
Retire Sooner with Wes Moss 5 Investing Pillars & Tax Tips for Retirement Planning
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Sep 18, 2025 Discover five essential investing pillars that guide decision-making in any market. Learn how capital gains tax rates can keep some investors in the 0% bracket and explore effective strategies for diversification. The discussion covers required minimum distributions and the 4% rule for retirement withdrawals. Plus, uncover the impact of tax-loss and tax-gain harvesting on returns. The conversation also highlights the increased senior tax deduction window for 2025-2028, and offers advice on choosing a trustworthy investment custodian for your assets.
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Avoid Concentration Risk
- Diversify beyond concentrated holdings or single legacy stocks.
- Avoid concentration risk because no trend or single sector lasts forever.
Diversify ESPP Proceeds Beyond S&P 500
- If your ESPP or company stock is large, diversify into broader or international funds.
- Consider equal-weight or international allocations to reduce mega-cap concentration.
Count RMDs Only When Spent
- Treat RMDs as spending only when money is actually consumed or used to pay taxes.
- Count toward your withdrawal rate only the portion of RMDs that leave your possession or are spent.


