
Selling the Family Business to Your Children Without Handing the IRS a Second Payday
An IRS Section 453 installment sale spreads the gain across your retirement, while $19,000 annual gifts and 20-40% valuation discounts move value tax-free.
#business-exit
Exit strategies and planning for business owners preparing to sell, retire, or transition

An IRS Section 453 installment sale spreads the gain across your retirement, while $19,000 annual gifts and 20-40% valuation discounts move value tax-free.

To close a 401(k) when selling or shutting down: board resolution, full vesting, distribute within 12 months, file a final Form 5500.

US law bars non-CPAs from owning an attest practice, so every CPA-firm PE deal splits in two — and only 30–50% of the headline price is cash at close.

Section 721 defers tax on the ~20% sellers roll into a PE buyout — but junior securities, leverage, and weak minority rights can erase the second bite.

Canada cancelled the two-thirds capital gains inclusion rate on March 21, 2025, but kept the $1.25M lifetime exemption — roughly $1,275,000 indexed for 2026. Here are the QSBC tests, CCA recapture, and 45(2)/45(3) elections that decide your bill.

A life settlement payout splits into three slices — basis tax-free, gain up to cash surrender value as ordinary income, the rest as capital gain. Here is how a business reports it, plus Forms 1099-LS, 1099-SB, 8925 and Section 101(j).

A step-by-step wind-down checklist — final 1040/1065/1120 returns, final 941/940/W-2 payroll filings, state dissolution, EIN account closure, Section 1245 and 1250 recapture on asset sales, and the 3-to-7-year record retention rules.

In a stock sale the seller reports one capital gain and the buyer inherits every liability; in an asset sale the price is allocated across seven Form 8594 classes, so depreciation recapture, inventory, and C corporation double taxation convert much of the gain to ordinary income. Here is how each structure taxes the seller, what the 338(h)(10) election and personal-goodwill carve-out change, and which liabilities follow you past closing.

Under BIR Revenue Memorandum Circular No. 47-2026, issued May 19, 2026, Philippine micro taxpayers with gross sales of 3 million pesos or less can close their registration without a mandatory audit and receive a tax clearance within three working days, and non-filing penalties stop accruing once a complete BIR Form 1905 packet is submitted. This guide lists the exact documents, the manual and electronic filing channels, the five-step closure sequence, and the mistakes that still delay an exit.

Medicare's IRMAA surcharge sets your 2026 Part B and Part D premiums from your 2024 tax return, and crossing a bracket by one dollar triggers the full tier — up to roughly $14,000 a year above standard premiums for a couple. Here is how business sales, Roth conversions and RMDs trigger it, the 2026 thresholds, and how to file Form SSA-44 after retirement or another qualifying life-changing event.

A March 2026 survey of about 1,000 U.S. small business owners found 40% expect to retire within a decade while 70% have no formal succession plan. Buyers price a small business on seller's discretionary earnings times a 2x–4x multiple, discounted for owner dependency, customer concentration and unreliable books. This guide lays out a six-part, three-to-five-year plan — two target numbers, three years of clean financials, operational replaceability, risk de-concentration, a deliberate exit path (third-party sale, family succession, management buyout or ESOP), and a reverse-built timeline with a CPA and attorney — plus the three mistakes that shrink exits.

An assignment for the benefit of creditors (ABC) lets an insolvent business liquidate under state law in months rather than a year, with an assignee the owner chooses instead of a court-appointed trustee — but it carries no automatic stay and no debt discharge. Here is how the five-step process works, how it compares to Chapter 7, and the bookkeeping that keeps a wind-down orderly.