Episode 27: Ask the Experts, Volume 2

Episode 29: Powwows, Prizes, and 1099s: Lessons from a 2026 IRS Ruling

In this episode of Information Return Intelligence, Jason breaks down a recent IRS private letter ruling that answers a deceptively simple question: Do tax-exempt organizations still have 1099 reporting obligations? The ruling involved a Native American tribe that awarded prize money at a powwow and questioned whether those payments required Form 1099 reporting. The tribe made three key arguments: They are not subject to income tax They are not a “person” under the tax code The activity was not a trade or business The IRS rejected all three. While private letter rulings only apply to the taxpayer who requested them, they provide valuable insight into how the IRS interprets the law. In this case, the takeaway is clear: Information reporting under IRC §6041 applies broadly—even to tax-exempt entities and activities that are not conducted for profit. Jason walks through: Why being tax-exempt does not eliminate 1099 obligations How the IRS defines a “person” under IRC §7701 Why “not-for-profit” activities can still trigger reporting requirements What nonprofits, government entities, and similar organizations should take away from this ruling He also raises an interesting open question: Could the IRS’s reasoning extend beyond tax-exempt entities to other non-profit-motivated activities, such as hobbies? If you work in accounts payable, finance, or compliance, this episode is a reminder that 1099 reporting rules are broader than many organizations assume—and exemptions are narrower than they appear. 📌 Key Takeaway: Even if your organization doesn’t pay income tax—or isn’t operating for profit—you may still be required to issue Forms 1099. This episode is sponsored by IOFM, the Institute of Finance and Management. Learn more at IOFM.com.

Episode 28: IOFM Conference Takeaways: Anxiety, Complexity, and AI

At this year’s IOFM Spring Conference in Orlando, one theme kept surfacing over and over again: uncertainty. In this episode of Information Return Intelligence, Jason shares his biggest takeaways from conversations with AP professionals, compliance teams, and attendees across the conference floor. While the sessions themselves were valuable, the real insights came from listening to the concerns people are facing every day in the information reporting world. Three major themes emerged: • Growing anxiety around information reporting compliance • Frustration with increasing complexity and constantly changing rules • Confusion and uncertainty surrounding artificial intelligence and AP technology Jason discusses the upcoming transition from the FIRE system to IRIS, the new 1099 reporting thresholds, ongoing worker classification confusion, and why so many professionals feel overwhelmed by overlapping IRS, DOL, and state rules. The episode also explores the current state of AI in the AP and information reporting space — including skepticism about vendor claims, pressure from management to “use AI,” and the challenge of figuring out what many AI products actually do. If you work with 1099s, W-9s, AP compliance, or information reporting in any form, this episode provides a candid look at what your peers are thinking — and worrying about — right now. Sponsored by IOFM, the Institute of Finance & Management. #1099 #AccountsPayable #AP #InformationReporting #IOFM #TaxCompliance #IRIS #ArtificialIntelligence #Finance #1099Guy

Episode 27: Ask the Experts, Volume 2

It's another Ask the Experts feature. The questions addressed this time: --What if you have to re-issue a check to the payee because they lost it, and it's the next year? Do you need to correct anything or issue new 1099s? --Is a collection agency associated with a medical facility providing a "medical service" reportable on 1099-MISC (box 6) --Is a non-cash amount, such as a book, given to a contractor considered contract labor? --How do you handle a legal settlement where interest payments are involved? As always, we are sponsored by IOFM, the Institute of Finance and Management. www.iofm.com

Episode 26: Latest W-9 Draft -- IRS Reverses Course on Sole Proprietor EIN Rule

The IRS has released a new draft of Form W-9—and this one brings welcome relief for accounts payable teams. In this episode, Jason breaks down the May 4 draft update and explains why the IRS’s decision to remove the proposed restriction on sole proprietors using EINs is a big deal. That controversial change would have created a massive compliance burden, forcing companies to re-solicit W-9s and revalidate vendor records at scale. For now, that headache is off the table. Jason also walks through what did change in the draft, including: *  A new backup withholding exemption code tied to broker and Form 1099-DA reporting  *  Updated (and much clearer) language around TIN reporting—specifically reinforcing that disregarded entity EINs should not be used  Even though the EIN restriction is gone, the IRS is making its expectations more explicit—and that has real implications for how W-9s are completed and reviewed. As always, this is still a draft. Jason closes with practical guidance on what AP professionals should be doing right now (hint: keep using the March 2024 version). If you deal with W-9s, vendor onboarding, or 1099 compliance, this is a must-listen update.

Episode 25: E-Delivery Rules for 1099s: Why Emailing PDFs Isn’t So Simple

This week on Information Return Intelligence, we break down one of the most overlooked areas of 1099 compliance: electronic delivery to recipients. Most organizations are used to thinking about e-filing with the IRS—but what about actually getting the form to the recipient? If you’re emailing PDFs of 1099s (and let’s be honest, most people are), there’s a good chance you’re not fully compliant with IRS rules. In this episode, Jason walks through: Why 1099 e-delivery rules are tied to W-2 regulations What the IRS actually says about furnishing statements electronically The three key requirements: consent, format, and notification Why a simple “sure, email it to me” isn’t enough How major e-filing platforms handle compliance (and why it matters) The real-world risk of ignoring these rules—even if “everyone else is doing it” The takeaway? This isn’t a gray area. The rules exist, they’re detailed, and they’re enforceable—even if they’re widely ignored. If your current process involves emailing 1099 PDFs without a formal consent workflow, this episode will make you rethink that approach. Key Topics Covered IRS Publication 1099 and electronic furnishing rules Reg. §31.6051-1 and its application to 1099s Recipient consent requirements (and why they’re more complex than expected) Substitute statement formatting (Pub. 1179) Website posting and notification requirements Practical compliance strategies for AP teams and tax professionals Who Should Listen Accounts Payable professionals Tax practitioners and accountants Anyone responsible for issuing Forms 1099 or W-2 Organizations using (or considering) electronic delivery methods About the Show Information Return Intelligence is a fast-moving weekly podcast focused on Forms 1099, W-9, 1042-S, and everything in the world of information reporting—brought to you by IOFM.