It’s Taxing - The IRS Podcast

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 – Introduction00:23 – Overview of Puerto Rican Residency Audits00:52 – Act 60 and Its Tax Benefits02:26 – IRS Scrutiny on Residency Claims03:39 – Misconceptions About the 183-Day Rule05:46 – State Tax Residency Comparisons08:03 – Invasive Nature of IRS Audits09:43 – Sourcing Income Disputes11:09 – Impact of Remote Work on IRS Audits12:54 – Importance of Documentation15:02 – Genuine Relocation Disputes16:47 – 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/

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 – Introduction00:55 – Understanding Captive Insurance Companies01:49 – IRS Focus on 831(b) Arrangements03:06 – Characteristics of Strong Captive Structures04:30 – Risk Distribution in Captive Insurance06:14 – IRS Examination of Captive Operations07:12 – Common Industries in Captive Disputes09:38 – Importance of Actuaries in Litigation12:06 – Recent Tax Court Decisions13:39 – Assumptions Creating Problems for Captives15:46 – 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/