All Episodes

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

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

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

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

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

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

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.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

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

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.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

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.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

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.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

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.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

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.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

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.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

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.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

Understanding the refund statute of limitations can mean the difference between claiming a refund and losing that money forever. This episode breaks down the complex rules around when taxpayers can file refund claims and how much they can recover, using the recent Hamilton v. US case as a cautionary tale. Whether you're dealing with late-filed returns, amended returns, or clients who've fallen behind on their taxes, these statute of limitations rules will determine what's possible and what's permanently lost.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

Most tax professionals assume joint filing is the default for married couples, but the tax code actually says the opposite. Jeremy Wells explores the surprising reality that married filing separately is technically the default status, requiring both spouses to elect joint filing under IRC Section 6013. He breaks down the key disadvantages of separate returns—from reduced credits to income limitations—while explaining legitimate scenarios where paying extra tax through separate filing can lead to better overall financial outcomes, particularly with student loan repayment strategies.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

Jeremy Wells breaks down the fundamentals of Section 1031 exchanges, explaining how real estate investors can defer capital gains taxes by swapping properties rather than selling and buying separately. He clarifies common misconceptions about these transactions, walks through the strict timing requirements including the 45-day identification and 180-day completion rules, and examines court cases that reveal when the IRS challenges whether replacement properties were truly intended for investment purposes. The discussion covers qualifying property types, disqualified persons, and the practical mechanics of using qualified intermediaries to facilitate these tax-advantaged exchanges.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

Jeremy dives deep into the critical red flags that should make tax professionals pump the brakes on S-corporation elections. From balance sheet debt ratios that could trigger unexpected taxable events to operating agreement provisions that can inadvertently terminate S-elections, this episode challenges the "default to S-corp" mentality that's become prevalent in tax advisory circles. Jeremy breaks down the specific scenarios where partnerships or sole proprietorships actually serve business owners better than the often-hyped S-corporation structure.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

The R&D tax credit offers significant tax-saving potential, yet remains misunderstood by many small business owners and their advisors. Jeremy breaks down the key components of the Section 41 credit, explaining qualified research activities, eligible expenses, and calculation methods. Small service-based businesses might qualify more often than they realize, especially when research activities relate to technological innovation, computer science, or engineering processes.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