Tax Day 2026 lands with the IRS in unprecedented shape: seven different people ran the agency in 2025, the Treasury Secretary’s acting authority has expired, and the day-to-day is being handled by the head of the Social Security Administration moonlighting as “IRS CEO.” Staff is down 25% post-DOGE. And somehow, 100 million returns have already been processed.
In this episode of The Tradeoff, Mattie breaks down what’s actually happening at the IRS, why the average refund is up 11% (and why that’s not the win the administration is selling), and the bigger structural story underneath it all: a tax code built for a 20th-century economy trying to enforce against digital assets, prediction markets, gig income, SPACs, and SPVs.
Plus: four tactical things to do before the April 15 deadline — including the W-4 update that pays for itself, what an extension actually means, and how to know if you’re overpaying for tax prep.
Mentioned in this episode: the One Big Beautiful Bill Act, IRS leadership turnover, Kalshi’s record $12.35B March, the 17-year lag on crypto tax reporting, federally-designated disaster zone extensions, and why complexity in the tax code functions as a regressive tax.
Run time: ~12 minutes. New episodes Tuesdays and Thursdays.
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