1099-Ks, Zelle, Venmo, and the P2P Confusion: What AP Needs to Know in 2025

With payment methods like Zelle, Venmo, PayPal, and Cash App blurring the lines between business and personal payments, it’s harder than ever to know when a 1099-NEC is required, or whether a 1099-K will be issued instead. And if the 1099-K rules apply, it means you don't need to issue a 1099-NEC. In some cases, no reporting form will be issued at all, and it's all legitimate within the law.

In this timely and actionable webinar, IOFM's "1099 Guy" Jason Dinesen breaks down the rules and reporting thresholds for Form 1099-K, explains when a third-party platform is considered a TPSO, and clarifies when the business must still issue its own 1099-NEC. You’ll also learn how to handle edge cases and misclassified payments before they become audit risks. We'll also look at proposed legislative changes to 1099-K, and the IRS's perspective.

This is must-know content for AP teams who want to get ahead of the curve and avoid 1099 reporting errors in a fast-evolving regulatory environment.

Learning Objectives:

• Define what qualifies as a Third Party Settlement Organization (TPSO) under IRS rules.
• Distinguish between when Form 1099-K is issued by platforms and when a 1099-NEC is required by the business.
• Analyze payment flows through platforms like PayPal, Zelle, Stripe, Cash App, and Venmo for proper tax treatment.
• Apply decision-making frameworks to ambiguous reporting situations involving payment apps.
• Document payment methods and 1099 determinations to maintain compliance and audit readiness.

Featured Speaker

Jason Dinesen

Jason Dinesen, EA, is a distinguished tax professional and educator with a fervent passion for demystifying complex tax concepts. Jason is the founder of Dinesen Tax & Accounting, P.C. and Dinesen Tax Advisory, LLC in the tax and accounting world. He also is founder of Dinesen Media Ventures, which provides a diverse range of media content, ranging from continuing education programs for accountants and tax professionals, to podcast production to radio and journalism content. 

Recognized for his sharp tax interpretations, Jason is renowned for promptly analyzing the latest tax updates and IRS guidance, sharing his insights with the professional community. Over his career, he has educated more than 200,000 accounting, tax, and HR professionals on various topics. Form 1099 was the very first thing he ever taught on, on April 26th, 2012, at a Sheraton Hotel next to a Lowe's in West Des Moines, Iowa. He still teaches on 1099s and around 30 other tax topics.

Continuing education credits available!

 Continuing Education for IOFM Certification

Receive 2 CEUs toward maintaining a certification with IOFM! IOFM's premier certification programs are designed to establish standards for the industry and recognize financial operations professionals who, by possessing related work experience and passing a comprehensive exam, have met stringent requirements for mastering the body of knowledge in their profession. Additional rules may apply, depending on your certification. See full guidelines here. 

 Continuing Professional Education for NASBA

Receive 1.5 CPEs towards a CPA license with NASBA. IOFM, A Diversified Business Communications Company, is registered with the National Association of State Boards of Accountancy (NASBA) as a sponsor of continuing professional education on the National Registry of CPE Sponsors (Sponsor number: 112048) State Boards of Accountancy have the final authority on the acceptance of individual course for CPE credit. Complaints regarding registered sponsors may be submitted to the National Registry of CPE Sponsors through its website: www.nasbaregistry.org. For more information about our NASBA CPE Policies, visit IOFM.com/nasba-cpe.

Accessibility Information:

IOFM is committed to accessibility. Disability-related accommodation requests for the live event (such as providing live captioning) should be sent to [email protected] by close of business the day before the live webinar. A captioned recording of this webinar can be made available upon request to [email protected].

Cancellation policy:

To cancel your registration for this event, simply contact IOFM customer service at [email protected] (or call 207-842-5557) no later than 24 hours prior to the scheduled start of the event. You can choose to access the full recorded event, or, your credit may be applied toward the purchase of any IOFM product or interactive event. If for any reason you are not completely satisfied with this program, we will provide a full refund — no questions asked!

For more information:

Contact Customer Service:

Phone: (207) 842-5557

Email: [email protected]