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On the show
Recent episodes
When Does Co-Ownership Become a Partnership
Jun 24, 2026
58m 20s
Cracking Open the Shell: How S Corp Asset Sales Actually Work
Jun 10, 2026
57m 28s
S Corp Ownership Changes: What Every Tax Advisor Needs to Know
May 27, 2026
1h 02m 51s
The S Corp's Three Ledgers: Retained Earnings, AAA, and Stock Basis
May 13, 2026
56m 48s
Your Business Doesn't Need to Own Your Car
Apr 29, 2026
58m 02s
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| Date | Episode | Description | Length | ||||||
|---|---|---|---|---|---|---|---|---|---|
| 6/24/26 | When Does Co-Ownership Become a Partnership | Two friends sharing a short-term rental, a married couple flipping houses, siblings splitting the income from a property they own together: any of these could be a partnership for federal tax purposes, often without the owners realizing it. This episode works through how federal tax law defines a partnership, when one actually forms, and why mere co-ownership does not automatically create one, drawing on Subchapter K, the regulations, and foundational cases like Tower and Culbertson. It also separates two regimes that frequently get conflated, the qualified joint venture under Section 761 and the community property LLC exception under Revenue Procedure 2002-69, and closes with a framework for making the call.(00:00) - Rental Friends Scenario (01:36) - Why Partnership Status Matters (02:28) - Aggregate Versus Entity (04:22) - Goals For This Episode (05:51) - IRS Partnership Definition (09:12) - Mere Co Ownership Tests (14:10) - LLCs And Entity Rules (17:20) - When A Partnership Forms (23:22) - Supreme Court Guidance (27:45) - Court Factors Checklist (33:50) - Electing Out Of Subchapter K (39:41) - Spouse Exceptions Explained (49:08) - Two Step Decision Framework (54:31) - Case Study Short Term Rental (57:01) - Key Takeaways And Wrap Up Connect with Jeremyhttps://www.linkedin.com/in/jwellstaxhttps://www.steadfastbookkeeping.comSubscribe on YouTubehttps://www.youtube.com/@TaxinActionEarn CPE for Listening to This Podcasthttps://www.earmark.app/This podcast is a production of Earmark Media | 58m 20s | ||||||
| 6/10/26 | Cracking Open the Shell: How S Corp Asset Sales Actually Work | A buyer who wants a business but not its liabilities will often buy the assets instead of the stock, and that one decision reshapes how the entire deal gets reported. This episode breaks down the S corporation asset sale from the ground up: allocating the purchase price across seven asset classes using the residual method under Section 1060, reporting it on Form 8594, and handling goodwill and other Section 197 intangibles. It also covers why each asset's character drives the gain that passes through to shareholders, and what documentation has to be locked down before you prepare a single return.(00:00) - Stock vs Asset Sales (03:32) - Course Goals Overview (06:04) - Lighthouse Example Setup (13:16) - Why Buyers Prefer Assets (16:29) - Section 1060 Basics (25:36) - Residual Method Classes (32:17) - Goodwill and Going Concern (40:45) - Personal Goodwill Cases (42:57) - Form 8594 Reporting (47:53) - Elections 338 and 336 (50:08) - Due Diligence Checklist (53:18) - Workflow and Wrap Up Connect with Jeremyhttps://www.linkedin.com/in/jwellstaxhttps://www.steadfastbookkeeping.comSubscribe on YouTubehttps://www.youtube.com/@TaxinActionEarn CPE for Listening to This Podcasthttps://www.earmark.app/This podcast is a production of Earmark Media | 57m 28s | ||||||
| 5/27/26 | S Corp Ownership Changes: What Every Tax Advisor Needs to Know | When ownership in an S corporation changes hands, the tax consequences routinely catch both clients and their advisors off guard. Jeremy walks through the two critical questions that drive correct reporting — who or what acquired the stock, and when did the transfer actually occur for tax purposes — and explains how the answers determine whether a transaction is treated as a capital sale, a stock redemption, or a distribution. He also covers the two close-the-books elections available under IRC Section 1377(a)(2) and Reg. 1.1368-1(g), and why locking in those elections before filing — ideally before the transaction closes — can make a significant difference in how income gets allocated between outgoing and incoming shareholders.Connect with Jeremyhttps://www.linkedin.com/in/jwellstaxhttps://www.steadfastbookkeeping.comSubscribe on YouTubehttps://www.youtube.com/@TaxinActionEarn CPE for Listening to This Podcasthttps://www.earmark.app/This podcast is a production of Earmark Media | 1h 02m 51s | ||||||
| 5/13/26 | The S Corp's Three Ledgers: Retained Earnings, AAA, and Stock Basis | S corporations maintain three separate ledgers — retained earnings, AAA, and shareholder stock basis — and each one answers a different question about the entity and its owners. Understanding why they diverge, and which one actually governs whether a distribution is taxable or a loss is deductible, is where a lot of tax professionals run into trouble. Jeremy walks through the mechanics of all three, including Form 7203, the order-of-operations rules for calculating stock basis, and what's really going on when a practitioner misclassifies distributions in excess of basis as shareholder loans.(00:00) - Why S Corps Are Hybrid (02:20) - Three Key Ledgers (06:35) - Retained Earnings Basics (10:52) - IRS Scrutiny of Retained Earnings (15:13) - AAA Explained and Origins (21:43) - AAA vs Retained Earnings (27:29) - Stock Basis and Common Mistakes (36:23) - Capital Contributions and Form 7203 (43:37) - Basis Ordering Rules and Elections (48:55) - Worked Example and Wrap Up Jeremy's Article on S Corp Ledgershttps://www.jwells.tax/p/the-three-ledgers-of-an-s-corporationConnect with Jeremyhttps://www.linkedin.com/in/jwellstaxhttps://www.steadfastbookkeeping.comSubscribe on YouTubehttps://www.youtube.com/@TaxinActionEarn CPE for Listening to This Podcasthttps://www.earmark.app/This podcast is a production of Earmark Media | 56m 48s | ||||||
| 4/29/26 | Your Business Doesn't Need to Own Your Car | Buying a vehicle through your business sounds like a clean tax win, but the rules around ownership, usage, and substantiation make it far more complicated — and far riskier — than most owners realize. Jeremy breaks down what actually determines whether a vehicle expense is deductible, why mileage logs are full of trips the IRS won't allow, and how a shift in business use percentage can trigger depreciation recapture that wipes out years of deductions.(00:00) - Influencer Tax Myths (03:32) - Core Tax Authority (07:25) - Business Trips vs Commutes (14:25) - Home Office Exception (19:09) - Strict Substantiation Rules (26:33) - Mileage Logs That Win (31:49) - Fringe Benefits and Accountable Plans (36:08) - Depreciation Limits and Recapture (43:51) - Standard Mileage Rate Option (45:54) - Three Question Framework (47:52) - Scenario Walkthroughs (55:58) - Key Takeaways and Wrap Up Connect with Jeremyhttps://www.linkedin.com/in/jwellstaxhttps://www.steadfastbookkeeping.comSubscribe on YouTubehttps://www.youtube.com/@TaxinActionEarn CPE for Listening to This Podcasthttps://www.earmark.app/This podcast is a production of Earmark Media | 58m 02s | ||||||
| 4/15/26 | Section 199A: Simple Below the Threshold… Complicated Above It | The Section 199A qualified business income deduction can put serious tax savings on the table for small business owners — but only if you understand how it actually works. Jeremy walks through who qualifies, how taxable income thresholds and specified service trade or business rules affect the deduction, and how wage and property limitations come into play for higher earners. He also covers the new $400 minimum QBI deduction introduced by the One Big Beautiful Bill Act, effective for tax year 2026.(00:00) - Why QBI Exists (02:22) - Episode Roadmap (03:16) - Qualified Trade or Business (05:21) - Base Deduction Basics (06:23) - New 2026 Minimum Deduction (07:50) - Defining Qualified Business Income (11:23) - What Income Is Excluded (16:46) - Taxable Income Thresholds (20:30) - Wage and Property Limits (24:22) - Planning With S Corp Wages (28:44) - Wage Limit Court Case (31:48) - Worked Example Jessica (34:16) - Aggregation Election Rules (36:03) - Specified Service Businesses (41:01) - SSTB Phaseout Example (43:27) - De Minimis and Anti Abuse (46:32) - Rental Real Estate Safe Harbor (52:16) - Key Takeaways and Wrap Up Connect with Jeremyhttps://www.linkedin.com/in/jwellstaxhttps://www.steadfastbookkeeping.comSubscribe on YouTubehttps://www.youtube.com/@TaxinActionEarn CPE for Listening to This Podcasthttps://www.earmark.app/This podcast is a production of Earmark Media | 55m 15s | ||||||
| 4/1/26 | Worker Classification, Part 2: Statutory Workers and Misclassification Relief | Part two of worker classification moves beyond the common law control test to cover the specific worker categories defined in the tax code — statutory employees, statutory non-employees, and the rare but real dual-status worker. Jeremy also walks through the relief options available to both employers and workers when a classification goes wrong, including Section 3509, Section 530, and Form SS-8.Connect with Jeremyhttps://www.linkedin.com/in/jwellstaxhttps://www.steadfastbookkeeping.comSubscribe on YouTubehttps://www.youtube.com/@TaxinActionEarn CPE for Listening to This Podcasthttps://www.earmark.app/This podcast is a production of Earmark Media | 55m 50s | ||||||
| 3/18/26 | Employee or Independent Contractor? How the IRS Actually Decides | Worker classification has never been more complicated—and the stakes for getting it wrong fall on both employers and workers. Jeremy breaks down how federal tax law defines "employee" using the common law control standard, walking through the three categories of evidence the IRS uses to evaluate any working relationship. This is part one of a two-part series on worker classification and misclassification.Connect with Jeremyhttps://www.linkedin.com/in/jwellstaxhttps://www.steadfastbookkeeping.comSubscribe on YouTubehttps://www.youtube.com/@TaxinActionEarn CPE for Listening to This Podcasthttps://www.earmark.app/This podcast is a production of Earmark Media | 56m 46s | ||||||
| 3/4/26 | S Corp Elections: The Rules, the Risks, and the Right Call | Electing S corporation status can be a powerful tax move — but only when it's the right move. Jeremy walks through the technical requirements of Form 2553, how to pursue relief for a late S election under Rev Proc 2013-30, and the ownership, balance sheet, and state tax factors that too many practitioners overlook before recommending the election. If you or your clients have been tempted by an overly simple "just elect S" rule of thumb, this episode is required listening.Connect with Jeremyhttps://www.linkedin.com/in/jwellstaxhttps://www.steadfastbookkeeping.comSubscribe on YouTubehttps://www.youtube.com/@TaxinActionEarn CPE for Listening to This Podcasthttps://www.earmark.app/This podcast is a production of Earmark Media | 59m 36s | ||||||
| 2/18/26 | Most Small Business Returns Are Getting Cost of Goods Sold Wrong | Cost of goods sold isn't just a special category of expenses — for tax purposes, it's actually part of the definition of gross income, and only manufacturing, merchandising, and mining businesses qualify to report it. Jeremy breaks down what Treasury Regulation 1.61-3 actually says, why service businesses shouldn't have COGS on their returns even when the financial statements show it, and why getting this wrong can be catastrophic for cannabis businesses operating under IRC Section 280E.Connect with Jeremyhttps://www.linkedin.com/in/jwellstaxhttps://www.steadfastbookkeeping.comSubscribe on YouTubehttps://www.youtube.com/@TaxinActionEarn CPE for Listening to This Podcasthttps://www.earmark.app/This podcast is a production of Earmark Media | 54m 42s | ||||||
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| 2/4/26 | You Can't Delegate Filing Deadlines | Jeremy walks through the case of a Florida surgeon who lost a $288,000 refund after his CPA failed to file three years of returns, exploring how the failure to file and failure to pay penalties work and why they matter so much. He breaks down the critical differences between these two penalties, explains why an extension to file is never an extension to pay, and covers the Supreme Court's position on taxpayer responsibility even when relying on professionals. The episode also details how first time abatement works, what qualifies as reasonable cause for penalty relief, and why the IRS applies its own administrative waivers before considering statutory reasonable cause exceptions.Connect with Jeremyhttps://www.linkedin.com/in/jwellstaxhttps://www.steadfastbookkeeping.comSubscribe on YouTubehttps://www.youtube.com/@TaxinActionEarn CPE for Listening to This Podcasthttps://www.earmark.app/This podcast is a production of Earmark Media | 56m 45s | ||||||
| 1/21/26 | Non-Cash Donations Gone Wrong: The Besaw Case and Form 8283 Requirements | Jeremy breaks down the 2025 Besaw v. Commissioner tax court case, where a taxpayer lost a $6,760 charitable deduction despite everyone agreeing the donation actually happened. The case reveals why blank Goodwill receipts aren't sufficient, what "contemporaneous written acknowledgement" really means under IRC Section 170, and exactly what documentation taxpayers must maintain—whether they're filing Form 8283 or not. Learn the substantiation requirements for non-cash donations under $250, over $250, and over $5,000, plus how to properly value donated household goods and clothing using fair market value standards.Connect with Jeremyhttps://www.linkedin.com/in/jwellstaxhttps://www.steadfastbookkeeping.comSubscribe on YouTubehttps://www.youtube.com/@TaxinActionEarn CPE for Listening to This Podcasthttps://www.earmark.app/This podcast is a production of Earmark Media | 56m 57s | ||||||
| 1/7/26 | Tax-Free Employee Benefits Part 3: Transportation, Moving, Retirement Planning & Athletic Facilities | Jeremy concludes the three-part series by examining the remaining four fringe benefits from IRC Section 132—qualified transportation, moving expense reimbursements, retirement planning services, and military base realignment benefits—many of which have been significantly limited by recent tax legislation. He also covers achievement awards, athletic facility exclusions, and provides essential guidance on accountable plans, explaining the three critical requirements employers must follow to ensure expense reimbursements remain tax-free for employees while maintaining deductibility for the business.Connect with Jeremyhttps://www.linkedin.com/in/jwellstaxhttps://www.steadfastbookkeeping.comSubscribe on YouTubehttps://www.youtube.com/@TaxinActionEarn CPE for Listening to This Podcasthttps://www.earmark.app/This podcast is a production of Earmark Media | 1h 00m 22s | ||||||
| 12/24/25 | Tax-Free Employee Benefits Part 2: Company Vehicles, Cell Phones, and Office Snacks | Jeremy continues his series on IRC Section 132 fringe benefits, focusing on working condition fringes and de minimis benefits—two categories that help employees be more productive or boost workplace morale. From company vehicle mileage tracking and employer-provided cell phones to why office snacks are excludable but gift cards never are, this episode clarifies which everyday workplace benefits can legally avoid taxation. Jeremy emphasizes the critical importance of documentation and explains the strict substantiation requirements that apply to many of these benefits.Connect with Jeremyhttps://www.linkedin.com/in/jwellstaxhttps://www.steadfastbookkeeping.comSubscribe on YouTubehttps://www.youtube.com/@TaxinActionEarn CPE for Listening to This Podcasthttps://www.earmark.app/This podcast is a production of Earmark Media | 1h 00m 39s | ||||||
| 12/10/25 | Tax-Free Employee Benefits Part 1: No-Cost Services and Employee Discounts | Section 132 allows employers to provide certain fringe benefits tax-free, but only if they follow specific rules. Jeremy breaks down no additional cost services, like airline employees flying on empty seats, and qualified employee discounts, explaining the 20% cap on services and the gross profit limitation on products. He covers the critical "line of business" requirement, who qualifies as an employee beyond current workers, and why highly compensated employees face stricter rules.Connect with Jeremyhttps://www.linkedin.com/in/jwellstaxhttps://www.steadfastbookkeeping.comSubscribe on YouTubehttps://www.youtube.com/@TaxinActionEarn CPE for Listening to This Podcasthttps://www.earmark.app/This podcast is a production of Earmark Media | 54m 57s | ||||||
| 11/26/25 | The Hobby Loss Rule: How to Defend Your Business Against the IRS | Jeremy explores the hobby loss rule through the landmark case of artist Susan Crile, who successfully defended her art business against IRS claims despite reporting losses in nearly all of 25 years. The episode breaks down the nine-factor test used to determine whether an activity has a genuine profit motive, examining how professional conduct, record-keeping, and business decisions matter more than consistent profitability. This case offers crucial lessons for practitioners working with creative professionals, startups, and any clients going through extended periods without turning a profit.Connect with Jeremyhttps://www.linkedin.com/in/jwellstaxhttps://www.steadfastbookkeeping.comSubscribe on YouTubehttps://www.youtube.com/@TaxinActionEarn CPE for Listening to This Podcasthttps://www.earmark.app/This podcast is a production of Earmark Media | 1h 01m 42s | ||||||
| 11/12/25 | Breaking Up with Your S-Corp Part 2 | Jeremy wraps up his two-part series on S corporation terminations by diving into what happens after an election ends, whether intentional or inadvertent. He explains the IRS's relief procedures for common mistakes like violating the one-class-of-stock rule, the crucial five-year waiting period before re-electing, and why a terminated S corp doesn't just revert back to an LLC but becomes a C corporation instead. The discussion includes real tax court cases and the specific steps needed to clean up termination issues before the IRS discovers them.(00:00) - Introduction and Recap of Part One (01:40) - Three Ways to Terminate an S Election (03:30) - Administrative Dissolutions at the State Level (08:00) - What Happens After S Election Termination (13:10) - Inadvertent Terminations Explained (17:00) - The One Class of Stock Rule (21:30) - Maggard v. Commissioner Tax Court Case (26:20) - Profit Interests and Phantom Equity Problems (29:40) - IRS Relief for Inadvertent Terminations (34:30) - Revenue Procedure 2022-19 (39:20) - Missing S Election Acceptance Letters (42:00) - Filing the Wrong Return Type (44:10) - Six Areas of Relief Without a PLR (47:10) - Short Year Returns and Pro Rata Allocation (51:30) - The Five-Year Rule Explained (54:20) - Reverting from C Corp Back to LLC Status (56:50) - Final Thoughts and Episode Wrap-Up Connect with Jeremyhttps://www.linkedin.com/in/jwellstaxhttps://www.steadfastbookkeeping.comSubscribe on YouTubehttps://www.youtube.com/@TaxinActionEarn CPE for Listening to This Podcasthttps://www.earmark.app/This podcast is a production of Earmark Media | 58m 07s | ||||||
| 10/29/25 | Breaking Up with Your S-Corp | Jeremy breaks down the three ways an S-corporation election can terminate: voluntary revocation (including the lesser-known withdrawal option from the IRM), ceasing to qualify as a small business corporation, and excessive passive investment income. He walks through the specific mechanics of each termination method, from shareholder consent requirements to the 100-shareholder limit and the one-class-of-stock rule.Connect with Jeremyhttps://www.linkedin.com/in/jwellstaxhttps://www.steadfastbookkeeping.comSubscribe on YouTubehttps://www.youtube.com/@TaxinActionEarn CPE for Listening to This Podcasthttps://www.earmark.app/This podcast is a production of Earmark Media | 54m 29s | ||||||
| 10/15/25 |  The Legal Case for Better Books: Why Recordkeeping Isn't Optional | Jeremy dives into the often-overlooked legal requirements for taxpayer recordkeeping under IRC Section 6001, explaining why accurate books aren't just nice to have: they're mandatory. He breaks down the Cohan rule (and why it's widely misunderstood), explores how good recordkeeping can shift the burden of proof to the IRS under Section 7491, and offers practical ways tax professionals can encourage better client recordkeeping without becoming bookkeepers themselves.SponsorsSafeSend - taxshow.promo/safesend(00:00) - Introduction: The Struggles of Accounting Firms (01:06) - Challenges with PBC Data (01:56) - Balancing Bookkeeping and Tax Services (04:03) - Legal Requirements for Bookkeeping (04:43) - The Cohan Rule Explained (10:23) - Penalties for Inadequate Record Keeping (23:26) - When Cohan Doesn't Apply (28:31) - Ethical Considerations for Tax Practitioners (33:04) - Encouraging Better Bookkeeping Practices (42:37) - Leveraging Technology for Record Keeping (45:33) - Offering Bookkeeping Review Services (51:31) - Building a Network of Preferred Partners (54:17) - Pricing and Providing Additional Services (01:01:02) - Conclusion: Adding Value Without Extra Work Connect with Jeremyhttps://www.linkedin.com/in/jwellstaxhttps://www.steadfastbookkeeping.comSubscribe on YouTubehttps://www.youtube.com/@TaxinActionEarn CPE for Listening to This Podcasthttps://www.earmark.app/This podcast is a production of Earmark Media | 1h 02m 15s | ||||||
| 10/1/25 |  The Aftermath: Tax Rules for Replacing Involuntarily Converted Property | Jeremy concludes his three-part series on losses by examining IRC Section 1033, the tax code's provision for what happens after you replace property lost to casualty, theft, or government condemnation. When clients receive insurance payouts or condemnation proceeds, they face a critical decision: recognize the gain immediately or defer it by purchasing qualifying replacement property within specific timeframes. Jeremy breaks down the "similar use" requirements, the two to four year replacement periods depending on property type, and how basis carries over to help clients avoid unexpected tax bills when bad things force them to start over.SponsorsSafeSend - taxshow.promo/safesend(00:00) - Welcome to Tax in Action (00:19) - Recap of Previous Episodes (00:53) - Involuntary Conversions Explained (04:06) - Case Study: Jessica's Print Shop (05:41) - Defining Involuntary Conversions (07:01) - Government Seizures and Condemnations (07:36) - Court Cases and Legal Precedents (18:52) - Replacement Property Rules (33:35) - Special Rules for Principal Residences (48:36) - State Tax Law Considerations (52:34) - Conclusion and Final Thoughts Connect with Jeremyhttps://www.linkedin.com/in/jwellstaxhttps://www.steadfastbookkeeping.comSubscribe on YouTubehttps://www.youtube.com/@TaxinActionEarn CPE for Listening to This Podcasthttps://www.earmark.app/This podcast is a production of the Earmark Media | 54m 49s | ||||||
| 9/17/25 |  From Discovery to Deduction: Modern Theft Loss Rules Explained | Jeremy explores the complex world of theft loss deductions, examining how digital asset scams have renewed interest in these tax provisions under the Tax Cuts and Jobs Act. The episode breaks down the three key criteria for claiming theft losses, explains why timing of discovery matters more than when the theft occurred, and analyzes five modern scam scenarios from IRS Chief Counsel guidance including pig butchering schemes and romance scams. Jeremy concludes with a fascinating 1984 court case involving Civil War veterans' land rights that shows even tax court judges can disagree on fundamental questions of tax law.SponsorsSafeSend - taxshow.promo/safesend(00:00) - Introduction: Digital assets spark new interest in theft losses (03:00) - The three types of losses under IRC Section 165 (08:00) - Three criteria for claiming a theft loss deduction (13:00) - When discovery matters more than when theft occurred (19:00) - State law defines theft for federal tax purposes (24:00) - Simple disappearance is not theft (27:00) - Casualty losses vs theft losses: Key differences (29:00) - Stock declines don't qualify as theft losses (33:00) - Ponzi schemes get special safe harbor treatment (41:00) - Five modern scam scenarios from IRS Chief Counsel (53:00) - Reporting theft losses on Form 4684 (56:00) - The Booth case: When smart judges disagree (01:02:00) - Wrap-up and final thoughts Connect with Jeremyhttps://www.linkedin.com/in/jwellstaxhttps://www.steadfastbookkeeping.comSubscribe on YouTubehttps://www.youtube.com/@TaxinActionEarn CPE for Listening to This Podcasthttps://www.earmark.app/This podcast is a production of the Earmark Media | 1h 02m 37s | ||||||
| 9/3/25 |  When Disaster Strikes: Navigating Casualty Loss Deductions | Natural disasters, accidents, and sudden destructive events can create significant financial hardship, but the tax code provides some relief through casualty loss deductions. This episode breaks down the complex rules governing what qualifies as a deductible casualty loss, including the critical distinction between personal and business losses under the Tax Cuts and Jobs Act. Jeremy walks through the three-part test for casualty losses, calculation methods using fair market value changes, and the reporting requirements on Form 4684, using a real-world hurricane damage scenario to illustrate these concepts.SponsorsSafeSend - taxshow.promo/safesend(00:00) - Introduction to the Series (01:08) - Understanding Casualty Losses (02:57) - Case Study: Jessica's Print Shop (05:16) - Types of Casualty Losses (06:57) - Tax Cuts and Jobs Act Impact (12:22) - Determining Deductible Casualty Losses (18:36) - An Identifiable Event (25:34) - Determining Casualty Loses or Gains (30:29) - Filing an Insurance Claim (39:44) - Reporting Casualty Losses (49:16) - What to Do For Casualty Gain (55:46) - Conclusion and Recap Connect with Jeremyhttps://www.linkedin.com/in/jwellstaxhttps://www.steadfastbookkeeping.comSubscribe on YouTubehttps://www.youtube.com/@TaxinActionEarn CPE for Listening to This Podcasthttps://www.earmark.app/This podcast is a production of the Earmark Media | 59m 07s | ||||||
| 8/20/25 |  Section 121: The $500k Exclusion Explained | Jeremy breaks down the complex rules surrounding Section 121's capital gains exclusion for home sales, using the Weber v. Commissioner tax court case to illustrate how taxpayers can lose out on excluding up to $500,000 in gains. The episode covers the critical two-out-of-five year ownership and use tests, explains how rental conversions can disqualify you from the exclusion, and details the partial exclusion exceptions for employment changes, health issues, and unforeseen circumstances. Understanding these nuances is essential since home sales often represent the largest financial transactions in taxpayers' lives.SponsorsSafeSend - taxshow.promo/safesend(00:00) - Section 121 (01:05) - Capital Gain Exclusion Introduction (03:21) - Case Study: Webert vs Commissioner (05:51) - Defining Principal Residence (15:58) - Ownership and Use Tests (26:08) - Understanding Spousal Eligibility for Exclusion (27:16) - Principal Residence Usage Requirements (29:17) - Counting Days and Periods of Absence (31:01) - Special Considerations for Older Taxpayers (32:22) - Ownership Through Trusts and LLCs (35:22) - The Once Every Two Years Rule (39:35) - Non-Qualified Use Explained (45:31) - Case Study: The Webers' Tax Court Case (46:37) - Partial Exclusions and Safe Harbors (55:16) - Conclusion and Key Takeaways Connect with Jeremyhttps://www.linkedin.com/in/jwellstaxhttps://www.steadfastbookkeeping.comSubscribe on YouTubehttps://www.youtube.com/@TaxinActionEarn CPE for Listening to This Podcasthttps://www.earmark.app/This podcast is a production of the Earmark Media | 56m 37s | ||||||
| 8/6/25 |  Repair vs. Improvement: When Can You Deduct It? | A rental property owner faces a $27,000 repair bill after a plumbing leak forces a complete bathroom renovation, water heater replacement, and structural repairs. Jeremy breaks down Treasury Decision 9636's framework for distinguishing between deductible repairs and capitalized improvements, using the three-part test of betterment, restoration, and adaptation. He also explains three valuable safe harbors including the de minimis election and routine maintenance provisions that can help property owners expense more costs immediately rather than depreciating them over time.SponsorsSafeSend - taxshow.promo/safesend(00:00) - Introduction to Repairs vs. Improvements (00:44) - Understanding the Basics of Repairs and Improvements (01:42) - Real Estate and Vehicle Examples (04:30) - IRS Guidelines and Treasury Decision 96-36 (06:53) - Case Study: Rental Property Repairs (18:39) - Determining Repairs vs. Improvements (37:30) - Safe Harbors for Taxpayers (54:22) - Conclusion and Key Takeaways Connect with Jeremyhttps://www.linkedin.com/in/jwellstaxhttps://www.steadfastbookkeeping.comSubscribe on YouTubehttps://www.youtube.com/@TaxinActionEarn CPE for Listening to This Podcasthttps://www.earmark.app/This podcast is a production of the Earmark Media | 54m 13s | ||||||
| 7/23/25 |  The Knowledge Economy Tax Trap: When Education Costs Aren't Deductible | Jeremy breaks down the complex world of work-related education tax benefits, revealing why most educational expenses aren't as deductible as business owners think. He explains the stark difference between limited educational assistance programs that cap benefits at $5,250 annually and business expense deductions that often get rejected by the IRS for qualifying taxpayers for "new trades or businesses." Through real tax court cases involving everyone from IRS agents trying to deduct law school to nurses upgrading their licenses, this episode exposes the narrow window where education costs actually qualify as legitimate business deductions.SponsorsSafeSend - taxshow.promo/safesend(00:00) - Introduction: The Knowledge Economy (01:00) - General Education Tax Benefits (04:20) - Business Owner Education Questions (05:20) - Two Main Approaches for Business Education Benefits (08:20) - Educational Assistance Programs Deep Dive (14:20) - Program Limitations and Restrictions (22:20) - What Educational Assistance Programs Cover (26:40) - Substantiation and Double Benefit Rules (30:20) - Business Expense Deduction Alternative (33:00) - Qualifying Education Expenses (37:40) - Non-Deductible Education: Two Key Exceptions (41:00) - Established in Trade or Business Requirement (44:20) - Law Degrees and New Trade or Business (48:00) - Professional Certifications as New Trade or Business (49:40) - MBA Programs: Split Tax Court Decisions (52:40) - Final Warnings and Best Practices Connect with Jeremyhttps://www.linkedin.com/in/jwellstaxhttps://www.steadfastbookkeeping.comSubscribe on YouTubehttps://www.youtube.com/@TaxinActionEarn CPE for Listening to This Podcasthttps://www.earmark.app/This podcast is a production of the Earmark Media | 54m 56s | ||||||
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