Fee-only advisors specializing in business sale and exit planning.
A business sale is the single largest liquidity event most owners experience. Structural choices (asset vs stock sale, installment sale, QSBS, rollover equity, ESOP) produce 10-40% differences in after-tax proceeds. Pre-transaction planning (entity structure, QSBS qualification, installment sale eligibility, 1202 stacking) matters more than post-tr
What our matched specialists handle
- Asset sale vs stock sale — which is right for my deal?
- QSBS — do I qualify and how much can I exclude?
- Installment sale — does it still make sense given my tax rate?
- Seller financing — should I hold a note?
- Rollover equity into PE — how do I value that?
- Post-sale: I just received $8M net after taxes, what's next?
Tools & guides
Capital Gains Tax on Selling a Business: 2026 Rates and Real Math
How much will you actually pay? Federal LTCG rates (0/15/20%), NIIT at 3.8%, depreciation recapture up to 37%, and state taxes — with a worked $10M example showing asset sale vs. stock sale side-by-side. Plus the strategies that legally reduce what you owe.
How to Reduce Taxes When Selling a Business: 7 Strategies for 2026
The structural choices made before and during a sale can mean a 10–30% difference in what you keep. Covers QSBS exclusion, deal structure, installment sale, CRT, pre-sale estate planning, ESOP, and asset allocation — and how to layer them.
Business Broker vs. M&A Advisor vs. Investment Banker: Which Do You Need?
Transaction advisors help you run a sale process — but they don't model your after-tax outcome, identify pre-sale tax planning windows, or plan what to do with the proceeds. Explains the three tiers, fee structures, how to vet each, and the planning gap that requires a separate fee-only financial advisor.
How to Choose a Financial Advisor for Business Exit Planning
The checklist for finding the right advisor — fee-only vs. commission, exit planning credentials (CFP, CEPA, CPA/PFS), and the six questions to ask before hiring. Includes the timing rule that determines whether pre-sale planning actually works: engage 2–5 years out, not after the LOI.
Opportunity Zone Investing After a Business Sale: 2026 Rules and OBBBA Changes
The OBBBA permanently overhauled QOZ — replacing the fixed December 31, 2026 deferral deadline with a rolling five-year deferral from investment date and launching new zone designations starting July 1, 2026. Explains what this means for 2026 business sellers, the 10-year appreciation exclusion, and how QOZ compares to QSBS, installment sale, and CRT.
Business Exit After-Tax Calculator
Model after-tax proceeds from different sale structures — asset vs stock sale, QSBS exclusion, installment sale.
Business Exit Planning Guide
Detailed framework — rules, tradeoffs, and common mistakes.
QSBS (Section 1202) Advisor Guide
Qualify, stack, and maximize your federal exclusion — potentially $15M+ tax-free per taxpayer. Updated for 2026 OBBBA rules.
Installment Sale Strategy Guide
When IRC § 453 deferral makes sense, the depreciation recapture trap, AFR requirements, and how QSBS interacts with seller notes.
Deferred Sales Trust (DST): Installment Deferral When the Buyer Pays Cash
A Deferred Sales Trust uses § 453 installment treatment even when the buyer pays in full at closing — the trust absorbs the cash and pays you over time. Covers the mechanics, the § 453(i) recapture trap that still applies, IRS step-transaction scrutiny, annual trust costs (1–2%/yr), and when DST beats a direct installment sale or CRT.
Asset Sale vs Stock Sale: Complete Tax Guide
The 2026 tax math, who prefers what, the §338(h)(10) hybrid, QSBS implications, and how to negotiate the structure premium.
What to Do After Selling Your Business
Tax settlement, portfolio construction, estate planning reset, Roth conversion windows, and charitable giving strategies for the first 90 days post-close.
ESOP Exit Strategy: Section 1042 Tax Deferral Guide
The only exit structure where C-corp owners can defer 100% of capital gains — potentially permanently. Deal mechanics, eligibility requirements, and how ESOPs compare to PE and strategic buyers.
PE Rollover Equity: Tax Treatment and the Second Bite Math
When PE asks you to roll 15–30% into Newco, three decisions matter: how much, which tax structure, and whether the second bite math works in your favor. Covers §351 deferral, carryover basis, QSBS interaction, and what to negotiate beyond the percentage.
Charitable Remainder Trust Before a Business Sale
Contribute appreciated stock to a tax-exempt trust before the sale, keep full pre-tax proceeds invested, receive a lifetime income stream, and take a charitable deduction. Covers IRC §664 requirements, the binding-commitment rule, CRUT vs. CRAT, and when CRT beats alternatives like DAF or installment sale.
Seller Financing: Should You Hold the Note?
When a buyer asks you to carry paper, you're trading liquidity for a higher price — and taking on real credit risk. Covers minimum terms, the subordination problem, the § 453A interest charge on large notes, and when to say no.
Earnout Agreements: Tax Treatment, Risks, and How to Negotiate
An earnout can close the deal or cost you millions in mischaracterized income. Covers the capital gains vs. ordinary income trap, IRC §453 contingent payment rules, which earnout metrics to agree to, and structural protections before you sign.
Estate Planning Before a Business Sale: GRAT, IDGT, and Gifting Strategies
Transfer business wealth to heirs before the sale closes using GRATs, IDGTs, SLATs, and direct gifting. Covers the 2026 $15M OBBBA permanent exemption, the §7520 hurdle rate, minority interest discounts, and the step-up vs. carryover basis trade-off.
Business Exit Planning Timeline: What to Do 1–5 Years Before You Sell
A year-by-year checklist: when to start QSBS qualification, when to fund a CRT, when to execute estate planning structures — and which windows close permanently at LOI. Most owners start too late; this guide maps the lead times for every major tax strategy.
Quality of Earnings Analysis: What Buyers Are Really Looking For
A QoE is not an audit — it is an analytical teardown of your EBITDA, revenue durability, and working capital. Covers how buyers normalize your earnings, what customer concentration and contract quality do to your multiple, and why running a sell-side QoE before launch can protect millions in purchase price.
Letter of Intent for Business Sale: What to Negotiate Before You Sign
The LOI is "non-binding" on paper — but the deal structure, exclusivity terms, and financial framework you agree to become the floor for the definitive agreement. Covers asset vs. stock sale at LOI stage, working capital pegs, earnout mechanics, exclusivity duration, and why getting a financial advisor before the LOI is the single most important timing decision you'll make.
Business Sale Due Diligence: What Buyers Examine and How to Prepare
After the LOI, buyers run parallel workstreams — financial, legal, tax, operational, HR — to verify your representations and find leverage. Covers what each workstream examines, how to build a data room that doesn't slow you down, common findings that reduce purchase price or kill deals, and how QSBS eligibility and asset vs. stock sale structure interact with what buyers uncover.
How to Prepare Your Business for Sale: A 3–5 Year Readiness Roadmap
The preparation that happens 2–5 years before a sale determines the multiple, the deal structure, and the after-tax proceeds. Covers financial normalization, customer concentration, owner-dependency, management depth, entity structure, QSBS qualification windows, and timing-sensitive estate planning strategies — all mapped to when each window opens and closes.
S-Corp vs C-Corp When Selling Your Business: Complete Tax Guide
Entity structure is the most overlooked pre-sale tax variable. On a $10M sale, the difference between an S-corp, a C-corp without QSBS, and a C-corp with QSBS can exceed $3M in after-tax proceeds. Covers the pass-through advantage, the §338(h)(10) election, the C-corp double-tax math, QSBS, and the built-in gains (BIG) tax trap for owners who recently converted from C to S.
Section 338(h)(10) Election: Complete Guide for Business Sellers
When a buyer asks you to elect §338(h)(10), they're asking you to let them treat the stock purchase as an asset deal for tax purposes — worth 13–15% of the purchase price in deductions to them. Here's how to calculate the structure premium you should demand, why QSBS holders should almost never agree to it, and the state conformity traps that can push your effective rate on recapture toward 50%.
Business Sale Retirement Calculator: Will Your Proceeds Last?
Model year-by-year portfolio sustainability from your after-tax proceeds. Enter your starting assets, annual spending, Social Security timing, and expected return — see whether the proceeds support your retirement through age 90+, when the portfolio might run short, and how Social Security timing affects the runway. Includes the 4% rule check and withdrawal-rate flag.
IRMAA After a Business Sale: The Medicare Premium Surcharge Nobody Warns You About
A $3M+ business sale almost always pushes MAGI into the top IRMAA tier, adding up to $13,872 per person over two years in Medicare surcharges. Explains the 2-year lookback, who is most exposed (ages 63+), and five strategies — QSBS exclusion, CRT, QOZ, installment sale, and pre-sale DAF — that can reduce the hit before closing.
Changing State Residency Before Selling Your Business: Can You Eliminate the State Tax?
A California business owner selling a $10M company owes $1.33M in state income tax. A Florida resident owes zero. Covers the domicile change requirements, California's statutory resident trap, the 546-day rule (it doesn't apply to most business owners), the asset-vs-stock-sale interaction that can void the strategy, and how far in advance you need to move.
How to Sell a Business: Step-by-Step Guide (2026)
A complete walkthrough of the M&A process from valuation through post-close — what happens in each phase, how to build the deal team, what buyers actually look for, and where the financial planning moves belong in the timeline. Hub page with links to 20+ supporting guides.
How matching works
Get matched with a specialist
Fee-only advisor with no commission conflict. Free match.
Business Exit Advisor Match is a matching service. We connect you with vetted fee-only financial advisors in our network — we don't manage money or provide advice ourselves. Advisors in our network are fiduciaries who charge transparent fees (not product commissions), and we match you based on your specific situation.