#business-exit
Business Exit
Exit strategies and planning for business owners preparing to sell, retire, or transition
The Silver Tsunami Is Here: How to Buy or Sell a Business in the $5 Trillion Great Ownership Transfer
About 6 million U.S. small and mid-sized businesses will change hands by 2035 as baby boomer owners retire, and McKinsey estimates more than 1 million of those are sellable, representing up to $5 trillion in enterprise value — yet only about 35% of owners have a succession plan. This guide covers the three-year seller timeline, how valuation multiples of 2x to 4x SDE are earned, SBA 7(a) and seller-financing structures for buyers, due diligence, and the bookkeeping habits that separate a sellable business from one that quietly closes.
How Small Businesses Are Actually Priced in 2026: SDE Multiples, Explained Before You List or Buy
Main street businesses are priced as Seller's Discretionary Earnings times a multiple — an all-sector average of 2.57x, ranging from 1.39x for dollar stores to 4.99x for car washes. Here is how SDE is calculated, which add-backs survive buyer diligence, why the multiple ladder moves, and how 2026 SBA lending rules reshape deal structure.
When the Business Is All You've Got: A Small Business Owner's Guide to Diversifying Wealth Outside the Company
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.
Business Valuation Methods Explained: What Your Company Is Really Worth Before You Sell, Raise, or Step Back
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.
The 24-Month Bookkeeping Cleanup: How Small Business Owners Get Their Books Buyer-Ready
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.
Donor-Advised Funds for Small Business Owners: Timing Charitable Giving Under the 2026 Rules
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 in Small Business M&A: How to Close a Deal With a Known Tax Risk
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 Just Eliminated Its Capital Gains Tax: What It Means for Business Owners Who Sell
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.
Letter of Intent for a Small Business Sale: What's Binding, What's Negotiable, and What Kills Deals
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.
The Deferred Sales Trust: How Business Owners Defer Capital Gains on an Exit Without a 1031 Exchange
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.
Disability Buy-Out Insurance: The Buy-Sell Agreement Gap Most Co-Owners Miss
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.
The Founder's Guide to ESOPs: Selling Your Business to Your Employees
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.