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Retire Sooner with Wes Moss

Wes Moss
Retire Sooner with Wes Moss
Latest episode

294 episodes

  • Retire Sooner with Wes Moss

    From Roth Rules to Small Caps: Today’s Headlines and Your Retirement Strategy

    02/19/2026 | 38 mins.
    Retirement decisions don’t often happen in isolation—they’re shaped by markets, policy shifts, career trends, and personal trade-offs. In this episode of the Retire Sooner Podcast, Wes Moss and Christa DiBiase translate timely financial headlines into practical retirement planning considerations.

    • Assess cash-flow strategies for small business owners, including how Roth IRA contribution rules may create flexibility.

    • Interpret the latest U.S. jobs report and education-level unemployment trends to help frame portfolio and career decisions.

    • Evaluate small-cap and value stock performance after years of lagging returns within a diversified allocation.

    • Examine why savings account rates may trail broader interest rate moves and what that can mean for cash positioning.

    • Compare long-term care insurance with self-funding approaches, including planning implications tied to Washington State’s LTC program.

    • Review 457 and 403(b) rollover considerations and clarify how early Social Security benefits are calculated.

    • Measure total investment results by factoring in dividends and interest income—not just price changes.

    Explore retirement planning considerations through balanced, long-term thinking grounded in real data and real scenarios. Listen and subscribe to the Retire Sooner Podcast to stay aligned with today’s evolving financial landscape.

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  • Retire Sooner with Wes Moss

    Inflation Is Back: Markets, Portfolios, and Retirement Trade-Offs

    02/12/2026 | 41 mins.
    Inflation is back in focus—and it’s reshaping how many people think about retirement decisions. In this episode of the Retire Sooner Podcast, Wes Moss and Christa DiBiase answer listener questions while providing clear context around markets, portfolios, and long-term planning trade-offs.

    • Explore how inflation cycles have historically resurfaced and how price shocks may influence spending and wage conversations.

    • Compare growth and value stocks using simple analogies that help clarify their role in retirement portfolios.

    • Break down how retirement withdrawals and tax planning are commonly coordinated, including Roth conversions and differences between 457 and 401(k) plans.

    • Explain key considerations around Employee Stock Ownership Plans, including diversification challenges in private companies.

    • Discuss where bonds and cash may fit when dependable income already covers everyday expenses.

    • Consider how lump sums and ongoing savings are often invested while balancing valuation concerns with disciplined approaches like dollar-cost averaging.

    • Review how buffered investment strategies are typically evaluated, including trade-offs involving downside limits, liquidity, and long-term return expectations.

    • Clarify pension payout choices by outlining common tax considerations and rollover mechanics tied to lump-sum decisions.

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    If inflation headlines and market swings have you rethinking your plan, this episode adds perspective without the noise. Listen and subscribe to the Retire Sooner Podcast to stay grounded in ongoing market and retirement conversations.

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  • Retire Sooner with Wes Moss

    When Markets Get Loud: A Clear Look at Retirement Planning Choices

    02/05/2026 | 35 mins.
    Concerned about retirement planning in a market full of uncertainty and noise? In this episode of the Retire Sooner Podcast, Wes Moss and Christa DiBiase bring practical context to today’s financial headlines and common retirement questions.

    • Analyze movements in gold prices and the U.S. dollar to clarify what currency shifts may indicate for markets and everyday economic conversations.

    • Explain why a modestly weaker dollar is not inherently negative and how it can affect U.S. company competitiveness.

    • Break down how the 4% retirement withdrawal rule of thumb is commonly discussed and why flexibility is central to long-term planning.

    • Compare viewpoints from prominent financial commentators on sustainable retirement withdrawals and why results may differ by household.

    • Outline considerations for retirement drawdowns, including when cash reserves versus equities are often referenced during market stress.

    • Evaluate diversification considerations for investors concerned about concentrated exposure to technology- and AI-focused funds.

    • Address the widespread concern about running out of money in retirement using commonly referenced planning frameworks.

    • Review how pension cost-of-living adjustments work and the factors considered when comparing lump-sum and annuity options.

    • Discuss the potential role and risks of high-yield bonds within balanced, income-focused portfolios.

    • Highlight why aligning brokerage account registrations with a living trust is frequently referenced in estate planning discussions.

    Listen to the Retire Sooner Podcast for clear, educational context on the retirement topics investors are talking about right now. Subscribe to stay connected to ongoing conversations focused on long-term planning, discipline, and perspective.

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  • Retire Sooner with Wes Moss

    The Middle Class Debate And Today’s Retirement Planning Landscape

    01/29/2026 | 40 mins.
    Is the American middle class actually shrinking, or evolving? In this episode of the Retire Sooner Podcast, Wes Moss and Christa DiBiase offer educational context on widely discussed economic, investing, and retirement planning topics shaping today’s financial conversations.

    Listen as long-term data, market history, and household-level considerations are used to frame—not forecast—how these issues connect.

    • Examine why the U.S. middle class is often described as shrinking and how income mobility, inflation-adjusted thresholds, and household dynamics influence that narrative.

    • Review how artificial intelligence is commonly discussed in relation to productivity, workforce demand, and labor market participation.

    • Outline general considerations around emergency savings, including income consistency, job stability, and insurance coverage.

    • Explain factors households often weigh when deciding whether to engage a financial professional for planning support.

    • Provide historical context on gold, market corrections, and why gold is sometimes referenced in diversification discussions.

    • Summarize why dividends are frequently included in long-term investing conversations across market cycles.

    • Highlight planning considerations for investment club assets, including potential capital gains implications during account or custodian transitions.

    • Examine variables that may influence retirement spending needs, reinforcing that planning outcomes vary by household.

    • Compare commonly discussed perspectives on dollar-cost averaging versus lump-sum investing during periods of market volatility.

    This episode focuses on education and perspective—not individualized recommendations. Listen and subscribe to the Retire Sooner Podcast for ongoing conversations that place investing and retirement topics into long-term context.

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  • Retire Sooner with Wes Moss

    Big Stocks, Small Caps, and Investor Behavior: What Today’s Markets Reveal

    01/22/2026 | 37 mins.
    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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About Retire Sooner with Wes Moss

Wes Moss is on a mission: help at least 1 million Americans of any age retire sooner and find joy along the way. A seasoned finance professional, best-selling author, broadcaster, and teacher, Wes has done extensive research on the habits of the happiest retirees. On this podcast, Wes shares key lifestyle and money habits you can implement now to prepare for a secure future while not depriving yourself of happiness in the present. In addition to leveraging his 20+ years of knowledge as an investment advisor, Wes brings in guests and specialists to teach you how to set and work towards your financial and lifestyle objectives. Refreshingly-free of mind-numbing financial jargon and unrealistic money goals, Retire Sooner with Wes Moss gives listeners the tools on how to retire sooner in the real world.
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