Drowning in Tax Debt: What to Do When You Can’t Pay the IRS

Drowning in Tax Debt: What to Do When You Can’t Pay the IRS

Episode Summary In this episode of Thorgood Tax Talk, Shamsey Oloko explains what happens when taxpayers face overwhelming IRS debt they cannot afford to pay. He breaks down the collection actions the IRS may take, such as liens, levies, and wage garnishments, and discusses the relief programs available to struggling taxpayers. Shamsey highlights installment plans, the Offer in Compromise program, and how the IRS evaluates a taxpayer’s true ability to pay. He also exposes the common myths behind “pennies on the dollar” ads, clarifies what financial disclosures are required, and explains why professional guidance often makes the difference between financial disaster and meaningful relief. Key Timestamps 01:00 – How the IRS enforces tax debt through liens, levies, and garnishments 03:20 – Payment plans and how they work for large debts 04:30 – Offer in Compromise: separating myth from reality 06:00 – How the IRS calculates ability to pay using income, assets, and expenses 08:20 – When a payment plan may be the only option 09:45 – What financial disclosures the IRS requires for debt relief 11:30 – Common mistakes taxpayers make when negotiating on their own 13:30 – How the IRS treats individuals vs. businesses differently 15:10 – Why quick action and professional help matter 16:20 – Case study: reducing $1.3 million in tax debt to zero About the Show Thorgood Tax Talk is a podcast dedicated to helping business owners and individuals navigate complex tax challenges with confidence. Shamsey Oloko a seasoned tax defense attorney and founder of Thorgood Law in New York, the show provides expert insights into IRS audits, tax investigations, and compliance strategies. With practical advice and real-world examples, Thorgood Tax Talk empowers listeners to protect their finances and avoid costly tax mistakes.

Criminal Tax Investigations: What Triggers Them and How to Respond

Episode Summary In this episode of Thorgood Tax Talk, Shamsey Oloko explains the critical differences between civil audits and criminal tax investigations, outlining the risks taxpayers face when matters escalate into criminal territory. He details common triggers for IRS criminal investigations, red flags during audits, and how early legal strategy can influence the outcome. Shamsey provides practical advice for individuals under investigation, emphasizing the importance of seeking immediate legal counsel and avoiding self-incrimination. Listeners will walk away with a clear understanding of what actions may attract IRS scrutiny, the warning signs that an audit may be shifting toward a criminal case, and why contacting a tax lawyer right away is the smartest move. Timestamps 00:40 – The difference between civil audits and criminal tax investigations 02:15 – What actions may trigger a criminal investigation 04:00 – Payroll tax violations and potential criminal liability 05:10 – What a criminal tax investigation looks like from the taxpayer’s perspective 07:00 – Warning signs an audit may escalate into a criminal case 08:45 – How early legal strategy can help resolve cases 10:15 – The single most important step if you’re under IRS investigation Show Description Shamsey Oloko breaks down what taxpayers need to know about IRS criminal tax investigations. From understanding the difference between civil audits and criminal cases to spotting red flags and knowing when to call a lawyer, this episode provides essential insights for anyone facing potential IRS scrutiny. If you’ve just learned you’re under criminal investigation, this episode delivers one clear message: stop talking and call your tax lawyer.

Sales Tax Audits: The Hidden Risk for Small Businesses

Episode Summary In this episode of Thorgood Tax Talk, tax defense attorney Shamsey Oloko explores the critical topic of sales tax audits, a significant concern for small business owners. The discussion covers the differences between sales tax and income tax audits, the types of businesses most at risk, common mistakes like commingling funds, and the severe consequences of non-compliance, including penalties and criminal charges. Listeners will gain practical strategies to minimize audit risks, such as timely filing, proper fund segregation, and professional assistance, ensuring their businesses remain compliant and protected. Key Timestamps 00:00 - Show Introduction and Welcome 01:30 - Overview of Sales Tax Audits 04:00 - Sales Tax Audits vs. Income Tax Audits 07:00 - Small Businesses Most Vulnerable to Sales Tax Audits 10:30 - Common Mistakes: Commingling Funds and Misreporting 14:00 - Consequences of Sales Tax Non-Compliance 18:00 - How States Track Sales Tax Irregularities 22:00 - Cash Transactions and Audit Challenges 26:00 - Common Misconceptions About Audit Risks 30:00 - How Far Back Can States Audit? 33:00 - Penalties and Enforcement Actions 36:00 - Preventing Criminal Charges in Sales Tax Audits 39:00 - Steps to Reduce Sales Tax Audit Risks 42:00 - Importance of Documentation and Professional Help 45:00 - Conclusion and Call to Action About the Show Thorgood Tax Talk is a podcast dedicated to helping business owners and individuals navigate complex tax challenges with confidence. Shamsey Oloko a seasoned tax defense attorney and founder of Thorgood Law in New York, the show provides expert insights into IRS audits, tax investigations, and compliance strategies. With practical advice and real-world examples, Thorgood Tax Talk empowers listeners to protect their finances and avoid costly tax mistakes.

Top Tax Mistakes That Can Land You in Hot Water

Episode Summary In this episode of Thorgood Tax Talk, tax defense attorney Shamsey Oloko addresses the most common tax mistakes that can lead to serious IRS consequences. The discussion covers underreporting income, overstating deductions, commingling personal and business funds, and relying too heavily on tax preparers. With real-world examples, such as a taxpayer hiding income through check-cashing schemes, the episode highlights the risks of non-compliance and offers practical strategies like maintaining accurate records and engaging professional help to avoid legal trouble. Key Timestamps 00:00 - Show Introduction and Welcome 01:30 - Introduction to Common Tax Mistakes 04:00 - Underreporting Income and Its Consequences 08:00 - Overstating Deductions and Audit Risks 12:00 - Risks of Commingling Personal and Business Funds 16:00 - Dangers of Poor Bookkeeping and Over-Reliance on CPAs 20:00 - Red Flag Deductions That Trigger Audits 24:00 - How Tax Mistakes Can Escalate to Criminal Investigations 28:00 - Differences in Tax Issues for Individuals vs. Businesses 32:00 - Correcting Tax Mistakes After the Fact 36:00 - Key Steps to Avoid Tax Pitfalls 40:00 - Importance of Accurate Record-Keeping 44:00 - Conclusion and Call to Action About the Show Thorgood Tax Talk is a podcast dedicated to explaining complex tax issues and helping listeners avoid legal pitfalls. Shamsey Oloko, a criminal tax defense attorney and founder of Thorgood Law in New York, the show provides expert insights into IRS audits, tax evasion, and compliance strategies. Through practical advice and real-world examples, Thorgood Tax Talk empowers individuals and businesses to navigate tax challenges with confidence.

What to Expect from an IRS Audit And How to Protect Yourself

In this insightful episode of Thorgood Tax Talk, attorney Shamsey Oloko breaks down the different types of IRS audits, the triggers that prompt them, and what taxpayers should know to avoid costly mistakes. Shamsey shares real-world examples, including high-stakes enforcement actions, and explains the importance of having the right professional support when facing an audit. Whether you’re a business owner, gig worker, or just trying to navigate your taxes, this episode offers clarity, expert advice, and actionable strategies to stay on the right side of the IRS. Key Moments and Timestamps: [00:00] Introduction to the episode [01:10] What triggers IRS audits and why underreporting is the biggest red flag [03:20] High-cash businesses and IRS audit patterns [05:00] How lifestyle and charitable donations can raise red flags [07:15] The role of whistleblowers in triggering audits [08:50] The four main types of IRS audits explained [13:30] Real-world example of a hybrid civil and criminal IRS raid [17:45] The most intense and rare audit: CCNP audit [20:15] Can one audit type escalate to another? [24:00] What to do when you first receive an audit notice [25:20] The importance of hiring a tax attorney over a CPA in serious audits [29:45] Documentation mistakes taxpayers often make [32:30] How tax preparer errors can create IRS issues [36:10] Real client stories: navigating IRS scrutiny and clearing your name [40:00] Key differences between CPAs and tax attorneys in audit defense [43:00] Final thoughts and practical advice for anyone facing an audit About the Show: Thorgood Tax Talk breaks down the real-world impact of IRS issues and enforcement. Led by trusted attorney Shamsey Oloko, the podcast offers expert legal insight into audits, collections, criminal tax investigations, and corporate tax compliance. Learn how to respond, how to protect your peace of mind, and how tax lawyers can make all the difference.