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 Brotman, J.D., LL.M.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.
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.
What is QSBS and how does it work?
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.
Asset sale vs. stock sale: which is better?
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.
How do installment sales reduce taxes?
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 Callor 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
Tax Strategies
Browse our library of tax strategies for business owners and investors.
Read the Guide → Free GuideBusiness Tax Optimization
Optimize your business tax position before — and after — the sale.
Read the Guide → Free GuideReal Estate Tax Strategy
Selling property as part of your exit? Learn about real estate tax optimization.
Read the Guide →
