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Retire Sooner with Wes Moss

Wes Moss
Retire Sooner with Wes Moss
Latest episode

305 episodes

  • Retire Sooner with Wes Moss

    Are AI and Job Fears Overblown? What the Data Shows

    05/07/2026 | 32 mins.
    Do headlines about AI, jobs, and markets feel overwhelming? Let this episode of the Retire Sooner Podcast help put things into perspective, using real data and relatable scenarios to connect today’s trends with everyday financial decisions.

    • Rethink college graduate unemployment and see how AI may be shaping hiring, with recent data pointing to more stability than disruption.

    • Put the U.S. job market in context by examining constant turnover, career shifts, and ongoing opportunity.

    • Consider what a midlife career change might look like while factoring in updated 529 plan rules that may offer more flexibility.

    • Clarify Roth IRA and Roth 401(k) rules to help keep timelines intact and simplify account management.

    • Assess the U.S. dollar’s global role and why it continues to anchor trade and reserves despite the noise.

    • Look inside mutual funds and ETFs to better understand what you own, while keeping diversification and allocation in focus.

    • Map out retirement income by considering dividends, distributions, and multiple cash flow sources working together over time.

    Listen to the Retire Sooner Podcast to hear Wes Moss and Christa DiBiase bring these topics to life with clarity and context. Subscribe for more grounded conversations designed to help support thoughtful, long-term financial decision-making.

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  • Retire Sooner with Wes Moss

    Retirement Planning Reset: Retirement Confidence, Roth Strategies, Fiduciary Standards & Income Planning Context

    04/30/2026 | 36 mins.
    Take a step back and get a clearer view of your retirement plan in this episode of the Retire Sooner Podcast with Wes Moss and Christa DiBiase. Enjoy a practical, easy-to-follow conversation that connects real data, real questions, and real-life planning: offering perspective to help guide decisions.

    • Explore why retirement confidence may be slipping, using insights from the Employee Benefit Research Institute and the University of Michigan, and see how inflation and oil prices have historically been associated with changing outlooks.

    • Break down the difference between fiduciary and non-fiduciary advisors to provide a backdrop when evaluating who you trust with your financial picture.

    • Walk through listener questions on 457(b) vs. 401(k) plans, Roth vs. traditional strategies, and how early retirement access rules actually work.

    • Get more clarity on VEBA HRA accounts vs. HSAs, and consider what may be affecting Roth IRA growth—including allocation choices and tools used.

    • Think through when a trust might make sense and how savings accounts, money markets, and bonds may play different roles as interest rates shift.

    • Consider ways to prepare for long-term care costs, including self-insuring concepts that tie into income planning and HSA savings over time.

    Looking to explore big picture retirement planning without getting lost in the weeds? This episode is a great place to start. Listen and subscribe to the Retire Sooner Podcast!

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  • Retire Sooner with Wes Moss

    What Drives a Fulfilling Retirement? Income Strategy, Location, and Purpose

    04/23/2026 | 31 mins.
    On this episode of the Retire Sooner Podcast, step back and reassess your retirement plan as Wes Moss and Christa DiBiase examine what may drive retirement happiness. Connect financial independence, taxes, and today’s economic backdrop into a clearer long-term perspective. See how big decisions, from pensions to property taxes to market uncertainty, may fit together to help evaluate what matters most for your own path.

    • Reimagine how achieving financial independence may shift your sense of purpose, and consider ways to redirect that drive toward a more fulfilling retirement.

    • Size up how property taxes may shape where you live and your retirement comfort level over time.

    • Stack up lump-sum versus pension-income options to help understand the trade-offs among flexibility, longevity risk, and steady income.

    • Map out retirement withdrawal strategies using historical market data and behavioral factors, while recognizing that outcomes may vary.

    • Make sense of today’s “mixed signals” economy by connecting jobs data, corporate margins, inflation, and Federal Reserve policy as context, not predictions.

    • Think through options for late starters and compare 529 plans with Solo Roth 401(k)s as potentially flexible ways to approach education funding within a broader plan.

    Listen to the Retire Sooner Podcast to hear the full conversation and explore how these ideas may apply to your situation. Subscribe for more thoughtful, real-world context on retirement planning, investing, and the decisions that shape long-term financial life.

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  • Retire Sooner with Wes Moss

    Where Should You Live in Retirement? (And How to Pay for It)

    04/16/2026 | 40 mins.
    Rethink retirement, and how the financial and lifestyle choices of today may shape tomorrow. In this episode of the Retire Sooner Podcast, Wes Moss and Christa DiBiase bring real-world context to retirement planning, housing decisions, investment strategies, and tax considerations.

    • Discover how consistent saving and long-term investing have historically supported greater flexibility in retirement, though past performance does not guarantee future results and may not indicate future market direction.

    • Picture how your retirement location, cost of living, and closeness to family may shape your day-to-day happiness.

    • Use a simple framework to research and test potential retirement destinations before making a big move.

    • Navigate housing transitions by thinking through timing gaps, home equity access, and tax considerations.

    • Compare ways to fund a home purchase using Roth IRAs, traditional IRAs, and brokerage accounts.

    • Understand how TSP, high-yield savings, mutual funds, and ETFs differ in fees, taxes, and flexibility.

    • Weigh whether keeping a TSP or rolling assets into an IRA may fit your broader financial picture.

    • Examine how investment fees and annuities may play a role in long-term planning decisions.

    • Consider early retirement scenarios by factoring in income variability, taxes, and sustainability over time.

    Take a fresh look at your retirement strategy with insights grounded in real-life decisions and long-term thinking. Listen and subscribe to the Retire Sooner Podcast for more educational content to help inform your financial decisions.

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  • Retire Sooner with Wes Moss

    Lump Sum vs Pension, Dividends & Market Risks Explained

    04/09/2026 | 41 mins.
    If the financial headlines feel overwhelming, Wes Moss and Christa DiBiase help bring things back into focus. This episode of the Retire Sooner Podcast ties real listener questions to long-term investing principles, offering context to support more informed decision-making.

    • Examine why many Americans feel financially behind while weighing the risks often associated with higher-risk areas such as crypto, meme stocks, options trading, and sports betting—and the behavioral pull of comparison-driven investing.

    • Evaluate pension choices by comparing lump sum payouts versus lifetime income streams in the context of longevity, income needs, and personal financial goals.

    • Understand how dividends may factor into total return and how reinvestment has historically contributed to long-term investment outcomes.

    • Assess how to use proceeds from a home sale by balancing debt reduction, investment opportunities, and liquidity for future flexibility.

    • Explore investment options often considered more conservative, such as Treasury money markets and short-term bond ETFs, while recognizing trade-offs between stability, income, and interest rate risk.

    • Differentiate between fixed annuities and CDs by reviewing guarantees, liquidity considerations, and how each may fit within a broader retirement income strategy.

    • Take a fresh look at your portfolio by balancing different time horizons, being mindful of taxes, and thoughtfully managing RSU stock (Restricted Stock Units) with an emphasis on diversification.

    Listen and subscribe to the Retire Sooner Podcast for more educational conversations about financial decisions and the world around them.

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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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