The 280E Trap & The Myth of Retroactive Refunds (w/ Jesse Alderman & Ray Owens)

2026-02-03

There is a dangerous rumor spreading in the cannabis industry: that with the "right" legal opinion, you can stop paying Section 280E taxes immediately.But the IRS has just drawn a line in the sand. They have released a specific list of "frivolous positions," and if your strategy is on that list, you don't just owe the tax—you face an automatic 20% negligence penalty.In this episode, we sit down with Jesse Alderman (Partner, Foley Hoag) and Ray Owens (Tax Lead, Withum) to separate the "Slam Dunk" myths from the financial reality.We cover:The IRS "Kill List": Why the "Opinion Letter" strategy might be an audit trap.Myth Busting: Why Schedule III almost certainly won't be retroactive (and why banking on a refund is a mistake).The "Reasonable Basis" Defense: What it actually protects you from—and what it doesn't.The Blueprint: Ray’s #1 piece of advice for operators trying to survive until 2026.If you are a cannabis operator trying to bridge the gap to rescheduling without going bankrupt, this is the playbook you need.