If the threads in this episode landed — relentless currency debasement, an oil market the U.S. seems determined to keep choked, a stock market topping out on money-losing trillion-dollar IPOs, and the case for owning real, tangible assets — even dividend-paying ones — then you already understand the why. Crisis Investing is the what and the when.
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