Pre-LOI stage (6 months out)
This is the planning window. We review structure, residency exposure, installment modeling, and coordinated reinvestment. Changes here can save hundreds of thousands in tax.
Selling a business
Selling a business: how much of the price you actually keep.
Two owners can sign the same headline number and walk away with materially different cash in the bank. Asset vs stock structure, goodwill allocation, installment terms, QSBS eligibility, and state residency are the levers that move the final net. This is the CPA-led view of how they fit together.
When timing matters
Exit planning only works if you have a window.
The real planning — structure, residency, asset allocation, installment terms — happens pre-LOI. Once the letter of intent is signed, the time to change the deal is mostly closed. That’s when you need someone who understands what you already agreed to.
Post-LOI stage (closing countdown)
The structure is locked. We focus on clean execution — purchase agreement tax sections, basis step-up planning, reinvestment coordination, and post-close tax positioning.
Where are you? If a sale or recap is actually on the table, the planning window is narrow. Let’s talk about timing. If you’re still exploring, the exit tax calculator shows what different scenarios cost.
The tax drivers
Six levers that move the net.
The goal isn’t a magic structure. It’s running each of these decisions honestly, together, and early enough that they still have leverage.
Asset sale vs stock sale
Asset sales usually favor the buyer; stock sales usually favor the seller. The difference can be sizable — ordinary-income recapture on assets, capital-gain treatment on equity, and who keeps which liabilities.
Asset vs stock explainerGoodwill allocation
Personal vs enterprise goodwill. The allocation line is negotiated, documented, and reported on Form 8594 — and it shows up in the tax character of the proceeds on both sides.
Goodwill in a business saleInstallment & earnouts
Deferred payments can spread gain across years and smooth the bracket. They also shift risk to the seller. Installment elections aren't automatic and aren't always the right call.
Model deal structuresQSBS (§1202)
Qualifying C-corp stock held more than five years may be eligible for a federal gain exclusion. Eligibility runs on the original acquisition — not the sale — and California doesn't always follow.
Check QSBS eligibilityCalifornia state tax
California taxes gain on a business sale at ordinary rates. Residency sourcing, pass-through entity tax elections, and the timing of any move across state lines all matter.
California business sale taxPost-close reinvestment
The day after close is when the financial plan changes, not before. Concentration becomes liquidity; cash has to meet a new schedule. The portfolio plan should exist before the wire lands.
Tax & wealth planningThe timeline
When each decision actually has leverage.
- 24–36 months out
Entity structure, QSBS qualification, basis cleanup, and residency planning. The moves with the largest leverage live here.
- 12 months out
Quality of earnings prep, deal structure analysis, and a multi-year tax model across asset vs stock scenarios.
- Pre-LOI
Allocation and structure negotiated with the buyer while leverage still exists. Installment, earnout, and rollover equity modeled.
- Close
Form 8594 allocation, 338(h)(10)/336(e) analysis if relevant, and estimated-tax coordination for the year of sale.
- Post-close
Liquidity becomes a portfolio. Distributions, charitable strategies, and the new tax baseline get built into an ongoing plan.
Run the numbers
Model your exit before you sign anything.
Exit Tax Estimator
Ballpark federal + California tax on an asset or stock sale at your expected price. See how the structure choice alone moves the final net.
Estimate my exit taxDeal Structure Simulator
See exactly what you net in an asset deal vs. a stock deal vs. an installment sale \u2014 side by side. The gap on a $3M sale is often $300K\u2013$500K.
Compare deal structuresEducational estimates only. Not tax or legal advice. Calculator assumptions.
Further reading
The topics owners dig into most.
Asset Sale vs Stock Sale
A plain-English comparison of the two structures and why buyers and sellers usually want opposite outcomes.
ReadCalifornia Tax When Selling a Business
How California sources the gain on a business sale, what residency actually requires, and where planning still moves the number.
ReadGoodwill in a Business Sale
Personal vs enterprise goodwill, why allocation matters, and how it shows up on the final tax bill.
ReadHow Much Tax Will I Pay Selling My Business?
A walkthrough of the key inputs behind the number — entity type, basis, state, and deal structure.
ReadReviews
What clients say.
“Matt is the best! Does a great job at explaining everything and answering all your questions. As a small business owner I trust Matt to handle my taxes and provide suggestions based on my business.”
Victoria G.
Small business owner · Google
“I'm a startup and it took me several months to find the right CPA. Matt is such an asset — a wealth of knowledge, passionate, straight-shooter, proactive, humble and kind-hearted. No need to look any further.”
MJ's Eatery
Startup, San Diego · Yelp
“We had to amend a few returns when a mortgage underwriter found a small error. Matt replied right away and made himself available on a Friday night to alleviate our concerns. Pay the money to have a CPA do it right the first time. Highly recommended.”
Justin A.
San Diego, CA · Yelp
Work with Matt
Ready to build a plan?
Matt Reese, CPA works with business owners preparing for a sale — pre-LOI structure, asset vs stock analysis, installment modeling, and post-close reinvestment plan.
Tax services provided through Matt Reese, CPA. This page is educational and does not constitute tax or investment advice.
Monthly tax planning reminders
One email per month — what’s due, what to do, and which tool to use. No fluff.