For tax years beginning after December 31, 2025, IRC §165(d) allows a deduction for only 90% of wagering losses, still capped at wagering gains. A bettor who wins $120,000 and loses $118,000 clears $2,000 and gets taxed on $13,800.
Read postThe Journal
Notes on tax strategy.
Weekly writing on the planning conversations that move the needle: S-Corp elections, equity compensation, real estate, and the IRS rules behind them.
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Defer Taxes on Private Company RSUs: The Section 83(i) Election Almost Nobody Can Use.
IRC §83(i) lets a qualified employee defer federal income tax on vested private company stock for up to 5 years. The 80% employee rule and a mandatory escrow keep most plans out, and the deferral locks in the vest-date value even if the shares fall to a quarter of it.
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Suspended Passive Losses When You Sell a Rental Property: The Whole Stack Releases at Once.
A decade of Form 8582 carryforwards comes loose in a single year when you sell, but only if the sale clears three tests. Here is what §469(g) requires, the four transactions that quietly fail it, and what the freed losses are worth on a 2026 return.
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Excess Premium Tax Credit Repayment in 2026: The Cap Is Gone.
The One Big Beautiful Bill Act repealed the limits on repaying excess advance ACA subsidies for tax years beginning after 2025. A self-employed filer who guessed low now hands back every dollar instead of stopping at $1,625.
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Roth Conversion Medicare Premium Surcharge: The Bill Comes Two Years Later.
A Roth conversion is ordinary income, and Social Security counts it when it sets your Medicare Part B and Part D premiums two years later. For 2026 premiums the first joint threshold is $218,000, and crossing it by a dollar costs a married couple $2,296.80.
Read postQBI Deduction Phase-Out for High Earners: The Wider 2026 Band.
For 2026 the 20% pass-through deduction starts phasing out at $201,750 of taxable income for singles and $403,500 for joint filers, and for service businesses it hits zero at $276,750 and $553,500. The One Big Beautiful Bill widened the band, so the deduction now falls more slowly.
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Qualified Charitable Distribution Rules for 2026: The $111,000 Cap.
For 2026 the QCD limit rises to $111,000 per person. Sent straight from your IRA to a charity, it satisfies your required minimum distribution and never lands in your adjusted gross income, which a normal donation cannot do.
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100% Bonus Depreciation Returns: The January 19, 2025 Cutoff.
The One Big Beautiful Bill made 100% bonus depreciation permanent, but only for property acquired after January 19, 2025. Sign the contract a day early and you are capped at 40%. The date you committed to buy matters more than the date the asset shows up.
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The 65-Day Rule for Trust Distributions: The Section 663(b) Election.
A trust hits the top 37% bracket at just $16,000 of income in 2026, plus a 3.8% surtax. The 65-day rule lets you move that income onto a beneficiary's return at a lower rate, if you distribute in time and check the box on Form 1041.
Read postCar Loan Interest Tax Deduction: The $10,000 US-Assembly Rule.
The One Big Beautiful Bill created a deduction of up to $10,000 a year for interest on a new car loan, but only for a vehicle with final assembly in the United States. The write-off phases out above $100,000 of income and requires the VIN on your return.
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Gift Splitting Form 709: How Couples Double the 2026 Exclusion.
Gift splitting lets a married couple treat one spouse's gift as made half by each, giving one recipient two $19,000 annual exclusions in 2026. The election covers every third-party gift that year and often requires two separate Forms 709.
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Job Move Home Sale Exclusion: The 50-Mile Partial-Exclusion Rule.
A job move can unlock a partial IRC §121 exclusion before you have owned and lived in the home for two years. The clean safe harbor requires the new workplace to be at least 50 miles farther from the home, then prorates up to $250,000 per spouse.
Read postS Corp Loss Basis Limit: Why Your K-1 Loss Can Be Suspended.
The S corp loss basis limit stops at the shareholder's stock basis plus loans made directly to the corporation. A bank guarantee adds nothing until the shareholder actually pays it, and Form 7203 carries the unused loss forward.
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