Retire Sooner with Wes Moss

Gain clear, educational context on today’s investing and retirement planning topics with the Retire Sooner Podcast, hosted by Wes Moss and Christa DiBiase. This episode places market trends, investor behavior, and retirement account considerations into long-term perspective using historical data and widely referenced research.

In this episode, you’ll hear discussions that:

• Define the differences between small-cap, mid-cap, and large-cap stocks and explain how market-capitalization classifications are commonly discussed in retirement planning.

• Examine why individual investors have historically experienced returns that differ from market benchmarks, referencing behavioral research frequently cited by DALBAR.

• Compare recent performance trends between the S&P 500 and small-cap indexes while reinforcing that market leadership shifts across cycles.

• Explain how trillion-dollar companies have reshaped modern definitions of large-cap and mega-cap stocks.

• Review the types of investment options typically available in employer-sponsored retirement plans and discuss why chasing recent performance is often identified as a behavioral risk.

• Discuss why small-cap equities remain part of long-term market history conversations while acknowledging higher volatility and variability.

• Compare Roth IRAs and Health Savings Accounts (HSAs) by outlining differences in tax treatment, eligibility, and planning considerations.

• Explain how dividend-focused ETFs are commonly referenced in retirement income discussions and the historical role of dividends in total return.

• Reinforce the importance of diversification and disciplined decision-making by addressing behavioral tendencies such as fear of missing out, or FOMO.

• Address listener questions on market timing, lump-sum investing, Roth versus traditional 401(k) contributions, and Roth IRAs for younger earners using educational frameworks rather than personalized guidance.

Listen to the Retire Sooner Podcast on Apple Podcasts, Spotify, YouTube, or your favorite podcast platform—and subscribe to stay connected to conversations designed to provide context, discipline, and long-term perspective on retirement and investing.

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The Retire Sooner Podcast welcomes Clark Howard alongside Wes Moss and Christa DiBiase for a special episode focused on market history, long-term investing principles, and today’s most talked-about financial transitions. The conversation emphasizes context over commentary and highlights how investors often think through uncertainty, change, and market structure.

• Highlight Clark Howard’s perspective on Warren Buffett stepping down as CEO of Berkshire Hathaway at age 95 and the transition to Greg Abel.

• Review Berkshire Hathaway’s long-term role in markets and why its history is frequently referenced alongside the S&P 500.

• Frame why long-term market participation is commonly emphasized during periods of leadership change at iconic companies.

• Discuss why Clark Howard views this transition as the close of a defining chapter in modern investing history.

• Explain how Berkshire Hathaway’s conglomerate structure differs from traditional private equity, including transparency and fee considerations.

• Examine growing market concentration and the shrinking number of U.S. public companies—and why those trends continue to matter.

• Outline how exposure to both public stocks and privately held businesses is often discussed when considering diversification.

• Summarize several big-picture themes shaping 2026 conversations, including artificial intelligence, tax-refund dynamics, and election-cycle uncertainty.

• Clarify what “dry powder” means and how cash, money market funds, and select bonds are commonly described in retirement safety discussions.

• Address listener questions by reviewing general considerations around investing settlement proceeds, tax-advantaged accounts, and dividend-oriented ETFs.

This episode offers a thoughtful conversation featuring Clark Howard with Wes Moss, focused on long-term perspective rather than short-term reaction. Listen and subscribe to the Retire Sooner Podcast for ongoing discussions that bring clarity and context to retirement and investing topics.

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Start the year with structured context around today’s most frequently discussed retirement planning questions on the Retire Sooner Podcast, hosted by Wes Moss and Christa DiBiase. This episode presents an educational review of real listener scenarios, placing retirement, investing, and planning topics within a long-term analytical framework.

• Review current U.S. wealth statistics by discussing commonly cited data on net worth, retirement account balances, and generational financial trends.

• Outline household risk considerations by examining how families often think about emergency savings, retirement contributions, and income stability.

• Discuss real estate planning considerations by evaluating factors involved in purchasing a condo for college-bound children, including cash flow and potential resale dynamics.

• Describe fiduciary planning relationships by outlining services commonly associated with comprehensive retirement planning, tax coordination, and advisory fee structures.

• Explain the “Rule of 55” by clarifying how early access to employer-sponsored retirement plans is typically referenced.

• Summarize shared characteristics of long-term savers by highlighting recurring themes reported by listeners with higher household savings levels.

• Compare buffered ETFs by discussing how downside buffers and capped upside features are typically weighed within diversified portfolios.

• Examine mortgage buyout scenarios by outlining considerations for co-owned property, interest-rate assumptions, and loan structure implications.

• Analyze bond duration risk by discussing how interest-rate changes and yield-curve movements may influence long-duration bond pricing.

If you’re searching for clear, educational discussions around retirement planning, investing considerations, and household financial decision-making, this episode may add perspective. Listen and subscribe to the Retire Sooner Podcast for ongoing conversations that help place financial topics in a long-term context.

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What actually shapes life in retirement—your finances, your relationships, or both? In this episode of the Retire Sooner Podcast, Wes Moss and Christa DiBiase walk through new research on happiness in retirement and unpack several financial and economic topics that often come up in retirement planning conversations.

• Share findings from a 2025 Money and Happiness in America study that looks at how social connection is commonly linked to reported retirement satisfaction.

• Talk through research showing how the number of close personal relationships is often discussed when measuring happiness among retirees.

• Reflect on how American friendships have changed over time and why staying socially connected is frequently part of retirement lifestyle discussions.

• Put into context recent government jobs reports by explaining what unemployment and labor-market numbers generally indicate.

• Walk through estate-planning considerations around life insurance, guardians, and trustees that many families review over time.

• Cover the core factors people often look at when evaluating bond funds, including yield, duration, expenses, and benchmarks.

• Discuss how Roth IRAs, traditional IRAs, brokerage accounts, and HELOCs are commonly weighed when addressing short-term cash needs during real-estate transitions.

• Answer listener questions about Roth IRA contributions, in-plan conversions, account-funding priorities, and retirement-plan considerations when changing jobs.

The episode keeps the focus on education, context, and real-world questions retirees and pre-retirees are already asking. Listen and subscribe to the Retire Sooner Podcast for ongoing conversations that connect money, lifestyle, and long-term planning—without the hype.

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Looking for clear context around today’s most talked-about retirement planning issues? In this episode of the Retire Sooner Podcast, Wes Moss and Christa DiBiase present an educational discussion covering healthcare planning, retirement income considerations, Social Security decisions, and how current economic conditions are commonly framed in retirement conversations.

• Review current healthcare enrollment periods, including Affordable Care Act considerations, and why coverage timing is often discussed by early retirees.

• Illustrate a real-world healthcare planning example that examines estimating and managing medical costs before age 65 using publicly available comparison tools.

• Explain recent healthcare policy changes by outlining how subsidy rules and updated federal poverty thresholds are referenced in retirement healthcare planning.

• Contextualize recent Federal Reserve rate cuts by discussing how interest-rate changes are typically viewed in relation to mortgages, housing activity, and broader economic conditions.

• Address listener questions by outlining commonly discussed considerations around retirement timing, asset allocation approaches, principal-protected notes, and early retirement trade-offs.

• Compare Social Security claiming considerations by reviewing trade-offs associated with different filing ages based on individual circumstances.

• Clarify how taxable, tax-deferred, and tax-free accounts are often viewed together when discussing overall portfolio allocation.

• Share perspectives from retirees on aligning lifestyle goals—such as travel, part-time work, or relocating abroad—with sustainable withdrawal planning discussions.

• Reinforce why significant financial and healthcare decisions are commonly reviewed with qualified professionals before implementation.

Interested in an educational retirement podcast focused on context, trade-offs, and long-term planning awareness? Listen to this episode and subscribe to the Retire Sooner Podcast for ongoing conversations designed to inform retirement planning decisions—not predict outcomes.

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