Episodes

  • Will Buying Your Dream Home Ruin Early Retirement? - 559

    Will Buying Your Dream Home Ruin Early Retirement? - 559
    Dec 9 2025

    Today on Your Money, Your Wealth® podcast 559 with Joe Anderson, CFP®, and Big Al Clopine, CPA, David wants to know if he and his wife (ages 47 and 53) are actually on track for retirement - without realizing they're creeping toward that .01% crowd that David swears he is not part of. Mia and Jessie from Seattle want to retire and still pick up a dream lake house with a combined ten million dollars saved. Can they pull it off? Yosemite Sam from Allen, Texas, wonders if he should wipe out the lake house mortgage or keep that low-rate loan to hang on to more flexibility as he approaches retirement. Joe and Big Al also spitball on whether Todd and Margo should shift more into pre-tax accounts to leave their corporate jobs at age 50, and whether early retirement at 55 plus a $500,000 beach home is in the cards for Birdie and Bogey from Williamsburg.

    Free Financial Resources in This Episode:

    https://bit.ly/ymyw-559 (full show notes & episode transcript)

    Financial Blueprint (self-guided)

    Financial Assessment (Meet with an experienced professional)

    REQUEST your Retirement Spitball Analysis

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    Apple Podcasts: leave your honest reviews and ratings

    Chapters:

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

    00:53 - Middle Class Retirement Spitball For Those Not in the .01%: Are We On Track at Age 47? (David)

    06:37 - $5 Million Roth, $5 Million Brokerage: Can We Retire and Buy a Dream Lake House? (Mia & Jessie, Seattle)

    17:26 - Pay Off the Lake House or Keep the Low Rate Mortgage? (Yosemite Sam, Allen, TX)

    25:23 - Should We Shift More Funds into Pre-Tax Retirement to Retire Early at 50? (Todd & Margo, TX)

    38:45 - Can We Afford Early Retirement at 55 and a $500K Beach Home? (Birdie & Bogie, Williamsburg, VA)

    46:27 - Outro: Next Week on the YMYW Podcast
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    48 mins
  • Roth IRA vs. Traditional IRA: Which is Better for Retirement Savings? - 558

    Roth IRA vs. Traditional IRA: Which is Better for Retirement Savings? - 558
    Dec 2 2025
    McDreamy Dempsey wants to know if converting to Roth in the 37% tax bracket ever makes sense, and Gary in La Crosse warns Joe Anderson, CFP® and Big Al Clopine, CPA about Roth conversion "lag" and when it DOESN'T make sense to convert, today on Your Money, Your Wealth® podcast 558. Plus, Wine Guy and Gal in Northern California want a spitball on whether they should protect their ACA subsidies or keep converting to Roth before Medicare kicks in. Then it's the classic question for Robert in Napa, Luke and Lorelai in Indiana, and Phil and Claire in California: should they save for retirement in their traditional, pre-tax, tax-deferred accounts, or their post-tax, tax-free Roth accounts? Different needs and situations, same big question: which strategy gives you the smarter tax outcome? Free Financial Resources in This Episode: https://bit.ly/ymyw-558 (full show notes & episode transcript) Top 10 Tax Tips Guide - limited time special offer, download yours before Friday, Dec 5, 2025! Ultimate Guide to Roth IRAs - free download 2025 Key Financial Data Guide - free download 10 Tax-Cutting Moves to Make Now - 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 00:57 - Should High Earners Do Roth Conversions in the 37 Percent Bracket? (McDreamy Dempsey) 06:50 - The Hidden Roth Conversion Lag: When Conversions Don't Actually Pay Off (Gary, LaCrosse, WI) 18:03 - Should You Prioritize the ACA Subsidy Cliff or Roth Conversions Before Medicare? (Wine Guy & Gal, No CA) 26:27 - Traditional vs Roth Contributions: What's Better When You Make $400K? (Robert, Napa) 33:09 - Roth or Traditional Contributions? Save More or Coast After Debt Payoff? (Luke & Lorelai, Indiana) 42:13 - Roth or Traditional at Age 48: Which Strategy Makes More Sense? (Phil & Claire, CA) 49:19 - Outro: Next Week on the YMYW Podcast
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    52 mins
  • UGMA, 529, HSA, RMD, and Inherited IRA Tax Bombs Defused - 557

    UGMA, 529, HSA, RMD, and Inherited IRA Tax Bombs Defused - 557
    Nov 25 2025
    Joe Anderson, CFP® and Big Al Clopine, CPA are defusing some confusing tax time bombs today on Your Money, Your Wealth® podcast number 557. George in Torrance wants to know the smartest way to deal with the giant UGMA account set up by his kids' grandparents. Suzanne in Detroit has a twist on the new 529 plan to Roth rollover rule. Homer and Marge need a spitball on whether they can build huge 529 plans for college savings and still retire early. Plus, Bill in Chicago just inherited a $950K IRA and needs a withdrawal plan before he triggers a tax explosion. Aaron in Cincinnati wonders whether maxing out his health savings account every year as part of his overall pre-tax contributions is a good idea. Carl in Western Maryland has questions about the required minimum distribution age and HSA rules, and wonders whether those who make the tax code are on drugs. And finally, Marc wants to know how to avoid the tax kaboom from $the 4M sitting in his traditional IRAs at age 73. Free Financial Resources in This Episode: https://bit.ly/ymyw-557 (full show notes & episode transcript) DIY Retirement Guide - limited time Special Offer, download yours by Friday November 28, 2025! Financial Advisors Expose the Internet's Worst Retirement Strategies! - 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 01:07 - Best Tax Moves When Your Kid Has a Huge UGMA Account (George, Torrance, CA) 06:23 - 529 to Roth Rollover or Save for Grad School: What's the Smarter Play? (Suzanne, Detroit) 14:47 - Can $650K High Earners Afford to Build Huge 529 Plans and Still Retire Early? (Homer and Marge, No CA) 24:01 - Inherited IRA Withdrawal Plan: How Much Should You Take Out Annually? (Bill, Chicago) 31:23 - Should You Really Max Out Your HSA Every Year? (Aaron, Cincinnati, OH) 33:07 - Do You Take RMDs at 73 or 75? Was the Government on Drugs When They Came Up with HSA Rules? (Carl, Western MD) 38:07 - 73 With $4 Million in IRAs: What's the Best Tax Strategy? (Marc, 92024 - Encinitas, CA) 39:31 - Outro: Next Week on the YMYW Podcast
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    41 mins
  • Roth Conversions vs. 0% Capital Gains Rate: a Retirement Tax Trap? - 556

    Roth Conversions vs. 0% Capital Gains Rate: a Retirement Tax Trap? - 556
    Nov 18 2025

    Joe Anderson, CFP® and Big Al Clopine, CPA spitball Roth conversions, capital gains, and retirement readiness from every angle, today on Your Money, Your Wealth® podcast number 556. Joe Momma from Virginia wants to know if his zero percent capital-gains strategy is too good to be true, if he can trust his advisor, and if it's finally time to start converting to Roth. David in Poway is already converting his IRA to Roth, but should they convert his wife Shannon's too? Thomas wonders when in retirement to finally start using the Roth money he's saved, instead of just admiring it. And Lizzy and Billy from Texas want to know if $3.5 million is enough for them to retire in 7 years at ages 62 and 65.

    Free Financial Resources in This Episode:

    https://bit.ly/ymyw-556 (full show notes & episode transcript)

    2025 Tax Planning Guide - free download

    Escape These 11 Tax Traps and You'll Save in Retirement - 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

    00:46 - Keep 0% Capital Gains or Convert to Roth? Should I Trust My Advisor? (Joe Momma, VA)

    12:03 - I'm Converting My IRA to Roth. Should We Convert My Wife's IRA Too? (David & Shannon, Poway, CA)

    17:39 - How to Use Roth IRA Money in Retirement (Thomas)

    25:34 - Can We Retire at in 7 Years at 62 and 65 on $3.5M? (Lizzy and Billy, TX)

    29:33 - Outro: Next Week on the YMYYW Podcast
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    31 mins
  • Retiring Before Social Security? Consider These Portfolio Changes - 555

    Retiring Before Social Security? Consider These Portfolio Changes - 555
    Nov 11 2025

    Joe Anderson, CFP® and Big Al Clopine, CPA spitball withdrawal strategies, Roth conversion timing, and saving priorities for every stage of life, today on Your Money, Your Wealth® podcast number 555. Christine just retired at 59 and wants the smartest way to draw income before Social Security, without letting taxes take a third of it. Prickly Richard and Margarita Maggie have a plan to "pull ahead" some Roth conversions now to dodge an RMD avalanche later. Will it work? And the Michigan Queen and Mississippi Boy are wondering whether to save harder for retirement or college for three kids currently under the age of 5.

    Free Financial Resources in This Episode:

    https://bit.ly/ymyw-555 (full show notes & episode transcript)

    Tax-Free Retirement Guide - NEW! Free download

    How To Retire Tax-Free With A Smart Income Plan on 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

    00:53 - I Retired at 59. What's My Best Retirement Withdrawal Strategy Before Social Security at 62? (Christine)

    13:50 - Should We Do Roth Conversions Before Being Hit With the RMD Avalanche? (Prickly Richard & Margarita Maggie, Tucson, AZ)

    26:20 - Saving for Early Retirement at 55 vs. Saving for Kids' Future (Michigan Queen & Mississippi Boy, TN)

    39:53 - Outro: Next Week on the YMYW Podcast
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    41 mins
  • Change of Roth Plans for the New Senior Tax Bonus? Tax-Loss Wins? - 554

    Change of Roth Plans for the New Senior Tax Bonus? Tax-Loss Wins? - 554
    Nov 4 2025
    Should the new temporary senior tax deduction change your Roth conversion strategy? Joe and Big Al spitball for Chris in Maple Grove, Minnesota, who wonders whether to keep converting to Roth now that the $6,000 Senior Bonus deduction phases out with higher income, today on Your Money, Your Wealth® podcast 554 with Joe Anderson, CFP®, and Big Al Clopine, CPA. Teri from Salt Lake City's broker has amassed $60,000 of losses in Teri's $1.1 million account due to tax-loss harvesting. When is enough… enough? Windy Chicago in Chino Hills, California, wonders what to do about their cost basis vanishing after transferring mutual funds to Vanguard, and Larry and Sally from Michigan are planning for retirement while facing significant health challenges. Can they afford to bridge the healthcare gap and still retire safely? Free Financial Resources in This Episode: https://bit.ly/ymyw-554 (full show notes & episode transcript) One Big Beautiful Bill Act Guide Retirement Income Strategies Guide Retirement Rebound: 5 Plays to Help You Score a Comeback - 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: 00:00:00 - Intro 00:00:56 - Should We Stop Roth Conversions for the New $6,000 Senior Bonus Tax Deduction? (Chris, Maple Grove, MN) 00:07:44 - Lost Cost Basis After Moving Funds to Vanguard. Now What? (Windy Chicago, Chino Hills, CA) 00:10:21 - Tax Loss Harvesting: When Is It Too Much? (Teri, Salt Lake City) 00:18:49 - Can We Retire with Rising Health Costs and Care Needs? (Larry & Sally Morgan, voice) 00:33:34 - Outro: Next Week on the YMYW Podcast
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    35 mins
  • Should You Convert to Roth Before or After You Retire? - 553

    Should You Convert to Roth Before or After You Retire? - 553
    Oct 28 2025
    Joe Anderson, CFP® and Big Al Clopine, CPA tackle one of the trickiest timing questions in retirement planning, today on Your Money, Your Wealth podcast number 553: when should you convert to Roth, while you're still earning, or after retirement? First, James from Texas wonders if it's worth maxing out his high-fee 457 plan, or if he's better off investing in a low-cost brokerage account. Full-time travelers "Lois and Clark" want to know how much they should keep converting to Roth now that they're on Medicare. Ray Charles in Chicago is burned out on corporate life and plans to quit at 55. Is that the perfect time for him to start Roth conversions? And finally, Gun and Rose from Louisiana ask if borrowing again from their 401(k) is a smart move. Free Financial Resources in This Episode: https://bit.ly/ymyw-553 (full show notes & episode transcript) Retirement Lifestyles Guide - free download Ultimate Guide to Roth IRAs - free download Will Your Money Last Through Retirement? - 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: 00:00:00 - Intro: This Week on the YMYW Podcast 00:00:56 - 457(b) vs. Brokerage: Are High Fees Worth the Tax Break? (James, TX) 00:06:43 - Roth Conversions in Retirement: Hitting the Road and the 12% Bracket ("Lois & Clark", FL) 00:19:54 - Early Retirement Pivot: Quit at 55 and Convert to Roth? ("Ray Charles", Chicago, IL) 00:33:28 - Should We Borrow From 401(k) For Home Repairs? (Gun & Rose, LA) 00:38:54 - Outro: Next Week on the YMYW Podcast
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    41 mins
  • Don't Let Money Anxiety Ruin Your Retirement - 552

    Don't Let Money Anxiety Ruin Your Retirement - 552
    Oct 21 2025

    Joe Anderson, CFP® and Big Al Clopine, CPA tackle the fears that mess with even the best-laid financial plans, today on Your Money, Your Wealth® podcast 552. Big Wallet Barbie and Ken from the Midwest have saved millions, but Barbie's still worried about retiring early, buying a new house, and converting to Roth. Is she second-guessing her plans? The fellas spitball for Dan from Florida, who's flying high in the 35% tax bracket and trying to decide between Roth 401(k) contributions and future Roth conversions. They also float a surprising idea - one that's rare on YMYW - for a listener from Chicago who is FIRE'd Up about Roth vs. pre-tax and making a tax-smart wealth transfer. We'll wrap up with a couple of your comments.

    Free Financial Resources in This Episode:

    https://bit.ly/ymyw-552 (full show notes & episode transcript)

    Emotionless Investing Guide

    The Truth About Your Love/Hate Relationship With Money - 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

    00:49 - Big Wallet Barbie and Ken's Roth Conversion, Retirement, and Home Purchase Strategy (Barbie Mattel, Midwest)

    08:58 - Roth 401(k) Contributions or Roth Conversions? Flying High in the 35% Tax Bracket (Dan, FL)

    17:23 - High-Earners Planning FIRE and Wealth Transfer: Roth, Pre-Tax… Life Insurance? (FIRE'd Up, Chicago)

    29:56 - Correction on Spousal Social Security Benefits After the Fairness Act (Cindy)

    33:37 - Follow Up: The Kids Are Pretty Alright (Lucas, MN)

    34:44 - Outro: Next Week on the YMYW Podcast
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    37 mins