Retire Sooner with Wes Moss

5 Investing Pillars & Tax Tips for Retirement Planning


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Gain clarity on investing and retirement planning with this engaging episode of the Retire Sooner Podcast, hosted by Wes Moss and Christa DiBiase. Whether you’re navigating strong markets or uncertainty, this conversation provides frameworks and explanations to help support your retirement planning.

• Unpack five pillars of investing that may guide decision-making across both strong and volatile markets.

Clarify how capital gains tax rates work, including how some investors may stay in the 0% long-term bracket under current tax law.

Address listener questions on diversification, from S&P 500 funds to total market and international fund considerations.

Examine how required minimum distributions (RMDs) may fit into retirement withdrawals alongside concepts such as the 4% rule.

• Break down cost basis options with Vanguard and explain how tax-loss and tax-gain harvesting may impact your returns.

Highlight the new, increased senior tax deduction window (2025–2028) and what it could mean for retirees.

Consider strategies for investing short- and intermediate-term savings for kids and teens by aligning time horizon with risk.

Evaluate why choosing a reputable investment custodian may matter and what questions can be asked about where assets are held.

Stay informed and proactive—listen now and seek to expand your understanding of investing and tax planning. Subscribe to the Retire Sooner Podcast for weekly conversations designed to keep you engaged with today’s financial landscape.


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Retire Sooner with Wes MossBy Wes Moss

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