

Retire Sooner with Wes Moss
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.
Episodes
Mentioned books

Aug 28, 2025 • 42min
Social Security, Taxes, REITs, and More: Exploring Key Retirement Planning Topics
Explore how today's financial choices impact your future happiness and confidence in retirement. Understand the implications of large IRA withdrawals on Medicare premiums and learn smart strategies for managing taxable income. Discover the intriguing concept of tokenization in investing and the potential for fractional ownership. Delve into Social Security survivor benefits and clarify dependency rules affecting grandchildren. Plus, assess the role of REITs in your investment portfolio and why withdrawal planning remains crucial for effective retirement planning.

Aug 21, 2025 • 38min
From Asset Allocation to Market Trends: Tools for Thoughtful Retirement Planning
Get ready to rethink retirement with Wes Moss and Christa DiBiase as they examine the realities of investing, financial security, and planning for a fulfilling future. This episode of the Retire Sooner Podcast delivers actionable insights, practical frameworks, and real-world examples to inform your retirement planning decisions.
Hear a retirement story illustrating how asset allocation strategies can change over longer time horizons.
Explore how retirees might evaluate investment choices when guaranteed income streams exceed spending needs.
Question the traditional “own your age in bonds” rule and consider how personal comfort with market risk can shape retirement planning.
Understand the Federal Reserve’s influence on interest rates and what rate changes may mean for savings, housing, and the broader economy.
Examine the inverted yield curve and consider historical patterns regarding economic slowdowns.
Identify market sectors, including consumer staples and utilities, that may show relative stability during market fluctuations.
Clarify misconceptions about global stock market capitalization and assess how international diversification may fit into a retirement plan.
Review the 6% test as a framework for comparing pension lump sum options and monthly payments.
Consider wealth-building benchmarks and habits for younger savers that support gradual accumulation over time.
Explore irrevocable trusts and other legal strategies that may help manage and protect certain assets.
Listen as Wes and Christa address listener questions covering retirement planning considerations across different life stages.
Empower yourself with knowledge and thoughtful considerations for your financial future. Listen and subscribe to the Retire Sooner Podcast for weekly discussions on investing, retirement planning, and financial security 🎧 Learn more about your ad choices. Visit megaphone.fm/adchoices

17 snips
Aug 14, 2025 • 49min
Balanced Investing, Roth Conversions & Estate Planning Strategies
In this discussion, Christa DiBiase, a financial expert who has collaborated with Clark Howard, dives into the evolution of balanced investing and challenges the traditional 60/40 strategy. She explains the intricacies of Roth conversions and highlights the importance of tailored financial advice versus self-management. Christa also explores the monumental $84 trillion Great Wealth Transfer, emphasizing the necessity of estate planning and family communication regarding inheritances. Listeners gain valuable insights into optimizing their portfolios and making informed financial choices.

Aug 7, 2025 • 44min
Retirement Catch-Up Strategies, Social Security Timing & Essential Planning Insights
Kickstart your journey to a happier, earlier retirement with this high-energy episode of the Retire Sooner Podcast, where Wes Moss and Christa DiBiase tackle real listener questions and spotlight flexible strategies that could help you build a more confident retirement plan. Whether you're in your 40s, 50s, or beyond, get motivated to consider meaningful actions—starting now.
• Jump-start your savings approach in your 40s and 50s, even if you're just beginning to focus on retirement.
• Unlock the “50+ Retirement Catch-Up Toolbox” with tools like Roth conversions, HSAs, and enhanced contribution limits.
• Discover what’s ahead with new “super catch-up” contribution rules and upcoming IRS changes that may impact your planning.
• Maximize your Social Security outlook by understanding how the timing of withdrawals could influence your benefits.
• Hear how annuities and home equity were discussed as potential components in long-term financial planning.
• Tune in to real-world stories from listeners managing late-in-life parenting, mortgages, and the pursuit of financial independence.
• Reconsider the risks and rewards of penny stocks with a balanced conversation about their place in a retirement portfolio.
• Weigh the role of pensions in your overall asset allocation for a more personalized investment approach.
• Rethink your withdrawal game plan with a closer look at the 4% rule—its origins and relevance today.
• Confront concerns around global exposure by reviewing how emerging markets and China-related investments might affect your portfolio.
• Strengthen your retirement mindset with income-focused planning designed to help support a more stable financial future.
Get energized with actionable ideas and relatable stories that help make retirement planning feel more approachable. 🎧 Listen and subscribe to the Retire Sooner Podcast to join a community focused on financial clarity and living a purpose-filled retirement.
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Jul 31, 2025 • 35min
Are You Richer Than You Think? Retirement Benchmarks and Planning Insights
Think you might be richer than you realize? In this episode of the Retire Sooner Podcast, Wes Moss and Christa DiBiase examine realistic benchmarks and practical frameworks for retirement planning.
• Define what the “rich ratio” means and consider how it may reframe your retirement outlook.
• Compare your savings habits to U.S. medians to understand the broader landscape.
• Acknowledge that building wealth typically occurs over long periods and that consistency can be meaningful.
• Discuss research on how happiness and financial confidence often plateau beyond certain savings levels.
• Evaluate the roles of traditional and Roth IRAs, 457(b)s, pensions, and brokerage accounts to support flexibility.
• Identify scenarios where a standalone brokerage account may be unnecessary for certain savers.
• Consider a target date fund allocation approach that may better align with your stated risk tolerance.
• Weigh convenience, costs, and tax features of index mutual funds versus ETFs, including changes following a major fund industry patent expiration.
• Clarify how the Net Unrealized Appreciation (NUA) rule for company stock in 401(k)s works and where tax treatment can differ.
• Review key factors when choosing between a state pension plan and a self directed plan for teachers and public employees.
• Position specialized pension income, including Railroad Retirement, as part of a base income layer within an overall plan, subject to program rules.
• Incorporate year round tax planning as a component of a well documented retirement strategy, noting that individual circumstances vary.
Listen and SUBSCRIBE to the Retire Sooner Podcast for weekly educational conversations that can inform more confident financial decision making.
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Jul 24, 2025 • 46min
What If Everything You Knew About Retirement Was Wrong?
Think you know the rules of thumb for retirement and investing? Think again. On this episode of the Retire Sooner Podcast, Wes Moss and Christa DiBiase examine common money myths and respond to listener questions that may reshape how you approach your financial future.
What you'll explore in this episode:
• Begin investing at any income level by seeing how access to markets has evolved.
• Focus on long-term participation instead of trying to perfectly time the market.
• Revisit the role of cash in your strategy and reflect on whether “cash is king” still holds.
• Understand why not all bonds carry the same level of risk, despite common assumptions.
• Consider how long-term investing differs from gambling based on historical probabilities.
• Explore modern tools and AI platforms that can support your portfolio analysis.
• Avoid the comparison trap by staying grounded in your personal financial goals.
• Compare the potential uses of whole life insurance versus long-term investing in special needs planning.
• Remember that market declines only become losses when assets are sold.
• Recognize the limitations of using past performance to estimate future outcomes.
• Examine whether real estate consistently appreciates by looking at real-life exceptions and patterns.
• Shift your perspective from outperforming the market to maintaining a long-term plan.
• Emphasize the importance of hobbies and social connections alongside financial readiness in retirement.
• Track your accounts and consider when changes to a managed portfolio may be appropriate.
• Reassess how supplemental funds—like vacation accounts—fit into your broader plan and tax picture.
• Simplify charitable giving by analyzing options such as donor-advised funds and intentional planning.
🎧 Listen today and subscribe to the Retire Sooner Podcast for thoughtful insights to help guide your retirement journey._
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Jul 17, 2025 • 44min
What Every Retiree Needs to Know About Social Security, Trusts, and Retirement Withdrawals
Take the next step in your retirement planning.
Tune in to the latest episode of the Retire Sooner Podcast with Wes Moss and Christa DiBiase, where you'll hear thoughtful, real-world insights designed to help you make informed financial decisions and pursue a more confident, purposeful retirement.
• Explore ways to optimize Social Security benefits, including timing strategies, spousal considerations, and personalized withdrawal approaches.
• Understand common sources of retirement anxiety, even among high-net-worth individuals, and consider approaches for managing emotional and financial uncertainty.
• Learn how trusts can support estate planning goals, from avoiding probate to managing real estate assets within your long-term financial plan.
• Consider retirement account strategies such as the Rule of 55, Roth conversion timing, and prioritizing tax-efficient cash flow.
Review your investment mix by comparing target date funds and balanced funds, and evaluate which may better align with your risk tolerance and retirement timeline.
• Weigh different withdrawal strategies by comparing the timing of distributions from retirement accounts versus claiming Social Security.
• Examine how 529 plans and Roth IRAs may fit into your education and retirement planning—especially if you’re part of a high-income household navigating recent tax law changes.
Compare the structure and features of S&P 500 mutual funds and ETFs to help determine which may be more appropriate for your investment preferences.
🎙️ Subscribe** and listen to the Retire Sooner Podcast today** for thoughtful conversations that can support your journey toward long-term financial well-being.
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Jul 10, 2025 • 39min
Roth Rules, Pension Puzzles, and Real Retirement Stories: Your Questions Answered
In this episode of the Retire Sooner podcast, Wes Moss and Christa DiBiase respond to listener questions and explore practical approaches to navigating retirement, investing, and financial planning.
• Discover a common Roth IRA misstep that can lead to unexpected taxes in retirement and learn how to approach it with more clarity.
• Explore the process of rolling over a Roth 401(k) into a Roth IRA and how the five-year rule of thumb might impact your withdrawal timeline.
• Hear real-world scenarios that highlight different outcomes based on how long your Roth accounts have been in place.
• Understand how to approach IRA rebalancing, including what to consider when dealing with concentrated stock positions and market changes.
• Compare Social Security and police pension benefits while examining updates to the Social Security Fairness Act and what it could mean for spousal coverage.
• Consider the use of retirement income projection tools and how applying more conservative assumptions may help you plan with greater confidence.
• Reflect on a “retirement love letter” that reveals three powerful themes behind a fulfilling retirement: financial flexibility, lifestyle design, and intentional planning.
• Follow the story of a couple who built a $6 million net worth, established six income streams, and prioritized meaningful pursuits and family in retirement.
• Explore why consistent movement and a sense of adventure are strongly connected to retirement satisfaction—and how shared community living can sometimes support both.
• Examine how changing family dynamics may shift your highest spending years later in life and why it matters for long-term planning.
• Get a clearer understanding of buffered index-linked notes, including their structure, potential costs, and how they differ from ETFs and other options.
• Learn how to calculate the present value of a pension using basic inputs such as years of service and average salary.
• Hear answers to more listener questions, including how stay-at-home spouses may qualify for Social Security and what pensions might mean for younger professionals.
Listen now to explore thoughtful planning strategies, real retirement stories, and insights that can help you design a future with more purpose and peace of mind.
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Jun 26, 2025 • 43min
From FOMO to Focused: Retirement Strategies for Market Volatility and Asset Allocation
In this episode of the Retire Sooner Podcast, Wes Moss and Christa DiBiase explore the role of dry powder assets in retirement planning and revisit “FOMO Freddie”—a cautionary character representing the risks of chasing investment trends without a long-term strategy. 🚀
They discuss why trend-chasing can be detrimental and how aligning with a consistent investment approach may help support long-term outcomes. You’ll hear comparisons of various investment styles—index, value, growth, momentum, and minimum volatility—and the potential drawbacks of “style timing” versus maintaining a steady allocation.
The episode also covers listener questions around portfolio transitions, including strategies for minimizing market disruption when moving IRAs or 401(k)s.
Additional topics include:
• Understanding TreasuryDirect accounts like I Bonds and EE Bonds
• Key risks of Market Linked Notes, including credit and liquidity concerns
• The “three-year dry powder” rule of thumb as a retirement buffer
• Age-based asset allocation considerations, including I Bonds as a potential emergency fund component for younger investors
• Considerations around high-yield municipal bond funds, especially for tax-conscious, high-net-worth retirees
• Factors to weigh when deciding whether to work with a financial advisor, including costs and allocation structure
Looking for help to strengthen your financial plan? Tune in for thoughtful insights to help you navigate market decisions with clarity and caution. For additional resources, visit yourwealth.com.
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Jun 19, 2025 • 45min
Keys to Early Retirement: Rule 72(t), New Research, Investing Insights, and Lasting Happiness
Dreaming about retiring early, but worried you’ll never have enough? On this episode of Retire Sooner with Wes Moss, Wes and Christa DiBiase break down powerful strategies and mindset shifts that could help folks retire sooner and happier, including:
• Tap Your IRA Early—Penalty-Free: Learn how Rule 72(t) and SEPPs can sometimes unlock your IRA before many expect and how that might help customize an early retirement plan.
• Rule of 55 vs. Rule 72(t): Compare two powerful early withdrawal strategies and discover which one could work for your retirement timeline.
• Smart Rollover and Roth Moves: Wes tackles listener questions on IRAs, dry powder strategy, and recovering from past investing mistakes.
• S&P 500 or Total Market Index? Find out which fund could fit your growth goals—and why broad diversification is often a winning strategy.
• The Real Source of Retirement Happiness: New research reveals it’s not just money—core pursuits like travel, hobbies, and connection can fuel lasting joy.
• Annuities & Life Insurance—Worth It? Explore the pros, cons, and ideal timing for annuities and whole life policies in your retirement plan.
Let years of retirement planning, actionable anecdotes, relatable listener questions, and eye-opening research fine-tune your investment and happiness game plan.
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