Transactional Tax Counsel
Selling Your Business Is a Tax Event Before It Is Anything Else
Counsel from an attorney who has sat on the other side of the table from private equity. I negotiate the structure, terms, and tax treatment of your sale so the price you accept is actually the money you take home.
Why I Started This Practice
I have watched family businesses get sold for far less than they were worth because the owner trusted the buyer's lawyer to be fair. Earn-outs designed to fail. Working-capital clawbacks that quietly recovered a quarter of the headline price. Indemnification provisions that let the buyer come back two years later with claims that the seller never saw coming.
Private equity firms are buying small businesses faster than at any point in the past decade. They walk into negotiations with full-time M&A attorneys, deal accountants, and a playbook refined across hundreds of acquisitions. Most family business owners walk in with a generalist attorney and the instinct that the buyer is being fair.
You deserve someone who knows the playbook. That's why this practice exists.
The Buyer's Playbook (and How I Counter It)
Five tactics I see in nearly every small business sale I work on, and what I do about each one.
Earn-outs that quietly transfer the upside
Earn-outs are pitched as fair, performance-based pay. In practice they let the buyer rewrite definitions, miss targets on purpose, or sell the business again before the earn-out vests. Owners walk away with a fraction of the headline number. I negotiate the earn-out language line by line, including who controls the books that determine whether targets are met.
Working capital adjustments designed to claw back
Almost every term sheet includes a working-capital target. The buyer's accountants get to define it, recompute it after closing, and demand a refund if the actual number falls short. Without a fair-value methodology specified up front, this is one of the most common ways money disappears between the LOI and the wire.
Deal structure that maximizes their tax benefit at your expense
Asset sales versus stock sales, allocations to goodwill versus equipment, and treatment of personal goodwill all sit in the deal documents. The buyer's lawyer drafts those allocations to minimize the buyer's future tax bill. The same allocations often increase the seller's tax bill. I model the after-tax outcome under each structure before the LOI is signed.
Indemnification baskets and caps that survive years
After closing, the buyer can come back with claims for breaches of representations. The basket, cap, and survival period determine how much of your sale proceeds you actually get to keep. Defaults favor the buyer. I rewrite them.
Non-competes that limit your next chapter
Buyers ask for broad geographic and industry non-competes that often have nothing to do with the business they're buying. I narrow them to what's actually defensible.
Who I Work With
- ✓An owner of a Michigan or U.S. small business considering a sale in the next 6-24 months
- ✓A family business owner being approached by private equity, search funds, or strategic buyers
- ✓A business owner who has received an LOI and wants a tax-aware second opinion before signing
- ✓An owner who plans to sell to a partner, employee group, or family member and wants the right structure for that transition
- ✓An owner exploring an ESOP, cross-purchase agreement, or other internal succession path
Outside my legal practice
My role is the legal and tax side of the sale: deal structure, the purchase agreement, and negotiating terms. I do not appraise or value your business, market it, or find buyers, and I do not act as your financial planner for the proceeds. For those pieces I can refer you to a licensed business appraiser, broker, or financial advisor.
How I Engage
Free 30-minute strategy session
Tell me where you are. I will tell you what your real options look like, including the tax implications of the path you are leaning toward. No retainer required to have this conversation.
Pre-LOI tax modeling
Before you respond to a buyer, I run after-tax outcome modeling under different deal structures (asset sale, stock sale, F-reorg, installment) so you know what the headline price actually nets you.
LOI and term sheet review
Most owners sign LOIs without realizing how many later-stage outcomes are decided in those documents. I negotiate the LOI before you commit to exclusivity.
Definitive agreement negotiation
Side-by-side with your other advisors, I negotiate the purchase agreement, escrow, indemnification, working-capital, earn-out, and tax representation provisions.
Closing and post-closing support
Closing is not the end. I coordinate the tax filings that follow the sale and stay engaged for the indemnification and earn-out windows.
Frequently Asked Questions
Why hire a tax attorney to sell my business when I already have a broker?
Your broker's job is to find a buyer and close the deal. Their economic interest is the closing fee. The tax attorney's job is to make sure the deal you close is the deal you actually walk away with after the IRS and the buyer's lawyers are done with it. Brokers, accountants, and attorneys each play a different role. Most owners discover too late that no one was specifically watching the after-tax math and the post-closing exposure.
What does it cost to engage you for a sale?
The free strategy session is no obligation. After that I typically work on a flat-fee or hourly basis, depending on the complexity of the transaction. For most small business sales, the total legal and tax counsel fee is a small fraction of the savings or recoveries I negotiate into the deal.
Are you really anti-private-equity? What if a private equity buyer is the best option for me?
No. Private equity buyers can be the right buyer. The problem is not the buyer category, it's the asymmetry. PE firms walk in with full-time M&A lawyers, accountants, and a playbook refined across hundreds of acquisitions. Most family business owners walk in with a generalist attorney and an instinct that the buyer is being fair. I level that playing field. If a PE buyer is the right fit for your situation, I will help you negotiate with them effectively.
I'm planning to sell to a family member. Do I still need this?
Yes. Internal sales have their own tax pitfalls, especially around valuation, installment notes, and gift-tax exposure. The IRS scrutinizes related-party transactions more closely than arm's-length sales. Getting the structure right protects both sides of the family.
What if I'm not selling for a few more years?
That's the best time to talk to me. The decisions that determine how much of the sale price you keep, capital gains versus ordinary income treatment, eligibility for QSBS, entity structure, and basis planning, are made years before the deal. The owners with the best outcomes started planning the exit five to ten years out.
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