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Buy-Sell Agreement Planning

A Buy-Sell Agreement provides a legally binding plan for the transfer of a business interest after a triggering event. It protects both business continuity and the financial security of the owner’s family.

Triggering Events Include:

  • Death
  • Disability
  • Retirement
  • Bankruptcy or Divorce
  • Termination of employment

Core Benefits of Buy-Sell Agreements

Provides Liquidity

Immediate cash flow to the deceased or disabled owner’s family.

Guaranteed Market

Creates a predetermined buyer for the business interest.

Avoids Outside Interference

Prevents unwanted third parties from entering the business.

Predetermined Value

Establishes clear valuation methods and terms of sale.

Types of Buy-Sell Agreements

Entity Purchase (Stock Redemption)

The business buys back the departing owner’s shares.

Best for: Single owners or when business has excess cash.

Cross Purchase

Co-owners buy each other’s shares directly.

Best for: 2-3 owners with similar financial capacity.

Wait-and-See

Business has first right to buy; if not, other owners can.

Best for: Provides flexibility for changing business conditions.

One-Way

Used when a third party (like a key employee) buys out the owner.

Best for: Succession planning to key employees.

Funding Your Buy-Sell Agreement

Funding method is critical — without proper funding, even the best agreement fails.

Life Insurance (Preferred)

Pros:

  • Funds immediately upon death or disability
  • Tax-efficient payout
  • Guaranteed availability

Cons:

  • Premiums required
  • Needs maintenance and review

Sinking Fund (Moderate)

Pros:

  • Build over time
  • Stable asset

Cons:

  • May be underfunded at trigger time
  • Subject to creditors

Installments (Moderate)

Pros:

  • Seller gets ongoing payments
  • Lower upfront cost

Cons:

  • Delays liquidity
  • Relies on new owner’s performance

Cash/Loans (Limited)

Pros:

  • Simple (cash)
  • No upfront cash needed (loans)

Cons:

  • Often unavailable when needed
  • May not qualify for loans

Life Insurance: The Preferred Funding Solution

Why Life Insurance is Most Common:

How It Works:

  • A policy is purchased on each owner
  • Death benefit is used to buy out shares
  • Cash value may be used for retirement/disability
  • Buy-sell documents reference the policies

Key Benefits:

  • Tax-free death benefit (IRC §101)
  • Immediate liquidity when needed
  • Smooth ownership transition
  • Guaranteed funding availability

Important: Connelly v. United States (2024)

Supreme Court Decision Impact: When a stock redemption is funded with life insurance, the insurance death benefit increases the business’s value, which increases the deceased owner’s estate.

Planning Consideration: This may create higher estate taxes. Planners must now account for this when using Entity Purchase methods.

Is Your Business Ready for Buy-Sell Planning?

Business Types:

  • C-Corporation
  • S-Corporation
  • Limited Liability Company (LLC)
  • Partnership
  • Sole Proprietorship

Owner Goals:

  • Create liquidity for family
  • Secure a guaranteed buyer
  • Reward key employees
  • Plan for retirement/disability
  • Maintain business continuity

Ready to Secure Your Business Future?

Don’t leave your business succession to chance. Let’s create a comprehensive buy-sell strategy that protects your business and your family’s financial security.

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Daniel Speiss

Daniel Speiss

RevOps & Operations Architect helping founders build clean, scalable operations infrastructure. Based in Miami, Austin, and NYC.

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