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