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  • Retirement Planning for Aging Parents - and Can You Retire Early? - 570

    Retirement Planning for Aging Parents - and Can You Retire Early? - 570
    2026/02/24

    Joe and Big Al spitball two sides of the retirement equation, today on Your Money, Your Wealth® podcast number 570. Daniel in Texas is 40 and worrying about how to support Mom and Dad if their money runs out. Can he build some kind of financial safety net for them without ruining his own retirement? Jemma's 82-year-old mom is drawing down her portfolio. Is locking in guaranteed income with an annuity a smart move, or could that create new problems down the road? Plus, "Cookie and Gerry" want to walk away from work before 50 with a big brokerage account and a pension. Are they positioned correctly? How can they avoid pulling the wrong levers at the wrong time? And "Fred and Wilma" are staring at a potential multi-million-dollar ESOP payout. What levers do they need to pull so they can retire at 46 and shout "Yabba Dabba Doo"?

    Free Financial Resources in This Episode:

    https://bit.ly/ymyw-570 (full show notes & episode transcript)

    10 Steps to Improve Investing Success - free download

    What to Do When the Stock Market Gets Crazy - YMYW TV

    Financial Blueprint (self-guided)

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    Chapters:

    00:00 - Intro: This Week on the YMYW Podcast

    00:57 - Can I Afford to Be My Parents' Retirement Plan? (Daniel, Texas)

    07:07 - Will an Annuity Really Save Mom From Running Out of Money? (Jemma)

    15:07 - Can We Retire in Our Early 50s With a Pension and a $190K Spend? (Cookie and Gerry)

    30:39 - Can We Retire Early at 46 With a $4M ESOP and a $210K Spend? (Fred and Wilma, CA)

    44:23 - Outro: Next Week on the YMYW Podcast
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    46 分
  • Retirement Changes at These 5 Major Financial Crossroads - 569

    Retirement Changes at These 5 Major Financial Crossroads - 569
    2026/02/17
    When you're standing at a major financial crossroads, the timing of your decisions can mean the difference between success and failure. Joe Anderson, CFP® and Big Al Clopine, CPA spitball on the "when" of five retirement decisions, today on Your Money, Your Wealth podcast number 569. We'll kick things off with a whale of an email: "Fine and Dandy" is 42 years old with a multimillion dollar private equity offer on the table. Should he sell his business now or hold out for a second bite of the apple later? He also wonders if it's crazy to spend more on his vacation home than on his primary residence. David calls himself an "elderly orphan," flying solo at 66 and in need of a plan to protect his million-dollar portfolio as he ages. BB and Shell are trying to time their final year of retirement contributions to save as much as possible before moving to a lower-tax state. Should they go Roth IRA or traditional? Joel wonders when to take required minimum distributions from retirement accounts for the maximum tax benefit, and Brian in New York needs a spitball on when it makes sense to have an emergency fund as a retiree, and for how much. Free Financial Resources in This Episode: https://bit.ly/ymyw-569 (full show notes & episode transcript) Growing Your Wealth Guide - free download Retirement Readiness Guide - free download Retire at 62: Great Idea or Huge Mistake? - YMYW TV Financial Blueprint (self-guided) Financial Assessment (Meet with an experienced professional) REQUEST your Retirement Spitball Analysis DOWNLOAD more free guides READ financial blogs WATCH educational videos SUBSCRIBE to the YMYW Newsletter Connect With Us: YouTube: Subscribe and join the conversation in the comments Podcast apps: subscribe or follow YMYW in your favorite Apple Podcasts: leave your honest reviews and ratings Chapters: 00:00 - Intro: This Week on the YMYW Podcast 01:09 - Should I Sell My Business or Wait? Is It Crazy to Spend More on My Vacation Home Than My Primary Residence? (Fine and Dandy, IL) 20:48 - Saving to Roth IRA vs Traditional IRA in the Final Year Before Retirement (BB and Shell) 23:50 - When to Take Your First RMD for the Maximum Tax Benefit (Joel, CA) 27:33 - Aging Alone in Retirement: How to Protect Assets Before Cognitive Decline (David, 68, Logan, NM) 35:37 - Why Some CPAs Cap Roth Conversions at $500K AGI (Shweta, CA) 37:05 - When Does It Make Sense for Retirees to Have an Emergency Fund - and How Much? (Brian, Albany, NY) 42:03 - Outro - Next Week on the YMYW Podcast
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    44 分
  • Tax-Smart Investing at Every Age: Starting Young or Catching Up - 568

    Tax-Smart Investing at Every Age: Starting Young or Catching Up - 568
    2026/02/10
    John Q. Taxpayer is in the home stretch of his career, looking for the best way to catch-up and build his tax-free bucket. Meanwhile, a pair of young financial nerds in Omaha are already strong savers, but they're wondering whether a simple "VOO for life" strategy is enough to help them reach multimillionaire status in retirement. Also, Janine retired unexpectedly. Can her remaining savings support a European retirement lifestyle? From Jonas Grumby's "glitch in the matrix" tax strategy to the potential tax nightmare of Dolly's literal sack of inherited gold coins, today on Your Money, Your Wealth® podcast 568, Joe Anderson, CFP® and Big Al Clopine, CPA. spitball on how folks from different generations with different situations can reach the same ultimate goal: positioning assets today to ensure the most tax-free wealth tomorrow. Plus, the fellas spitball on the "double taxation" trap of retirement plan loans for Pete in North Carolina, and the affordability of 50-year mortgages for Semper Fi in Michigan. Free Financial Resources in This Episode: https://bit.ly/ymyw-568 (full show notes & episode transcript) Why Asset Location Matters - free guide All About Asset Location - more free resources 15 Maneuvers to Duck an Unplanned Early Retirement Knockout - YMYW TV Financial Blueprint (self-guided) Financial Assessment (Meet with an experienced professional) REQUEST your Retirement Spitball Analysis DOWNLOAD more free guides READ financial blogs WATCH educational videos SUBSCRIBE to the YMYW Newsletter Connect With Us: YouTube: Subscribe and join the conversation in the comments Podcast apps: subscribe or follow YMYW in your favorite Apple Podcasts: leave your honest reviews and ratings Chapters: 00:00 - Intro: This Week on the YMYW Podcast 01:05 - After-Tax 401(k) Catch-Ups vs Taxable Investing (John Q Taxpayer) 06:16 - Forced Early Retirement: Social Security and Roth Conversion Timing? (Janine, Bothell, WA) 11:30 - Are 50-Year Mortgages Actually Affordable? (Semper Fi, Stevensville, MI) 17:59 - 401(k) Loan vs Mortgage Payoff (Pete, NC) 21:27 - Can You Manufacture a Step-Up in Basis? (Jonas Grumby, The Colony, TX) 25:03 - Inherited Gold Coins and Capital Gains Taxes (Dolly, 63, TN) 29:35 - Spitball for Young Investors Who Don't Have Millions (Young Financial Nerds, Omaha, NE) 42:13 - Outro: Next Week on the YMYW Podcast
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    44 分
  • Rising Costs and Retirement Unknowns? Here's What to Do - 567

    Rising Costs and Retirement Unknowns? Here's What to Do - 567
    2026/02/03

    Should Al and Peggy in Illinois keep hammering pre-tax retirement savings or should they pivot to post-tax Roth for better tax diversification? Which pension option is best for their early retirement plans? Long-term care insurance premiums are going up endlessly for Eloise in Connecticut. Is she walking into an insurance industry trap? How do Eric and Tami in Baton Rouge help their kids with college without blowing up their own retirement, and when do student loans make sense? Finally, should Lana and Sterling harvest capital gains or prioritize Roth conversions before moving to a much higher-tax state? The basic question in all of these is the same: how do you protect your future from rising costs and unknowns that are out of your control? We'll find out what it takes, today on Your Money, Your Wealth podcast number 567.

    Free Financial Resources in This Episode:

    https://bit.ly/ymyw-567 (full show notes & episode transcript)

    Key Financial Data Guide - free download

    Retirement Panic Button: 7 Ways to Avoid Hitting It - YMYW TV

    Financial Blueprint (self-guided)

    Financial Assessment (Meet with an experienced professional)

    REQUEST your Retirement Spitball Analysis

    DOWNLOAD more free guides

    READ financial blogs

    WATCH educational videos

    SUBSCRIBE to the YMYW Newsletter

    Connect With Us:

    YouTube: Subscribe and join the conversation in the comments

    Podcast apps: subscribe or follow YMYW in your favorite

    Apple Podcasts: leave your honest reviews and ratings

    Chapters:

    00:00 - Intro: This Week on the YMYW Podcast

    00:55 - Pre-Tax vs. Late Roth Savings? Pension Lump Sum vs. Lifetime Income in Early Retirement? (Al & Peggy, Illinois)

    14:14 - Should I Drop Long-Term Care Insurance Now at Age 70? (Eloise, Connecticut)

    20:41 - College Costs vs Retirement Security for Parents (Tami & Eric, Baton Rouge, LA)

    35:59 - Roth Conversions or Capital Gains Before Moving to a High Tax State? (Lana & Sterling, Nebraska)

    48:14 - Next Week on the YMYW Podcast
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    50 分
  • High Net Worth Pre-Retirees Share Their Biggest Fear (Here's How to Calm It) - 566

    High Net Worth Pre-Retirees Share Their Biggest Fear (Here's How to Calm It) - 566
    2026/01/27
    "Mr and Mrs Smith" have nearly $850,000 saved at age 43, but they're very concerned about retirement. "Lucy and Desi" are 58 and 64 with nearly $7 million saved, but they still lie awake wondering if it's enough for their high-expense life. "Tony and Carmela" are in a similar boat with millions saved at 61 and 59, but they're worried their asset allocation won't get them through their retirement. No matter the numbers, the fears sound exactly the same: will you run out of money in retirement? Turns out overcoming that fear is not about hitting a magic number. We'll find out what it's all about today on Your Money, Your Wealth podcast number 566 with Joe Anderson, CFP®, and Big Al Clopine, CPA. The fellas also spitball Roth conversions, long/short direct indexing capital gains tax strategies for "Juicy Squeeze", working after retirement for Wendi, and how one confusing word can completely change a retirement timing decision for "Jacques and Johana." Free Financial Resources in This Episode: https://bit.ly/ymyw-566 (full show notes & episode transcript) Withdrawal Strategy Guide - free download Financial Blueprint (self-guided) Financial Assessment (Meet with an experienced professional) WATCH 6 Signs You Truly Have "Enough" For Retirement on YMYW TV REQUEST your Retirement Spitball Analysis DOWNLOAD more free guides READ financial blogs WATCH educational videos SUBSCRIBE to the YMYW Newsletter Connect With Us: YouTube: Subscribe and join the conversation in the comments Podcast apps: subscribe or follow YMYW in your favorite Apple Podcasts: leave your honest reviews and ratings Chapters: 00:00 - Intro: This Week on the YMYW Podcast 01:01 - 43 With $850K. Am I Too Late to Build Enough Roth Money? (Mr & Mrs Smith, Dallas, TX) 11:29 - Nearly $7M Saved at 58 and 64. Do We Have Enough for a High-Spend Retirement? (Lucy & Desi, Jersey Shore, NJ) 23:38 - 61 and 59 With $4.5M Saved. Can I Retire Now With a 50/50 Portfolio? (Tony & Carmela, San Ramon, CA) 32:09 - Mid-50s with $685K Saved. Can One Spouse Retire While the Other Works? (Jacques & Johana, Florida) 38:53 - Are Long-Short Direct Indexing Tax Strategies Worth the Fees? (Juicy Squeeze) 47:04 - Should I Work as an Employee or Contractor After 70 on Social Security? (Wendi) 52:04 - Outro: Next Week on the YMYW Podcast
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    53 分
  • 48 and Worried About Early Retirement? This Changes the Math - 565

    48 and Worried About Early Retirement? This Changes the Math - 565
    2026/01/20
    Lucky Lou is 48, burned out and wants to punch at 50. How should he bridge the gap before pensions and Social Security? Joe Anderson, CFP®, and Big Al Clopine, CPA walk through the Rule of 55, 72(t)s, and the psychological reality of spending down a taxable account, today on Your Money, Your Wealth® podcast number 565. Alexei and Anna are high earners in their mid-20s who want to save aggressively and keep taxes low. Which retirement accounts should they prioritize, and can they afford a downpayment on a house? Jay and Gloria are wrestling with the classic question of whether to save to Roth or traditional 401(k), especially since their state doesn't tax retirement income. Is taking the deduction now and backdooring Roths the smarter move? Plus, Sleepless in Seattle wants to know, can her 28-year-old daughter afford to buy a condo in a high-cost housing market? Finally, Jennifer in Texas wonders how to invest and withdraw an inherited IRA over the 10-year rule with the least tax damage. Free Financial Resources in This Episode: https://bit.ly/ymyw-565 (full show notes & episode transcript) The Last 5 Years Before Retirement Will Decide Your Lifestyle - Here's How - YMYW TV Guides: Growing Your Wealth Tax-Free Retirement One Big Beautiful Bill Act Blogs: A Market of Stocks Why AI May Not Be a Bubble Should You Own Gold Instead of Stocks? Financial Blueprint (self-guided) Financial Assessment (Meet with an experienced professional) REQUEST your Retirement Spitball Analysis DOWNLOAD more free guides READ financial blogs WATCH educational videos SUBSCRIBE to the YMYW Newsletter Connect With Us: YouTube: Subscribe and join the conversation in the comments Podcast apps: subscribe or follow YMYW in your favorite Apple Podcasts: leave your honest reviews and ratings Chapters: 00:00 - Intro: This Week on the YMYW Podcast 01:04 - Can I Retire at 50 with $5M and Bridge the Gap to Pensions and Social Security? (Lucky Lou) 10:51 - Which Retirement Accounts Should Young High Earners Max First? Can We Afford a House Downpayment? (Alexei & Anna, Cincinnati) 17:57 - Save to Roth 401(k) or Traditional If Our State Doesn't Tax Retirement Income? (Jay & Gloria, People's Republic of IL) 28:21 - Should a 28-Year-Old Buy a Home in an Expensive Market? (Sleepless in Seattle) 37:15 - How to Invest for Most Growth and Least Tax on an Inherited IRA? (Jennifer, TX) 41:04 - Outro: Next Week on the YMYW Podcast
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    43 分
  • Social Security Timing and When Family Wrecks Retirement - 564

    Social Security Timing and When Family Wrecks Retirement - 564
    2026/01/13
    Hana's mom is 92. Mom's husband is 74, and after years of trying to help a family member, nearly a million dollars is gone. How do they stop the bleeding before it's too late, and how much can they spend each year from what's left? That's today on Your Money, Your Wealth® podcast number 564 with Joe Anderson, CFP® and Big Al Clopine, CPA. Plus, "Peter and Gwen" from Virginia have a pension, Roths, and a shrinking IRA. With the new tax law, IRMAA, and Social Security decisions all colliding, should they keep converting to Roth, and when should they actually collect Social Security? Also, does it make sense for "Mr. and Mrs. Scarecrow" to claim Social Security early and invest it? Finally, "Rosie and Astro" from Pennsylvania ask if they can retire in just three years with $1.3 million, and whether it's time to hire an advisor to help them get there. Free Financial Resources in This Episode: https://bit.ly/ymyw-564 (full show notes & episode transcript) Social Security Handbook Retirement Readiness Guide 6 Biggest Financial Pitfalls in America (Avoid These Traps!) - YMYW TV Financial Blueprint (self-guided) Financial Assessment (Meet with an experienced professional) REQUEST your Retirement Spitball Analysis DOWNLOAD more free guides READ financial blogs WATCH educational videos SUBSCRIBE to the YMYW Newsletter Connect With Us: YouTube: Subscribe and join the conversation in the comments Podcast apps: subscribe or follow YMYW in your favorite Apple Podcasts: leave your honest reviews and ratings Chapters: 00:00 - Intro: This Week on the YMYW Podcast 02:21 - Family Wrecking Retirement: How Much Can Benevolent Retirees Afford to Spend? (Hana) 10:30 - We Have a Pension. Should We Do Roth Conversions After the OBBBA? When to Claim Social Security? (Peter Parker & Gwen Stacy) 23:29 - Should We Claim Social Security Early and Invest It? (Mr & Mrs Scarecrow) 29:56 - We're 60 and 57 with $1.3M. Can We Retire in 3 Years? Should We Hire an Advisor? (Rosie & Astro, PA) 41:04 - Outro: Next Week on the YMYW Podcast
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    43 分
  • How to Beat the "Fire Hydrant" of Future Taxes: YMYW Best of 2025 - 563

    How to Beat the "Fire Hydrant" of Future Taxes: YMYW Best of 2025 - 563
    2026/01/06
    YMYW friends, welcome to 2026. What actually mattered most to you in 2025? It turns out to be tax-free gains on investments, retirement timing, and claiming Social Security. Today on Your Money, Your Wealth® podcast number 563, Joe Anderson, CFP® and Big Al Clopine, CPA break down the smartest tax moves, the biggest Roth mistakes to avoid, and how real people solve real retirement problems - with the help of special guests Susan Brandeis CFP® and the IRA guru, Ed Slott, CPA. Find out when Roth conversions help or hurt, how to lower lifetime taxes for you and your heirs, what it really takes to retire confidently, even without a massive portfolio, and more. Watch or listen and steal the financial strategies that made YMYW's most popular episodes of the year. Free Financial Tools & Resources in This Episode: https://bit.ly/ymyw-563 (full show notes & episode transcript) The Complete Roth Papers Package - 3 free downloads in one! Don't Let These 10 Risks Break Your Retirement - YMYW TV Financial Blueprint (self-guided) EASIRetirement (self-guided) Financial Assessment (Meet with an experienced professional) LISTEN to the Best of the YMYW Podcast 2021, 2022, 2023, 2024 LISTEN to the Top Funniest Moments from the YMYW Podcast Vol. 1, Vol. 2 REQUEST your Retirement Spitball Analysis DOWNLOAD more free guides READ financial blogs WATCH educational videos SUBSCRIBE to the YMYW Newsletter Connect With Us: YouTube: Subscribe and join the conversation in the comments Podcast apps: subscribe or follow YMYW in your favorite Apple Podcasts: leave your honest reviews and ratings Chapters: 00:00 - Intro: This Week on the YMYW Podcast00:54 - Roth IRA is "The Greatest Account Ever" Per Ed Slott. But Why?from ep. 526: YMYW most listeners and plays in 2025 on Apple Podcasts, YMYW most downloaded in 2025 across all podcast platforms 20:46 - Is There a Point Where Roth Conversions No Longer Make Sense? (Jerry, Phoenix, AZ)from ep. 535: YMYW most views, watch time, and new subscribers in 2025 on YouTube, most engaged listeners in 2025 on Apple Podcasts 32:13 - Roth Conversions vs. Taking Advantage of Zero Percent Cap Gains (Skipper, CA)from ep. 517: YMYW most consumed episode in 2025 on Apple Podcasts 43:06 - We're in Our Early 40s with $795K Saved. Can We Retire at 55? (Mr Buckeye, OH)from ep. 546: YMYW longest average view duration in 2025 on YouTube 55:12 - Is My Husband Eligible for Spousal Social Security Benefits Now that WEP and GPO Are Gone? (Cherilyn, El Cajon, CA)from ep. 536: YMYW most plays, most listeners, and most viewers in 2025 on Spotify 59:53 - Outro: 2025 Stats and Next Week on the YMYW Podcast
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