One of the first structural questions in any M&A transaction is whether the deal will be an asset sale or an equity sale. While the distinction can feel abstract — in both cases, the business is being sold — in practice, this choice affects taxes, complexity, risk allocation, and even whether the deal can close smoothly.

More importantly, structure shapes how risk shows up in a deal, not just who bears it.

This post explains the practical differences between asset sales and equity sales, including how structure affects taxes, risk allocation, diligence, and whether a deal can realistically close.

What Is an Asset Sale?

In an asset sale, the buyer purchases specific assets and assumes specific liabilities of the business. Everything not expressly included stays with the seller.

Commonly transferred assets include:

• customer contracts
• equipment and inventory
• intellectual property
• goodwill
• certain employees
• Liabilities are assumed only if the buyer agrees to take them.

A Critical Reality About Asset Deals: Liability Doesn’t Disappear

Asset sales are often described as “safer” for buyers — but that safety is frequently overstated.
When a buyer acquires substantially all of a business’s operations and continues it as a going concern, successor liability risks can still apply, regardless of structure. Certain liabilities (including employment, tax, environmental, and product-related claims) can follow the business based on substance rather than form.
Asset deals reduce risk, but they do not eliminate it. Buyers still need contractual protections, diligence, and insurance — and sellers should not assume asset structure alone resolves liability concerns.

What Is an Equity Sale?
In an equity sale, the buyer purchases the ownership interests of the entity itself (stock in a corporation or membership interests in an LLC).

That means:

• all assets stay with the entity
• all liabilities stay with the entity
• contracts usually continue automatically
• ownership changes, but the business remains intact

From an operational perspective, equity sales are often simpler.

Why Structure Is Not Just a Negotiation Issue
It’s common to hear that buyers prefer asset deals and sellers prefer equity deals — and often that’s true. But in practice, structure is not always a matter of leverage or preference.

In many transactions:

• an equity sale is the only practical way to preserve licenses, permits, or regulatory approvals
• an asset sale would require dozens of third-party consents and assignments
• fragmented ownership or tax elections make one structure clearly superior
• attempting the “wrong” structure creates friction that threatens the deal

In other words, some businesses are simply better sold one way than the other — and sometimes there is no realistic alternative.

How Structure Affects Timing and Deal Risk

Structure also affects how difficult the deal is to execute.

Asset deals often:

• require asset-by-asset diligence
• trigger more third-party consents
• involve complex transfer mechanics
• extend timelines
• Equity deals often:
• simplify transfer mechanics
• reduce consent risk
• but concentrate diligence on historical liabilities

These differences matter in small and mid-market transactions, where momentum and management bandwidth are often decisive.

So Which Structure Wins?

Neither structure is inherently better. The “right” structure depends on:

• the business
• the tax profile
• regulatory constraints
• diligence realities
• and how the deal needs to close

Price often adjusts to reflect these realities — but structure frequently determines whether the deal works at all.

Why This Matters

Structure is not a technicality, and it’s not just a negotiating position. It’s a strategic decision that shapes risk, complexity, and closing certainty from the outset.

Understanding the implications early — before structure hardens and price adjusts — is one of the most important advantages experienced counsel can provide.

Indemnification provisions define who bears the financial risk when issues arise after a business is sold.

They don’t change the headline price, but they often determine how much money remains at risk after closing — and for how long.

This post explains how indemnification works in business sales, including caps, baskets, and escrows, and how these terms determine a seller’s real post-closing exposure.

What Is Indemnification?

Indemnification is the seller’s obligation to compensate the buyer for losses caused by breaches of representations and warranties, or certain specified liabilities.

In plain terms:
If something you promised turns out not to be true, indemnification determines whether — and how much — you might have to pay back.

What Is an Indemnification Cap?

The cap is the maximum amount the seller can be required to pay for indemnification claims.

• General representations typically have a lower cap
• “Fundamental” representations (authority, title, capitalization, etc.) often have higher caps — sometimes up to the full purchase price

For sellers, the cap is one of the most important risk-limiting provisions in the deal.

What Is a Basket?

The basket is a threshold that must be exceeded before the buyer can recover anything.

There are two common types:

• Deductible basket: the seller pays only losses above the basket
• Tipping (first-dollar) basket: once the basket is exceeded, the seller pays all losses

Which structure applies can materially change exposure — even when the basket amount is the same.

How Escrows and Holdbacks Work

To secure indemnification obligations, buyers often require:

• an escrow (funds held by a third-party escrow agent), or
• a holdback (funds withheld directly by the buyer)

These funds are released over time as indemnification periods expire.

Typical escrows last 12–24 months for general reps, longer for fundamental or special risks.

Why This Matters in Practice

Indemnification provisions define how much risk you carry after the check clears.

Poorly negotiated indemnity terms can result in:

• unexpected post-closing claims
• money tied up longer than anticipated
• disputes that drag on well after closing

Sophisticated sellers focus not just on price, but on how risk is capped, secured, and released.