Retire Sooner with Wes Moss

Latest Episodes:

What Makes Retirement Fulfilling? Friendships, Investing, and Financial Planning Jul 16, 2026

Show notes

Retirement is about more than growing your nest egg; it’s also about building friendships, finding purpose, and making informed financial decisions along the way. Join Wes Moss and Christa DiBiase on this episode of the Retire Sooner Podcast as they blend listener questions, new research, and practical conversations about retirement planning, retirement investing, and personal finance.

• Hear an inspiring listener story about trading everyday life for a full-time adventure aboard a sailboat in the Caribbean.

• Discover new research on how long it may take to build close friendships and why those relationships may matter throughout retirement.

• Learn why making new friends often gets tougher with age—and what may help create more meaningful connections.

• Explore how The Retire Sooner Method encourages balancing financial security with purpose, relationships, and the experiences often associated with making retirement meaningful.

• Explore portfolio diversification, pensions, liquidity, and how stocks, bonds, and cash may work together in a retirement portfolio.

• Compare working with a financial advisor versus DIY investing, including what research suggests about each approach.

• Review how financial planning may extend beyond investing to include tax planning, estate planning, and family priorities.

• Consider ways to balance retirement savings, mortgage payments, and emergency cash reserves when extra income comes your way.

• Understand portfolio rebalancing during market volatility and what Treasury notes and yield to maturity mean for fixed-income investors.

Whether you're counting down to retirement or already there, this episode offers thoughtful perspectives to help you navigate the road ahead. Listen and subscribe to the Retire Sooner Podcast for more conversations about retirement planning, investing, and living well in retirement.

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The Retire Sooner Method: The Research Behind a Happier, More Fulfilling Retirement Jul 09, 2026

Show notes

In this special episode of the Retire Sooner Podcast, Wes Moss shares the story behind The Retire Sooner Method and explores the research on the financial and lifestyle habits associated with greater retirement satisfaction.

• Discover five habits that research has associated with greater retirement satisfaction.

• See how saving a little time today may create more flexibility in retirement.

• Hear the story behind the "Happiest Retiree on the Block" and The Retire Sooner Method.

• Explore how purpose, core pursuits, close friendships, and a written financial plan may support retirement well-being.

• Learn how the Money Red, Yellow, and Green Zones may relate to financial confidence.

• Consider how healthy routines, meaningful activities, and quality sleep have been associated with overall well-being.

• Access the research, charts, and resources behind The Retire Sooner Method at retiresoonermethod.com.

Whether retirement is years away or already here, this episode offers research-based perspectives on retirement planning and financial well-being. Listen, subscribe, and join the conversation on the Retire Sooner Podcast for more educational discussions about investing, retirement, and living a life of purpose.

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Target-Date Funds, Retirement Income & 401(k)s: Listener Questions Answered Jul 02, 2026

Show notes

Retirement planning comes with plenty of questions, and this episode of the Retire Sooner Podcast is built around answering them. Join Wes Moss and Christa DiBiase as they tackle listener questions on retirement income, investing, 401(k)s, Roth IRAs, target-date funds, and career changes.

• Compare the bucket strategy with other approaches to generating retirement income.

• Learn how withdrawal guardrails may help shape spending decisions in different market environments.

• Consider 401(k) and Roth IRA options if you're working to build your retirement savings.

• Find out how target-date fund fees and expense ratios really work and how they may fit into a retirement withdrawal strategy.

• Explore what a second-act career may look like in education, healthcare, technology, or financial services.

• Review what to expect when moving from a financial advisor to a self-directed investment account.

• Understand why compounding and asset allocation may matter whether you own one fund or several.

Whether you're saving for retirement, approaching retirement, or already there, you'll find thoughtful perspectives on some of today's most common financial questions. Listen and subscribe to the Retire Sooner Podcast for more conversations about retirement planning, investing, and retirement income.

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Clark Howard Joins Wes Moss to Take On Your Toughest Retirement Questions Jun 25, 2026

Show notes

Consumer advocate Clark Howard joins Wes Moss and Christa DiBiase for a special Retire Sooner Podcast episode packed with listener questions, thoughtful debate, and real-world financial scenarios. From retirement planning and investing to tax considerations and the pursuit of a more fulfilling retirement, this conversation explores a wide range of topics through the lens of everyday decisions.

• Explore how technology stocks, index funds, IPOs, and diversification continue to shape the current investing landscape.

• Examine retirement timing, market volatility, and the role consistent investing may play over time.

• Consider mortgage, refinancing, capital gains, and tax-planning questions raised by listeners navigating major financial decisions.

• Compare Target Date Funds and ETF portfolios while weighing different approaches to diversification and risk.

• Evaluate the tradeoffs of selling versus renting a home before an extended move overseas.

• Explore the role core pursuits, purpose, and meaningful activities may play in discussions about retirement satisfaction.

• Learn about the **pre-sale of Wes Moss's new book, **The Retire Sooner Method, including available bonuses and how to reserve a copy.

Whether you're thinking about your portfolio, your next chapter, or both, this episode offers plenty to consider. Listen and subscribe to the Retire Sooner Podcast for more conversations about retirement planning, investing, and the financial and lifestyle decisions that may shape life after work.

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The Ultimate Dividend of Retirement: Freedom, Flexibility, and Financial Planning Jun 18, 2026

Show notes

Is retirement just about accumulating assets, or is it also about creating the flexibility to spend your time in ways that matter most to you? Join Wes Moss and Christa DiBiase on this episode of the Retire Sooner Podcast as they explore retirement planning, investor behavior, and the financial decisions that may influence long-term outcomes.

• Discover why building wealth and preserving wealth often involve different financial considerations.

• Examine how emotions, habits, and investor behavior may affect financial decision-making over time.

• Explore the transition from asset accumulation to retirement income planning and risk management.

• Consider listener questions on pensions, Social Security claiming decisions, longevity, and retirement income strategies.

• Evaluate factors investors may weigh when considering Roth conversions and portfolio rebalancing.

• Learn about the **five-step **Retire Sooner Method from Wes’s new book, and the role financial and happiness "green zones" may play in retirement planning.

• Understand what some may refer to as the "ultimate dividend"—the freedom and flexibility many people seek through thoughtful financial preparation.

• Compare perspectives on equity-indexed annuities, bonds, fiduciary standards, and financial product considerations.

• Review financial planning concepts for younger investors, including Roth IRAs, long-term saving, and preparing for future homeownership.

Whether you're preparing for retirement or already navigating it, this episode examines the intersection of financial planning, investor behavior, and personal fulfillment. Listen and subscribe to the Retire Sooner Podcast, and pre-order Wes Moss's new book, The Retire Sooner Method, to learn more about the planning principles discussed in this episode.

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What the Happiest Retirees Do Differently: Insights from The Retire Sooner Method Jun 11, 2026

Show notes

What if a happier retirement has as much to do with how you spend your time as how you invest your money? In this episode of the Retire Sooner Podcast, Wes Moss and Christa DiBiase explore the research behind retirement happiness, answer listener questions on retirement planning, and share how you can pre-order Wes’s new book, The Retire Sooner Method, and unlock exclusive bonuses!

• Discover why core pursuits—the activities that get you excited to start the day—are often linked to greater retirement satisfaction.

• Explore the hobbies, passions, and routines most commonly found among retirees who report higher levels of happiness and fulfillment.

• Review how retirement withdrawal frameworks work, including considerations around cash reserves and 4%+ distribution strategies.

• Compare Equity Indexed Annuities (EIAs), dividend-focused approaches, and pension-versus-lump-sum options when evaluating retirement income choices.

• Consider Roth conversions, required minimum distributions (RMDs), and other tax-planning factors that may influence long-term retirement strategies.

• Evaluate the opportunities and risks that may come with concentrated RSU and company stock positions.

• Understand how FDIC insurance works and what to know about coverage for savings accounts and CD ladders.

Whether you're years from retirement or already there, this episode blends retirement happiness research with practical financial planning conversations. Listen to the Retire Sooner Podcast and subscribe for more discussions about retirement, investing, personal finance, and building a life you look forward to living.

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When and How to Help Adult Children: Roth Conversions, Social Security & Retirement Planning Topics Jun 04, 2026

Show notes

Retirement planning doesn’t always follow a straight line, and this episode of the Retire Sooner Podcast tackles the pressing money decisions families are talking about. Join Wes Moss and guest host Mallory Boggs for a lively conversation about helping adult children buy homes, Roth conversions, Social Security timing, investing, taxes, and the lifestyle choices often associated with a happy retirement.

• Explore the financial and emotional tradeoffs that may come with helping adult children buy a home while still protecting your own retirement goals.

• Examine how higher home prices, rising mortgage rates, and ongoing family support may help shape retirement planning and financial flexibility.

• Evaluate Roth conversions, Social Security claiming strategies, IRA withdrawals, and HELOC financing through the lens of taxes and long-term retirement income planning.

• Reconsider how spending on travel, family experiences, health, hobbies, and social connections may play a role in retirement satisfaction.

• Assess portfolio diversification considerations beyond concentrated “Magnificent 7” exposure while tackling listener questions on IRAs, emergency funds, taxable accounts, and retirement investing.

Listen and subscribe to the Retire Sooner Podcast for more conversations on retirement planning, investing, taxes, and navigating today’s financial landscape with a practical long-term perspective.

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Retirement Curveballs: Early Retirement, Taxes, and Market Volatility May 28, 2026

Show notes

Retirement rarely goes exactly according to plan—and this episode of the Retire Sooner Podcast tackles the real-life financial curveballs that may affect the timeline. Join Wes Moss and special guest host Mallory Boggs for a fast-moving conversation on early retirement, market volatility, taxes, rollover IRAs, annuities, direct indexing, and diversification strategies.

• Explore why many Americans retire earlier than expected and how health issues, caregiving responsibilities, and job loss may reshape retirement plans.

• Learn how thoughtful retirement income planning, IRA rollover decisions, and mortgage strategies may help create more financial flexibility.

• Compare the pros, cons, and tradeoffs of annuities, direct indexing, tax-loss harvesting, and alternative investment strategies beyond the traditional 60/40 portfolio.

• Understand why unusually fast stock market recoveries have historically been less common, and why long-term investors often focus on perspective over prediction.

• Examine practical planning considerations for high-income earners, looking at tax efficiency, portfolio diversification, and varying levels of investment risk.

Listen and subscribe to the Retire Sooner Podcast for more conversations on retirement planning, investing, taxes, and navigating today’s financial landscape with a clear, practical long-term perspective.

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What Does a Fiduciary Advisor Really Do? Taxes, Retirement Income & Investing Explained May 21, 2026

Show notes

Retirement planning is about far more than picking investments, and this episode of the Retire Sooner Podcast shows just how many moving pieces may shape your financial life over time. Join Wes Moss and Christa DiBiase for a fast-moving conversation covering retirement income planning, tax strategy, dividend investing, market volatility, and the potential value of working with a fiduciary, fee-only advisor.

• Compare fiduciary advisors and non-fiduciary advisors through a simple “orange pepper” analogy.

• Explore how tax planning, behavioral coaching, retirement forecasting, and portfolio strategy may work together in long-term financial planning.

• Evaluate real estate decisions, business transitions, and career planning during peak earning years and retirement.

• Review dividend investing, ETF selection, cash reserves, and sequence-of-returns risk considerations for retirees and near-retirees.

• Organize retirement rollovers, trusts, pensions, and tax records with greater clarity and flexibility.

Whether you’re building a retirement plan or fine-tuning an existing strategy, this episode delivers practical financial conversations grounded in long-term thinking and real-life investor questions. Listen and subscribe to the Retire Sooner Podcast for more discussions on retirement investing, financial planning, and navigating today’s changing economic landscape.

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Clark Howard Joins Wes Moss to Talk Roth Strategies, Taxes, and Retirement May 14, 2026

Show notes

Clark Howard joins Wes Moss and Christa DiBiase for a fun, fast-moving Retire Sooner Podcast episode packed with conversations about retirement planning, Roth conversions, HSAs, taxes, investing, and the lifestyle choices that may help to shape financial life. From boats and horse racing to tax strategies and retirement income planning, this episode blends practical financial conversations with the relatable chemistry listeners love.

• Compare **Roth vs. traditional **401(k) contribution approaches as Clark Howard and Wes Moss sort through taxes, future flexibility, and retirement income planning considerations.

• Consider how state income taxes, Roth conversions, required minimum distributions (RMDs), and Medicare IRMAA (Income-Related Monthly Adjustment Amount) surcharges may influence retirement cash flow over time.

• Explore HSA strategies, backdoor Roth IRAs, and mega backdoor Roth opportunities while reviewing contribution rules and planning considerations for higher earners.

• Weigh whether buying a boat aligns with lifestyle goals and retirement spending priorities by comparing personal value and real-world price-per-use scenarios.

• Enjoy Christa DiBiase’s stories about horse racing, sports fandom, and finding balance between financial goals and enjoying life along the way.

Listen and subscribe to the Retire Sooner Podcast to hear Clark Howard, Wes Moss, and Christa DiBiase bring retirement planning and investing conversations to life with humor, perspective, and approachable discussions about financial independence, retirement income, and long-term planning strategies.

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