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Tax Strategy

Exit Planning & Corporate Transactions
Sell Smart. Keep More.

We’ve structured over 150 multimillion-dollar corporate transactions. When you sell your business, the tax structure of the deal determines how much you actually keep.
Sam BrotmanSam Brotman, J.D., LL.M.
Last updated July 2026

Key Takeaway

The difference between a well-planned business exit and an unplanned one is often 15-20% of the total sale price. Tax structuring — installment sales, entity conversion, QSBS — must begin years before the transaction.

The Wrong Deal Structure Can Cost You Millions in Taxes.

You’ve spent years building your business. When it’s time to sell, the difference between a well-structured deal and a poorly structured one can be millions of dollars in taxes. Asset sale vs. stock sale, installment terms, earnout provisions, QSBS exclusions, and entity restructuring — each decision has massive tax consequences.
Most business brokers and M&A attorneys focus on the headline purchase price. They don’t always optimize for after-tax proceeds. That’s where we come in. We work alongside your deal team to structure the transaction for maximum tax efficiency from day one.
Whether you’re selling outright, merging, bringing in partners, or restructuring ownership, we ensure the tax tail doesn’t wag the deal dog.

From Our Practice

We’ve guided business owners through exits ranging from $2M to $50M+, structuring each transaction to minimize capital gains, optimize installment sale treatment, and preserve wealth across generations. The difference between a well-planned exit and an unplanned one is often 15-20% of the total sale price.

Talk to a Tax Attorney

Free 15-minute call. No obligation. We'll tell you exactly where you stand.

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(619) 378-3138

What We Handle

Transaction Tax Services

Business Sale Structuring

Asset sale vs. stock sale analysis, purchase price allocation, installment sale planning, and earnout structuring to minimize tax on the sale.

QSBS Tax Exclusion

Section 1202 Qualified Small Business Stock can exclude up to $10M+ in capital gains from federal tax. We identify and preserve QSBS eligibility before the sale.

Mergers & Acquisitions

Tax-free reorganizations, Section 368 mergers, and partnership mergers that allow business combinations without triggering current taxation.

Entity Restructuring

Pre-sale entity conversions, holding company formation, and ownership restructuring to optimize the tax treatment of transaction proceeds.

Installment Sales

Spreading gain recognition over multiple years to reduce the effective tax rate and manage bracket impact from a large sale.

Post-Transaction Planning

After the sale, we help you invest, structure, and plan for the proceeds — including estate planning, charitable strategies, and reinvestment optimization.

How It Works

Exit Planning: What You Need to Know

When should I start exit planning?
Ideally, 2-5 years before you plan to sell. Many of the most powerful tax strategies — QSBS qualification, entity restructuring, installment sale planning — require advance setup. If you wait until you have a buyer, many options are no longer available.
That said, even if you’re already in negotiations, there are strategies we can implement quickly to improve your tax outcome.
Section 1202 allows founders and early investors in Qualified Small Business Stock to exclude up to $10 million (or 10x their basis) in capital gains from federal tax. For a founding team of two, that’s potentially $20 million+ in tax-free gains.
QSBS has specific requirements: the company must be a C-Corp, under $50M in gross assets at issuance, and engaged in a qualifying active business. The stock must be held for more than 5 years. We verify eligibility and help structure transactions to maximize the exclusion.
Buyers prefer asset sales (they get a stepped-up basis). Sellers prefer stock sales (capital gains treatment). The optimal structure depends on entity type, asset composition, and negotiating leverage. In many cases, creative structures can give both parties what they want.
We model both scenarios and help negotiate deal terms that minimize your tax burden while keeping the transaction attractive to the buyer.
By spreading the gain recognition over multiple years, you can keep more income in lower tax brackets. For a business owner selling for $5M, the difference between recognizing all gain in one year vs. over five years can be hundreds of thousands in tax savings.
Installment sales also provide cash flow flexibility and can be combined with other strategies like opportunity zone investments for additional tax deferral.

Talk to a Tax Attorney

Not Sure Where You Stand?

Schedule a free 15-minute call. We’ll assess your situation, outline your options, and tell you exactly what to expect — no obligation.
Book Your Free Call

or call (619) 378-3138

Why Brotman Law

150+ Transactions. Millions in Tax Savings.

150+ Deals Closed

We've structured over 150 multimillion-dollar transactions. This isn't theoretical knowledge — it's battle-tested experience.

Attorney-Led Strategy

We're attorneys, not accountants. We can implement strategies that require legal restructuring, entity formation, and transactional documentation.

Pre-Sale Planning

The biggest savings come from planning years ahead. We start early to maximize your options.

QSBS Specialists

We've helped founders secure tens of millions in tax-free gains through proper QSBS structuring and preservation.

Deal Team Integration

We work alongside your M&A attorney, business broker, and CPA as the tax specialist on your deal team.

Both Sides Experience

We've worked on both buy-side and sell-side transactions, giving us insight into what the other side wants.

Learn More

Exit Planning Guides & Resources

Free Guide

Tax Strategies

Browse our library of tax strategies for business owners and investors.

  • Read the Guide

Free Guide

Business Tax Optimization

Optimize your business tax position before — and after — the sale.

  • Read the Guide

Free Guide

Real Estate Tax Strategy

Selling property as part of your exit? Learn about real estate tax optimization.

  • Read the Guide

Free Guide

Read our Multistate Tax Guide

A comprehensive, attorney-written resource covering everything you need to know about this topic.
Related services: Individual Tax Optimization • Residency & Multi-State Tax • Exit Planning

Also consider: IRS Audits • Criminal Tax Defense

Frequently Asked Questions

Exit Planning FAQs

How much tax will I owe when I sell my business?
It depends on the deal structure, your entity type, your basis, and how the proceeds are allocated. Federal capital gains rates top out at 20%, plus 3.8% NIIT and state taxes. We model exact tax liability for each potential deal structure.
C-Corps with QSBS-eligible stock can achieve tax-free treatment on significant gains. S-Corps provide single-level taxation. LLCs offer flexibility. The best entity depends on your specific situation, and restructuring before the sale may improve your outcome.
Yes — through installment sales, opportunity zone investments, and other deferral strategies. In some cases, you can combine QSBS exclusion with installment treatment to eliminate or defer the majority of your tax liability.
2-5 years is ideal. QSBS requires 5-year holding periods. Entity restructuring needs time to settle. Even one year of advance planning can significantly improve your tax outcome compared to structuring the deal at the last minute.
Yes. We serve as the tax strategist on your deal team, working alongside your M&A counsel, business broker, and CPA. We don’t replace them — we add the tax optimization layer that’s often missing from deal negotiations.
Real estate sales within a business transaction require careful allocation and structuring. We coordinate the sale of real estate assets with the overall business transaction to optimize the tax treatment of each component.

As Featured In & Recognized By

Forbes Business Council

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