2026-02-03
Section 280E Tax Strategies: Risk or Reward? With the potential of Schedule III on the horizon, cannabis operators are weighing the risks and rewards of different 280E tax positions. But what separates a "reasonable basis" from a red flag? In this episode, Jesse Alderman (Partner, Foley Hoag) and Ray Owens (Tax Lead, Withum) discuss the myths and realities of the rescheduling executive order and what comes next for cannabis businesses. We cover the legal and accounting best practices for Section 280E treatment, the "Opinion Letter" strategy, and how to prepare your team for the future. TIMESTAMPS: 00:00 - Intro & Pre-roll 01:05 - The "High Functioning" Reality (Episode Start) 05:06 - Rescheduling: Myth vs. Reality 20:19 - Section 280E vs. The CSA: Why It’s Separate 30:26 - The "Frivolous Positions" List (Defining the Risk) 32:18 - The Harborside Case & The 20% Penalty 54:42 - Retroactivity: Will refunds actually happen? 1:06:11 - Debunking the "471c" Small Business Myth 1:17:52 - Best Practices: Ray’s #1 Advice for Operators Disclaimer: This content is for educational purposes only and does not constitute legal or tax advice.