Episode Summary: In this episode of Bankruptcy Through the Looking Glass, host Kevin Rosenquist is joined by bankruptcy expert Barry Levine to dive deep into the issue of tax debt and its intersection with bankruptcy. They discuss the complexities of dealing with overwhelming tax liabilities, including common reasons individuals find themselves in tax debt, options like bankruptcy, and the IRS’s approach to collecting taxes. Barry shares valuable insights on strategies like offers in compromise and asset liquidation, along with practical advice on how to navigate these challenges. With over four decades of experience, Barry also reflects on his many stories of clients and the realities of tax collection. Timestamps: 00:00 - 00:05: Intro 00:05 - 00:31: Kevin introduces the topic and welcomes Barry 00:31 - 02:33: How common is tax debt and why it’s growing? Barry discusses real-life examples of individuals failing to file tax returns 02:33 - 04:06: Common reasons for falling into tax debt, including self-employment taxes and withholding issues 04:06 - 05:26: IRS tactics for dealing with tax debt: Estimated returns and tax liens 05:26 - 06:29: What is an offer in compromise? Barry explains how this process works 06:29 - 07:09: The importance of asset liquidation in resolving tax debts 07:09 - 08:33: Real stories from Barry's clients dealing with tax debt and the IRS 08:33 - 09:23: Bankruptcy vs. offers in compromise: How to evaluate your best option 09:23 - 11:35: Pros and cons of filing bankruptcy to discharge tax debts 11:35 - 13:43: Why people end up with years of tax debt and how the IRS handles long-term tax issues 13:43 - 16:20: The importance of being proactive with the IRS and avoiding mistakes like hiding financial transactions 16:20 - 16:44: Barry signs off with his trademark saying "Zygazook!" About the Show: Bankruptcy Through the Looking Glass is a podcast hosted by Kevin Rosenquist and bankruptcy attorney Barry Levine, where they discuss real-life issues in bankruptcy law. Each episode dives into the intricacies of financial troubles, debt relief, and strategies to regain control over your finances. With Barry’s decades of experience in bankruptcy law, listeners get insightful, expert advice on navigating complex situations, including tax debt, creditor negotiations, and the nuances of various bankruptcy chapters.