Podcast Summary:

Title: Deadlines, Deductions & Decisions: Year-End Planning for the New Tax Era with Bob Keebler
Podcast: AICPA Personal Financial Planning (PFP)
Date: October 17, 2025
Host: Kari Sinnett (AICPA & CIMA)
Guest: Bob Keebler, CPA (Keebler & Associates)

Main Theme & Purpose

This episode explores the rapidly evolving landscape of year-end tax planning for high-income clients, emphasizing how new legislation, shifting phaseouts, and potential government-induced changes upend usual strategies. Renowned CPA and wealth transfer expert Bob Keebler provides practical, detailed guidance on optimizing client outcomes in this "new tax era," while encouraging deeper client conversations about long-term goals, philanthropy, and wealth transfer.

Key Discussion Points & Insights

1. The New Year-End Tax Planning Paradigm

• Significant Shifts:
  The traditional playbook for year-end planning "has changed" (03:00), with new rules from recent legislation (OBVBA), government shutdown impacts, and shifting thresholds. Bob urges advisors to rethink familiar approaches and adapt to new opportunities and hazards.
• Top Seven Planning Areas:
  1. Charitable Giving & Itemized Deductions: Consider new phaseouts and deduction limitations post-OBVBA.
  2. Qualified Small Business Stock (QSBs): Review opportunities under Section 1202.
  3. SALT & Senior Deduction: Examine the interplay of state and local tax with the new thresholds.
  4. Section 199A (199cap) Phase-Outs: High phaseout ranges create “tax cliffs” and anomalous marginal rates.
  5. Roth Conversions: Remain attractive but with new IRMAA (Medicare) premium side-effects.
  6. Gain and Loss Harvesting: Broadly similar but needs sharper timing.
  7. Tax Shelters: Heightened IRS scrutiny; caution clients about aggressive social media promotions.

Quote:
“Everything we thought we knew about year end planning has changed. We need to shatter that prior paradigm and basically start all over.”
— Bob Keebler (01:49)

2. Bracket Management & Timing Complexity

• More Moving Parts:
  The sheer number of overlapping phaseouts means “no one can memorize all these different phaseouts” anymore (05:10) — advanced software is essential.
• Critical Phaseouts:
  • Senior deduction
  • SALT deduction
  • Charitable deduction phaseout at $237k+ incomes
• Strategy Example:
  Roth conversions and IRA withdrawals must be balanced against potential bracket creep and deduction limits.

Quote:
“There are like eight or ten different phaseouts… you have to use your software, balance that out.”
— Bob Keebler (05:04)

3. Integrating Charitable Giving, Capital Gains, and Roth Conversions

• Start with Client Life Goals:
  Planning should be led by client objectives—income needs, legacy, philanthropy—particularly as they approach their 60s and 70s (06:50).
• Long Horizon Projections:
  Keebler’s team models out 15-year projections to anticipate effects of RMDs, tax bracket changes, and strategic withdrawals (07:10).
• Case Study Warning:
  Waiting too long to draw down IRAs may result in forced distributions at much higher tax rates.

Quote:
“He proudly told me...he hadn’t taken any money out of his IRA...but...he now had like $9 million in his IRA. I didn’t have the heart to say...his plan was a plan of fools.”
— Bob Keebler (07:31)

• Double-Layered Strategy:
  • Use Roth conversions to fill up targeted brackets.
  • Dial taxable income down by making charitable gifts—optimally coordinated in late November/December for better accuracy (12:10).

Host Reflection:
“Using your charitable strategies to keep it back down into the bracket you want...I love how all of those things overlay each other.”
— Kari Sinnett (11:47)

4. Managing Tax Uncertainty and Avoiding Pitfalls

• Run Multiple Projections:
  Advisors should run initial tax scenarios now, fine-tune closely as December approaches (14:10).
• Beware of “Tax Cliffs”:
  Clients near $500–600k AGI may face effective tax rates over 45% due to phaseouts. Strong caution and precise calculation are vital.

Quote:
“If I made exactly $500,000...and I do a Roth conversion of $100,000, I’m going to pay tax at 45.5% on that conversion because of the phase out of the SALT. And that is so critical to understand.”
— Bob Keebler (14:12)

5. Deeper Client Conversations: Beyond the Numbers

• Springboard for Legacy & Wealth Transfer:
  Use year-end technical planning as a way to win client trust and open broader goal-setting conversations (16:10).
• Goal-Setting Exercise:
  Keebler asks spouses to separately list their top 10 goals, then negotiate a shared list before planning. This crystallizes real objectives and minimizes later conflicts with attorneys or other advisors (16:50).

Quote:
“I ask husband and wife to sit at opposite ends of a table and write down their 10 goals...and then come up with 10 common goals...Her insight is going to be much different than mine—most of the time I think better.”
— Bob Keebler (16:24)

• Example – Concentrated Stock & Charitable Trusts:
  If a client has most net worth in one stock and wishes to give to charity, charitable trusts can mitigate capital gains and secure income tax benefits (18:20).

6. Client-Centered Planning & Professional Collaboration

• Define Goals Before Recommending Techniques:
  Clearly defined goals ensure smoother implementation and reduce advisor disagreements (18:56).

Quote:
“If you can define the goals, the techniques just speak for themselves...that’s the critical thing—is just to know what people really want to achieve.”
— Bob Keebler (19:49)

• Advisor’s Role:
  Provide technical expertise, but keep the client’s voice and wishes central in all planning.

Notable Quotes & Memorable Moments

| Time | Speaker | Quote | |-----------|---------|----------------------------------------------------------------------------------------------------------------------------| | 01:49 | Bob | “Everything we thought we knew about year end planning has changed. We need to shatter that prior paradigm and start over.” | | 05:04 | Bob | “There are like eight or ten different phaseouts… you have to use your software, balance that out.” | | 07:31 | Bob | “…he now had like $9 million in his IRA. I didn’t have the heart to say...his plan was a plan of fools.” | | 11:47 | Kari | “Using your charitable strategies to keep it back down into the bracket you want...all of those things overlay each other.” | | 14:12 | Bob | “I’m going to pay tax at 45.5% on that conversion because of the phaseout of the SALT.” | | 16:24 | Bob | “I ask husband and wife to sit at opposite ends of a table and write down their 10 goals...Her insight is...better.” | | 19:49 | Bob | “If you can define the goals, the techniques just speak for themselves…” |

Important Timestamps

| Time | Segment/Topic | |----------|--------------------------------------------------------------------------------------------------------------------------| | 01:30 | Introduction to Bob Keebler and episode urgency | | 01:49 | Bob’s overview: The seven most critical year-end issues for advisors | | 05:00 | Discussion on the need for advanced software and the complexity of overlapping phaseouts | | 06:47 | Integrating planning strategies; importance of projecting 15 years out | | 11:47 | Layered Roth and charitable strategy | | 12:31 | Coordinating December charitable gifts and Roth conversions for bracket management | | 14:07 | Running projections to manage phaseouts and avoid stealth taxation for $500k–$600k earners | | 16:08 | Using year-end meetings to deepen client relationships on legacy & wealth transfer topics | | 16:24 | Spouse goal-listing exercise as a foundation for meaningful planning | | 18:20 | Example of addressing concentrated stock through charitable trusts | | 18:56 | Importance of concrete goals before technical recommendations |

Takeaways for Advisors

• Abandon “autopilot”; each client must be recalibrated under new rules.
• Don’t rely on mental checklists—advanced planning software is now a necessity.
• Run detailed, future-oriented scenarios; avoid bracket creep and stealth taxes.
• Leverage December for final income and deduction timing, using Roth conversions and philanthropy in concert.
• Proactively educate clients about new tax shelter risks.
• Move beyond the numbers to uncover clients’ deepest goals—use facilitated exercises to align spouse and family visions.
• Let clients “write their own plan,” with your expertise guiding, not dominating, the process.

This episode is a must-listen for any advisor facing a turbulent year-end planning season under the new tax regime.