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.
Section 368 Tax-Free Reorganizations: How Type A Mergers, Type B Stock Swaps, and Type C Asset Deals Defer Tax in Strategic M&A
Section 368 defines seven reorganization types (A through G) that defer corporate and shareholder tax in M&A. This guide covers the 40% Continuity of Interest test, Type A statutory mergers, Type B stock-for-stock swaps with the 80% control requirement, Type C asset deals, and forward/reverse triangular merger structures with their consideration limits.
Section 754 Election and 743(b) Basis Adjustments: How Partnerships Step Up Inside Basis When a Partner Buys In or Dies
A Section 754 election triggers a 743(b) inside-basis step-up when a partner dies, sells, or is bought in — preventing heirs and incoming partners from paying tax twice on the same appreciation. This guide covers 743(b) and 734(b) mechanics, Section 755 allocation across asset classes, the substantial built-in loss rule, Form 15254 revocation, and when the administrative cost outweighs the benefit.
Section 83(b) Election: The 30-Day Window That Saves Founders From a Phantom Tax Bill
How the IRS Section 83(b) election converts phantom ordinary income on unvested startup stock into long-term capital gains, what the new Form 15620 online portal requires, and when filing is the wrong move.
Earnouts in M&A: Bridging the Valuation Gap Without Walking Into a Lawsuit
About one third of 2024 private-target M&A deals included an earnout, and median earnout potential rose to roughly 43% of the closing payment. This guide explains contingent purchase price structure, Section 453 installment-sale tax mechanics, the compensation-versus-purchase-price trap, and the recurring drafting mistakes behind six of the last seven major Delaware decisions favoring sellers.
Form 8594 and Section 1060: Allocating Purchase Price Across Asset Classes I–VII in a Business Sale
Buyers and sellers in an asset acquisition must each file Form 8594 under Section 1060, allocating consideration across seven asset classes using the residual method. Mismatched filings can trigger $50,000 penalties and audit cascades; a single dollar moved between Class IV inventory and Class VII goodwill can swing after-tax cash by 17 cents.
Section 1045 QSBS Rollover: How Founders Defer Capital Gains by Reinvesting Within 60 Days
Section 1045 lets non-corporate taxpayers defer capital gains from a QSBS sale by reinvesting proceeds into new qualifying small business stock within 60 days. After the 2025 OBBBA expansion (75M gross assets cap, tiered 50/75/100 percent exclusion at 3/4/5 years), the rollover can convert a missed Section 1202 exclusion into a deferred, and potentially excluded, gain.
Trader Tax Status and the Section 475(f) Mark-to-Market Election: How Active Traders Escape the Wash Sale Rule and the $3,000 Capital Loss Cap
Active traders can convert capital losses into ordinary deductions and eliminate the wash sale rule by filing a Section 475(f) mark-to-market election — but the statement must be attached to the prior year's April 15 return. A working guide to qualifying for trader tax status, the three big benefits of the election, Form 3115 mechanics, and the mistakes that invalidate it.
Form 1099-DA Arrives in 2026: A Crypto Investor's Guide to the IRS's First Digital Asset Reporting Form
U.S. digital asset brokers must issue Form 1099-DA for sales after December 31, 2024. This guide explains what each box reports, why 2025 forms cover only gross proceeds while 2026 forms add cost basis, and how to reconcile broker data with your own records on Form 8949.
Installment Sales and Form 6252: Spreading Capital Gain Across Future Years
How IRC Section 453 and Form 6252 let sellers spread capital gain on seller-financed real estate or business sales across the years payments arrive — including the gross profit percentage formula, the depreciation recapture trap, the Section 453A interest charge on installment balances above $5 million, and when to elect out.
Section 1374 Built-In Gains Tax: The Five-Year Window That Catches C-Corp to S-Corp Conversions
When a C corporation converts to an S corporation, Section 1374 imposes a 21% corporate-level tax on appreciated assets disposed of during a five-year recognition period. This guide walks through NUBIG, NRBIG, the 2026 rules, a worked example, and seven planning moves to avoid a six-figure surprise.
ESOP Section 1042 Rollover: How C-Corp Owners Can Sell to Employees and Defer (or Eliminate) Capital Gains Tax
Section 1042 of the IRC lets a C-corporation owner selling shares to an ESOP defer federal capital gains tax indefinitely — and potentially eliminate it through step-up at death. This guide covers the five qualifying conditions, what counts as Qualified Replacement Property, the floating-rate-note diversification strategy, and the trade-offs founders should weigh against a strategic sale.