#business-exit
Exit strategies and planning for business owners preparing to sell, retire, or transition
80% of owners have most wealth tied to the business and only 20-30% of listings sell. Learn how to build outside wealth while you run the company, not just when you exit.
Learn how appraisers value small businesses using market comparables, discounted cash flow, and asset-based methods — plus how to normalize earnings and avoid the five mistakes that quietly destroy sale price.
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.
