A Legal Wake-Up Call for Business Owners and Advisors

The Massachusetts court ruling in CONNELLY v. UNITED STATES has raised serious questions about the way life insurance should be owned or structured when used to fund a buy/sell agreement. If you advise or operate a closely held business, this case could have major implications for your planning strategies.
 
We recently hosted a focused, one-hour panel discussion with legal, tax, and valuation experts. The panel broke down what Connelly means for your clients and your business—and what to do next.
 
This discussion explored the legal, tax, and valuation challenges related to improperly structured buy-sell agreements, particularly in light of recent IRS scrutiny (e.g., the Connelly case).
 

You can listen to the recording here

What you will learn

  • Legal fallout from CONNELLY v. UNITED STATES
  • Structuring buy-sell agreements to withstand IRS scrutiny
  • Avoiding tax surprises and valuation disputes
  • Insurance and funding considerations
  • Real-world case studies and action steps

Our expert panel brought together seasoned professionals from law, tax, valuation, and insurance planning, each offering practical insights and actionable guidance.

Meet the Moderator

Aviva Sapers

CEO

Sapers & Wallack

Aviva E. Sapers is the President and CEO of Sapers & Wallack, leading the firm in its third generation. Recognized in the 2024 Forbes/SHOOK Top Financial Security Professionals Ranking as #17 in Massachusetts, she brings extensive expertise in wealth management and insurance planning. She holds Chartered Life Underwriter and Chartered Financial Consultant designations, a Certification in Long Term Care, and is a licensed Insurance Advisor. Aviva is an active member of FINSECA, NALU, the Million Dollar Round Table’s Court of the Table, and several community advisory councils.

Meet the Panelists

Jeffrey Levine

Director of Financial Strategies

LGA, LLP

Jeffrey Levine, CPA, MST, is Director of Financial Strategies at LGA, LLP, with over four decades of experience. Previously, he co-founded a successful Boston-area accounting firm, personally serving 700+ business and individual clients in tax and financial planning. At LGA, Jeff leads efforts to deliver holistic services, including estate planning and insurance assessment. He’s a recognized financial expert featured by NBC, WGBH, WBZ, Fortune, and the Boston Globe. 

Jeffrey Davis

Chairman & CEO

Mage, LLC

Jeffrey Davis is a renowned organisational and leadership advisor who has guided over 700 entrepreneurial and family-run businesses. He hosts the Radio Entrepreneurs podcast and previously led three nationally syndicated radio segments. A best-selling author and columnist for the Boston Business Journal, Jeffrey also founded the Massachusetts Family Business Association. His expertise spans leadership, strategic marketing, sales, and family business transitions, with prior roles at Johnson & Johnson’s Ethicon Sutures and global agency Doyle Dane Bernbach. He taught entrepreneurship at Babson College.

Jane Gorham Ditelberg

Director of Tax Planning

Northern Trust Institute

Jane Ditelberg is an attorney with more than 30 years of experience in the tax and trusts and estates fields.  She is the Director of Tax Planning at The Northern Trust Company where she analyzes new developments in income and transfer taxes and provides insights and guidance on tax topics for individuals, closely-held businesses, estates and trusts.  Her newsletter on tax topics for professional advisors is available at Tax News You Can Use | Northern Trust.

Mark Tarallo,

Partner

Nutter

Mark J. Tarallo is a partner in Nutter’s Corporate and Transactions Department. He represents clients in a broad array of corporate matters, including mergers and acquisitions, venture capital financings, private equity transactions, and securities offerings. Mark works with clients of all sizes ranging from startups to publicly listed international companies.

Mark regularly counsels buyers, sellers, investors, and issuers on business planning, corporate governance, and transaction due diligence. He has extensive experience advising private funds and investment advisers in connection with regulatory and securities matters.

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