Retire Sooner with Wes Moss

Hosted by Wes Moss

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Episodes

321

Latest episode

Aug 2026

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About the show

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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60 recent

September 3, 202634 min

Can You Retire Sooner? Mortgages, Rental Income, Investing & Retirement Risks

When should you retire, and what might shape the years that follow? On this episode of the Retire Sooner Podcast, Wes Moss and Christa DiBiase tackle listener questions about retirement planning, investing, retirement income, and the surprises life may throw your way. ·       Consider why retiring sooner may provide more time to enjoy healthy, active retirement years. ·       See what certain retirement stories may reveal about health, longevity, and planning for the unexpected. ·       Explore Wes’s new book, The Retire Sooner Method, and his latest research on happy retirees. ·       Examine how rental property income may factor into retirement cash flow and diversification, along with the risks and responsibilities of owning real estate. ·       Weigh paying down the mortgage against keeping cash available for a future home or land purchase. ·       Meet what some refer to as the “boomer candy” of investing—buffered ETFs—and learn how their potential benefits, limitations, and risks may function. ·       See why sequence of returns risk may matter when you start withdrawing money in retirement. ·       Untangle the tax, diversification, and emotional considerations that may come with selling a concentrated stock position. ·       Navigate the investing, tax, and financial questions that may come with retiring abroad. Join Wes and Christa for real questions, relatable stories, and an educational look at the decisions that may shape retirement planning. **Listen and subscribe to the **Retire Sooner Podcast for more conversations about investing, retirement income, and the pursuit of an earlier, happier retirement. Learn more about your ad choices. Visit megaphone.fm/adchoices

August 27, 202625 min

Rapid-Fire Retirement Q&A: Roths, College Savings, Bonds, and More

Got retirement questions? Wes Moss and Christa DiBiase tackle them in this rapid-fire episode of Retire Sooner Podcast. Take an educational look at retirement planning, investing, Roth accounts, college savings, bonds, and more. ·       Explore considerations for when high-yield savings account rates start heading south, including evaluating brokerage money market funds. ·       Balance daycare bills, taxable investing, and 529 college savings when there never seems to be enough room in the budget for every goal at once. ·       Understand how backdoor Roth and mega backdoor Roth strategies work and factors to consider. ·       Consider the tricky question of whether a potential inheritance belongs in a retirement plan. ·       Look beyond the higher distributions of high-yield ETFs to the potential risks hiding underneath. ·       See what it’s like for financial advisors to juggle client concerns, annual planning, and a steady stream of market and economic news. ·       Review The Retire Sooner Method, from getting the financial pieces in place to finding purpose, nurturing friendships, and getting better sleep. ·       Compare individual bonds, bond funds, and bond ETFs when weighing income characteristics, diversification, and simplicity. ·       Evaluate whether boosting Roth or after-tax contributions may make sense as retirement gets closer. Hear Wes and Christa take on the retirement questions that may be on your mind, too. **Listen and subscribe to the **Retire Sooner Podcast for more educational conversations about money, retirement, and building toward a happy retirement. Learn more about your ad choices. Visit megaphone.fm/adchoices

August 20, 202644 min

Stock Market All-Time Highs: What Could They Mean for Your Retirement?

The stock market may be hitting all-time highs, but is that a reason to celebrate or worry about what comes next? On the Retire Sooner Podcast, Wes Moss and Christa DiBiase turn current headlines and listener questions into a lively conversation about investing, retirement, Social Security, housing, 55+ communities, healthcare, and more. ·       See what history may tell us about stock market all-time highs, why they have historically arrived in bunches, and how corrections may fit into the picture. ·       Track the S&P 500’s historical performance and put today’s market highs into historical perspective. ·       Ask whether early retirement might work by weighing spending, taxes, healthcare, Social Security, and retirement withdrawals. ·       Consider how much your adult children should know about your net worth, inheritance, and estate plans. ·       Weigh the pros and cons of using 529 plan funds for private education, including a potential wrinkle for families in New York. ·       Picture life in a 55+ community and explore ways to test-drive the lifestyle before making a move. ·       Think through renting in retirement and how rising housing costs may affect a long-term retirement budget. ·       Navigate the tougher side of retirement planning, including healthcare, Social Security, long-term care costs, and caregiving. ·       Revisit when to claim Social Security as questions continue around the program’s future funding and potential changes. ·       Discover the Retire Sooner Method and explore a framework intended to help you think through the financial and lifestyle pieces of an earlier, happier retirement. Listen and subscribe to the Retire Sooner Podcast for an engaging, educational take on the money and life questions that often come along with planning for retirement. Learn more about your ad choices. Visit megaphone.fm/adchoices

August 13, 202638 min

How to Retire Sooner: The Rule of 55, 4% Rule, Roth Conversions, and the Keys to a Happier Retirement

What does it really take to retire sooner and enjoy the years you’ve worked so hard for? On this episode of the Retire Sooner Podcast, Wes Moss and Christa DiBiase tackle listener questions about retirement planning, investing, taxes, retirement income, and the pursuit of a happier life after work. ·       Examine the idea of building a retirement life map around what matters most to you. ·       Discover what Aristotle can teach us about retirement happiness, purpose, and fulfillment. ·       Confront spending anxiety and why letting yourself enjoy your savings can be surprisingly difficult. ·       Consider when it might be time for a change of scenery—and what a move may mean for your finances. ·       Compare **cost-of-living **calculators when sizing up potential retirement destinations. ·       Analyze strategies for untangling concentrated stock positions, diversification, and the potential tax tradeoffs. ·       Explore the Rule of 55 and when it may provide penalty-free access to certain 401(k) funds. ·       Experience the Retire Sooner Method, from the Money & Happiness Green Zones and Core Pursuits to relationships and sleep. ·       Break down the 4% rule of thumb, withdrawal rates, and the fear of running out of money. ·       Weigh a HELOC versus IRA withdrawal while considering taxes and potential Roth conversions. ·       Walk through listener scenarios involving retirement readiness, withdrawal strategies, and investment allocation. Retirement is about more than hitting a number—it’s also about figuring out what you want those years to look like. Listen and subscribe to the Retire Sooner Podcast for more educational conversations about the money and life behind a happier retirement. Learn more about your ad choices. Visit megaphone.fm/adchoices

August 6, 202637 min

When Should You Claim Social Security? Plus Mortgage and College Planning

When should you claim Social Security? Should you pay off your mortgage before retirement? And how do you balance saving for retirement while helping pay for college? Join Wes Moss and Christa DiBiase on this episode of the Retire Sooner Podcast as they tackle listener questions and explore practical perspectives on retirement planning, retirement income, taxes, pensions, and planning for a more fulfilling retirement. planning for a more fulfilling retirement • Compare Social Security claiming approaches and the factors that may influence your decision. • Consider how health, longevity, your spouse, and taxes may shape your retirement plan. • Explore the research behind Core Pursuits and why they may play an important role in retirement satisfaction. • Balance retirement savings and college funding while weighing different education-planning options. • Evaluate pension survivor benefits, cash reserves, and mortgage payoff as part of your broader financial picture. • Access preorder bonus information for The Retire Sooner Method, no matter where you purchase it, including your favorite local bookstore. Listen and subscribe to the Retire Sooner Podcast for more educational conversations about retirement planning, Social Security, retirement income, investing, taxes, and financial independence—and discover new ideas to consider as you prepare for retirement. Learn more about your ad choices. Visit megaphone.fm/adchoices

July 30, 202632 min

Retirement Planning: The Retire Sooner Method, Sleep & Smart Money Strategies

Retirement planning isn't just about the numbers—it's also about trying to create a life you'll enjoy living. Join Wes Moss and Christa DiBiase on this episode of the Retire Sooner Podcast as they tackle listener questions, share fresh retirement planning perspectives, and explore the habits that may help shape a more fulfilling future, including sleep! • Discover The Retire Sooner Method, including the Money & Happiness Green Zones, the Retirement Superpower, and the role Core Pursuits may play in retirement. • See how sleep, net worth benchmarks, liquid investable assets, income, and mortgage payoff may influence long-term retirement planning. • Hear practical discussions about long-term care, IRMAA (Income-Related Monthly Adjustment Amount), healthcare before Medicare, and managing short-term cash. • Compare the bucket strategy, retirement account consolidation, fixed annuities, and structured notes while weighing flexibility, liquidity, and risk. Listen and subscribe to the Retire Sooner Podcast with Wes Moss and Christa DiBiase for engaging and educational conversations about retirement planning, retirement investing, retirement income, and financial independence. Learn more about your ad choices. Visit megaphone.fm/adchoices

July 23, 202634 min

How to Build a Happy Retirement: The 5-Step Retire Sooner Method, Roth Conversions & Retirement Planning

What does it really take to build a happy retirement? Join Wes Moss and Christa DiBiase on this episode of the Retire Sooner Podcast as they blend retirement planning research with listener questions to explore the financial and lifestyle choices that may help shape life after work. • Learn how the five-step Retire Sooner Method brings together the financial and personal sides of retirement planning. • See how retirement "green zones" may help you think about savings, income, liquidity, and mortgage decisions. • Explore why core pursuits, strong friendships, and even better sleep have been linked to greater retirement satisfaction. • Hear practical conversations about written financial plans and other habits that may help reduce money-related stress. • Get answers to listener questions about AI financial tools, Roth conversions, bond funds versus money markets, spousal IRAs, retirement income, paying off a mortgage, reverse mortgages, and annuities. Listen and subscribe to the Retire Sooner Podcast for more educational conversations about retirement planning, retirement investing, and personal finance. Learn more about your ad choices. Visit megaphone.fm/adchoices

July 16, 202634 min

What Makes Retirement Fulfilling? Friendships, Investing, and Financial Planning

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

July 9, 202632 min

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

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

July 2, 202630 min

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

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