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Hey folks,
This one went completely off the rails in the best possible way.
Jack Cocchiarella and I got right into it and we started where everybody’s attention is right now: Trump, insider trading, the Iran war, and whether the people around him are cashing in while the rest of the country gets screwed. But then the conversation cracked open into something way bigger — power, corruption, billionaires, the future of the Democratic Party, and whether America’s entire obsession with “rugged individualism” is breaking us apart.
We got personal. We disagreed. We pushed each other hard. And honestly? These are the kinds of conversations I think we need a lot more of right now.
Here’s what we got into:
[00:01:37] We dig into the DOJ probe surrounding suspicious oil trades tied to Trump’s Iran escalation — and ask who inside Trumpworld may have been cashing in.
[00:12:59] The conversation shifts to billionaires, Wall Street, and why some of the most powerful people in America actually benefit from chaos and instability.
[00:20:07] Jack breaks down the insane private equity takeover of youth sports — including parents getting punished for taking photos at hockey games.
[00:33:00] We debate how Democrats should actually use power if they win in 2028 — from nuking the filibuster to taking on monopolies and corporate corruption.
[00:45:37] The second half turns into a full-on philosophical fight over individualism, expertise, freedom, systems, and whether Americans are being sold a myth about success and self-reliance.
This episode covers a lot of ground, but underneath all of it is one question: what kind of country are we actually trying to build? If you’re frustrated with performative politics and want deeper conversations about power, class, media, democracy, and where this movement goes next, this one is essential. And if you value conversations that are honest, messy, thoughtful, and real — help us keep building this thing.
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With urgency,
—Mike
