Key Takeaways
- ✓ Asset purchases let buyers cherry-pick assets and avoid liabilities, with a stepped-up tax basis - but require individual transfer of every contract, permit, and employee
- ✓ Stock purchases transfer the entire entity (simple, fast) but saddle buyers with all liabilities - known and unknown
- ✓ Mergers combine entities by operation of law - most common for larger deals via reverse triangular merger structures
- ✓ The tax impact alone can swing the net proceeds by 15-25% - getting the structure wrong is one of the most expensive mistakes in M&A
- ✓ Section 338(h)(10) elections can give you the best of both worlds - but only if both parties agree and the entity qualifies
- ✓ Earnouts, escrow holdbacks, and working capital adjustments are structural tools that determine how risk is allocated between signing and closing
Every M&A deal starts with a question most people don't spend enough time on: how are we actually doing this?
Not the price. Not the timeline. The structure. Are you buying assets or stock? Is this a merger? What about a reverse triangular merger? Should you make a 338(h)(10) election? How does the seller get paid - all cash, seller note, earnout, rollover equity?
Most buyers and sellers treat deal structure as a technical detail - something the lawyers and accountants figure out. That's a mistake. The structure of your deal determines:
- Tax treatment - who pays capital gains vs. ordinary income, and whether you face double taxation
- Liability exposure - whether the buyer inherits every lawsuit, environmental claim, and tax obligation the seller ever had
- Contract continuity - whether key customer contracts, leases, and licenses survive the transaction
- Employee retention - whether employees transfer automatically or have to be rehired (and whether they walk away)
- Closing timeline - whether you close in 45 days or 120
- Post-closing risk allocation - how losses from undisclosed problems are handled after the deal closes
In my practice, I've seen structure choices save deals and I've seen them destroy them. I once worked on a deal where the buyer saved significant taxes by switching from an asset purchase to a stock purchase with a 338(h)(10) election - a change that took one conversation with the seller's tax advisor. I've also seen deals collapse because a seller's key customer contract had an anti-assignment clause that nobody caught until two weeks before closing, and the asset purchase structure meant that contract couldn't transfer.
This guide is the complete reference for M&A deal structure. It covers the three primary transaction types, the tax and legal mechanics of each, and the structural components - earnouts, working capital adjustments, escrow holdbacks, seller notes, reps and warranties - that determine how risk is allocated between buyer and seller. For a detailed comparison of asset and stock purchases specifically, see our asset purchase vs. stock purchase guide. If you're at the beginning of the process, our complete guide to buying a business covers all seven phases from search to close.
Structure your deal wrong and you'll pay for it in taxes, inherited liabilities, or lost contracts. Structure it right and you start day one with a clean foundation.
The Three M&A Deal Structures at a Glance
Before we go deep on each structure, here's the high-level comparison:
| Factor | Asset Purchase | Stock Purchase | Merger |
|---|---|---|---|
| What transfers | Selected assets and assumed liabilities only | Entire entity - all assets and all liabilities | Everything by operation of law |
| Buyer's tax basis | Stepped up to fair market value | Carryover (seller's old basis) | Depends on structure (tax-free vs. taxable) |
| Seller's tax treatment | Mixed (ordinary + capital gains); double tax risk for C-corps | Capital gains (single level) | Can be tax-free if structured as reorganization |
| Liability exposure | Limited to assumed liabilities | All liabilities (known and unknown) | All liabilities (surviving entity) |
| Contract transfer | Requires individual assignment + consent | Automatic (but watch change-of-control clauses) | Automatic by operation of law |
| Employee transfer | Must be rehired by buyer | Automatic - same employer | Automatic (surviving entity) |
| Typical timeline | 60-120 days | 45-90 days | 60-120+ days |
| Best for | Small-to-mid deals, distressed assets, cherry-picking | Clean companies, few shareholders, contract-dependent businesses | Larger deals, public companies, tax-free reorganizations |
Structure 1: Asset Purchase
An asset purchase is the most common structure for small and mid-market M&A deals. The buyer identifies specific assets they want - equipment, inventory, intellectual property, customer lists, contracts - and specific liabilities they're willing to assume. Everything else stays with the seller's entity. Our asset purchase agreement guide covers the key provisions of these documents in detail.
Think of it as buying the contents of a house without buying the house itself. You pick the furniture, appliances, and artwork you want. The seller keeps the mortgage, the property taxes, and the leaky roof.
Asset Purchase vs. Stock Purchase: Tax and Liability Trade-offs
The core tension between asset and stock purchases is a tax trade-off. Buyers want asset deals because of the stepped-up basis - the buyer's tax basis in the acquired assets is reset to the purchase price, not the seller's depreciated book value. This means more depreciation deductions in the years following the acquisition, which reduces taxable income. For a business with significant equipment or intangibles, this can be worth hundreds of thousands of dollars in tax savings over the first 5-7 years.
Sellers want stock deals because they avoid double taxation. For C-corporation sellers, an asset sale triggers tax at the corporate level on the gain from the asset sale, and then again at the shareholder level when the proceeds are distributed. The combined effective rate can approach 40% or more. A stock sale taxes the proceeds only once, at capital gains rates. For S-corporations, partnerships, and LLCs, the double-tax problem doesn't exist - the gain flows through to owners' personal returns in either structure - but sellers still prefer capital gains treatment over ordinary income on any portion of the proceeds. For a deeper dive on state-specific tax treatment, see our guide on Florida asset vs. stock sale tax treatment.
On the liability side, buyers favor asset deals because they leave behind the seller's historical liabilities. Pending litigation, environmental claims, tax deficiencies, and undisclosed obligations stay with the seller's entity. But this protection is not absolute. Courts have carved out successor liability exceptions - the de facto merger doctrine, mere continuation theory, and product liability rules - that can impose the seller's obligations on the buyer even in a properly structured asset deal.
Tax Advantages for Buyers
- Stepped-up basis - The buyer's tax basis in the acquired assets equals the purchase price (fair market value), not the seller's depreciated book value
- Higher depreciation deductions - That stepped-up basis means more depreciation and amortization deductions in the years following the acquisition
- Section 1060 allocation - The purchase price is allocated across asset classes (I through VII), and smart allocation can front-load tax benefits
- Goodwill amortization - Any purchase price above the fair market value of tangible assets becomes amortizable goodwill (15 years)
Liability Protection
- Cherry-pick liabilities - Only assume the liabilities explicitly listed in the purchase agreement
- Leave behind the unknown - Pending litigation, environmental claims, tax disputes, and undisclosed obligations stay with the seller
- Clean entity - The buyer operates through a new (or existing) entity without the seller's historical baggage
- Reduced diligence scope - You only need to diligence what you're buying (though you should still review what you're not)
The Problems with Asset Purchases
Asset purchases aren't free money. They come with significant operational friction:
Contract Assignment Headaches
Every contract must be individually assigned from the seller to the buyer. Many contracts contain anti-assignment clauses requiring the other party's consent. Key risks:
- Landlords can refuse to assign leases (or demand higher rent)
- Customers can use the assignment as leverage to renegotiate terms
- Government permits and licenses often can't be assigned at all
- IP licenses may have restrictions on assignment
Employee Transfer Risks
Employees don't transfer automatically. They must be terminated by the seller and rehired by the buyer. This creates:
- WARN Act exposure if 100+ employees (60 days notice required)
- Benefits gaps - employees lose seniority, PTO, retirement vesting
- Key employee flight - the transition window lets talent walk away
- Non-compete complications - seller's non-competes may not transfer
Real example:
A buyer structured a $4M acquisition as an asset purchase to avoid the seller's pending litigation. During due diligence, we discovered that the target's three largest customer contracts - representing 60% of revenue - contained anti-assignment clauses requiring written consent. One customer used the assignment request as an opportunity to reduce their annual spend by 25%. Another refused to consent entirely. The buyer ultimately renegotiated the price down and restructured two of the contracts pre-closing. Without catching this early, the buyer would have acquired a business missing a third of its revenue base.
The Seller's Double Tax Problem
For C-corporation sellers, asset sales create a double taxation event. Here's why:
| Step | What Happens | Tax Impact |
|---|---|---|
| 1. Corporate-level sale | The C-corp sells its assets to the buyer | Corporation pays corporate income tax on any gain (up to 21% federal) |
| 2. Liquidation distribution | Corporation distributes net proceeds to shareholders | Shareholders pay capital gains tax on the distribution (up to 23.8% with NIIT) |
| 3. Net result | Combined effective tax rate on the same dollars | Effective rate can approach 40%+ vs. ~24% for a stock sale |
This is why C-corp sellers push so hard for stock deals. For S-corporations, partnerships, and LLCs, the double-tax problem doesn't exist because these are pass-through entities - the gain flows directly to the owners' personal returns.
Successor Liability: The Exception That Swallows the Rule
Buyers choose asset purchases to avoid inheriting liabilities. But courts have developed exceptions that can pierce that protection:
- De facto merger doctrine - If the transaction looks, walks, and quacks like a merger (same employees, same location, seller dissolves), courts may treat it as one and impose successor liability
- Mere continuation - If the buyer is essentially a continuation of the seller (same ownership, same management, same operations), the corporate separateness doesn't hold
- Fraud exception - If the asset sale was structured specifically to defraud the seller's creditors
- Product liability - Many states impose successor liability for product liability claims regardless of deal structure
- Environmental liability - CERCLA (federal Superfund law) can impose environmental cleanup liability on current property owners regardless of how they acquired the property
The lesson: an asset purchase doesn't guarantee liability protection. How you structure the post-closing operations matters as much as how you structure the deal itself.
Structure 2: Stock Purchase
In a stock purchase, the buyer acquires the seller's ownership interests (stock in a corporation, membership interests in an LLC). The company itself doesn't change - it keeps its assets, liabilities, contracts, employees, tax ID number, everything. What changes is who owns the company. For a comprehensive look at the documents involved, see our business purchase agreement guide.
Using the house analogy: you're buying the house itself, not the contents. The mortgage, the property taxes, the leaky roof - they all come with it.
Why Stock Purchases Work
Simplicity
- No individual transfers - The entity continues to own everything it already owns. No bills of sale, no assignment agreements, no title transfers
- Contracts stay in place - The entity that signed the contracts still exists, so no consent or assignment needed (usually)
- Employees remain employed - No termination/rehire process, no WARN Act issues, no benefits gaps
- Permits and licenses - Government permits typically stay with the entity
Seller Tax Advantages
- Single level of tax - Proceeds go directly to shareholders, avoiding double taxation
- Capital gains treatment - Sale of stock is a capital transaction (lower rates than ordinary income)
- Cleaner exit - No need to dissolve the entity, liquidate, or distribute assets
- Potential QSBS exclusion - If the stock qualifies under Section 1202, sellers may exclude up to $10M or 10x basis from gain
Stock-for-Stock vs. Cash Consideration
In addition to choosing between asset and stock structures, parties must decide how the buyer pays. All-cash is the simplest: the seller receives a fixed amount at closing and exits completely. But there are several alternatives that affect how risk and reward are shared:
Stock-for-stock transactions occur when the buyer pays with its own equity rather than cash. The seller receives shares in the acquiring company instead of a cash payment. The primary advantage is tax deferral - if the transaction qualifies as a reorganization under IRC Section 368, the seller doesn't recognize gain at closing. They hold the buyer's stock with a carryover basis, and tax is deferred until they sell those shares. This structure is most common in public company acquisitions and private equity roll-ups.
The seller's risk in a stock-for-stock deal is obvious: they're betting that the buyer's stock will hold or increase in value. If the buyer's business deteriorates post-closing, the seller's consideration shrinks accordingly. This is why sellers in stock-for-stock deals often negotiate registration rights, lockup waivers, and price adjustment mechanisms to protect the value of what they receive.
Mixed consideration deals - part cash, part stock - are common in larger transactions. They give the seller immediate liquidity on the cash portion while keeping some upside in the combined entity. The allocation between cash and stock is a negotiating point that affects both parties' tax positions and the seller's post-closing exposure.
The Risks Buyers Must Manage
Stock purchases are simple, but simplicity comes at a price:
| Risk | What Can Go Wrong | How to Protect Yourself |
|---|---|---|
| Unknown liabilities | You inherit every obligation the company ever had - lawsuits, tax deficiencies, regulatory violations, environmental contamination | Thorough due diligence + comprehensive reps and warranties + indemnification with escrow |
| Change-of-control clauses | Key contracts may allow termination when ownership changes - even though the entity survives | Identify all change-of-control provisions in diligence; get consents or waivers pre-closing |
| No stepped-up basis | Buyer inherits seller's depreciated basis - lower deductions, higher future gain on resale | Consider 338(h)(10) election if entity qualifies; factor tax cost into purchase price |
| Minority shareholders | If not all shareholders agree to sell, you have a holdout problem (especially without drag-along rights) | Confirm shareholder count and drag-along provisions early; consider merger structure instead |
| Tax history | Unfiled returns, unpaid taxes, and aggressive positions all become your problem | Tax diligence + tax indemnification + escrow for known exposures |
Change-of-control traps are more common than you think:
In a recent transaction, the target had a master service agreement with its largest customer (45% of revenue). The contract contained a change-of-control clause allowing termination on 30 days' notice. The seller had never triggered it because ownership hadn't changed in 15 years. During due diligence, we flagged the clause, approached the customer before closing, and negotiated a 3-year extension commitment. Without that pre-closing conversation, the buyer would have been one certified letter away from losing nearly half their revenue.
Not Sure Which Structure Fits Your Deal?
The right structure depends on entity type, tax situation, contract portfolio, and deal size. Get it wrong, and you'll pay for it in taxes or inherited liabilities. Get it right, and you start day one in a stronger position.
Submit Transaction DetailsThe Best of Both Worlds: Section 338(h)(10) Elections
What if you could buy stock (simple transaction) but get the tax benefits of an asset purchase (stepped-up basis)? That's exactly what a Section 338(h)(10) election does.
When both buyer and seller agree to make this election, the IRS treats the stock purchase as if the target corporation sold all its assets and then liquidated. The buyer gets a stepped-up basis in the assets. The transaction mechanics remain a stock purchase - no individual asset transfers, no contract assignments, no employee terminations.
When 338(h)(10) Works
| Requirement | Details |
|---|---|
| Entity type | Target must be an S-corporation or a subsidiary of a consolidated group (not available for standalone C-corps) |
| Buyer requirement | Must be a corporation (or entity treated as corporation for tax purposes) |
| Purchase threshold | Must acquire at least 80% of the target's stock within a 12-month period |
| Joint election | Both buyer and seller must agree to the election - seller faces deemed asset sale treatment |
| Filing deadline | Election must be filed by the 15th day of the 9th month after the acquisition date (Form 8023) |
The Negotiation Dynamic
Here's where it gets interesting. The 338(h)(10) election benefits the buyer (stepped-up basis) but can hurt the seller (the deemed asset sale may allocate proceeds to ordinary income categories rather than capital gains). So sellers typically ask for a gross-up payment - the buyer pays the seller extra to compensate for the additional tax burden.
Whether this makes economic sense depends on the math: if the buyer's present value of future tax savings from stepped-up basis exceeds the gross-up payment, the election creates value for both parties. If not, stick with a straight stock purchase.
Note on timing:
Run the 338(h)(10) analysis early - before LOI if possible. I've seen deals where both sides assumed the election was obvious, only to discover during due diligence that the entity didn't qualify (because it was an LLC taxed as a partnership, not an S-corp). By that point, the purchase price had been negotiated based on stock-deal tax assumptions, and the entire economic model had to be reworked.
Structure 3: Mergers
A merger is fundamentally different from an asset or stock purchase. Instead of one party buying from another, two entities combine by operation of law - meaning the state statute governs how assets and liabilities transfer, not the parties' agreement. The surviving entity automatically holds everything the merged entity had.
Types of Mergers
| Merger Type | How It Works | When It's Used |
|---|---|---|
| Forward merger | Target merges into buyer; target disappears, buyer survives | Simple deals where buyer wants to absorb target entirely |
| Reverse merger | Buyer merges into target; buyer disappears, target survives | When target has valuable licenses, permits, or contracts that shouldn't transfer |
| Forward triangular merger | Target merges into a buyer-created subsidiary; target disappears, subsidiary survives | Buyer wants to keep target's business separate in a subsidiary |
| Reverse triangular merger | Buyer's subsidiary merges into target; subsidiary disappears, target survives as buyer's subsidiary | Most common - preserves target entity, contracts, and permits while giving buyer full control |
Forward Merger vs. Reverse Triangular Merger
The choice between a forward merger and a reverse triangular merger is one of the most common structural decisions in mid-market M&A, and it hinges on one question: do you need the target entity to survive?
In a forward merger, the target merges into the buyer (or into the buyer's subsidiary in a forward triangular structure). The target entity ceases to exist. Everything the target owned - assets, contracts, permits, employees - transfers to the surviving entity by operation of law. This works well when the target's contracts don't have anti-assignment restrictions that are triggered by entity dissolution, and when the buyer wants to fully integrate the target rather than maintain it as a separate subsidiary.
The problem with a forward merger: many contracts define "assignment" to include a merger where the contracting party disappears. If the target's key licenses, regulated permits, or major customer agreements contain this kind of language, a forward merger can trigger the same assignment consent issues as an asset purchase - with less flexibility to address them individually.
A reverse triangular merger sidesteps this problem. The buyer creates a new subsidiary (a shell company with no history, no liabilities). That subsidiary merges into the target. The target survives - the shell disappears. The target becomes a wholly-owned subsidiary of the buyer. Because the target entity continues to exist as the surviving legal entity, most contracts remain in place, most permits stay with the entity, and most anti-assignment clauses are not triggered (though change-of-control clauses still apply).
The reverse triangular merger also handles minority shareholders. Unlike a stock purchase, which requires each shareholder to individually agree to sell, a merger can force dissenting shareholders to accept the deal (subject to their statutory appraisal rights). This is why reverse triangular mergers are the default structure when the target has a complex cap table, employee stock options, or investors who may not cooperate with a voluntary stock purchase.
Why Reverse Triangular Mergers Dominate
The reverse triangular merger is the default structure for most mid-market and larger M&A transactions because it solves the biggest problems of both asset and stock purchases:
- Target entity survives - All contracts, permits, licenses, and employee relationships stay intact (like a stock purchase)
- No consent issues for most contracts - Since the target entity continues to exist, most anti-assignment clauses aren't triggered (though change-of-control clauses may still apply)
- Squeeze-out minority shareholders - Unlike a stock purchase, a merger can force dissenting shareholders to accept the deal (subject to appraisal rights)
- Tax flexibility - Can be structured as tax-free (Type A reorganization) if paid with buyer stock, or taxable if paid in cash
- Clean structure - Buyer's parent company isn't directly exposed to target's liabilities - they're housed in the subsidiary
The downside: mergers are more complex legally. They require board approvals, shareholder votes (in most cases), state filings, and compliance with statutory merger procedures. For smaller deals, this overhead isn't worth it - an asset or stock purchase is simpler.
Earnout Mechanics and Common Dispute Points
An earnout is a contingent payment structure where part of the purchase price is paid after closing, tied to the target business hitting specific performance milestones. Earnouts bridge valuation gaps - when buyer and seller disagree on what the business is worth based on projected performance, the earnout lets them share the upside if projections come true. For a comprehensive breakdown of how these agreements are drafted, see our earnout agreements guide.
The basic mechanics: the purchase price includes a fixed amount paid at closing (the "base price") and a variable amount payable over a defined period (typically 1-3 years) if certain metrics are achieved. Common metrics include revenue, EBITDA, gross profit, or specific operational targets (customer retention, project completion, regulatory approval). The earnout period, the metrics, and the payment schedule are all negotiable.
Earnouts sound straightforward, but they generate more post-closing litigation than almost any other deal element. The disputes cluster around three areas:
1. Metric Definition Disputes
What exactly counts as "revenue" for earnout purposes? Are intercompany transactions included? What about one-time items, returns, or disputed invoices? The contract defines the metric, but ambiguous definitions get litigated. If the earnout says "EBITDA," whose accounting policies apply - the seller's historical practices or the buyer's post-closing policies?
2. Buyer Conduct Disputes
The seller has a legitimate concern: what stops the buyer from running the business in a way that suppresses earnout metrics? Shifting revenue to other business units, cutting sales resources, integrating the target into a larger operation that dilutes its standalone financials, or simply neglecting the business. Sellers typically negotiate "covenants" requiring the buyer to operate the business in the ordinary course during the earnout period and to use commercially reasonable efforts to achieve the targets.
3. Accounting Method Disputes
When the buyer applies different accounting methods post-closing, earnout calculations can shift dramatically. Accelerating or deferring revenue recognition, changing expense classification, or applying different depreciation policies can all affect whether the earnout target is reached. The purchase agreement should specify which accounting standards apply to earnout calculations - ideally, the same ones the target used historically.
The best earnout provisions are simple, measurable, and tied to metrics that are easy to calculate and hard to manipulate. Revenue is better than EBITDA (which depends on expense allocation choices). Gross profit is better than net income. If the earnout metric requires the parties to make subjective judgments about costs, integration, or accounting, you're building in a future dispute.
Working Capital Adjustment at Close
A working capital adjustment is a post-closing price mechanism designed to ensure the seller delivers the business with a normalized level of working capital - the current assets (cash, receivables, inventory) minus current liabilities (payables, accrued expenses) that the business needs to operate at its current level. For a full technical breakdown of how these adjustments are calculated and disputed, see our guide on working capital adjustments at closing.
Here's the problem working capital adjustments solve: without one, a seller has an incentive to drain cash, delay paying invoices (to inflate receivables), or sell off inventory before closing. The buyer shows up to close expecting a normally functioning business and instead gets a shell with depleted working capital. A working capital adjustment punishes sellers for this behavior and rewards them for delivering above-target working capital.
The mechanics work like this: the parties agree on a "target working capital" - typically the average working capital over the prior 12 months, adjusted for seasonality. At closing, the parties calculate actual working capital. If actual exceeds the target, the purchase price increases by the difference. If actual falls short, the purchase price decreases. The adjustment is usually made against an escrow account, settled within 60-90 days after closing.
Working capital adjustments generate significant post-closing disputes in their own right, usually because the parties disagree about how to calculate specific line items (what's collectible in receivables, what's saleable in inventory, which accruals to include). The purchase agreement should define the calculation methodology in detail, including the accounting principles to apply and which items to include or exclude.
Escrow and Holdback Structures
An escrow holdback is the primary mechanism for enforcing post-closing indemnification in smaller M&A deals. At closing, a portion of the purchase price - typically 5-15% - is placed in a third-party escrow account rather than paid to the seller. The escrow remains in place for a defined period (the "survival period"), usually 12-24 months. If the buyer discovers a breach of the seller's representations after closing, they make a claim against the escrow rather than suing the seller directly.
The escrow account serves two purposes: it provides a readily accessible fund for buyer claims, and it gives the buyer negotiating leverage against a seller who might otherwise dispute small claims rather than pay them.
Holdbacks are a related concept but structured differently. A holdback is a portion of the purchase price withheld by the buyer (not placed in escrow) until specific conditions are met post-closing. Common holdback triggers include the seller completing a transition period, a key employee remaining with the business, or regulatory approvals coming through. Unlike an escrow, a holdback is controlled by the buyer - which creates risk for sellers who may not receive it if the buyer disputes whether the conditions were met.
Key terms to negotiate in any escrow or holdback arrangement:
- Amount - What percentage of the purchase price goes into escrow
- Duration - How long the escrow stays open (typically matches the survival period of the reps)
- Release schedule - Whether the escrow is released in one lump sum or in tranches over time
- Claim threshold - Whether the buyer must meet the indemnification basket before drawing on escrow
- Resolution procedure - How disputes over claims are resolved (arbitration, litigation, independent expert)
Seller Notes and Rollover Equity
All-cash at closing is not always how deals get done. Two structures - seller notes and rollover equity - give buyers flexibility in how they finance the acquisition and give sellers ongoing participation in the upside.
Seller Notes
A seller note (also called seller financing) is when the seller agrees to receive part of the purchase price over time rather than all at closing. The buyer pays a portion at close and finances the rest through a promissory note to the seller, paid over a defined period at an agreed interest rate. Seller notes are common in SBA deals (where the SBA may require a seller note as the equity injection) and in deals where the buyer has limited liquidity but the seller trusts the business's ability to service the debt.
Seller notes change the risk profile of the deal for both parties. The seller now has ongoing credit exposure to the buyer - if the business fails post-closing, the seller may not collect the balance of the note. The buyer takes on debt service obligations that reduce cash flow available for operations and growth. Sellers must negotiate carefully for protections: interest rate, payment schedule, prepayment penalties, acceleration on default, and subordination terms relative to any senior lender.
When a senior lender (bank or SBA) is also financing the deal, they typically require the seller note to be subordinated - meaning the bank gets paid first, and the seller only receives payments from the seller note after senior debt obligations are met. Some lenders require a standstill period during which the seller cannot receive any payments on the seller note if the business is in financial difficulty.
Rollover Equity
Rollover equity is a structure where the seller reinvests a portion of their sale proceeds back into the acquiring entity, retaining an ownership stake post-closing. Instead of receiving 100% cash, the seller might take 80% cash and roll 20% of their equity value into the buyer's holding company. This retained equity position keeps the seller economically aligned with the business's ongoing performance.
Private equity buyers frequently use rollover equity because it serves multiple purposes: it reduces the cash needed at close, it aligns the seller's incentives during any post-closing transition, and it signals that the seller believes in the business's future value. The seller is betting that their retained equity stake will be worth more when the PE firm eventually exits - typically 3-7 years later.
From a tax perspective, rollover equity can be structured to defer recognition of gain on the rolled portion. The seller recognizes gain only on the cash they receive at closing, not on the equity they retain. The deferred gain becomes taxable when they eventually sell their rollover equity in the buyer's entity. This structure requires careful coordination between M&A counsel and tax advisors to ensure the rollover qualifies for non-recognition treatment.
Sellers considering rollover equity should understand that they're exchanging a known value (the cash they could receive) for an illiquid interest in a private company. Negotiate for information rights, governance protections, anti-dilution provisions, and a defined path to liquidity on the retained equity stake.
Representations and Warranties Overview
Representations and warranties (reps and warranties) are statements of fact made by each party in the purchase agreement about the state of the business and the transaction at closing. They are how the seller tells the buyer: "Here is what you're getting. Everything I've told you is true. Here is what I'm promising about the condition of the business."
Seller reps typically cover: organization and authority (the seller actually owns what they're selling), financial statements (the financials are accurate), material contracts (all significant agreements are disclosed), litigation (there are no undisclosed pending claims), intellectual property (the IP belongs to the company), compliance (the business has followed applicable laws), and taxes (returns are filed, no undisclosed liabilities). For a deeper look at how indemnification flows from these representations, see our guide to indemnification provisions in M&A.
If a rep is false - if the seller represented there was no pending litigation but there was - the seller has "breached" the representation. That breach triggers the seller's indemnification obligation: they must pay the buyer for losses the buyer suffers as a result. The disclosure schedules attached to the purchase agreement serve as exceptions to reps - if the seller discloses something on a schedule, they're not "breaching" the rep by disclosing it.
Reps and warranties survive closing for a defined period (the "survival period") - typically 12-24 months for general reps, longer for fundamental reps (like ownership and authority) and tax reps. After the survival period, the seller's liability for breach generally expires.
Indemnification Caps and Baskets
Indemnification is the mechanism by which the seller compensates the buyer for losses arising from breaches of the seller's representations and warranties (and other agreed indemnifiable events). The scope of indemnification is always negotiated, and two concepts - caps and baskets - define the financial limits of that obligation.
The indemnification cap is the maximum amount the seller must pay in indemnification. It is typically expressed as a percentage of the purchase price - commonly 10-20% for general reps and warranties. This cap protects sellers from being wiped out by a buyer's aggressive indemnification claims. For fundamental reps (ownership, authority, capitalization), the cap is usually the full purchase price. For fraud, the cap is typically unlimited.
The indemnification basket is the threshold of losses the buyer must absorb before the seller's indemnification obligation kicks in. Think of it as a deductible. There are two types:
- True deductible (or threshold) - The seller only pays losses above the basket amount. If the basket is $100K and the buyer suffers $150K in losses, the seller pays $50K.
- Tipping basket (or dollar-one basket) - Once cumulative losses exceed the basket, the seller pays the full amount from dollar one. If the basket is $100K and losses reach $101K, the seller pays the full $101K, not just the $1K above the basket. Buyers prefer tipping baskets; sellers prefer true deductibles.
Basket amounts are typically 0.5-1% of the purchase price for deals under $50M. Above the basket and below the cap, the seller pays claims. Below the basket, the buyer absorbs the loss. Above the cap, the buyer absorbs the loss.
Some categories of claims - fraud, intentional misrepresentation, certain tax obligations, environmental liabilities - are often carved out from both the cap and the basket. These "special indemnities" allow claims above the cap without the basket applying.
Reps and Warranties Insurance (RWI)
Reps and Warranties Insurance (RWI) is a specialized M&A insurance product that covers losses arising from breaches of the seller's representations and warranties. Instead of relying solely on the seller's indemnification obligation backed by an escrow, the buyer purchases an RWI policy that pays claims directly - and typically provides broader coverage than the seller's negotiated indemnity would.
RWI has become standard in deals above $10M and is increasingly common in the $5-10M range. Its growth reflects the interests of both sides:
Benefits for Sellers
- Cleaner exit with less escrowed capital (or no escrow at all)
- Reduced personal indemnification exposure post-closing
- Ability to distribute proceeds to equity holders immediately at closing
- Lower negotiating friction over indemnification terms
Benefits for Buyers
- Coverage often extends beyond the survival period of the reps
- Insurer has deeper pockets than individual sellers
- Less adversarial post-closing relationship with the seller
- Higher coverage limits than typical escrow holdbacks
RWI policies typically cover losses from unknown breaches - things the seller didn't know about when they made the representations. Known issues (items on the disclosure schedules, things identified in diligence) are not covered. Exclusions also commonly include forward-looking representations, pricing or valuation matters, and certain regulatory issues.
The underwriting process for RWI mirrors due diligence: the insurer reviews the purchase agreement, disclosure schedules, and the buyer's diligence materials. The insurer may require enhanced diligence in certain areas (tax, environmental, IP) as a condition to coverage. Premiums typically run 2-4% of the coverage amount. For a deal with $20M in coverage, expect a premium of $400K-$800K.
Whether RWI makes sense depends on the deal size, the risk profile of the target, and how clean the diligence process has been. For most deals above $15M with a motivated seller who wants a clean exit, RWI is worth evaluating.
Closing Conditions and MAC/MAE Clauses
Every M&A purchase agreement includes closing conditions - the set of requirements that must be satisfied before either party is obligated to close the transaction. Standard closing conditions include: the accuracy of representations and warranties as of the closing date, compliance with pre-closing covenants, no material adverse change (MAC) in the target, receipt of required regulatory approvals, and receipt of required third-party consents.
The Material Adverse Change (MAC) or Material Adverse Effect (MAE) clause is the most heavily negotiated closing condition. It gives the buyer a right to walk away from the deal (without paying a termination fee) if the target's business suffers a material adverse change between signing and closing. But what counts as a MAC is defined and limited by the contract - and the definition is fought over intensely.
Sellers push to carve out from the MAC definition: general economic downturns, industry-wide conditions, changes in law or regulation, and pandemic-type events. Buyers push to remove those carve-outs or to add back exceptions when the target is disproportionately affected relative to peers. Delaware courts (where most M&A litigation lands) have set a very high bar for what qualifies as a MAC - there are almost no precedents of courts allowing a buyer to walk based on a MAC claim.
Closing conditions also define what happens if they aren't met. Most purchase agreements include a "drop-dead date" - if the deal hasn't closed by that date, either party can terminate. Some deals include reverse termination fees: if the buyer walks for a non-MAC reason, they pay the seller a breakup fee. These provisions are increasingly common in competitive deal environments where sellers want certainty of close.
How Deal Structure Affects SBA Financing
If SBA financing is part of the acquisition plan, deal structure is not a free choice - SBA lending requirements create strong structural constraints. Understanding these constraints before you sign the LOI will save you from having to restructure the deal mid-process. For buyers and sellers working through the broader process of selling a small business, our guide to selling a small business covers the full timeline and process.
SBA 7(a) lenders strongly prefer asset purchases for several reasons:
- In an asset purchase, the collateral is clearly defined and free of the seller's historical encumbrances
- The buyer starts with a clean entity - the lender doesn't have to underwrite the seller's historical liabilities
- SBA loan guaranty is tied to the acquired assets, which are easier to value and perfect liens against
- The seller's representations about the assets are directly aligned with what the lender is financing
Stock purchases are possible with SBA financing but create additional underwriting complexity. The lender must evaluate the entire acquired entity - including historical liabilities, pending litigation, and contingent obligations - rather than just the specific assets being financed. Many SBA lenders decline stock deals or require additional due diligence and collateral as a result.
SBA financing also affects how seller notes and earnouts can be structured. The SBA's Standard Operating Procedure (SOP) limits seller financing: seller notes are permitted but often must be on "full standby" (no payments allowed for a defined period) and the seller note equity injection requirements vary by deal size and leverage. Earnouts are permitted but the SBA requires specific terms and may count the earnout as part of the purchase price for eligibility purposes.
The equity injection requirement - typically 10% of the total project cost - must come from the buyer's own funds, not borrowed funds. If the seller is rolling over equity or providing a seller note that the SBA counts as the buyer's equity, the math gets complex. Get SBA lender involvement early in the process, before you've committed to a deal structure.
How LOIs Lock In Structure Terms
The Letter of Intent is where deal structure decisions have their most lasting consequences. Most buyers treat the LOI as a preliminary document - a starting point for negotiation. That framing is dangerous. The structure terms in the LOI - asset vs. stock, purchase price, deposit, exclusivity period - establish anchors that are very difficult to change later in the process. For a comprehensive comparison of what the LOI covers versus what the purchase agreement covers, see our guide on LOI vs. purchase agreement. For broader LOI guidance, see our LOI guides.
If the LOI says "asset purchase," you will very likely close an asset purchase. Switching to a stock purchase after LOI requires renegotiating the purchase price (because tax treatment changes for both sides), restarting lender approval (if SBA financing is involved), and redrafting the purchase agreement from a different template. The seller - who was expecting an asset deal - now faces a different tax outcome and may demand more money. You've introduced instability into the deal at its most vulnerable point.
Similarly, if the LOI doesn't address the working capital adjustment methodology or the escrow holdback amount, those gaps will be filled later under time pressure. Sellers who don't read the LOI carefully may agree to a purchase price that is actually lower than they understood when the working capital peg and escrow holdback are applied. Getting these terms right in the LOI stage - with proper M&A counsel - protects both parties from post-LOI surprises.
For buyers working with a small business acquisition attorney, the LOI review is one of the highest-leverage points in the entire deal process. It's when the structure is established, the terms are anchored, and the parties' expectations are aligned. Don't treat it as a formality.
How to Choose the Right Structure for Your Deal
There's no universal "best" structure. The right choice depends on a matrix of factors specific to your deal. Here's the decision framework I walk clients through:
Start with Entity Type
| Seller's Entity | Default Structure | Why |
|---|---|---|
| C-Corporation | Stock purchase or merger | Asset sale triggers double taxation; stock sale or merger avoids it |
| S-Corporation | Stock purchase with 338(h)(10) election | Pass-through avoids double tax; election gives buyer stepped-up basis |
| LLC (partnership-taxed) | Asset purchase (or membership interest purchase) | Pass-through entity - no double tax; membership interest sale is similar to stock sale but with different mechanics |
| Sole proprietorship | Asset purchase (only option) | No separate entity exists - you can only buy the assets |
Then Layer in Deal-Specific Factors
| If the deal has... | Lean toward... | Because... |
|---|---|---|
| Known or suspected liabilities | Asset purchase | Leave the liabilities behind |
| Non-assignable contracts or permits | Stock purchase or merger | Entity survives, contracts stay in place |
| Many shareholders (including minority) | Merger | Squeeze-out dissenters via statutory merger |
| Healthcare, defense, or regulated industry | Stock purchase or merger | Regulatory permits and licenses usually can't be assigned |
| Buyer wants tax benefits from purchase price | Asset purchase or 338(h)(10) | Stepped-up basis = more depreciation deductions |
| Distressed seller or bankruptcy | Asset purchase (363 sale) | Bankruptcy court can convey assets free and clear of liens |
| Buyer wants to pay in stock (tax-free to seller) | Merger (Type A reorganization) | Qualified reorganization defers seller's tax |
| SBA financing involved | Asset purchase | SBA lenders prefer clean asset acquisitions over entity acquisitions with legacy liabilities |
The Five Most Expensive Structure Mistakes I See
1. Defaulting to asset purchase "because it's safer"
Yes, asset purchases limit liability. But if the target is a C-corp, the seller's after-tax proceeds drop dramatically - which means they'll demand a higher purchase price to compensate. A $5M asset deal might cost the same as a $4.2M stock deal when you factor in the seller's tax gross-up. Run the math before picking the structure.
2. Ignoring anti-assignment clauses until closing
If you're doing an asset deal and the target has material contracts, you need to identify anti-assignment and change-of-control provisions during LOI diligence - not during the purchase agreement phase. Discovering that your largest customer can walk away two weeks before closing is a nightmare that's entirely preventable.
3. Assuming 338(h)(10) is available without checking
I've seen buyers negotiate purchase prices based on the tax savings from a 338(h)(10) election, only to discover in diligence that the target is an LLC taxed as a partnership - which doesn't qualify. Or that the target's S-corp election was terminated years ago. Verify entity status and election eligibility before you build it into your financial model.
4. Not modeling the Section 1060 allocation
In asset purchases, the purchase price must be allocated across seven asset classes under Section 1060. How you allocate directly affects both parties' taxes - allocating more to depreciable assets (Class V) benefits the buyer with faster deductions, while allocating to goodwill (Class VII) means 15-year amortization. Buyers and sellers have opposing interests here, and failing to negotiate the allocation in the purchase agreement leads to post-closing disputes.
5. Picking the structure without involving tax counsel
Deal structure is a joint legal-and-tax decision. I've seen M&A attorneys draft purchase agreements for a structure that their client's CPA later realized was tax-inefficient - requiring a restructure that added significant legal fees and two months to the timeline. Get your M&A attorney and tax advisor in the same room before you sign the LOI.
Quick Reference: Which Structure When?
Asset Purchase
Best when you want control
- ✓ Small-to-mid deals (<$10M)
- ✓ Known liability risks
- ✓ S-corp or LLC sellers
- ✓ Distressed acquisitions
- ✓ SBA-financed deals
- ✓ Buyer wants specific assets only
- ✗ Avoid if target has non-assignable contracts
Stock Purchase
Best when you want simplicity
- ✓ Clean target with few liabilities
- ✓ C-corp sellers (avoid double tax)
- ✓ Contract-dependent businesses
- ✓ Regulated industries (permits)
- ✓ Few shareholders
- ✗ Avoid if significant unknown liabilities
Merger
Best when you want flexibility
- ✓ Larger transactions ($10M+)
- ✓ Many or minority shareholders
- ✓ Tax-free reorganizations
- ✓ Public company targets
- ✓ Complex ownership structures
- ✗ Avoid for simple, small deals
Deal structure and business valuation are closely linked - the structure affects how the purchase price is taxed, which in turn affects the true economic cost to the buyer and the true net proceeds to the seller. Before finalizing your structure, make sure you understand how the business has been valued and what assumptions underlie the price. Our complete guide to business valuation for M&A covers the methodologies and how they interact with deal terms. And if you're evaluating whether you need M&A counsel for your transaction, our guide on what an M&A attorney does explains the five core functions and when specialized counsel is warranted.
Structure Your Deal Right the First Time
The wrong deal structure costs you in taxes, inherited liabilities, or lost contracts. I've structured transactions across every entity type and deal size - and the structure conversation is always the first one I have with clients.
Experienced M&A representation. Senior counsel on every deal. Nationwide practice.
Request Engagement AssessmentFrequently Asked Questions About M&A Deal Structures
What is the difference between an asset purchase and a stock purchase?
In an asset purchase, the buyer selects specific assets (equipment, IP, contracts, inventory) and specific liabilities to assume. The seller's legal entity stays behind. In a stock purchase, the buyer acquires the seller's ownership shares, which means the entire entity transfers - every asset, every liability, every contract, every lawsuit. Asset purchases give buyers more control over what they're buying; stock purchases are simpler but riskier because you inherit everything.
Is asset purchase or stock purchase better for the buyer?
Buyers generally prefer asset purchases because they get a stepped-up tax basis (higher depreciation deductions), they can leave unwanted liabilities behind, and they choose exactly which assets to acquire. However, stock purchases are better when the target has non-assignable contracts, government permits, or licenses that would be lost in an asset sale. The right structure depends on your specific deal - there is no universal answer.
Is asset purchase or stock purchase better for the seller?
Sellers generally prefer stock purchases because the proceeds are taxed at capital gains rates (lower than ordinary income), there is no double taxation issue for C-corporation sellers, and the transaction is simpler since the entity transfers as a whole. Asset sales can trigger double taxation for C-corp sellers - the corporation pays tax on the asset sale, then shareholders pay again when they receive the proceeds.
What is a Section 338(h)(10) election?
A Section 338(h)(10) election lets you structure a stock purchase but treat it as an asset purchase for tax purposes. The buyer gets the stepped-up basis and depreciation benefits of an asset deal, while the transaction mechanics are simpler because you're still buying stock. Both buyer and seller must agree to the election, and it only works for S-corporations and certain subsidiary acquisitions. It's one of the most powerful tools in M&A tax planning.
What is a working capital adjustment?
A working capital adjustment is a post-closing price mechanism that ensures the seller delivers the business with a normalized level of working capital (current assets minus current liabilities). The parties agree on a target working capital amount during negotiations. If actual working capital at closing is above the target, the buyer pays the seller more. If it's below the target, the seller owes the buyer the shortfall. This prevents sellers from draining cash or inventory before closing.
How does an earnout work?
An earnout is a contingent payment structure where part of the purchase price is paid after closing, tied to the business hitting specific performance targets. For example, the seller receives $500K at closing and up to $200K more if the business generates $2M in revenue in the first year post-closing. Earnouts bridge valuation gaps when buyer and seller disagree on future performance. The risk: disputes over whether targets were met and whether the buyer ran the business in a way that allowed the seller to hit the targets.
What is an indemnification basket?
An indemnification basket (also called a deductible) is the threshold of losses the buyer must absorb before the seller becomes obligated to indemnify. If the basket is $100K and the buyer suffers $75K in losses from a seller breach, the buyer gets nothing. If losses reach $150K, the buyer can recover the excess above the basket. There are two types: a true deductible (seller pays only the excess over the basket) and a tipping basket (seller pays the full amount once the threshold is crossed).
What is an escrow holdback?
An escrow holdback is a portion of the purchase price (typically 5-15%) placed in a third-party escrow account at closing to secure the seller's indemnification obligations. If the buyer discovers a breach of the seller's representations after closing, they make a claim against the escrow instead of suing the seller directly. The escrow is released to the seller at the end of the survival period if no claims are made. It's the primary mechanism for enforcing post-closing indemnification in smaller deals.
When do deals use a reverse triangular merger?
A reverse triangular merger is used when the buyer wants the operational simplicity of a stock purchase (contracts, permits, and employees stay in place) but also wants to keep the target as a separate subsidiary rather than absorbing it directly. The buyer creates a shell subsidiary, that shell merges into the target, and the target survives as a wholly-owned subsidiary. It's also used when the target has many shareholders, because a merger allows squeeze-out of dissenters - unlike a stock purchase which requires each shareholder to agree.
Does deal structure affect SBA financing?
Yes, significantly. SBA lenders strongly prefer asset purchases because the buyer gets a clean start without inherited liabilities, and the assets serve as clean collateral. Stock purchases require the lender to underwrite the entire entity including historical liabilities, which most SBA lenders avoid. The SBA 7(a) program also has specific rules about seller notes, earnouts, and equity injections that vary by deal structure. If SBA financing is on the table, structure the deal as an asset purchase from the start.
Can the LOI lock in the deal structure?
Yes, and this is often overlooked. LOIs typically specify whether the deal is an asset purchase or stock purchase, and changing the structure after LOI means renegotiating price (because tax treatment changes for both sides), redrafting the purchase agreement, and potentially restarting lender approval. The structure decision should be made before you sign the LOI - not treated as a detail to sort out during drafting. Getting it right at the LOI stage saves weeks and significant legal fees.
What is Reps and Warranties Insurance?
Reps and Warranties Insurance (RWI) is a policy that covers losses arising from breaches of the seller's representations and warranties in the purchase agreement. Instead of (or in addition to) an escrow holdback, the buyer can purchase an RWI policy that pays claims directly. This benefits sellers because they get cleaner exits with less escrowed capital and lower personal indemnification exposure. It benefits buyers because coverage often extends beyond the survival period and the insurer has deeper pockets than the individual seller.
How does seller financing change the structure?
When a seller carries a note (agrees to receive part of the purchase price over time rather than at closing), it changes the risk allocation of the deal. The seller now has ongoing exposure to the buyer's performance and creditworthiness. From a structure standpoint, seller notes are more common in asset purchases and often required in SBA deals as the seller equity injection. The note terms - interest rate, payment schedule, subordination to senior debt, and default provisions - must be negotiated alongside the purchase price.
What is rollover equity?
Rollover equity is when the seller reinvests a portion of their sale proceeds back into the acquiring entity, retaining an ownership stake in the business post-closing. Instead of receiving 100% cash, the seller might take 80% cash and roll 20% into equity in the buyer's holding company. Private equity buyers frequently structure deals this way because it aligns seller incentives post-closing and reduces the cash required at close. The seller bets that their retained equity will be worth more when the buyer eventually exits.
Related Resources
Asset Purchase vs. Stock Purchase
Deep dive on the tax and liability trade-offs between the two most common acquisition structures.
Earnout Agreements Explained
How earnouts work, how to structure them to minimize disputes, and what sellers need to watch out for.
Indemnification in M&A
Caps, baskets, survival periods, and special indemnities - how post-closing liability is allocated.
LOI vs. Purchase Agreement
What gets locked in at the LOI stage and what gets negotiated in the definitive agreement.
Working Capital Adjustments
How the working capital peg works, common disputes, and how to protect your position at closing.
How to Buy a Business
The complete acquisition guide - all 7 phases from search to close.