By Raymond Nash

Business Planning

Looking Forward - Buy/Sell Arrangement Options

During the month of July, we are focusing on business planning in the wake of the Supreme Court ruling in Connelly v. U.S. On June 6, 2024, the U.S. Supreme Court affirmed the 8th U.S. Circuit Court of Appeals’ decision in Connelly v. U.S. This ruling determines that the value of the business at a shareholder’s death will be increased by any life insurance proceeds that are received without an offsetting reduction for the amount of the stock redemption liability.

When establishing a new buy/sell agreement for a company, the shareholders should consider the possible ramifications of the Supreme Court’s ruling when determining their preferred arrangement.

The first thing to consider is that this holding will not affect every business owner. Per Treas. Reg. 25.2703-1(b)(3), a company automatically meets the criteria for an exclusion if more than 50% is owned directly or indirectly by individuals who are not members of the same family. Additionally, if a business owner’s net worth, including their business equity and portion of any death benefit payable upon their mortality, falls below the projected estate tax exemption threshold, they might not incur any estate taxes. Of course, the unpredictability of where the estate tax exemption could lie in the coming years is another consideration altogether.

Future interpretation of the language used by the Supreme Court might have a narrow or broad effect to the landscape of buy/sell life insurance held within a company; time will tell. In the short-term, family-owned companies with shareholders who will incur estate taxes and might have considered stock redemption for their buy/sell arrangements in the past, are exploring different arrangements in the wake of the Connelly Supreme Court decision. Outlined in the graphic below is a comparison of stock redemption and three alternative buy/sell arrangements to consider.

Each arrangement has its pros and cons, so there is no one size fits all solution. When considering the preferred buy/sell arrangement for a family-owned business, there are extenuating circumstances that can affect which arrangement will work for each company. For instance, family dynamics can play a huge part in how to structure the agreement. Other factors include the age of the shareholders (to determine an approximation of how far back the Connelly decision will be in the rearview at life expectancy), if their succession plan includes passing the company down within the family, and the shareholders’ sophistication for planning techniques that might require routine maintenance.

We will continue to monitor the ramifications of the Supreme Court ruling in Connelly v. U.S. and provide any updated details as we are made aware of them. Contact us with any questions or opportunities to help you or your clients achieve identified goals. This is what we enjoy doing for only a select number of families, businesses, and charitable institutions each year, and we look forward to hearing from you.

Heirmark operates on a different model.

As a member of M Financial Group, we’re part of a select network of independent firms focused on advanced insurance planning for high-net-worth individuals and complex needs. This provides access to more customized structuring, deeper underwriting collaboration, and solutions not typically available through traditional channels—allowing us to approach each case with greater flexibility and design strategies around the client, not the product.

Heirmark is a premium life insurance advisory firm dedicated to helping affluent families, business owners, and their trusted advisors acquire custom-designed life insurance solutions that protect assets and preserve legacies.

Cleveland Office

PS Executives Center, Crown Centre, 5005 Rockside Road, Suite 600, Cleveland, OH 44131

Office of Supervisory Jurisdiction

1125 NW Couch Street, Suite 900, Portland, OR 97209

Copyright © 2026 HEIRMARK, LTD All Rights Reserved.

Securities and Investment advisory services offered through M Holdings Securities, Inc., a registered broker/dealer and investment advisor, member FINRA/SIPC. HEIRMARK, LTD is independently owned and operated. HEIRMARK, LTD is a member of M Financial Group. Please go to mfin.com/DisclosureStatement for further details regarding this relationship.


For important information related to M Securities, refer to the M Securities’ Client Relationship
Summary (Form CRS) by navigating to https://mfin.com/m-securities.


Check the background of this Firm and/or investment professional on FINRA's BrokerCheck.


Registered representatives are registered to conduct securities business and licensed to conduct insurance business in limited states.  Response to, or contact with, residents of other states will only be made upon compliance with applicable licensing and registration requirements.  The information in this website is for U.S. residents only and does not constitute an offer to sell, or a solicitation of an offer to purchase brokerage services to persons outside of the United States.


This site is for information purposes and should not be construed as legal or tax advice and is not intended to replace the advice of a qualified attorney, financial or tax advisor or plan provider.


Raymond Nash CA License #0G32030

Raymond Nash AR License #7081134

Heirmark CA License #0K00803

5784256 

Heirmark operates on a different model.

As a member of M Financial Group, we’re part of a select network of independent firms focused on advanced insurance planning for high-net-worth individuals and complex needs. This provides access to more customized structuring, deeper underwriting collaboration, and solutions not typically available through traditional channels—allowing us to approach each case with greater flexibility and design strategies around the client, not the product.

Heirmark is a premium life insurance advisory firm dedicated to helping affluent families, business owners, and their trusted advisors acquire custom-designed life insurance solutions that protect assets and preserve legacies.

Cleveland Office

PS Executives Center, Crown Centre, 5005 Rockside Road, Suite 600, Cleveland, OH 44131

Office of Supervisory Jurisdiction

1125 NW Couch Street, Suite 900, Portland, OR 97209

Copyright © 2026 HEIRMARK, LTD All Rights Reserved.

Securities and Investment advisory services offered through M Holdings Securities, Inc., a registered broker/dealer and investment advisor, member FINRA/SIPC. HEIRMARK, LTD is independently owned and operated. HEIRMARK, LTD is a member of M Financial Group. Please go to mfin.com/DisclosureStatement for further details regarding this relationship.


For important information related to M Securities, refer to the M Securities’ Client Relationship
Summary (Form CRS) by navigating to https://mfin.com/m-securities.


Check the background of this Firm and/or investment professional on FINRA's BrokerCheck.


Registered representatives are registered to conduct securities business and licensed to conduct insurance business in limited states.  Response to, or contact with, residents of other states will only be made upon compliance with applicable licensing and registration requirements.  The information in this website is for U.S. residents only and does not constitute an offer to sell, or a solicitation of an offer to purchase brokerage services to persons outside of the United States.


This site is for information purposes and should not be construed as legal or tax advice and is not intended to replace the advice of a qualified attorney, financial or tax advisor or plan provider.


Raymond Nash CA License #0G32030

Raymond Nash AR License #7081134

Heirmark CA License #0K00803

5784256 

Heirmark operates on a different model.

As a member of M Financial Group, we’re part of a select network of independent firms focused on advanced insurance planning for high-net-worth individuals and complex needs. This provides access to more customized structuring, deeper underwriting collaboration, and solutions not typically available through traditional channels—allowing us to approach each case with greater flexibility and design strategies around the client, not the product.

Heirmark is a premium life insurance advisory firm dedicated to helping affluent families, business owners, and their trusted advisors acquire custom-designed life insurance solutions that protect assets and preserve legacies.

Cleveland Office

PS Executives Center, Crown Centre, 5005 Rockside Road, Suite 600, Cleveland, OH 44131

Office of Supervisory Jurisdiction

1125 NW Couch Street, Suite 900, Portland, OR 97209

Copyright © 2026 HEIRMARK, LTD All Rights Reserved.

Securities and Investment advisory services offered through M Holdings Securities, Inc., a registered broker/dealer and investment advisor, member FINRA/SIPC. HEIRMARK, LTD is independently owned and operated. HEIRMARK, LTD is a member of M Financial Group. Please go to mfin.com/DisclosureStatement for further details regarding this relationship.


For important information related to M Securities, refer to the M Securities’ Client Relationship
Summary (Form CRS) by navigating to https://mfin.com/m-securities.


Check the background of this Firm and/or investment professional on FINRA's BrokerCheck.


Registered representatives are registered to conduct securities business and licensed to conduct insurance business in limited states.  Response to, or contact with, residents of other states will only be made upon compliance with applicable licensing and registration requirements.  The information in this website is for U.S. residents only and does not constitute an offer to sell, or a solicitation of an offer to purchase brokerage services to persons outside of the United States.


This site is for information purposes and should not be construed as legal or tax advice and is not intended to replace the advice of a qualified attorney, financial or tax advisor or plan provider.


Raymond Nash CA License #0G32030

Raymond Nash AR License #7081134

Heirmark CA License #0K00803

5784256