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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?