Retire Sooner with Wes Moss

Wes Moss
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Nov 6, 2025 • 39min

COLA Updates, AI, and Diversification: Mapping the Modern Retirement Landscape

Stay informed about the changing retirement landscape with hosts Wes Moss and Christa DiBiase as they unpack today’s relevant financial topics—from the growing influence of AI-related stocks to strategies for maintaining a well-balanced retirement plan. This episode of the Retire Sooner Podcast focuses on education, awareness, and practical insights to help you better understand the factors that can potentially shape your long-term financial journey. • Explore how AI-related stocks are influencing the S&P 500 and what increased market concentration may mean for maintaining a diversified investment mix. • Review thoughtful rebalancing considerations designed to help preserve diversification across asset classes—including small caps, mid caps, international equities, and fixed income. • Understand the structure and potential risks of employee stock purchase plans (ESPPs), including holding periods and portfolio exposure considerations. • Clarify what the idea of a “million-dollar retirement” represents by examining how individual goals, income needs, and household spending habits differ. • Consider long-term planning concepts such as Roth IRA conversions for inherited assets and the potential benefits of engaging multiple generations in family financial discussions. • Examine the latest Social Security Cost of Living Adjustment (COLA), how it compares historically, and common perspectives regarding future program sustainability. • Evaluate options for managing excess savings allocated toward shorter-term goals—such as travel or home projects—based on time horizon and comfort with potential market movement. • Discuss flexible withdrawal and income planning considerations that may help support the transition from early retirement to Social Security eligibility. Enhance your financial awareness and stay up to date with the Retire Sooner Podcast. Listen and subscribe for educational discussions on market trends, retirement fundamentals, and strategies to help you make well-informed financial decisions. Learn more about your ad choices. Visit megaphone.fm/adchoices
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Oct 30, 2025 • 50min

Clark Howard Joins Wes Moss to Discuss Market Context, Investor Behavior, and Retirement Trends

In this special episode of The Retire Sooner Podcast, Wes Moss speaks with nationally recognized consumer advocate Clark Howard about current topics shaping the financial and retirement landscape. Their conversation centers on how investors can think more clearly about markets, behavioral finance, and long-term planning in today’s changing economy. • Discuss how shifting economic conditions are influencing how Americans view retirement readiness. • Review market valuation trends and how historical context can inform today’s conversations around investing. • Compare different investment philosophies that emphasize patience, discipline, and perspective. • Examine how technological advancements, including artificial intelligence, may affect corporate performance and investor sentiment. • Consider the concentration of large-cap companies in market indexes and what that means for diversification discussions. • Recognize the role of behavior and emotion in financial decision-making, especially during market volatility. • Reflect on lessons from past market cycles that highlight the importance of long-term participation and steady perspective. • Address common retirement concerns, such as inflation and uncertainty, through the lens of thoughtful financial planning. • Explore the emergence of private equity options in retirement plans and potential considerations around structure, transparency, and access. • Emphasize the value of continued education and awareness in navigating evolving retirement landscapes. This conversation between Wes Moss and Clark Howard focuses on education, context, and perspective—helping listeners stay informed about financial and retirement trends. Listen and subscribe to The Retire Sooner Podcast for ongoing discussions that encourage thoughtful understanding of markets, money, and financial planning concepts. Learn more about your ad choices. Visit megaphone.fm/adchoices
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10 snips
Oct 23, 2025 • 37min

How Private Equity, 401(k) Changes, and Emerging Trends May Be Reshaping Retirement Planning

Discover how private equity could soon be part of 401(k) plans, reshaping retirement investing. Explore the impact of the FIRE movement and the flexibility a $1 million nest egg can offer. Learn about the nuances between Roth and traditional 401(k) options. Delve into conservative investment strategies and the role of private equity in today’s market. The hosts also provide tips on teaching family wealth values and insights on covered call ETFs for income generation!
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Oct 16, 2025 • 46min

From “Set” to “Settled”: Finding Confidence and Calm in Your Financial Life | Retire Sooner Podcast

Join Wes Moss and Christa DiBiase on the Retire Sooner Podcast, where real-life financial questions meet clear, grounded discussions about retirement planning, investing, and financial wellbeing. This episode explores practical ways individuals can make informed decisions, manage uncertainty, and approach retirement with more clarity and confidence. • Review how the current bull market compares to past market cycles and what history may suggest about long-term investment behavior. • Reflect on the difference between being financially “set” and emotionally “settled” when preparing for retirement. • Evaluate potential considerations when choosing to pay down a mortgage or allocate extra cash toward long-term financial goals. • Understand how 401(k) providers record traditional and Roth contributions and maintain accurate tax reporting for participants. • Compare UGMA/UTMA custodial accounts and 529 plans as common education savings options, each with unique features and limitations. • Recognize that effective financial planning includes lifestyle, estate, tax, withdrawal, and healthcare considerations—not just investment management. • Discuss common causes of retirement-related anxiety and explore approaches that can help promote greater financial peace of mind. • Clarify how management fees appear in fund performance and why transparency matters when reviewing investment options. • Comprehend the pros and cons of financial planners who communicate clearly, align with your comfort level, and structure their services to support your individual needs. • Consider how consistent investing through dollar cost averaging has sometimes reduced emotional reactions to short-term market volatility. Listen and subscribe to the Retire Sooner Podcast for thoughtful conversations about retirement planning, financial confidence, and long-term investing strategies that can help you navigate your own financial journey with purpose. Learn more about your ad choices. Visit megaphone.fm/adchoices
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Oct 9, 2025 • 46min

The American Dream Reset: Retirement Costs, Inflation, and Savings Strategies

Curious how today’s costs, inflation trends, and shifting expectations are shaping the American Dream? Join Wes Moss and Christa DiBiase on the Retire Sooner Podcast as they provide context on financial headlines, explore common planning questions, and share research-informed insights for your retirement journey. • Explore the discussion around what it may take to reach the American Dream and whether a $5 million lifetime target is a realistic benchmark. • Review how inflation has historically influenced the stock market and why the concept of a “Goldilocks zone” may be relevant for long-term investors. • Compare how inflation can affect different categories of stocks, including dividend-paying and growth-oriented companies. • Discuss what pursuing a CFP designation or considering a late-stage career shift into financial planning might involve. • Consider how high-yield bond ETFs are typically viewed in the marketplace and why “junk bonds” continue to spark debate among investors. • Examine different ways couples might think about retirement savings benchmarks—whether by age-based charts or total household goals. • Illustrate the role of compound growth in both saving and investing when working toward retirement readiness. • Highlight factors to weigh when assessing whether to maintain or drop life insurance as retirement approaches, including debt, dependents, and overall assets. • Outline new Secure 2.0 provisions that allow certain 529 plan funds to be redirected to Roth IRAs for children. • Showcase how automation and behavioral systems can encourage consistent savings habits across different income levels and career stages. Every financial situation is unique, but gaining context can help make more informed choices. Listen now and subscribe to the Retire Sooner Podcast for ongoing conversations that keep you engaged with today’s retirement and financial planning landscape. Learn more about your ad choices. Visit megaphone.fm/adchoices
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Oct 2, 2025 • 39min

Retirement Planning Insights, TSP Education, and Family Money Conversations

Explore practical retirement planning strategies and gain clarity on key financial decisions in this engaging episode of the Retire Sooner Podcast. Wes Moss and Christa DiBiase discuss common questions and considerations for savers and soon-to-be retirees, providing perspectives on investment options and long-term planning frameworks. • Discover how a focused 30-minute financial conversation between spouses about income, assets, and liabilities can reduce uncertainty and help families feel more organized and informed in their money matters. • Understand why nearly half of Americans do not have a written financial plan and what this may indicate for retirement preparedness. • Clarify retirement account protections within TSPs, along with rules for required minimum distributions (RMDs) and available investment options after age 73. • Examine UTMA and UGMA accounts for minors, including potential tax implications, gifting considerations, and impact on financial aid eligibility. • Consider when a financial planner may be appropriate, approaches to managing planning-related FOMO, and the features of advisory services offered by various firms. • Explore the 0.01% Rule of thumb and how it may guide thinking about saving versus spending without implying specific outcomes. • Review historically effective withdrawal rates, including whether a paid-off home could influence planning assumptions and evolving perspectives on the 4% rule of thumb. • Assess strategies such as “buy, borrow, die”, including potential tax considerations, leverage, and portfolio risk factors. • Compare keeping assets in a TSP for Roth conversions versus transferring them to another custodian, considering fees and investment options. Gain perspective and knowledge to help support thoughtful retirement planning decisions—listen now to the Retire Sooner Podcast. Learn more about your ad choices. Visit megaphone.fm/adchoices
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Sep 25, 2025 • 39min

Fed Actions, 72(t) Rules, and Investment Strategies: Retirement Planning Made Clear

Gain a clear perspective on retirement planning in this episode of the Retire Sooner Podcast, hosted by Wes Moss and Christa DiBiase, where listener questions meet the latest financial planning insights. Discover practical considerations that can help inform decisions about your long-term financial strategy. • Examine how the Federal Reserve’s interest rate cut may influence mortgages, loans, and stock market activity. • Understand why homeowners may appear “locked in” to current mortgage rates and explore potential shifts in housing trends. • Explore how the Fed balances inflation with employment data and what this could mean for your financial outlook. • Review historical stock market outcomes following Fed rate cuts near all-time highs. • Consider strategies for small business growth, including business checking accounts and high-yield options. • Compare dividend reinvestment with manual reallocation to assess approaches for your retirement phase. • Navigate backdoor Roth IRA contributions, conversions, gains, and tax-efficient dollar-cost averaging. • Address common retirement questions and explore planning steps that may provide financial clarity. • Benchmark savings against national averages and examine actionable retirement milestones. • Utilize spousal IRAs to maintain contributions while transitioning toward retirement. • Understand 72(t) IRA withdrawals and evaluate flexibility for early retirement considerations. • Assess ultra-high-yield ETFs and review the potential risks of concentrated portfolios. Listen and subscribe to the Retire Sooner Podcast to stay informed and explore considerations that can support your financial planning and retirement goals. Learn more about your ad choices. Visit megaphone.fm/adchoices
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21 snips
Sep 18, 2025 • 38min

5 Investing Pillars & Tax Tips for Retirement Planning

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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Sep 11, 2025 • 42min

Maximize Retirement Income & Plan for Early Financial Freedom

Curious how to manage your 401(k), Social Security, and retirement withdrawals in today’s market? On this episode of the Retire Sooner Podcast, Wes Moss and Christa DiBiase break down practical strategies for navigating retirement planning, taxes, and investment decisions so you can make informed choices for your financial future. • Examine why a strong stock market may not reflect the real economy and what seems to be influencing current market movements. • Break down company stock in 401(k)s and explore how net unrealized appreciation (NUA) can affect tax planning. • Explore listener examples of balancing Social Security benefits and retirement account withdrawals to create a thoughtful income plan. • Review early retirement rules, including 457 plans, 72(t) distributions, and the rule of 55, and how they often impact access to funds. • Analyze estate planning mistakes, even among high-profile cases, to understand potential pitfalls and planning considerations. • Compare brokerage accounts, investment research tools, and target-date funds to evaluate what may fit your individual situation. • Evaluate the trade-offs between mortgage payoff strategies and staying invested when interest rates fluctuate. • Clarify how Roth 401(k) and IRA withdrawal rules differ before age 59 ½ and what that could mean for accessing retirement funds. Gain actionable insights and considerations to help make informed retirement planning decisions. Listen now and subscribe to the Retire Sooner Podcast to stay updated on the key factors shaping today’s financial planning and retirement strategies. Learn more about your ad choices. Visit megaphone.fm/adchoices
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Sep 4, 2025 • 47min

Balancing Stability and Growth in Today’s Retirement Landscape

Ready to explore new perspectives on retirement planning? In this episode of the Retire Sooner Podcast, Wes Moss and Christa DiBiase examine money, markets, and financial strategies, highlighting ways thoughtful planning may help support financial confidence. ·       Review how stock dividends have historically compared with bond interest over the long term. ·       Explain total return as the combination of growth and income, and discuss how it relates to inflationand purchasing power. ·       Compare the historical performance of stocks and bonds and outline the effects of compounding over decades. ·       Consider the role of bonds in a portfolio, particularly for those seeking stability and diversification. ·       Address listener questions on money supply, cash reserves, risk tolerance, and the potential influence of guaranteed income sources on retirement timelines. ·       Explore options for self-employed retirement savings, including the flexibility of solo 401(k) plans. ·       Reflect on the psychological value of having a financial plan during periods of market uncertainty. ·       Highlight trends in U.S. manufacturing productivity, including the impact of AI, robotics, and Midwest innovation. ·       Discuss approaches to balancing an emergency fund with retirement contributions, and review considerations around Roth accounts. ·       Examine practical examples of retirement-related decisions, such as early home purchases, Roth IRA conversions, and considerations for taxes, Social Security, and pensions. Gain insights into the discussions shaping retirement planning and investing today. Listen and subscribeto the Retire Sooner Podcast to explore more perspectives that can help guide your financial journey. Learn more about your ad choices. Visit megaphone.fm/adchoices

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