Episode 118: New Bill, New Breaks: What Families and Investors Should Know
Release Date: 06/13/2025
Episode 147: The 10-Year Tax Play: Deferring Capital Gains the Right Way
Accounting and Accountability
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.
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Episode 146: Hobby Losses, Gambling Wins, and the IRS's Fine Print
Accounting and Accountability
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...
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Episode 145: Marketplace Money Trouble: The Subsidy Surprise Coming Your Way
Accounting and Accountability
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.
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Episode 144: New Tax Credits, Crypto, and IRS Chaos
Accounting and Accountability
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...
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Episode 143: QSBS, SALT, HSAs & More: Mid-Year Tax Moves for Taxpayers
Accounting and Accountability
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...
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Episode 142: IRS Notices, Hidden Tax Credits, and the Tax Traps Costing People Money
Accounting and Accountability
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...
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Episode 141: From Kids' First Jobs to High Earners: Your Mid-Year Tax Playbook
Accounting and Accountability
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...
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Episode 140: Fewer Audits, More Red Flags: What’s Really Changing at the IRS
Accounting and Accountability
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...
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Episode 139: Avoid IRS Penalties!
Accounting and Accountability
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...
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Episode 138: Tax Traps and Smart Moves: What Taxpayers Should Fix Before It Costs Them
Accounting and Accountability
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...
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The benefits of long-term capital gains tax rates and how to qualify
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The impact of the 3.8% Net Investment Income Tax (often called the “Obamacare tax”)
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The key differences between long-term and short-term capital gains
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New increases to the standard deduction for 2025
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A proposed tax-advantaged “Trump Account” for children under age 8, including contribution limits and withdrawal rules
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The House-passed bill’s broader context, including its 100+ tax provisions still awaiting Senate approval
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Why it's important to wait for legislation to be finalized before planning around it
In this episode, our guest, Debora Gorman, dives into Maryland’s sweeping tax changes for 2025, aimed at closing a $3.3 billion budget gap—while giving entrepreneurs a crash course in how these changes will hit their bottom lines. If you own or operate a business in Maryland (or sell into it), this is your cheat sheet to staying compliant and tax-savvy in the face of some major shifts.
What You’ll Learn:
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New High-Income Tax Brackets:
Maryland has introduced two new tax tiers for top earners—up to 6.5% for individuals making over $1 million and joint filers over $1.2 million. Business owners should reassess employee withholdings and estimated tax payments now. -
Capital Gains Surtax:
A new 2% surtax applies to net capital gains for individuals with federal AGI over $350,000. Some exceptions apply (think retirement accounts and primary residences under $1.5M), but high-income entrepreneurs will want to revisit their investment strategies and tax planning. -
Standard Deduction Boosts:
Maryland has raised its standard deduction significantly. It could tip the scales for some taxpayers, especially small business owners juggling itemized deductions. Gorman urges entrepreneurs to run both scenarios before filing. -
New 3% Sales Tax on Digital & IT Services:
Starting July 1, 2025, certain digital subscriptions and tech services will be taxed. This includes cloud storage, custom software, and IT consulting under specific NAICS codes. If you’re selling these services, you’ll need to start collecting and remitting the tax. If you’re buying, plan for increased costs. -
Out-of-State Sellers Beware:
If your company sells into Maryland and hits $100K in revenue or 200 transactions/year, you’re likely on the hook for sales tax collection—even without a physical presence. -
Custom Software No Longer Exempt:
With the expansion of what’s taxable, the custom software exemption is gone. If it’s tied to taxable IT services, it’s now subject to the 3% rate. -
Help Is Available:
Gorman highlights resources like MarylandTaxConnect.gov and the Comptroller’s legislative updates page, which includes step-by-step videos, withholding calculators, and FAQs. Bonus: There’s no underpayment penalty for 2025 if your miscalculation is due to the new rates.
This episode delivers exactly what every entrepreneur needs: clarity, direction, and tools to stay ahead of the changes—without the legalese. Stay sharp and compliant, Maryland business owners. July’s coming fast.