FROM POLICY TO PITFALL: ESTATE TAX LESSONS FROM CONNELLY FOR BUSINESS OWNERS
This session will unpack what the Connelly case means for business owners and how current structures involving life insurance can inadvertently inflate estate tax exposure. We’ll explore the implications of the ruling and how it may reshape valuation practices for closely held businesses. Attendees will gain a clearer understanding of the potential risks within existing buy-sell agreements and funding mechanisms. The session will also highlight proactive planning strategies to help minimize unintended tax consequences.
Learning Objectives:
- Explain the Connelly holding
- Distinguish between entity redemptions and cross purchase buy-sell arrangements
- Common drafting pitfalls
- Discuss proactive planning strategies
About the Presenter:
Hear from industry expert Gerrard Grant
Event Location
Event Details
Who Should Attend?
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Business Owners & Their Trusted Advisors
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Business Owners
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Other Business Professionals
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Business Consultants
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Professional Advisors
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Members of Family Business Boards
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Private Business Owners
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Other Professional Advisors
Regardless of your unique specialty, there is seat at the exit planning table for you. Learn more at www.EarnCEPA.com.
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Family Business Advisors
More than 50% of lower middle market business owners would prefer to transition to the next generation. Help them succeed with exit planning strategies.
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Commercial Lenders
One of the best relationships a business owner makes is with their banker. How can you help your corporate clients think about the future and ensure financial continuity? Answer: exit planning.
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Mergers & Acquisition Advisors
Proper exit planning causes less deals to fall through at the last minute. Connect with CEPAs to build your healthy deal flow network.
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Insurance Professionals
Exit planning addresses the 5 D's. So do you. Approach the risk conversation differently with exit planning.
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Strategic Consultants
One of the most critical roles in exit planning is building transferable value. Strategic consultants have the ability to expand options and drive rapid business value that affect performance today.
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Estate Planners
Exit planning is a natural fit for estate planners who want to operate more holistically with their owner clients.
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Investment Bankers
Only 2 of every 10 businesses that come to market actually sell. Learn how exit planning can bring attractive AND ready business to your purview.
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Valuation Analysts
Valuation is both a billable engagement AND an opportunity to provide owners some perspective on how to accelerate value drivers (and deal with value killers). Use exit planning to make that valuation into a longer term value acceleration engagement.
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Financial Advisors
One of the critical ‘legs of the stool’ is personal financing planning. An owner must have a strong financial plan & contingency plan post-transition to enable them to thrive in the next act of the lives personally and financially. Exit planning brings this future mindset into the present. Exit is now.
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Wealth Managers
You’re a skilled relationship person. Being entangled into your clients’ professional lives matters as you build a strategy to manage their wealth upon them harvesting it from their business. Exit planning allows you to build a deeper relationship with your client, expands your COI network, while giving you an early seat at table well before the liquidity event.
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CPAs/Accountants
Owners participating in the State of Owner Readiness research continue to indicate that you are the No. 1 "Most Trusted Advisor." You are a natural fit to lead the exit planning team and deepen your relationship (and retention) of next generation owners.
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Attorneys
You have close relationships with clients, and can benefit from being the first advisor to introduce the idea of exit planning.
EXIT PLANNING IS GOOD BUSINESS STRATEGY
The Exit Planning Institute, provides Financial Advisors, Accountants, Consultants, and other advisors of business owners with the critical education to differentiate themselves and add value to their existing client relationships through a credential, conference, courses, and content. Download the CEPA brochure for more information.
ABOUT THE PRESENTER
Gerrard is a trusted business and tax advisor to entrepreneurs, closely held family businesses, and startups. He is a Florida Bar Board Certified Tax Attorney and serves clients across various industries including finance, hospitality, technology, real estate, healthcare, manufacturing, and entertainment. His experience as both a business-tax attorney and CPA is the best of both worlds for many clients and the skillsets he mastered in both areas stand out among his peers. Gerrard understands the financial implications of tax matters while navigating the legal aspects of complex tax law and business law matters for his clients and their advisors.
His law practice includes representing early-stage startups to mid-size businesses and advising on capital raising, M&A, debt-refinancing, structuring complex transactions, and estate planning and asset protection. Gerrard serves as outside general counsel to for-profit organizations which include a registered investment advisory firm with $300 million in AUM and multiple non-profit organizations. In that capacity, he advises management on issues ranging from minimizing legal exposure and contract drafting and review, to daily operational matters.
Having over a decade of experience representing taxpayers against the Tax Division of the U.S. Department of Justice, the Internal Revenue Service, and state and local taxing authorities, Gerrard devotes a significant part of his practice to helping taxpayers both domestically and internationally navigate all aspects of federal and state tax controversy matters. These matters include but are not limited to IRS liens and levies, employment and payroll tax, IRS appeals, CDP hearings, IRS audits, and examinations, IRS installment agreements, offer in compromise, and when needed, litigation in the U.S. Tax Court.
Gerrard serves in various leadership roles within the Florida Bar and in his community. He is the 2023 – 2024 Chair of the Florida Bar Tax Certification Committee and serves on the Executive Council of the Tax Section where he is a Co-Chair of the IRS Collection Activities Subcommittee. He is a member of the Real Property Probate and Trust Law Section. He is also a proud board member of the UCF Alumni Board and sits on the Advisory Board of the Orlando Sports Foundation, Inc.
As an attorney, Gerrard received the esteemed AV Preeminent rating by Martindale-Hubbell, the highest rating for attorneys who are ranked by their peers for exhibiting the highest level of professional excellence for their legal expertise, communication skills, and ethical standards. He has been recognized in publications such as Best Lawyers®, Super Lawyers, Florida Trend Legal Elite, and Orlando Family Magazine as an Awesome Attorney in Tax Law.
In his spare time, Gerrard enjoys spending time with his family and is an avid sports fan of the Toronto Raptors NBA basketball team and enjoys rooting for the UCF Knights and Florida Gators sports teams. He is a supporter of Orlando City SC and Chelsea FC football clubs.


