College tuition didn’t spiral out of control by accident. This episode examines how unlimited access to subsidized money, non-dischargeable student loans, and administrative bloat turned higher education into one of the most profitable—and least disciplined—industries in America. From the Bennett Hypothesis to the explosion of bureaucracy and low-value degrees, the discussion argues that the crisis in higher education isn’t about learning or compassion, but about incentives—and why prices will keep rising until those incentives change.

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Healthcare in America isn’t broken—it’s perfectly aligned with the incentives that govern it. This episode examines how scale, insurance design, and cultural expectations have transformed medicine into a system where costs rise invisibly, accountability dissolves, and intermediaries thrive. From Medicare’s role as a dominant buyer to the psychological separation between patients and prices, the conversation explores why reform is endlessly discussed yet rarely achieved—and why the system continues to serve those closest to the money far better than the people who fund it.

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Most investors ask the wrong first question. Instead of “How much can I make?” this episode asks something far more revealing: “Why is this opportunity being offered to me at all?”

This conversation explores what access really signals in investing—how scarcity, liquidity, and incentives shape both public and private markets. From private deals to publicly traded stocks, the episode unpacks why broadly marketed “opportunities” often exist to provide an exit for others, and why skepticism should scale with availability.

Investment success, it argues, is less about finding hidden gems and more about understanding who needs your capital—and why.

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Most people never consciously decide what role money will play in their lives—they drift into it. In this episode, we examine why that quiet drift is so costly, and why your relationship with money should be chosen early and deliberately. We explore two coherent paths that actually work—intentional frugality and aggressive ambition—and why the unfocused middle ground produces stress rather than security. Along the way, we unpack hedonic adaptation, the modern rat race, and how small, intentional choices can restore alignment between effort and satisfaction. This is a conversation about clarity, coherence, and choosing a financial life that fits—before default choices make the decision for you.

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Every industry divides into two roles: those who do the work and those who control access to money. This episode examines why technicians—often the most skilled and indispensable people in the system—are routinely out-earned by relationship owners who sit closest to the transaction. From law and medicine to music, film, and corporate leadership, we unpack the structural reasons effort and difficulty fail to determine pay, and why owning relationships scales in ways technical mastery never can. Understanding this asymmetry is uncomfortable—but it’s also a competitive advantage.

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Why does someone entrusted with thousands of lives earn less than someone brokering expensive deals with little personal risk? Because pay is rarely about responsibility, difficulty, or social value. This episode breaks down how modern compensation actually works: income flows to those positioned near large pools of money, not those bearing the greatest consequences. We explore deal-size thinking, reference bias, executive pay rationalizations, and why access to big transactions matters more than skill or effort. Once you see the pattern, much of the economy stops being confusing—and starts being predictable.

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Colleges insist they want well-rounded students. In reality, they want something very different: a carefully engineered, well-rounded class. This episode unpacks the quiet distinction between individual breadth and institutional design, and why genuine intellectual range—formed through curiosity and free choice—often works against modern admissions incentives. We examine how the language of “well-roundedness” obscures social engineering, explains many of the contradictions in elite admissions, and rewards conformity over organic development.

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Home ownership is treated as a moral good in American life—question it and you risk sounding heretical. But beneath the spreadsheets, tax deductions, and rent-vs-buy calculators lies a deeper set of costs few are willing to confront. This episode examines home ownership not as a financial decision, but as an existential one: how it shapes mobility, opportunity, influence, and exposure to the state. We explore how government policy distorted housing markets, why ownership often means distance from cultural and economic centers, and how property quietly turns flexibility into friction. The real question isn’t whether buying is cheaper than renting—it’s what kind of life ownership makes possible, and what it silently forecloses.

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