Building Your Post-Sale Investment & Legacy Plan For Middle-Market Business Owners

1. Introduction 

As a registered investment advisor, we work closely with business owners who face a defining moment: the sale of a company that generates significant investable assets. Our goal is to help translate that liquidity event into lasting wealth—addressing short-term and long-term investment needs, optimizing tax and estate strategies, and empowering generational legacy.   

2. Investment Planning: Short-Term & Long-Term Goals

A. Short-Term: Liquidity, Stability & Cash Flow 

• Immediately post-sale, capital preservation and liquidity are paramount. We construct a cash and short- duration fixed-income strategy to focus on capital preservation and fund near-term spending or transition needs.
• A standard approach: a laddered portfolio of high-quality bonds, money market funds, and cash equivalents in an effort to cover 3–5 years of personal living expenses and obligations. 

B. Long-Term: Wealth Growth & Legacy  

• After establishing a stable liquidity base, the remainder is invested for growth or income, or a combination of both: diversified across equities, fixed income, real assets, and alternatives—tailored to your risk tolerance, timeframe, and legacy objectives.   
• We align portfolio construction with your long-term goals: retirement lifestyle, family gifting, philanthropic ambitions, and generational transfer.  

3. Tax & Estate Planning Strategies 

A. Minimizing Capital Gains and Income Tax 

• By collaborating with your accountant and attorney, we explore structuring the sale (asset sale vs. stock sale), installment or structured sale options, and other deferral strategies to reduce immediate capital gain impact.   
• Section 1042 rollover: selling business stock to an ESOP can defer federal (and state) tax by reinvesting into qualified replacement property, a powerful tool for owners with an existing employee-ownership plan.   

B. Estate Planning & Preservation for Generations  

• Estate planning must begin early (ideally before sale) to avoid forcing heirs to liquidate assets to pay estate taxes. Effective tools include family-limited partnerships, grantor trusts, irrevocable life insurance trusts (ILITs), dynasty trusts, and generational skip-trust strategies.   
• We suggest reviewing your plan every 2-3 years or after major events to support its continued effectiveness.

4. Legacy & Family Governance

A. Defining & Preserving Family Legacy 

• Our private banking approach emphasizes structuring wealth in alignment with core family values—creating structures (e.g. family trusts, “family bank” lending frameworks) that promote responsibility, stewardship, and entrepreneurial continuity across generations.   

B. Preparing Heirs & Governance Structures 

• We help facilitate family financial education sessions, regular meetings, and governance frameworks to enable smooth generational transitions and prevent the common “fails by third generation” heritage loss scenario.  

5. Integrated Advisory Model

We serve as your fiduciary advisor, building a coordinated team with your bank’s trust, wealth planning, tax, and legal specialists:      

• Pre-Sale Advisory: Align exit timing, legal structure, and valuation with long-term objectives.    
• Post-Sale Investment Strategy: Establish short-term liquidity and construct a long-term diversified growth portfolio.    
• Tax & Estate Professionals: Collaborate on structuring, gifting strategies, trusts, and insurance tools for tax-efficient wealth preservation.    
• Generational Planning: Family engagement, governance, and legacy education.

7. Why Partner with Courier Capital

• Integrated trust & estate expertise: Access to bank trust services, estate attorneys, and tax professionals.  
• Fiduciary standard: We act in your best interest with full transparency.  
• Generational focus: Not just growth, but stewardship, family cohesion, and mission alignment.  
• Referral alignment: We welcome introductions from your commercial banker—ensuring coordinated service across your banking and wealth needs.

8. Conclusion

Selling your business is one of life's most significant financial milestones—and the opportunity to secure a legacy that lasts. Through disciplined short-term planning, tax-efficient execution, long-term portfolio design, and structured family and estate governance, you can convert the sale into multigenerational security and purpose. We stand ready to partner with you and your bank referral team—helping you turn your liquidity event into lasting impact for your family and beyond.

Next Steps:  

• Review your professional advisory team (CPA, attorney, succession consultant, wealth advisor) ahead of sale.  
• Work with us to design immediate liquidity and longterm investment strategy.  
• Establish estate and legacy structures that reflect your vision for your family. 

We welcome conversations with your commercial banker about how we can collaborate in serving you and your family at this pivotal time. 

Sources

Private Wealth Management+8BBH+8Business Insider+8Kiplinger.

Morgan StanleyU.S. Bank.

U.S. Bank+15Private Wealth Management+15Kiplinger+15.

BNY.

Kiplinger.

Mercer Advisors+2Tom Kelly+2Financial Times+2.

U.S. Bank+1Truist+1.

advisors.ubs.com+4wellsfargo.com+4epwealth.com+4BBH+4epwealth.com+4Finley Davis Private Wealth+4Wikipedia+1Wikipedia+1Regions+2Kiplinger+2Finley Davis Private Wealth+2.

Courier Capital, LLC (“Courier Capital”) is an SEC registered investment adviser located in Buffalo, NY, Rochester, NY, Jamestown, NY, Sarasota, FL and Pittsburgh, PA. For information pertaining to the registration status of Courier Capital, as well as its fees and services, please refer to our disclosure statement as set forth on Form ADV, available upon request or via the Investment Advisor Public Disclosure Website(www.adviserinfo.sec.gov). The information contained herein should not be construed as personalized investment advice or a solicitation to buy or sell any security. Investing in the stock market involves risk of loss, including loss of principal invested, and may not be suitable for all investors. Past performance is no guarantee of future results. This material contains certain forward-looking statements which indicate future possibilities. Actual results may vary. Additionally, this material contains information derived from third party sources. Although we believe these sources to be reliable, we make no representation as to the accuracy of any information prepared by an unaffiliated third party incorporated herein, and take no responsibility therefore. All expressions of opinion reflect the judgement of the authors as the date of publication and are subject to change without prior notice. Investment products and services are not FDIC Insured, are not a deposit or bank guaranteed, are not insured by any Federal governmental agency, and are subject to investment risks, including possible loss of the principal invested.