
This detailed program explores the unique tax challenges and considerations faced by entertainers, performers, and influencers. It covers the complexities of income reporting, expense deductions, and compliance issues specific to individuals in the entertainment and social media industries. The program shows how to correctly categorize income, distinguish between business and personal expenses, and apply IRS guidelines to ensure accurate tax reporting. The program also examines recent legal cases, IRS audits, and common pitfalls in the taxation of entertainers and influencers. Lastly, the program provides case studies, and practical examples, to equip tax professionals with the knowledge needed to navigate the intricacies of taxation in the entertainment sector effectively.
Moderator: Kelley C. Miller, Esq., Reed Smith LLP
Panelists:
Alyssa Maloof Whatley, Esq.,
Law Offices of Alyssa Maloof Whatley, LLC
Anthony J. DeRiso, Esq., Jones Day
Carneil D. Wilson, Dentons Sirote
Lani Rosado-Espinal, IRS Criminal Investigation
Sarah Green, Esq., Dentons Sirote
This webinar is available for Virtual or LIVE In-Person attendance.
Tax Professionals that attend are encouraged to accept a pro bono tax controversy case assignment from NYCLA, an ABA-sponsored Tax Court Pro program or a NY or NJ low-income Tax Clinic.
IRS Program #: 7Q3WU-T-00766-25
CTEC Course #: 6248-CE-00129

John began his tax career in 1987 and passed the IRS Special Enrollment Exam in 1995. A National Tax Practice Institute fellow and SUNY Oswego graduate, he specializes in taxation for non-resident aliens, U.S. citizens living abroad, S corps, legal marijuana businesses, and cryptocurrency.
John is passionate about giving back to the profession. Every year on Giving Tuesday, Tax Practice Pro offers a free ethics webinar, and its weekly Tax Update webinars keep tax professionals informed on the latest developments. These programs combine practical guidance, strategies, and insights to help practitioners work smarter, faster, and with confidence.
Whether you’re just starting your career or expanding an established practice, Tax Practice Pro and John Sheeley, EA provide the education, coaching, and community support tax professionals need to succeed.
3 Free NY & NJ CLE, CPE and IRS CE/NASBA CPE Credits
Tax Professionals that attend are encouraged to accept a pro bono tax controversy case assignment from NYCLA, an ABA-sponsored Tax Court Pro program or a NY or NJ low-income Tax Clinic.
4 Free NY & NJ CLE, 4CPE and 4IRS CE/ 4 NASBA CPE Credits
This program delves into the evolving role of artificial intelligence (AI) in the realm of tax controversy. The program covers the use of AI tools for legal research, document automation, and predictive analytics, highlighting their applications in tax dispute resolution. It explores the benefits and challenges of AI-powered eDiscovery, the ethical considerations of AI in legal contexts, and best practices for integrating AI into tax practices. The program reviews the IRS's use of AI for audit selection, taxpayer assistance, and litigation. Lastly, this program addresses bias, privacy, and the ethical implications of AI in tax and legal contexts.
4 Free NY & NJ CLE, CPE and 4 IRS CE/4 NASBA CPE Credits
This detailed program explores the unique tax challenges and considerations faced by entertainers, performers, and influencers. It covers the complexities of income reporting, expense deductions, and compliance issues specific to individuals in the entertainment and social media industries. The program shows how to correctly categorize income, distinguish between business and personal expenses, and apply IRS guidelines to ensure accurate tax reporting. The program also examines recent legal cases, IRS audits, and common pitfalls in the taxation of entertainers and influencers. Lastly, the program provides case studies, and practical examples, to equip tax professionals with the knowledge needed to navigate the intricacies of taxation in the entertainment sector effectively.
2 IRS CE/2 CTECT/2 NASBA CPE*
Whether your clients rent out a spare bedroom or operate multiple vacation properties, short-term rentals come with unique tax challenges—and opportunities. This course dives into the latest IRS guidance and practical strategies for navigating the tax rules surrounding short-term rental activity. You'll learn when rental income is tax-free, how to allocate deductions between personal and rental use, and how to handle reporting obligations—even when your client receives a 1099. The course covers depreciation, safe harbor elections and loss limitations and more!
1 IRS CE/1 CTEC/1 NASBA CPE*
This webinar is only available to monthly subscribers. Join us for our third webinar in our "2025 Tax Office Cyber Security Series", designed to help accounting and tax firms enhance their security posture and protect their sensitive data.
2 IRS CE/2 CTEC/2 NASBA CPE*
Unlock key strategies for navigating the complexities of passive loss limitations and grouping elections in this essential webinar for tax professionals. This course will provide a comprehensive breakdown of passive loss rules, how they apply in real-world scenarios, and the critical decisions taxpayers must make when electing to group activities. It will demystify the differences between passive loss grouping elections and other aggregation elections, ensuring you understand their distinct tax implications. With a focus on strategic tax planning, we’ll explore when grouping can maximize tax benefits and when it might lead to unintended consequences.
1 IRS CE/1 CTEC/1 NASBA CPE*
The Tax Cuts and Jobs Act introduced the Qualified Business Income (QBI) deduction under IRC §199A, creating powerful tax savings for qualifying trades and businesses. But what about rental real estate? This course explores one of the most nuanced areas in modern tax law—when and how rental activities qualify as a trade or business for purposes of the §199A deduction. Through detailed analysis of statutory language, court decisions, and IRS guidance (including Rev. Proc. 2019-38), participants will learn to assess whether rental activities rise to the level of a trade or business under IRC §162. We will break down the safe harbor rules, examine case law, and explore various scenarios including triple-net leases, single-property landlords, and self-rentals. This course offers practitioners the tools to perform due diligence, evaluate facts and circumstances, and properly document their conclusions.
2 IRS CE/2 CTEC/2 NASBA CPE*
Join us for an in-depth webinar covering Depreciation, Depletion, and Amortization for tax preparers. This program will explore critical topics such as Depreciation methods, Special (Bonus) Depreciation, and Section 179 expensing. We'll also discuss the Depletion deduction, including percentage and cost depletion methods, and tax treatment of royalties and timber sales. Additionally, we'll cover the use of Form 3115 for changes in accounting methods. Enhance your knowledge and ensure accurate reporting for your clients with this essential tax webinar.
2 IRS CE/2 CTEC/2 NASBA CPE*
Join us for an engaging and informative webinar exploring the challenges and opportunities tax preparers face when working with clients who own rental properties. This program will provide a comprehensive overview of key tax forms, including Form 1040, Schedule E (Page 1) - Supplemental Income and Loss from rental real estate, and Form 8825 - Rental Real Estate Income and Expenses of a Partnership or an S Corporation. Gain valuable insights, practical tips, and expert guidance to confidently navigate rental property taxation for your clients.
Varies
Get ready to unlock the secrets of real estate taxation with our month-long webinar series designed for tax professionals! Whether you’re navigating short-term rentals, passive activity losses, grouping, or real estate professional status, this series delivers the strategies and insights you need to stay sharp and compliant.
2 IRS CE/2 CTEC/2 NASBA CPE*
"Our best deal is always to become a monthly subscriber" *Self-Study recording not available for NASBA CPE credit.
2 IRS CE/2 CTEC/2 NASBA CPE*
“Knock & Talks” are unannounced visits by IRS agents designed to catch tax professionals off guard—often during tax season—to verify compliance on everything from due diligence forms to security practices. This webinar walks you through what to expect if the IRS comes knocking, what the agents are looking for, and how to maintain proper documentation and procedures to protect your practice from hefty penalties or sanctions.