It’s Taxing - The IRS Podcast

The Legal Podcast Network (LPN)
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It’s Taxing - The IRS Podcast is a comprehensive resource for individuals and businesses navigating the complexities of tax law and IRS regulations. Hosted by former IRS attorneys, the show offers expert insights into tax disputes, compliance, and planning strategies. Each episode breaks down intricate tax topics into understandable discussions, providing listeners with practical advice and the latest updates in tax law. Whether you're a business owner, tax professional, or simply interested in understanding the tax landscape, this podcast delivers valuable information with clarity and depth.

Episodes

  1. 21h ago

    Puerto Rico Bona Fide Residency Audits and IRS Scrutiny

    Episode Summary:  In this episode of It's Taxing- The IRS Podcast, host Lisa Mosbey and guest Derek W. Kaczmarek, co-founder of Kaczmarek and Jojola and former IRS Senior Trial Attorney, delve into the complexities of Puerto Rican bona fide residency audits. They explore the surge in popularity of Puerto Rican residency among high earners due to Act 60, which offers significant tax benefits.  Derek explains the IRS's rigorous scrutiny of residency claims, highlighting the invasive nature of audits and the importance of understanding the three tests used to determine bona fide residency. The discussion also covers the challenges faced by remote workers and online businesses in maintaining compliance with IRS regulations. Listeners will gain valuable insights into the documentation required for audits and the common pitfalls to avoid, ensuring they are well-prepared to navigate the intricacies of Puerto Rican residency. Key Timestamps: 00:01 – Introduction 00:23 – Overview of Puerto Rican Residency Audits 00:52 – Act 60 and Its Tax Benefits 02:26 – IRS Scrutiny on Residency Claims 03:39 – Misconceptions About the 183-Day Rule 05:46 – State Tax Residency Comparisons 08:03 – Invasive Nature of IRS Audits 09:43 – Sourcing Income Disputes 11:09 – Impact of Remote Work on IRS Audits 12:54 – Importance of Documentation 15:02 – Genuine Relocation Disputes 16:47 – Underestimating Puerto Rican Residency Audits About the Show:  It's Taxing- The IRS Podcast is designed for individuals and businesses navigating the complexities of tax law and IRS regulations. Hosted by Lisa Mosbey, the show features expert guests who provide insights into tax disputes, compliance, and strategic planning.  With a focus on clarity and practical advice, the podcast aims to demystify the often daunting world of taxes, offering listeners the knowledge they need to make informed decisions. Whether you're a business owner, tax professional, or simply interested in understanding tax issues, It's Taxing- The IRS Podcast provides valuable content to help you stay ahead. For more information, visit our website:  https://kjtaxlaw.com/

    Puerto Rico Bona Fide Residency Audits and IRS Scrutiny

  2. Sep 1

    Captive Insurance Audits and IRS Litigation

    Episode Summary: In this episode of It's Taxing - The IRS Podcast, hosts Derek W. Kaczmarek, a former IRS senior trial attorney, and Lisa Mosbey delve into the complexities of captive insurance arrangements. They explore why these arrangements have become a significant focus for the IRS and the implications for businesses involved. Derek explains the legitimate use of captive insurance companies for small to medium-sized businesses and the tax benefits under code section 831(b). The discussion highlights the IRS's scrutiny of these arrangements, particularly focusing on risk distribution and the real-world operations of captives. Listeners gain insights into the characteristics that differentiate compliant captives from those challenged by the IRS, and the role of actuaries and other expert witnesses in litigation. This episode is essential for business owners and advisors navigating the intricate landscape of captive insurance and tax compliance. Key Timestamps: 00:01 – Introduction 00:55 – Understanding Captive Insurance Companies 01:49 – IRS Focus on 831(b) Arrangements 03:06 – Characteristics of Strong Captive Structures 04:30 – Risk Distribution in Captive Insurance 06:14 – IRS Examination of Captive Operations 07:12 – Common Industries in Captive Disputes 09:38 – Importance of Actuaries in Litigation 12:06 – Recent Tax Court Decisions 13:39 – Assumptions Creating Problems for Captives 15:46 – Final Advice for Business Owners About the Show: It’s Taxing - The IRS Podcast is a comprehensive resource for individuals and businesses navigating the complexities of tax law and IRS regulations. Hosted by former IRS attorneys, the show offers expert insights into tax disputes, compliance, and planning strategies. Each episode breaks down intricate tax topics into understandable discussions, providing listeners with practical advice and the latest updates in tax law. Whether you're a business owner, tax professional, or simply interested in understanding the tax landscape, this podcast delivers valuable information with clarity and depth. For more information, visit our website: https://kjtaxlaw.com/

    Captive Insurance Audits and IRS Litigation
  • 2 Episodes

About

It’s Taxing - The IRS Podcast is a comprehensive resource for individuals and businesses navigating the complexities of tax law and IRS regulations. Hosted by former IRS attorneys, the show offers expert insights into tax disputes, compliance, and planning strategies. Each episode breaks down intricate tax topics into understandable discussions, providing listeners with practical advice and the latest updates in tax law. Whether you're a business owner, tax professional, or simply interested in understanding the tax landscape, this podcast delivers valuable information with clarity and depth.

Information

  • Creator
    The Legal Podcast Network (LPN)
  • Years Active
    2026
  • Episodes
    2
  • Rating
    Clean
  • Copyright
    © Copyright 2026 All rights reserved.
  • Show Website
    It’s Taxing - The IRS Podcast