Love, your Money - Wealth, Money, and Financial Advisor for Women

280: Maximize Gains and Minimize Taxes: Introducing Ultra Tax Efficient Wealth Management℠, Part One

May 13, 2025
Robert Hendershott, Chief Investment Officer with decades in investments and hedge funds, explains Ultra Tax Efficient Wealth Management. He and Hilary unpack tax deferral, long-short overlays using individual stocks, and why personalized tax-aware strategies can multiply long-term wealth. They also cover risks, implementation challenges, and who benefits most.
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INSIGHT

Tax Deferral Multiplies Wealth

  • Tax deferral compounds wealth by letting you earn returns on money you would otherwise pay in taxes.
  • Hilary illustrates with a $1M home vs $750k after taxes: deferral creates an extra $10k/year at 4% that compounds into material wealth.
INSIGHT

Create Losses To Offset Gains Without Losing Returns

  • Ultra Tax Efficient Wealth Management (UTEWM) generates predictable realized losses to offset capital gains without materially changing portfolio returns.
  • Robert explains the overlay creates losses in a slice of the portfolio while the overall portfolio remains intact.
ANECDOTE

How They Would Rotate ETFs To Realize Losses

  • Robert gives a simplified Amazon example: convert $1M Amazon position into a paired long/short S&P ETF overlay to book losses while keeping net exposure.
  • They rotate among SPY, IVV, VOO to sell the losing ETF and immediately replace it, locking tax losses like $20k per cycle.
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