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Mike Thrift

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ISO AMT in 2026: Bargain Element, Form 6251 Line 2i, and the OBBBA Phase-Out Cliff
·mike

ISO AMT in 2026: Bargain Element, Form 6251 Line 2i, and the OBBBA Phase-Out Cliff

Under OBBBA, the 2026 AMT exemption phases out at $500K single / $1M joint with a 50-cent rate, doubling the stealth bracket on ISO exercises. Here is exactly how the bargain element flows into Form 6251 line 2i, when a same-year disqualifying disposition eliminates the AMT adjustment, and how to plan exercises to avoid a six-figure phantom-income tax bill.

equity-instruments
tax-planning
stock-basis
OFAC Sanctions Compliance for Small Businesses: SDN Screening, the 50% Rule, and Voluntary Self-Disclosure
·mike

OFAC Sanctions Compliance for Small Businesses: SDN Screening, the 50% Rule, and Voluntary Self-Disclosure

OFAC enforcement now targets fintech, crypto, real estate, and small e-commerce firms with civil penalties up to $377,700 per violation. A practical guide to SDN list screening, the 50 percent ownership rule, voluntary self-disclosure under the 2026 portal, and the five-pillar compliance program Treasury expects from any company touching cross-border money.

compliance
small-business
legal
PCI DSS 4.0.1 in 2026: The Small Merchant's Guide to SAQ A, Script Tampering, and MFA
·mike

PCI DSS 4.0.1 in 2026: The Small Merchant's Guide to SAQ A, Script Tampering, and MFA

PCI DSS v4.0.1 governs every 2026 assessment, and FAQ 1588 has narrowed who qualifies for SAQ A. This guide walks small merchants through the new script-tampering rules (6.4.3 and 11.6.1), the 12-character password and MFA requirements, what non-compliance actually costs, and a 12-step checklist for getting it right.

compliance
security
payments
Qualified Charitable Distributions in 2026: A $111,000 Tax-Free Path From IRA to Charity
·mike

Qualified Charitable Distributions in 2026: A $111,000 Tax-Free Path From IRA to Charity

A complete 2026 guide to Qualified Charitable Distributions — the IRS-sanctioned strategy that lets retirees age 70½ and older route up to $111,000 from an IRA directly to a qualified charity without recognizing the distribution as taxable income.

charitable-giving
ira
tax-planning
S-Corp Basis, Form 7203, and the Phantom Distribution Trap: A Section 1366(d) Guide
·mike

S-Corp Basis, Form 7203, and the Phantom Distribution Trap: A Section 1366(d) Guide

Section 1366(d) caps S-corporation loss deductions at stock basis plus direct shareholder debt, and Form 7203 is how the IRS verifies the math. A working guide to suspended losses, phantom capital gains on distributions, the $25,000 open-account debt rule, why personal guarantees do not create basis, and how the Regulation 1.1367-1 ordering rules decide which losses survive each year.

s-corp
s-corporation
stock-basis
Schedules K-2 and K-3: The Domestic Filing Exception, the 1-Month Rule, and the $250,000 Small-Entity Carve-Out for 2026
·mike

Schedules K-2 and K-3: The Domestic Filing Exception, the 1-Month Rule, and the $250,000 Small-Entity Carve-Out for 2026

How U.S. partnerships and S corporations qualify for the Schedule K-2/K-3 domestic filing exception, manage the 1-month-date partner request rule, and use the new small-entity exception for entities with under $250,000 in total receipts.

partnerships
s-corporation
international-tax
Section 1061 Carried Interest Three-Year Holding Period: How Hedge, PE, and VC Fund Managers Lose Long-Term Capital Gains Without It
·mike

Section 1061 Carried Interest Three-Year Holding Period: How Hedge, PE, and VC Fund Managers Lose Long-Term Capital Gains Without It

Section 1061 recharacterizes carried interest gains from long-term to short-term unless the underlying asset was held more than three years — a 17-point federal rate swing for hedge, PE, and VC fund managers. A practitioner guide to applicable partnership interests, Worksheet A and B reporting, the capital interest exception, and 2026 planning moves.

tax
tax-planning
tax-compliance
Section 1212 Capital Loss Carryover: The $3,000 Annual Cap, Indefinite Carryforward, and Why Character Survives Across Tax Years
·mike

Section 1212 Capital Loss Carryover: The $3,000 Annual Cap, Indefinite Carryforward, and Why Character Survives Across Tax Years

A practical guide to IRS Section 1212 for individual investors: the $3,000 annual ordinary-income cap, indefinite carryforward, short-term vs. long-term character preservation, the Schedule D ordering rules, and how wash sales interact with carryovers.

tax
tax-planning
capital-gains
Section 1244 Small Business Stock: How Founders Convert a Failed Startup Into a $50,000 Ordinary Loss
·mike

Section 1244 Small Business Stock: How Founders Convert a Failed Startup Into a $50,000 Ordinary Loss

Section 1244 lets eligible founders and early investors convert up to $50,000 ($100,000 joint) of capital loss on failed C-corporation stock into ordinary loss deductible against W-2 wages, freelance income, or interest. This guide covers who qualifies, the $1 million capital ceiling, Form 4797 reporting, and the formation steps that keep the deduction defensible.

tax
tax-deductions
tax-planning
Section 1245 vs. Section 1250: How Depreciation Recapture Erodes Your Bonus Depreciation Benefits
·mike

Section 1245 vs. Section 1250: How Depreciation Recapture Erodes Your Bonus Depreciation Benefits

When you sell depreciated business property, Section 1245 recaptures prior depreciation as ordinary income (up to 37%), while Section 1250 caps the recapture on real estate at 25% — turning a 100% bonus depreciation deduction into a large tax bill at exit unless you plan with cost segregation, 1031 exchanges, and a clean fixed-asset register.

depreciation
bonus-depreciation
cost-segregation
Section 1259 Constructive Sales: How Hedging Appreciated Stock Can Trigger a Phantom Tax Bill
·mike

Section 1259 Constructive Sales: How Hedging Appreciated Stock Can Trigger a Phantom Tax Bill

Section 1259 treats short-against-the-box trades, equity swaps, and tight collars on appreciated stock as constructive sales — taxable today, even with no proceeds. Covers the variable prepaid forward workaround, the 30-day closing exception, and the related-party trap.

tax-planning
capital-gains
equity-instruments
The Self-Employed Health Insurance Deduction: How Section 162(l) Beats Itemizing
·mike

The Self-Employed Health Insurance Deduction: How Section 162(l) Beats Itemizing

Section 162(l) lets sole proprietors, partners, and more-than-2% S-corp shareholders deduct health, dental, vision, LTC, and Medicare premiums above the line on Schedule 1, line 17 — bypassing the 7.5%-of-AGI floor that gates itemized medical deductions. Form 7206 enforces three limits — earned income, subsidized-coverage months, and PTC coordination — and S-corp owners must include premiums in W-2 Box 1 (not Box 3 or 5) to preserve the deduction.

tax-deductions
self-employment
health-insurance
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