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Jeff and Scott talk with Tyler Menzer, an assistant professor of accounting at Texas Christian University, about his recent research on cryptocurrency tax reporting. In the project, Tyler submitted the same set of cryptocurrency transactions to multiple crypto tax software and reporting services, many of which present themselves as tracking or reporting tools rather than tax preparation providers. He found that these services often produced very different calculations of taxable income from identical transactions. The conversation explores why these discrepancies arise and uses them as a starting point for a broader discussion of cryptocurrency taxation, compliance, and reporting challenges.

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Jeff and Scott chat with Mike Kaercher, Deputy Director of the Tax Law Center at NYU Law, about where tax law comes from. We often refer to “tax law,” but in this episode we unpack what that actually means—how the Internal Revenue Code, Treasury Regulations, and court cases, all the rest, all fit together, and who actually writes the words on the pages we consider to be tax law.

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Jeff and Scott chat with Conor Clarke, a law professor at Washington University in St. Louis, about the Supreme Court case challenging President Trump’s sweeping tariffs imposed by executive order. The key questions are whether the International Emergency Economic Powers Act authorizes the types of tariffs President Trump has put in place, if it does, whether Congress can delegate tariff-setting power that broadly even if they want to. What will the Court decide?

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Jeff and Scott chat with Joe Thorndike about how the United States moved from relying heavily on tariffs to building the modern income-tax-based system we know today. Joe is a tax historian and journalist, and writes for Tax Notes, where he writes widely on the history and politics of U.S. tax policy. They walk through the political and economic forces that made tariffs both attractive—and eventually untenable—as a main source of revenue. Along the way, they discuss the creation of the federal income tax, the rise of new revenue needs, and what this history can teach us about today’s debates over trade and taxation.

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Jeff and Scott talk with Jason DeBacker about his new paper, Learning from 25 Years of Changes in Business Tax Policy (with Aerfate Haimiti). Jason is an associate professor of economics at the University of South Carolina and the director of the Policy Simulation Library, an open-source effort that helps researchers and policymakers analyze policy. They discuss his work at PSL and what the last 25 years of business tax changes have taught us—whether bonus depreciation boosts investment, how firms respond to shifts in business tax rates, and more.

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Jeff and Scott chat with David Mitchel, a Senior Fellow at the Washington Center for Equitable Growth, about the small business stock exclusion, recent changes to it, and an article that David wrote with Kyle Pomerleau about why we should get rid of it.

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Luke 2 tells us that Mary and Joseph went to Bethlehem "to be taxed", and while there, the baby Jesus was born. But, what do we know about that taxing from history? Did everyone travel? What was the general tax environment in the Roman world at the time? Did they actually remit a tax, or, what was the purpose of this trip? Jeff and Scott chat with Roman historian Anna Dolganov about these questions, and more.

Anna's previous appearance on the show: https://www.buzzsprout.com/1878989/episodes/17860482 .

One note: On the podcast we talk about how burdensome the tax imposed by the Romans in situations like this was, in terms of days of labor (a la Tax Foundation's "Tax Freedom Day"). Here is a follow-up note from Anna: "A Roman legionary's salary was about 225 denarii per year, and the poll tax rate in Egypt was 8-40 drachmas per year (depending on location and tax privilege). So, not quite Austrian level taxation, but still quite a considerable sum."

A denarii and a drachma are equivalent. So, Tax Freedom Day for Mary and Joseph, based only on the poll tax, may have been sometime in mid-February.

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Jeff and Scott talk with Justin Schein. They discuss Justin's newest film, and the issues and questions it brings up. Justin's newest film is Death and Taxes, which "is a feature documentary about wealth, inequality and the American Dream, viewed through the lens of the estate tax and the very personal story of a father and son at odds over what kind of inheritance we want to leave our kids and our country."

Learn more about the film here: https://www.deathandtaxesfilm.com/.