#family-business
Family Business
Guidance for family-owned businesses on governance, succession, and managing family dynamics
The $15 Million Estate Tax Exemption: What OBBBA Means for Business Succession Planning
The One Big Beautiful Bill Act permanently raised the federal estate and gift tax exemption to $15 million per person ($30 million per couple) starting in 2026, eliminating the scheduled TCJA sunset to roughly $7 million. Here's what changed, which existing plans are now outdated, and the succession moves business owners should make — from portability filings to buy-sell agreement reviews and state estate tax exposure.
Lewis v. Commissioner: What a $53 Million QTIP Trust Dispute Teaches About Defensible Valuations
In Lewis v. Commissioner, the Tax Court valued remainder interests surrendered when a $117.6 million QTIP trust terminated early — the IRS said $53.4 million per child, the taxpayers said $156,000, and the court's four rulings on state law, powers of appointment, net-gift math, and actuarial tables landed at $35.1 million.
When a Deficit Restoration Obligation Isn't One: What CCA 202628009 Means for Partnership Loss and Liability Allocations
IRS Chief Counsel Advice CCA 202628009 (July 10, 2026) held that a demand-based deficit restoration obligation enforceable only by withholding future distributions is not unconditional, failing both the §1.704-1(b) economic-effect safe harbor and the §1.752-2(b) recourse-liability test — a fact pattern common in family LP boilerplate that can reallocate recourse debt and suspend previously deducted losses.
When Capital Gain Becomes Ordinary Income: Section 1239 and the Family Business Trap
Section 1239 converts capital gain to ordinary income on sales of depreciable property between related parties — including a controlling owner and their own corporation, partnership, or trust. The constructive ownership rules under Section 267(c) make the more-than-50% threshold easier to cross than family business owners expect.
Section 267 Explained: Related-Party Loss Disallowance and the Matching Rule
Section 267 disallows losses on sales between related parties and defers deductions on accrued payments to related cash-basis payees. A practical guide to who counts as related, how constructive ownership works, the 267(d) gain offset, the 2.5-month payment safe harbor, and the bookkeeping habits that keep family businesses and partnerships audit-ready.
Section 414 Controlled Group and Affiliated Service Group Rules: How Multiple Businesses Can Sabotage Your 401(k)
Section 414(b), (c), and (m) treat related businesses as one employer for retirement-plan testing. This guide explains controlled-group and affiliated-service-group rules, the spousal and minor-child attribution traps, and the steps multi-business owners should take before opening a 401(k).
Schedule B-1 of Form 1065: Disclosing 50% Owners in Tiered Partnerships, Family LLCs, and Private Equity Funds
Schedule B-1 of Form 1065 uses Section 267(c) attribution — not Section 318 — to identify partners who own 50% or more of profit, loss, or capital. A practical guide for tiered partnerships, family holding LLCs, and private equity fund structures.
Section 2032A Special-Use Valuation: Cut Up to $1.46 Million Off the Estate Value of a Family Farm or Closely Held Business in 2026
Section 2032A lets executors value qualifying farm or closely held business real property at productive use rather than fair market value, with a 2026 reduction cap of $1,460,000 — worth up to $584,000 in federal estate tax at the 40% rate. The election is irrevocable, requires material participation, and triggers a 10-year recapture period.
Section 302 Stock Redemptions: Sale vs. Dividend Treatment in Closely-Held C Corporations
A practical guide to Section 302 stock redemptions in closely-held C corporations — when a buyback gets capital gain treatment versus dividend treatment, how Section 318 family attribution disqualifies most family redemptions, and how the four 302(b) tests plus the 302(c)(2) waiver preserve sale treatment.
ESBT vs QSST: Choosing the Right Trust to Hold S-Corporation Stock
A side-by-side comparison of Electing Small Business Trusts (ESBT) and Qualified Subchapter S Trusts (QSST) under Section 1361, including who pays the tax, the 2-month-and-16-day election window, and a worked example showing a $118,000 annual tax swing between the two structures on $1M of K-1 income.
ESBT vs QSST: How Trusts Can Hold S-Corporation Stock Without Killing the S Election
A trust holding S-corporation stock must qualify as a QSST or ESBT under Section 1361 or the S election terminates retroactively. A QSST taxes pass-through income at the single beneficiary's personal rate; an ESBT permits multiple beneficiaries but traps S-portion income at the 37% top trust rate. The election deadline is two months and sixteen days from the triggering event.
Family Limited Partnership Valuation Discounts in 2026: How Wealthy Families Quietly Shave 25–40% Off Estate and Gift Tax Bills
A practical 2026 guide to Family Limited Partnership valuation discounts — how high-net-worth families combine 10–25% lack-of-control and 20–35% lack-of-marketability discounts to cut estate and gift tax exposure, with worked numerical examples, the IRC Section 2036 traps that have collapsed estates in Tax Court, setup costs, and the bookkeeping required to defend the structure on audit.