Tax Season Is Our Super Bowl

EPIC list of tax planning moves we just saw pay off on a client’s 2025 return

  • $300K+ of harvested capital losses to offset gains from private investments
  • ~$250K of ordinary losses to shield RMDs and Roth conversion income (while moving PE into Roth)
  • ~$350K of depreciation deductions to offset rental income for years to come
  • Donated highly appreciated stocks into a donor‑advised fund (DAF) instead of cash
  • Used margin interest expense from a long/short SMA to reduce taxable dividends

This is why I say your investment portfolio and your tax plan should be the same conversation, not separate silos.

We genuinely have fun doing this work and 4/15 is our Super Bowl, because we get to see all the planning show up on the return.

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