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Deal Structuring

Optimize deal terms to maximize value and minimize risk

Structure Deals for Maximum Value

How you structure a deal is often more important than the headline purchase price. Poor deal structure can cost small business owners 20-40% of their expected proceeds through excessive taxes, unfavorable payment terms, or post-close liabilities.

Our deal structuring expertise helps you navigate complex decisions about asset vs. stock sales, payment terms, tax implications, and risk allocation. We work with your tax and legal advisors to create structures that maximize your net proceeds while protecting you from future liabilities.

From simple cash deals to complex earn-outs and seller financing arrangements, we ensure deal terms align with your goals and provide the security you need for a successful exit.

Our Structuring Services

  • Asset vs. stock sale analysis and recommendations
  • Tax impact modeling for different structures
  • Payment terms optimization (cash, notes, earn-outs)
  • Risk mitigation through proper indemnification
  • Earn-out and performance milestone design
  • Post-closing obligation negotiation

Common Deal Structures

Understanding your options is key to maximizing value

Asset Sale

Buyer purchases specific business assets rather than stock/equity

Pros:

  • Buyer gets step-up in basis
  • Can exclude liabilities
  • Clean transaction

Cons:

  • May trigger more taxes for seller
  • Transfer of contracts/licenses needed

Best for: Most small business transactions, especially C-corps

Stock/Equity Sale

Buyer purchases ownership interests in the business entity

Pros:

  • Simpler transfer process
  • Often better tax treatment for seller
  • Contracts stay in place

Cons:

  • Buyer inherits all liabilities
  • No step-up for buyer

Best for: S-corps, LLCs, and businesses with significant contracts

Hybrid Structure

Combines elements of asset and stock sales with creative terms

Pros:

  • Flexible to meet both parties needs
  • Can bridge valuation gaps
  • Tax-efficient for both sides

Cons:

  • More complex documentation
  • Requires sophisticated advisors

Best for: Complex situations or when parties have conflicting priorities

Key Deal Components

Purchase Price

Key Considerations:

  • Cash at closing
  • Seller financing
  • Earn-outs
  • Equity rollovers

Pro Tip:

Balance certainty of payment with maximizing total value

Representations & Warranties

Key Considerations:

  • Scope of seller guarantees
  • Survival periods
  • Indemnification caps
  • Escrow holdbacks

Pro Tip:

Limit exposure while providing reasonable buyer protections

Post-Close Terms

Key Considerations:

  • Transition assistance
  • Non-compete agreements
  • Employment/consulting
  • Contingencies

Pro Tip:

Clearly define expectations and compensation for ongoing involvement

Why Structure Matters

Tax Optimization

Structure deals to minimize tax burden and maximize net proceeds

Risk Protection

Protect yourself from post-sale liabilities and earn-out disputes

Value Maximization

Creative structuring can bridge valuation gaps and close deals

Terms Optimization

Balance cash at close, seller financing, and earn-outs strategically

Deal Structuring Questions

What is deal structuring in an M&A transaction?

Deal structuring determines how a business sale is organized — including payment terms, asset vs. stock sale classification, earnout provisions, seller financing, non-compete agreements, and transition arrangements. The structure directly impacts how much the seller nets after taxes, the risk profile for both parties, and the likelihood of the deal closing successfully.

What is an earnout and should I accept one?

An earnout is a portion of the purchase price that is contingent on the business achieving certain performance targets after closing. Earnouts can bridge valuation gaps between buyer and seller, but they introduce risk — the seller may not receive full payment if targets are missed. Whether to accept an earnout depends on the specific terms, your confidence in post-sale performance, and the overall deal structure.

What is the difference between an asset sale and a stock sale?

In an asset sale, the buyer purchases specific business assets (equipment, inventory, customer contracts) rather than the company entity itself. In a stock sale, the buyer acquires ownership of the entire entity. Asset sales are more common for small businesses and generally favor buyers (tax benefits, limited liability). Stock sales are simpler structurally but transfer all liabilities. The choice significantly impacts tax consequences for both parties.

Get Expert Deal Structuring Advice

Maximize your net proceeds with strategic deal structuring.