Thorgood Tax Talk

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 garnishments03:20 – Payment plans and how they work for large debts04:30 – Offer in Compromise: separating myth from reality06:00 – How the IRS calculates ability to pay using income, assets, and expenses08:20 – When a payment plan may be the only option09:45 – What financial disclosures the IRS requires for debt relief11:30 – Common mistakes taxpayers make when negotiating on their own13:30 – How the IRS treats individuals vs. businesses differently15:10 – Why quick action and professional help matter16:20 – 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.

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 investigations02:15 – What actions may trigger a criminal investigation04:00 – Payroll tax violations and potential criminal liability05:10 – What a criminal tax investigation looks like from the taxpayer’s perspective07:00 – Warning signs an audit may escalate into a criminal case08:45 – How early legal strategy can help resolve cases10:15 – 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.

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.

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.

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.

Episode Summary:
In this premiere episode of Thorgood Tax Talk, attorney Shamsey Oloko, founder of the Thorgood Law Firm in New York and a former Wall Street professional turned tax defense attorney, Shamsey shares his journey into tax law, demystifies what tax lawyers really do, and explains why taxpayers facing IRS audits, enforcement actions, or criminal investigations need legal defense rooted in expertise. From peace of mind to powerful representation, this episode sets the tone for a show that takes the fear out of dealing with the IRS.
Key Timestamps:
00:01 – Introduction to Thorgood Tax Talk and host Sophia Morales01:00 – Shamsey Oloko’s journey from Wall Street to tax law03:00 – Why tax law affects every American and how Shamsey found his niche04:45 – Difference between CPAs and tax attorneys in IRS matters07:10 – What is a tax lawyer? Who needs one and when?09:20 – Real-world IRS defense strategies: audits, payroll issues, criminal tax investigations12:40 – Common myths and mistakes when dealing with the IRS15:05 – Why “telling the truth” to the IRS without legal counsel can backfire17:30 – Shamsey’s client-centered approach: restoring peace of mind19:50 – Preview of future episodes and tax topics the show will explore21:40 – Free consultations, client success stories, and real outcomes24:35 – Final advice: tax debts don’t get better with age—take action now26:00 – How to connect with Shamsey Oloko and the Thorgood Law Firm
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.