Tuesday Feb 11, 2025

Episode 47 - From IRS Insider to America's Tax Defender The Battle Against Tax Crimes

Tax Crime Junkies | Episode 47 - Inside the IRS with Pietro Canestrelli (Part 1)

Show Notes:

In this thrilling episode of Tax Crime Junkies, we dive into the mind of Pietro Canestrelli, a seasoned tax attorney who has spent years navigating both the world of tax law and the inside of the IRS. From battling audits to understanding the inner workings of the IRS, Pietro brings a wealth of experience and colorful stories that will keep you on the edge of your seat!

In part one of our conversation, Pietro gives us an inside look at the absurdities, inefficiencies, and the fascinating world of tax enforcement. You’ll hear about:

  • The IRS Work Culture: Pietro shares what it was like to step into the IRS as a fresh law school graduate and the frustrations of working within a system with little incentive to get work done. Get the inside scoop on what it’s like to navigate this giant bureaucracy.
  • Unforgettable Characters: Meet some of the quirky characters Pietro encountered inside the IRS, from The Phantom, a mysterious woman who wandered the halls, to The Walker, a man who defied dress codes by wearing running shorts. These stories give you a glimpse into the strange world behind the IRS’s serious image.
  • The Knife Incident: One of the most jaw-dropping stories Pietro shares is about a guy who threatened his boss with a knife—and still didn't get fired! You won’t believe how things work (or don’t work) inside the IRS.

Pietro also opens up about the lack of empathy often found within the IRS and how this impacts tax disputes, leading to mistakes that can escalate into tax crimes.

Stay tuned for part two, where we’ll dive into the Weekend Warrior case, management fee deductions, and the critical concept of economic substance. You won’t want to miss the dramatic continuation of Pietro’s story!

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:

  • The bizarre and frustrating realities of working at the IRS
  • Insight into how empathy (or the lack thereof) can affect the outcome of tax disputes
  • The importance of understanding both sides of the tax law for effective representation

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

Subscribe wherever you get your favorite podcasts and find us on X and instragram @TaxCrimeJunkies

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