Behind Closed Books

Craig Sheets

Behind Closed Books is where raw business stories meet real financial turning points. It is not about glossy success; it is about the breakdowns, pivots, and gut-punch lessons that came from finally paying attention to the numbers. Each episode delivers unaltered insight from entrepreneurs and advisors who have faced the hard calls and came out sharper.This show brings on bold founders, sharp consultants, and those who have been deep in the trenches of business chaos and clarity. They unpack what actually moved the needle and what nearly broke it. If you think accounting is boring, you have not heard these stories.

  1. 6d ago

    Decoding the Alphabet Soup: ERISA, COBRA, HSAs & What Every Employer Gets Wrong About Benefits | Kevin Mathis | EP 123

    What do ERISA, COBRA, Section 125, FSA, HSA, and HDHP actually mean — and why do the details cost employers and employees real money? In this episode of Behind Closed Books, Craig Sheets sits down with Kevin Mathis, Compliance Counsel for the Gallagher Benefit Services team at Arthur J. Gallagher & Co. in Atlanta, for a plain-English tour through the alphabet soup of employee health and welfare benefits. Kevin explains what an employee benefits attorney actually does, then works through the statutes one by one: how ERISA's two "houses" split retirement from welfare benefits, why fiduciary responsibility is the highest standard in the field, how COBRA continuation coverage works and why the premium lands at 102% of your total cost, and how Section 125 cafeteria plans let employees defer compensation pre-tax to lower their taxable income — sometimes enough to drop into a lower bracket. The conversation gets practical on spending accounts: the use-it-or-lose-it rule on health FSAs and the two ways employers can soften it, the four rules that govern HSA eligibility, and the triple tax advantage that makes HSAs one of the most underused accounts in benefits. Kevin also walks through a decision most employees make without advice — whether to pay disability premiums pre-tax or post-tax — and why checking the wrong box means your disability benefit gets taxed at exactly the moment you need it most. For employers, Kevin covers the ACA's pay-or-play mandate at 50 full-time equivalents, the two penalty structures and what triggers each, and the step most businesses skip entirely: the written plan documents required separately under both ERISA and Section 125 once the plan is in place. He closes with what's trending — state-level paid family medical leave, the dependent care account increase under the 2025 tax act, and the HSA reforms that didn't make the bill. Kevin also shares his own path: growing up in Zephyrhills, Florida, watching Perry Mason reruns with his grandmother, a cancer scare in his late twenties that pushed him to finally apply to law school, and the scholarship that landed him in Atlanta and, eventually, in healthcare law. In This Episode: What an employee benefits attorney actually does day to day ERISA's two houses — retirement benefits vs. health and welfare Why fiduciary responsibility is the highest standard in benefits Plan assets, self-dealing, and where rebates and refunds have to go COBRA explained: qualifying life events and the 102% premium Section 125 cafeteria plans and pre-tax compensation deferral Health FSAs: the $3,400 limit, use-it-or-lose-it, carryover vs. grace period HSA eligibility: high deductible health plans, Medicare, and disqualifying coverage The triple tax advantage of an HSA — and tying one to an investment account HSA-compatible limited-purpose FSAs Pre-tax vs. post-tax disability premiums and why the choice matters Why employers offer benefits when they aren't legally required to Wellness programs and lifestyle spending accounts The ACA employer mandate, 50 full-time equivalents, and pay-or-play penalties Affordability thresholds and the second penalty most employers miss Written plan documents under ERISA and Section 125 — the step everyone skips The irrevocability rule and mid-year qualifying events Auto-enrollment, participation rates, and how they affect premiums Trending: state paid family medical leave and the dependent care account increase Kevin's path from Zephyrhills to Georgia State Law to benefits compliance Subscribe to Behind Closed Books for more conversations about the financial decisions, strategies, and turning points that shape successful businesses. #EmployeeBenefits #ERISA #COBRA #HSA #FSA #HealthInsurance #HR #Compliance #BenefitsAdministration #BusinessGrowth

    Decoding the Alphabet Soup: ERISA, COBRA, HSAs & What Every Employer Gets Wrong About Benefits | Kevin Mathis | EP 123
  2. Sep 30

    Why AI Can't Replace Accountants: Dyron Bush on Tax Errors and Human Judgment | Dyron Bush | EP 122

    AI is changing accounting, but technology still needs human judgment to get the numbers right. In this episode of Behind Closed Books, Craig Sheets sits down with Dyron Bush, Senior Tax Consultant at M&A Business Advisors, CEO of Theogeny Financial, tax strategist, accountant, financial consultant, and host of the Mechanics of Money podcast, to discuss how AI is changing accounting and why experienced professionals still matter. Dyron shares real examples of where technology can help and where it can go wrong, including a scanning error that created an incorrect million-dollar tax refund. He explains why AI should be treated as a useful tool rather than a replacement for professional judgment, and why accountants still play a critical role in reviewing financial information, finding errors, and helping clients make better decisions. The conversation also explores how clients can make tax preparation easier by sending complete information, naming documents clearly, organizing files properly, and understanding which tax documents their accountant needs. In this episode you'll learn: Why AI cannot replace experienced accountants How technology errors can create major financial mistakes Where AI can help with reports, research, and efficiency Why AI-generated work still needs human review How Dyron uses tools such as ChatGPT, Claude, Gemini, Kling, and Canva Why clients should send complete tax documents How properly naming and organizing files saves time Why tax results can change from one year to the next How accountants help clients plan beyond tax preparation Why professional judgment remains important as technology improves Dyron also shares his journey from studying accounting at Xavier University to building his career in finance, tax, technology, and business, along with his perspective on where AI may take the industry next. If you're a business owner, accountant, tax professional, entrepreneur, or anyone interested in how AI is changing financial work, this episode offers practical lessons on using technology without losing the value of human expertise. 👍 Like this video if you found it valuable. 💬 Share your biggest takeaway in the comments. 🔔 Subscribe for more conversations with entrepreneurs, experts, and business leaders. #ArtificialIntelligence #Accounting #TaxStrategy #TaxPreparation #AI #BusinessFinance #Entrepreneurship #BusinessGrowth #FinancialStrategy #BehindClosedBooks

    Why AI Can't Replace Accountants: Dyron Bush on Tax Errors and Human Judgment | Dyron Bush | EP 122

About

Behind Closed Books is where raw business stories meet real financial turning points. It is not about glossy success; it is about the breakdowns, pivots, and gut-punch lessons that came from finally paying attention to the numbers. Each episode delivers unaltered insight from entrepreneurs and advisors who have faced the hard calls and came out sharper.This show brings on bold founders, sharp consultants, and those who have been deep in the trenches of business chaos and clarity. They unpack what actually moved the needle and what nearly broke it. If you think accounting is boring, you have not heard these stories.