Episode 48 - From IRS Insider to America’s Tax Defender The Battle Against Tax Crimes (Part 2)

Tax Crime Junkies | Episode 48 - Inside the IRS with Pietro Canestrelli (Part 2)

Show Notes:

Welcome back to Tax Crime Junkies for part two of our conversation with Pietro Canestrelli, a seasoned tax attorney with an insider’s view of the IRS. If you missed part one, make sure to go back and listen to Pietro’s jaw-dropping stories about life inside the IRS, quirky characters, and the inefficiencies that make this massive organization so fascinating.

In part two, we’re diving deeper into the world of tax law, tax crimes, and the Weekend Warrior case. Get ready for more intriguing insights, real-world examples, and stories that will make you rethink everything you thought you knew about tax law. Here’s what you can expect in this episode:

• The Weekend Warrior Case: Pietro takes us through the famous Weekend Warrior Trailers v. Commissioner case. We discuss the key issues surrounding management fee deductions and the IRS’s challenge to their economic substance. What does it take to prove a business decision has a legitimate purpose beyond tax avoidance? Pietro gives us a breakdown.
• The Importance of Economic Substance: We dive into the critical concept of economic substance, especially when it comes to structuring transactions that stand up to IRS scrutiny. How do tax pros ensure their clients’ moves are legally sound and not deemed abusive?
• Tax Schemes and the Role of Tax Pros: Pietro offers advice for tax professionals on how to protect themselves from getting caught up in questionable tax schemes and promoter penalties. Whether it’s spotting red flags or making sure transactions are properly vetted, Pietro shares crucial tips to keep you on the right side of the law.

Pietro also discusses the changing dynamics of tax enforcement, the aggressive nature of IRS criminal investigations, and how tax professionals can navigate these challenges while providing the best service to their clients.  You can get your own copy of Pietro's book, America's Tax Defender: Stories of Taxpayers Who Fought the IRS and Won" on Amazon.  

Key Takeaways:

• How the IRS assesses the economic substance of business decisions and transactions
• The dangers of getting involved in abusive tax schemes and the importance of due diligence
• Why maintaining good relationships with clients and IRS personnel is crucial in resolving tax disputes

Stay curious, stay vigilant, and stay on the right side of the law.

Make sure to subscribe wherever you get your favorite podcasts, and follow us on X and Instagram @TaxCrimeJunkies for more updates!