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Strategic & Tactical Roth Conversions after the SECURE Act



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Strategic & Tactical Roth Conversions after the SECURE Act

Roth conversions have always had the potential to unlock hidden value. In the past, it was perhaps simple nominal conversions to take advantage of a low-income year. However, the SECURE Act expands the impact of Roth conversions beyond a quantitative arbitrage game to a strategic estate planning set of issues that should be of interest to all lawyers, trust officers, insurance and financial advisors and CPAs.

The paradigm shift from life expectancy distributions to a 10-year distribution is at its core a mathematical problem. Therefore, quantitative driven strategies can mitigate the impact of lost deferral and Roth conversions will be the primary tool for most families.

IMPORTANT NOTE: This is not a class designed to help wealthy clients, but rather will provide advice for the mass-affluent. The webinar materials will include easy to follow flowcharts, graphs and tables.

In this exclusive LISI Webinar, Bob review the following issues:

  • Critical Roth conversion concepts after SECURE
  • Critical strategies by profession and objectives
  • Roth conversions for rate arbitrage compared to traditional IRAs to trusts
  • 10+ Reasons to convert to a Roth IRA
  • Taxation of Roth IRA conversions and distributions
  • Easy to read conversion tables by common scenarios
  • How to use and analyze conversion software
  • Mathematics of Roth IRA conversions
  • Timing of Roth IRA conversions to gain tax rate arbitrage
  • Estate tax considerations
  • Why a Roth conversion is much better when an estate tax exists
  • The SECURE Act’s ten-year payout rule and the high tax rates to follow
  • “Stretch” Roth IRAs for eligible designated beneficiaries
  • Roths for SNTs and asset protection trusts
  • Roths to fund long-term care strategies
  • Hedging Roth conversions with life insurance
  • Using insurance to preserve post-death “stretch-out”
  • Tax-sensitive withdrawal strategies
  • Why a conversion is a “Bet-to-Live” Strategy and why insurance is a “Bet-to-Die” Strategy
  • Hedging Roths with Insurance
  • Easy to read charts, graphs and tables


There will be no CE for this webinar


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Robert S. Keebler, CPA/PFS, MST, AEP (Distinguished) is a partner with Keebler & Associates, LLP and is a 2007 recipient of the prestigious Accredited Estate Planners (Distinguished) award from the National Association of Estate Planners & Councils. He has been named by CPA Magazine as one of the Top 100 Most Influential Practitioners in the United States and one of the Top 40 Tax Advisors to Know During a Recession. Mr. Keebler is the past Editor-in-Chief of CCH's magazine, Journal of Retirement Planning, and a member of CCH's Financial and Estate Planning Advisory Board. His practice includes family wealth transfer and preservation planning, charitable giving, retirement distribution planning, and estate administration. Mr. Keebler frequently represents clients before the National Office of the Internal Revenue Service (IRS) in the private letter ruling process and in estate, gift and income tax examinations and appeals. In the past 20 years, he has received over 250 favorable private letter rulings including several key rulings of "first impression." Mr. Keebler is nationally recognized as an expert in estate and retirement planning and works collaboratively with other experts on academic reviews and papers, and client matters. Mr. Keebler is the author of over 75 articles and columns and editor, author, or co-author of many books and treatises on wealth transfer and taxation, including the Warren, Gorham & Lamont of RIA treatise Esperti, Peterson and Keebler/Irrevocable Trusts: Analysis with Forms. Mr. Keebler is the Chair of the AICPA's Advanced Estate Planning Conference. He is a featured columnist for CCH's Taxes Magazine - "Family Tax Planning Forum," Bob is also a contributing author to the American Bar Association's The ABA Practical Guide to Estate Planning. Robert.Keebler@KeeblerandAssociates.com

Jonathan G. Blattmachr is director of estate planning for Peak Trust Company, formerly Alaska Trust Company, and a director of Pioneer Wealth Partners LLC, a boutique wealth advisory firm in Manhattan. He is a retired member of Milbank, Tweed, Hadley & McCloy and of the New York and California bars. He is the author and co-author of eight books and over 500 articles, and has been chair of several committees of the New York and American Bar Associations and the American College of Trust and Estate Counsel. He is co-developer of Wealth Transfer Planning, a computerized system for lawyers that automatically generates estate planning documents such as wills and trusts, and provides specific client advice using a form of artificial intelligence. Jonathan served two years of active duty in the US Army, rising to the rank of Captain and was awarded the Army Commendation Medal. He is an instrument rated land and seaplane pilot and a licensed hunting and fishing guide in the Town of Southampton, New York.


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