A podcast focusing on the top things business taxpayers need to know. Updated information that is easy to digest and will keep you on the cutting edge of business finance news.
Listen to episodes
60 recent
August 7, 2026Episode 14715 min
Episode 147: The 10-Year Tax Play: Deferring Capital Gains the Right Way
In this episode: Inflation-indexed IRS deductions, credits, and thresholds for 2026. Non-indexed thresholds that haven't changed in decades (e.g., home sale gain exclusion). New above-the-line charitable deduction for non-itemizers. Rules for deducting donated vehicles. Conservation easements and farmland preservation. Tax treatment of donated timeshares and vacation home rentals. Qualified opportunity zone capital gains deferment. Health insurance marketplace premium tax credit pitfalls. Upcoming tax filing deadlines. IRS interest vs. penalty abatement rules.
July 24, 2026Episode 14621 min
Episode 146: Hobby Losses, Gambling Wins, and the IRS's Fine Print
In this episode: Hobby loss rules – refresher on when the IRS may reclassify a business as a hobby. Trump accounts – contributing up to $5,000 for a minor without triggering a gift tax filing. Gift tax basics – $19,000 annual exclusion, filing requirements above that, and the $15M lifetime exemption. Gambling loss changes – losses now deductible only up to 90% of winnings (previously 100%), and only if itemizing. Online sports betting – winnings are taxable income regardless of platform. Standard mileage rate increase – 76 cents/mile for July–Dec 2025 vs. 72.5 cents for Jan–June. Foreign bank account disclosure – steep penalties for not reporting foreign accounts/access to funds. IRS penalty relief – automatic first-time penalty abatement for compliant taxpayers (no longer needs to be requested). IRS penalty statistics – $1.25 trillion assessed in 2025, 92% from unpaid payroll taxes, with most later abated. Maryland's new tax portal – launching September 1st, with a blackout period and no penalties during the transition.
July 10, 2026Episode 14514 min
Episode 145: Marketplace Money Trouble: The Subsidy Surprise Coming Your Way
In this episode: Premium tax credit changes affecting Marketplace health coverage enrollees. Long-term care insurance premium deductions and new retirement plan withdrawal rules. A proposed Newborn Tax Credit and updates to ABLE accounts. IRS partnership audit trends and lingering ERC (Employee Retention Credit) claim backlog. A rundown of current IRS-impersonation scam tactics targeting seniors.
June 29, 2026Episode 14421 min
Episode 144: New Tax Credits, Crypto, and IRS Chaos
In this episode: Federal Scholarship Tax Credit (2027) — Up to $1,700 non-refundable credit for K–12 scholarship donations; no income limits; requires state opt-in Cryptocurrency staking rewards — Tokens taxable as income upon receipt; deferral legislation proposed but not yet law 1099-DA reporting (2027) — Brokers must report digital asset sales; provide all 1099s to your preparer Charitable contribution rules — Cash must be documented; GoFundMe not deductible; large non-cash donations require appraisals $4.2M charitable deduction denied — Tax court disallowed due to inadequate documentation Hobby loss rules — Losses only deductible if activity is run with genuine profit motive Family limited partnership discounts — Court upheld IRS challenge; deemed tax-motivated with no business purpose Estate tax Form 706 & closing letters — Portability elections, new request fee, and 2–3 year processing delays 2027 Social Security wage base — Increases to $190,200; effectively a tax hike for higher earners Amended returns (Form 1040-X) — 3-year filing window; e-file for faster refunds IRS workforce decline — Staffing down 28%; enforcement agents down 33%; fewer audits and slower service
In this episode: IRS call strategies – A tip for getting through when the IRS won't accept calls • Tax identity theft – How fraudsters file returns using stolen Social Security numbers • Qualified Small Business Stock (QSBS) – A little-known tax exclusion that could eliminate gains for eligible investors • IRS First-Time Abatement – An automated penalty relief process coming soon for late filers • Investment fee deductibility – Why individuals can no longer deduct these fees, but businesses still can • IRS interest rate increases – Higher rates on underpayments and overpayments starting Q3 2026 • 2026 W-2 changes – New codes to identify deductible tips and overtime pay • SALT cap – The $40,000 state and local tax deduction limit reaffirmed through 2029 • 2027 HSA limits – Contribution limits going up, with a reminder of the long-term savings benefits
May 29, 2026Episode 14218 min
Episode 142: IRS Notices, Hidden Tax Credits, and the Tax Traps Costing People Money
In this episode: A recent court case that could allow some taxpayers to recover certain IRS penalties and interest assessed during the COVID-era, and what steps may be available to protect refund claims. The growing problem of erroneous IRS and state tax notices, including what taxpayers should do before reacting to unexpected letters. Valuable but often-overlooked tax credits, including significant updates to the adoption tax credit and how proper communication with your tax preparer can prevent missed opportunities. A refresher on the Net Investment Income Tax (NIIT) and additional Medicare taxes, including why more taxpayers are being affected than ever before. Important considerations for farmers, landowners, and others exploring conservation easements or land preservation programs, including common compliance pitfalls. Tax-saving opportunities that may be disappearing soon, including credits related to electric vehicle charging equipment. Current mileage reimbursement rates, the importance of maintaining accurate mileage logs, and why mid-year IRS changes could matter. New direct deposit requirements for federal tax refunds, common IRS notice issues related to those requirements, and how to avoid unnecessary refund delays. Delaware-specific tax notice concerns that are affecting taxpayers across the state. A look at potential tax and legislative developments on the horizon, including discussions surrounding a possible federal gas tax holiday and what it could mean for consumers.
May 15, 2026Episode 14119 min
Episode 141: From Kids' First Jobs to High Earners: Your Mid-Year Tax Playbook
In this episode: 2026 Tax Legislation Outlook — No major tax changes expected this year; budget reconciliation and new proposals remain largely on hold. Retirement Savings Updates — Expanded 401(k) investment options (real estate, private equity), new IRA access for those without workplace plans, and spousal IRA contribution rules. Roth IRA Benefits — Tax-free growth advantages and AGI threshold increases for contributions. Summer Tax Tips for Families — Tax withholding rules for dependent children working summer jobs, and how to hire your child if you're self-employed to reduce payroll taxes. Child and Dependent Care Credit — Enhanced credit limits for 2026, including eligibility for summer camps. Kids' Roth IRAs — Opening retirement accounts for children with earned summer income. Employee Fringe Benefits — IRS guidance on taxable vs. non-taxable benefits, including employer-paid tuition assistance (up to $5,250 annually, indexed for inflation starting 2027). Marijuana Tax Developments — Medical marijuana reclassified to Schedule III, removing the 280E deduction limitation for medical operators. Nonprofit Filing Deadline — May 15th deadline for calendar-year exempt organizations; upcoming Form 990 revisions for increased transparency. Tax Rates for High Earners — Breakdown of effective tax rates vs. tax brackets for top 1% earners, including capital gains and net investment income tax.
May 1, 2026Episode 14016 min
Episode 140: Fewer Audits, More Red Flags: What's Really Changing at the IRS
In this episode: What IRS funding cuts actually mean in the real world, fewer audits, but slower responses and more frustration when you do need answers Why "audit rates are down" doesn't mean you're off the hook, and how AI-driven red flags are quietly replacing old-school enforcement The growing role of automation in tax processing, and how it's leading to confusing notices, mismatched payments, and head-scratching letters Why you should never ignore a tax notice, even when it looks wrong, and how often they actually are New and finalized tax rules that could create real savings opportunities, especially for service-based businesses with tipped income A new 1% tax that could quietly affect personal cash transfers overseas starting in 2026 Eye-opening tax data on who is actually paying the bulk of federal taxes, and what that means for business owners thinking about growth Hidden traps inside common entity structures, especially S corporations, that can trigger unexpected taxes if handled incorrectly Advanced planning strategies like micro captive insurance, where the upside is real, but so is the IRS scrutiny if you get it wrong What the lack of major tax law changes (for now) means for planning ahead, and why stability might actually be your biggest advantage going into the next couple of years
April 17, 2026Episode 13915 min
Episode 139: Avoid IRS Penalties!
In this episode: Why most taxpayers don't itemize anymore, and when it still actually makes sense to do so The hidden fine print on mortgage interest deductions, including caps that quietly limit what high-balance homeowners can write off How home equity loans can either save you on taxes, or cost you the deduction entirely depending on how you use the money The real story behind points, refinancing, and why timing matters more than most people realize Why some common "write-offs" like mortgage insurance premiums rarely benefit higher earners A major shift in state and local tax deductions, and why some business owners may suddenly see bigger write-offs The growing cost pressure of employee health insurance, and the moment your business is legally required to offer it How benefits strategy isn't just an expense, it's a recruiting weapon if you play it right A surprising tax change around gambling income that quietly increases what people owe Why the IRS insists you pay taxes throughout the year, not just in April, and how that impacts cash flow The concept of "safe harbor" payments and how it can protect you even if your income swings wildly A lesser-known payroll strategy some business owners use to legally manage timing of tax payments Why tax planning isn't just a nice-to-have, it's the difference between scrambling in April and being in control year-round
April 3, 2026Episode 13826 min
Episode 138: Tax Traps and Smart Moves: What Taxpayers Should Fix Before It Costs Them
In this episode: A practical look at proposed IRS reform and why better customer service, clearer appeals rights, and stronger taxpayer advocacy matter to everyday taxpayers and business owners. A timely reminder about April tax deadlines, including the difference between an extension to file and an extension to pay. What taxpayers should know about the IRS shift away from paper checks, and how that could affect refunds, estimates, and tax payments. A candid discussion about what happens when you owe the IRS, including payment plan options, costly mistakes, and why tax planning matters more than panic. Easy-to-follow insights on gift and estate planning strategies, including annual gifting rules and key filing requirements families often miss. A useful overview of charitable giving strategies through IRAs and how they may benefit certain taxpayers. Important filing issues that can come up after the death of a spouse, including deadlines and portability considerations. Common audit triggers, popular tax scams, and the kinds of "too good to be true" tax advice business owners should avoid.
Is this your show?
Claim this listing to keep it up to date, reach guests who want to pitch you, and manage bookings with Guestify.
