#business-exit
Exit strategies and planning for business owners preparing to sell, retire, or transition
More than half of small business sales that reach a signed letter of intent still fail to close, often because the seller's books can't survive a buyer's Quality of Earnings review — a 24-month, four-phase bookkeeping cleanup is how owners get financials buyer-ready before going to market.
Starting in 2026, itemized charitable deductions only count above a 0.5%-of-AGI floor, while the new non-itemizer deduction excludes donor-advised funds. This guide shows small business owners how to respond — bunching several years of giving into one high-income year, donating appreciated stock to avoid capital gains, and using the 60%/30% AGI limits and five-year carryforward around a business sale.
Tax liability insurance transfers one specific, identified tax risk — an invalid S-corp election, a Section 382 NOL limit, QSBS eligibility — to an insurer instead of a price cut, escrow, or seller indemnity. Premiums run 2–5% of the insured limit, underwriting takes two to four weeks, and most carriers want exposure above roughly $1 million. Here's how it works and when to raise it before a closing deadline.
Missouri's HB 594, signed July 10, 2025, made it the first state to fully exempt individuals from state capital gains tax — a 100% subtraction covering stocks, real estate, crypto, and pass-through business sales, with C corporations waiting on a 4.5% rate trigger. Here's who qualifies, what's excluded, and how it changes exit timing for business owners.
Most letters of intent are labeled non-binding, but exclusivity, confidentiality, and break-up-fee clauses inside them are typically enforceable. This guide covers LOI terms in sub-$10M business sales — asset vs. stock structure, 30–90 day exclusivity windows, working capital true-ups, price allocation, and the mistakes that cost sellers deals.
A deferred sales trust lets a business owner spread capital gains tax from a sale over 10-20 years under IRC Section 453 with no like-kind reinvestment requirement, but setup and management fees commonly total $100,000-$300,000+ over a decade and the IRS has never issued formal guidance approving the structure.
A 35-year-old is six times more likely to become disabled than to die before 65, yet most buy-sell agreements only plan for death. How disability buy-out (DBO) insurance funds a co-owner buyout — elimination periods, cross-purchase vs. entity redemption, and why premiums are nondeductible but proceeds are tax-free.
How an ESOP lets founders exit on their own terms — 6,411 US ESOPs hold $2.1 trillion for 15.1 million employees. Covers Section 1042 capital gains deferral, the S-corp federal tax exemption, 2–4% deal costs, fiduciary and repurchase obligations, and which businesses actually fit the structure.
A practical walkthrough of the Section 368(a)(1)(F) reorganization — the six regulatory requirements, the six-step Rev. Rul. 2008-18 choreography, why PE buyers prefer it to a 338(h)(10) election, and how it preserves the operating EIN while giving the buyer asset-basis step-up and the seller tax-deferred rollover equity.
How the net working capital peg and post-closing true-up quietly transfer cash from sellers to buyers in mid-market M&A, and the monthly accrual-basis bookkeeping discipline that protects sale price.
A Quality of Earnings (QoE) report decides whether a buyer accepts your EBITDA or re-trades the deal price. This guide breaks down the 12 add-backs buyers accept, the 8 they reject, and how the working capital peg quietly cuts seller proceeds at closing.
Learn how a 1377(a)(2) election lets an S corp split its tax year when a shareholder leaves midyear, allocating pass-through income fairly.
