Portability Denied: The Compliance Misstep That Cost Millions with Bob Keebler
AICPA Personal Financial Planning (PFP)
Release Date: 08/22/2025
Cracking the AI Code for CPA Financial Planners
AICPA Personal Financial Planning (PFP)
Host Cary Sinnett is joined by Dr. Brianne Smith, a PFP practitioner, CPA firm owner, and accounting professor at Auburn University, for a timely conversation on artificial intelligence in financial planning. Artificial intelligence is moving quickly into financial planning workflows, but not all “AI” tools are created equal. For CPA financial planners, the opportunity is significant: increased efficiency, deeper insights, and more client-centered communication. The risk lies in adopting technology without fully understanding what it does, how it works, and where human judgment must...
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Jeff Levine on the Planning Tug-of-War: Income vs. Estate
AICPA Personal Financial Planning (PFP)
In this episode, host Cary Sinnett is joined by Jeff Levine, CPA, CFP, a nationally recognized tax planning thought leader, to examine one of the most persistent dilemmas in personal financial planning: the tension between income tax strategies and estate tax minimization. They explore why these two priorities often conflict and walk through practical examples CPA financial planners face when advising clients on gifting, step-up in basis, trust structures, and navigating compressed tax brackets. Jeff explains how changes to the federal estate tax exemption, evolving client...
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Carl Richards on Precision and Purpose
AICPA Personal Financial Planning (PFP)
What happens when technical excellence meets deep human empathy? In this episode, Carl Richards, CFP®, author of and creator of the famed “Sketch Guy” column in The New York Times, joins host Cary Sinnett to explore how CPA financial planners can foster trust through simplicity, storytelling, and purposeful conversation. Carl shares how sketches can cut through complexity, how planners can create space for real client understanding, and why listening with intention may be your most powerful technical skill. Whether you're coaching a client through uncertainty or explaining a nuanced...
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Smart Planning with AI: Real-World Strategies with Chris Benson
AICPA Personal Financial Planning (PFP)
Artificial intelligence is transforming how CPA financial planners approach research, analysis, and communication. In this episode, Chris Benson shares how he moved from curiosity to confident integration of AI in his daily practice. He explains how AI helps him generate first drafts of client communication, brainstorm planning strategies, and reduce research time from hours to minutes. Chris also provides a balanced perspective on data privacy, compliance risks, and how planners should evaluate new tools without getting distracted by every new release. Whether you are just beginning to...
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How CPAs Are Shaping the Future of Financial Planning with Jimmy Williams
AICPA Personal Financial Planning (PFP)
Jimmy Williams, CPA/PFS, shares how the role of the CPA is evolving from compliance technician to holistic financial planner. In this episode, Jimmy and host Cary Sinnett explore how trust, technical excellence, and human connection are converging in a new era of planning, and why CPAs are uniquely positioned to lead it. · Learn how CPAs can step into their fullest potential as advisors. · Hear about the added value to your clients and to your practice. · Discover what’s driving...
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Deadlines, Deductions & Decisions: Year-End Planning for the New Tax Era with Bob Keebler
AICPA Personal Financial Planning (PFP)
Bob Keebler joins Cary Sinnett to unpack why this year-end is anything but routine. With shifting tax thresholds and surprise penalties lurking under the surface, every decision matters more than ever. This rapid-fire episode arms CPA financial planners with critical year-end strategies, from Roth conversions to trust distribution traps. Don’t miss your chance to finish strong and plan ahead with confidence. AICPA Resources: This episode is brought to you by the AICPA’s , the premier provider of information, tools, advocacy, and guidance for professionals who...
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Wealth, Meaning and the Future of Advice with Dr. Brian Portnoy
AICPA Personal Financial Planning (PFP)
Building wealth is one thing. Defining what wealth means is another. In this episode, Cary Sinnett sits down with Dr. Brian Portnoy, one of the world’s leading experts on the psychology of money, to explore why the future of financial advice isn’t just about technical expertise — it’s about emotional intelligence, perspective, and purpose. Brian unpacks his powerful concept of “funded contentment” — the idea that true wealth is the ability to live a meaningful life, not just grow a bigger balance sheet. He shares practical ways advisors can help clients escape the hedonic...
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Building Financial Capability Across Generations
AICPA Personal Financial Planning (PFP)
When families look to CPA financial planners, they’re often asking more than just tax or investment questions. They want to know: Will my kids be ready when it’s their turn to inherit? In this episode, Cary Sinnett welcomes Mindy Kalinowski Earley, consultant to ultra-high-net-worth families and Chief Learning Officer at Family Office Exchange. With two decades of experience at the intersection of family dynamics and education, Mindy challenges planners to move beyond balance sheets and into legacy stewardship. Together, they explore: · Why preparing...
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The Exit Blueprint: Strategies to Maximize Value and Minimize Risk
AICPA Personal Financial Planning (PFP)
When business owners skip exit planning, the fallout can be brutal; value lost, families divided, legacies diminished. But with the right strategy, an exit isn’t chaos, it’s a launchpad: valuations climb, transitions smooth out, and owners step confidently into their next chapter. In this episode of the AICPA Personal Financial Planning Podcast, host Cary Sinnett welcomes Daniel D. Meiklejohn, JD, CPA, PFS. With his rare combination of legal, tax, and financial planning expertise, Daniel helps business owners turn exits from reactive scrambles into deliberate successes, covering everything...
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Portability Denied: The Compliance Misstep That Cost Millions with Bob Keebler
AICPA Personal Financial Planning (PFP)
What happens when one overlooked detail turns a thoughtful estate plan into a multi-million-dollar tax disaster? In this episode of the AICPA Personal Financial Planning Podcast, nationally recognized tax and estate planning expert Bob Keebler joins Cary Sinnett to unpack the cautionary tale of Estate of Rowland v. Commissioner. Despite well-crafted trusts and modest estates, a simple misstep in making the portability election led to the loss of $3.7 million in estate tax exemption. The case underscores the reality that “substantial compliance is not enough” when filing Form 706—and the...
info_outlineWhat happens when one overlooked detail turns a thoughtful estate plan into a multi-million-dollar tax disaster? In this episode of the AICPA Personal Financial Planning Podcast, nationally recognized tax and estate planning expert Bob Keebler joins Cary Sinnett to unpack the cautionary tale of Estate of Rowland v. Commissioner.
Despite well-crafted trusts and modest estates, a simple misstep in making the portability election led to the loss of $3.7 million in estate tax exemption. The case underscores the reality that “substantial compliance is not enough” when filing Form 706—and the reputational and financial risks that follow.
You’ll learn:
- Why the IRS and courts denied the portability election—and what it means for practitioners.
- How valuation, appraisals, and strict filing compliance can make or break an estate.
- What CPA financial planners can do to collaborate effectively with attorneys and safeguard clients from hidden estate administration landmines.
- Practical risk management steps firms should adopt to prevent similar outcomes.
Listen in to protect your clients’ legacies, preserve your professional reputation, and avoid the quiet traps buried in estate planning compliance.
Resources:
Guide: Guide to Financial and Estate Planning Vol. 4
Podcast: Estate Planning & Portability
Learning: Estate Planning Certificate Program
Video: Critical Income, Estate and Trust Planning for 2023 and Beyond
This episode is brought to you by the AICPA’s Personal Financial Planning Section, the premier provider of information, tools, advocacy, and guidance for professionals who specialize in providing tax, estate, retirement, risk management and investment planning advice. Also, by the CPA/PFS credential program, which allows CPAs to demonstrate competence and confidence in providing these services to their clients. Visit us online to join our community, gain access to valuable member-only benefits or learn about our PFP certificate program.
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