Investing Unscripted

135. 2025 and Beyond

6 snips
Jan 1, 2025
The hosts reflect on the past year's investment journeys and evolving strategies, emphasizing a move towards more conservative investments. They dive into tax loss harvesting tactics and the emotional nuances of selling underperforming stocks. Long-term financial goals and the balance between growth and dividend stocks take center stage as they outline actionable steps for 2025. The discussion also highlights the importance of pensions and the benefits of consulting with financial advisors for better retirement planning.
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ANECDOTE

Tax-Loss Harvesting Excuse

  • Jeff Santoro uses tax-loss harvesting to sell stocks he wants to sell anyway.
  • He disguises his desire to sell by calling it tax-loss harvesting.
ADVICE

Offsetting Gains

  • Consider selling losing stocks to offset large gains and reduce your tax bill.
  • Wait at least 31 days to repurchase them to avoid the wash rule.
ADVICE

Selling Losers

  • Sell losing stocks if you've lost conviction in the underlying business, not just because the price dropped.
  • Maximize tax opportunities like 401(k) contributions and Roth IRAs.
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