Retire Sooner with Wes Moss

Wes Moss
  • 4.4 (417)
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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.

  1. 5D AGO

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

    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. Learn more about your ad choices. Visit megaphone.fm/adchoices

    37 min

  2. JAN 15

    Clark Howard Joins Retire Sooner to Break Down Buffett, Markets, and 2026 Themes

    The Retire Sooner Podcast welcomes Clark Howard alongside Wes Moss and Christa DiBiase for a special episode focused on market history, long-term investing principles, and today’s most talked-about financial transitions. The conversation emphasizes context over commentary and highlights how investors often think through uncertainty, change, and market structure. • Highlight Clark Howard’s perspective on Warren Buffett stepping down as CEO of Berkshire Hathaway at age 95 and the transition to Greg Abel. • Review Berkshire Hathaway’s long-term role in markets and why its history is frequently referenced alongside the S&P 500. • Frame why long-term market participation is commonly emphasized during periods of leadership change at iconic companies. • Discuss why Clark Howard views this transition as the close of a defining chapter in modern investing history. • Explain how Berkshire Hathaway’s conglomerate structure differs from traditional private equity, including transparency and fee considerations. • Examine growing market concentration and the shrinking number of U.S. public companies—and why those trends continue to matter. • Outline how exposure to both public stocks and privately held businesses is often discussed when considering diversification. • Summarize several big-picture themes shaping 2026 conversations, including artificial intelligence, tax-refund dynamics, and election-cycle uncertainty. • Clarify what “dry powder” means and how cash, money market funds, and select bonds are commonly described in retirement safety discussions. • Address listener questions by reviewing general considerations around investing settlement proceeds, tax-advantaged accounts, and dividend-oriented ETFs. This episode offers a thoughtful conversation featuring Clark Howard with Wes Moss, focused on long-term perspective rather than short-term reaction. Listen and subscribe to the Retire Sooner Podcast for ongoing discussions that bring clarity and context to retirement and investing topics. Learn more about your ad choices. Visit megaphone.fm/adchoices

    38 min

  3. JAN 8

    Retirement Planning, Investing Trade-Offs, and Household Risk Explained

    Start the year with structured context around today’s most frequently discussed retirement planning questions on the Retire Sooner Podcast, hosted by Wes Moss and Christa DiBiase. This episode presents an educational review of real listener scenarios, placing retirement, investing, and planning topics within a long-term analytical framework. • Review current U.S. wealth statistics by discussing commonly cited data on net worth, retirement account balances, and generational financial trends. • Outline household risk considerations by examining how families often think about emergency savings, retirement contributions, and income stability. • Discuss real estate planning considerations by evaluating factors involved in purchasing a condo for college-bound children, including cash flow and potential resale dynamics. • Describe fiduciary planning relationships by outlining services commonly associated with comprehensive retirement planning, tax coordination, and advisory fee structures. • Explain the “Rule of 55” by clarifying how early access to employer-sponsored retirement plans is typically referenced. • Summarize shared characteristics of long-term savers by highlighting recurring themes reported by listeners with higher household savings levels. • Compare buffered ETFs by discussing how downside buffers and capped upside features are typically weighed within diversified portfolios. • Examine mortgage buyout scenarios by outlining considerations for co-owned property, interest-rate assumptions, and loan structure implications. • Analyze bond duration risk by discussing how interest-rate changes and yield-curve movements may influence long-duration bond pricing. If you’re searching for clear, educational discussions around retirement planning, investing considerations, and household financial decision-making, this episode may add perspective. Listen and subscribe to the Retire Sooner Podcast for ongoing conversations that help place financial topics in a long-term context. Learn more about your ad choices. Visit megaphone.fm/adchoices

    35 min

  4. JAN 1

    Inside the Research: Happiness, Jobs Data, and Retirement Questions

    What actually shapes life in retirement—your finances, your relationships, or both? In this episode of the Retire Sooner Podcast, Wes Moss and Christa DiBiase walk through new research on happiness in retirement and unpack several financial and economic topics that often come up in retirement planning conversations. • Share findings from a 2025 Money and Happiness in America study that looks at how social connection is commonly linked to reported retirement satisfaction. • Talk through research showing how the number of close personal relationships is often discussed when measuring happiness among retirees. • Reflect on how American friendships have changed over time and why staying socially connected is frequently part of retirement lifestyle discussions. • Put into context recent government jobs reports by explaining what unemployment and labor-market numbers generally indicate. • Walk through estate-planning considerations around life insurance, guardians, and trustees that many families review over time. • Cover the core factors people often look at when evaluating bond funds, including yield, duration, expenses, and benchmarks. • Discuss how Roth IRAs, traditional IRAs, brokerage accounts, and HELOCs are commonly weighed when addressing short-term cash needs during real-estate transitions. • Answer listener questions about Roth IRA contributions, in-plan conversions, account-funding priorities, and retirement-plan considerations when changing jobs. The episode keeps the focus on education, context, and real-world questions retirees and pre-retirees are already asking. Listen and subscribe to the Retire Sooner Podcast for ongoing conversations that connect money, lifestyle, and long-term planning—without the hype. Learn more about your ad choices. Visit megaphone.fm/adchoices

    35 min

  5. 12/25/2025

    Healthcare, Social Security, and Rate Cuts: Retirement Planning in Today’s Economy

    Looking for clear context around today’s most talked-about retirement planning issues? In this episode of the Retire Sooner Podcast, Wes Moss and Christa DiBiase present an educational discussion covering healthcare planning, retirement income considerations, Social Security decisions, and how current economic conditions are commonly framed in retirement conversations. • Review current healthcare enrollment periods, including Affordable Care Act considerations, and why coverage timing is often discussed by early retirees. • Illustrate a real-world healthcare planning example that examines estimating and managing medical costs before age 65 using publicly available comparison tools. • Explain recent healthcare policy changes by outlining how subsidy rules and updated federal poverty thresholds are referenced in retirement healthcare planning. • Contextualize recent Federal Reserve rate cuts by discussing how interest-rate changes are typically viewed in relation to mortgages, housing activity, and broader economic conditions. • Address listener questions by outlining commonly discussed considerations around retirement timing, asset allocation approaches, principal-protected notes, and early retirement trade-offs. • Compare Social Security claiming considerations by reviewing trade-offs associated with different filing ages based on individual circumstances. • Clarify how taxable, tax-deferred, and tax-free accounts are often viewed together when discussing overall portfolio allocation. • Share perspectives from retirees on aligning lifestyle goals—such as travel, part-time work, or relocating abroad—with sustainable withdrawal planning discussions. • Reinforce why significant financial and healthcare decisions are commonly reviewed with qualified professionals before implementation. Interested in an educational retirement podcast focused on context, trade-offs, and long-term planning awareness? Listen to this episode and subscribe to the Retire Sooner Podcast for ongoing conversations designed to inform retirement planning decisions—not predict outcomes. Learn more about your ad choices. Visit megaphone.fm/adchoices

    47 min

  6. 12/18/2025

    Roth Conversions and Withdrawal Frameworks: Retirement Income Planning

    Looking for an educational overview of today’s most commonly searched retirement planning topics? In this episode of the Retire Sooner Podcast, Wes Moss and Christa DiBiase provide context around retirement income planning, tax considerations, and widely referenced financial frameworks, helping listeners better understand how these concepts are typically discussed. • Review how Roth IRA conversions are generally evaluated and why converting an entire retirement account balance in a single tax year can materially affect taxable income calculations. • Explain how marginal tax brackets apply to large conversions and why simplified terms like “tax bomb” may not fully reflect how tax liability is determined. • Highlight considerations associated with forgotten or inactive 401(k) accounts and why consolidation is often discussed from an organizational or administrative perspective. • Examine how withdrawal flexibility prior to Social Security eligibility is commonly framed when discussing early-retirement income planning. • Outline factors frequently reviewed when evaluating whether life insurance coverage remains appropriate as family and financial circumstances change. • Clarify how Secure 2.0 legislation outlines limited 529 plan–to–Roth IRA rollovers, including applicable statutory rules, eligibility criteria, and contribution constraints. • Compare the traditionally cited 4% withdrawal framework with alternative retirement income scenarios that include pensions or guaranteed fixed-rate income sources. • Discuss how “dry powder” reserves are often described using bond ETFs or money market ladders within retirement planning conversations. • Evaluate the role small- and mid-capitalization stocks may play alongside large-cap equities within diversified, long-term portfolio discussions. • Reframe home value benchmarks in an inflationary environment while noting why mortgage status is often considered when assessing retirement readiness. Listen and subscribe to the Retire Sooner Podcast for ongoing discussions that explore retirement planning concepts, market context, and long-term financial considerations. Learn more about your ad choices. Visit megaphone.fm/adchoices

    38 min

  7. 12/11/2025

    The Saver-to-Spender Shift: Behavioral Drivers of Thoughtful Retirement Planning

    Gain a grounded, research-informed perspective on retirement planning in this episode of the Retire Sooner Podcast, where Wes Moss and Christa DiBiase examine the emotional, behavioral, and organizational factors that often influence how individuals approach life after work. This conversation highlights commonly referenced frameworks and planning considerations, offering context for listeners seeking to better understand the many moving parts of a thoughtful retirement process. • Explore the behavioral and psychological dynamics behind transitioning from a saver mindset to a spending mindset in retirement, including the frequently cited “millionaire’s paradox.” • Understand how creating a written retirement plan may help provide structure, along with why general withdrawal frameworks—such as the commonly referenced 4%+ rule—are used for discussion rather than as recommendations. • Consider approaches for maintaining emotional objectivity when making financial decisions throughout retirement. • Reflect on why some financial professionals continue working and how their experience may contribute to broader retirement-planning conversations. • Review the potential role a fiduciary or financial advisor may play in helping individuals identify common planning pitfalls, organize long-term strategies, and evaluate tax and estate considerations. • Identify widely used criteria for assessing whether a fiduciary advisor aligns with an individual's values, communication preferences, and planning philosophy. • Explore end-of-year tax-related considerations—including SALT limits, charitable deduction rules, HSAs, clean-energy credits, bonus depreciation provisions, and updates to 529 plan flexibility—while recognizing that tax implications depend on each household’s specific circumstances. • Evaluate the educational value some families see in establishing custodial investment accounts for children or grandchildren as part of broader financial learning. • Assess the administrative reasons some individuals review whether consolidating retirement accounts may support clearer oversight of their financial landscape. If you're interested in expanding your understanding of the factors that may shape retirement decision-making, this episode offers context to help you think through your own process. Listen and subscribe to the Retire Sooner Podcast for ongoing discussions centered on thoughtful, well-informed retirement planning. Learn more about your ad choices. Visit megaphone.fm/adchoices

    39 min

  8. 12/04/2025

    Your Guide to Today’s Highly Searched Retirement Questions

    Stay informed about today’s highly-searched retirement and financial planning topics in this new episode of the Retire Sooner Podcast with Wes Moss and Christa DiBiase. Gain clear, accessible context on economic trends, retirement rules, portfolio structures, and planning conversations that are shaping long-term decision-making discussions. • Explore how the proposed 50-year mortgage is influencing conversations around affordability, home-equity timelines, and shifting real estate structures. • Recognize how the K-shaped economy reflects differing financial experiences across households and shapes discussions about consumer sentiment and wealth-building patterns. • Clarify how mortgage leverage and ultra-long terms relate to borrowing structures, payoff timelines, and the considerations homeowners may evaluate. • Understand how equal-weighted investing frameworks are designed to help distribute exposure more evenly across sectors to address concentration awareness. • Review how equal-weighted and sector-weighted ETFs and mutual funds structure market exposure and present alternative allocation methodologies. • Assess the factors often discussed when evaluating early Social Security filing, especially when immediate income needs are already met. • Compare modeled scenarios that illustrate how different 401(k) contribution timelines can affect projected balances under various assumptions. • Examine informational considerations for highly compensated employees, including restoration plan structures, tax mechanics, and withdrawal rules. • Weigh the structural differences between W-2 and 1099 income in high-income medical professions, including taxation, liability frameworks, and benefits access. • Explore available approaches for high earners encountering Roth IRA limits, such as after-tax contributions, mega-backdoor Roth structures, and ETF allocation strategies. • Hear listener questions addressing savings habits, employer-plan options, and retirement-plan mechanics discussed in real-world scenarios. • Identify informational steps that may support ongoing awareness throughout different stages of retirement planning. If you want to stay current on the retirement conversations shaping today’s financial landscape, listen and subscribe to the Retire Sooner Podcast. Join Wes Moss, Christa DiBiase, and the Retire Sooner community for grounded, ongoing discussions aimed at helping listeners stay informed and intentional about long-term planning. Learn more about your ad choices. Visit megaphone.fm/adchoices

    42 min
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4.4
out of 5
417 Ratings

About

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.

Information

  • Creator
    Wes Moss
  • Years Active
    2014 - 2026
  • Episodes
    290
  • Rating
    Clean
  • Copyright
    Copyright © 2004 – 2021 Wes Moss
  • Show Website
    Retire Sooner with Wes Moss

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