22 tagged with "Business Exit"
Exit strategies and planning for business owners preparing to sell, retire, or transition
Personal Goodwill in M&A Asset Sales: How Martin Ice Cream and Norwalk Help Owners Avoid Double Taxation
Personal goodwill, anchored in the Martin Ice Cream and Norwalk Tax Court decisions, lets closely held C corporation owners shift a portion of an asset-sale price out of the corporate tax layer and onto the shareholder as long-term capital gain. This guide explains the doctrine, when it works, the documentation that survives an IRS audit, and the mistakes that have sunk allocations.
Section 280G Golden Parachute Payments: The 3× Trigger, 20% Excise Tax, and the Private Company Cleansing Vote
Section 280G disallows the corporate deduction and imposes a 20% Section 4999 excise tax once parachute payments to a disqualified individual reach three times the executive's five-year average W-2 compensation, with the penalty applying to everything above 1× the base amount. Private companies can eliminate the consequences entirely through a 75% disinterested shareholder vote paired with conditional waivers signed before closing.
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.
Valuing a Closely-Held Business: Asset, Income, and Market Approaches for Exits, Buyouts, and Estate Transfers
Three valuation approaches — asset, income, and market — can produce 50% differences in indicated value for the same closely-held business. This guide explains when each fits, how DLOM and DLOC discounts apply, and what records owners need before a sale, partner buyout, or estate transfer.
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.
Asset Sale vs Stock Sale: How M&A Deal Structure Decides Who Pays the Tax
An asset sale vs stock sale changes who pays tax, who carries liability, and how a deal closes. Compare 2026 tax math, successor liability doctrines, and the S-corp hybrid structures — Section 338(h)(10) and F-reorganizations — that now dominate mid-market deals.
Business Succession Planning: A Complete Guide for Small Business Owners
Learn how to create a business succession plan that protects your legacy. Covers the five main succession options, buy-sell agreements, business valuation, tax planning, and a step-by-step timeline for small business owners.
Estate Planning for Small Business Owners: Protect Your Legacy and Your Business
A complete guide to estate planning for small business owners. Covers trusts, buy-sell agreements, the 2026 estate tax exemption changes, tax-smart transfer strategies, succession planning, and a practical estate planning checklist.