Your Money, Your Wealth

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 platforms20:46- 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 Podcasts32:13- Roth Conversions vs. Taking Advantage of Zero Percent Cap Gains (Skipper, CA)from ep. 517: YMYW most consumed episode in 2025 on Apple Podcasts43:06- 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 YouTube55:12- 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 Spotify59:53- Outro: 2025 Stats and Next Week on the YMYW Podcast

Today on Your Money, Your Wealth podcast 562 (an encore of episode 513), Joe Anderson, CFP® and Big Al Clopine, CPA spitball for YMYW listeners in their 40s who are ready to call it quits at work, become financially independent, and retire early. Can they afford to do it? Peter and Joanna want to retire in the next two years. Burned Out and Ready to Retire wants out of his toxic office. If Maryland Chicken Man never earns another dollar, how much can he afford to withdraw from his retirement accounts each year? And Suzanne in Massachusetts is 69 and needs $60K a year for the next 30 years. Is she all right? (While Joe and Big Al enjoy a little seasonal downtime and Andi recovers from surgery, enjoy this encore presentation of these questions from an early 2025 episode.) Free Financial Resources in This Episode: https://bit.ly/ymyw-562 (full show notes & episode transcript) 2025 Key Financial Data Guide - free download 10 Big Retirement Regrets to Avoid (Before It's Too Late) - 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 01:30 - We're 45 and 44. Can We Retire in the Next 2 Years? (Peter & Joanna, NJ) 10:45 - Watch 10 Big Retirement Regrets to Avoid (Before It's Too Late) on YMYW TV, Calculate your Free Financial Blueprint 11:44 - I'm 42 and I Work in a Toxic Office. Can I Afford to Retire? (Burned Out and Ready to Retire, NJ) 21:53 - Download the 2025 Key Financial Data Guide for free 22:53 - I'm 69 and Need $60k/Year for the Next 30 Years. Am I All Right? (Suzanne, MA) 25:40 - I'm 45. If I Never Earn Another Dollar How Much Can I Withdraw Every Year? (Maryland Chicken Man) 35:15 - Outro: Next Week on the YMYW Podcast

Financially speaking, should Old Bear in Northern Kentucky marry his Honey? How should Sebastian in Virginia navigate the financial aspects of his separation? Plus, Famous Missourians want to know, how much is enough for retirement and when can you take your foot off the gas? Can Paul with the Big Wallet Bridge the long gap between retiring and claiming Social Security benefits? And can Aspiring Adventurer in Oregon retire single at age 58? (While Joe and Big Al enjoy a little seasonal downtime and Andi recovers from surgery, enjoy this encore presentation of these questions from an early 2025 episode.) Free Financial Resources in This Episode: https://bit.ly/ymyw-561 (full show notes & episode transcript) DOWNLOAD The Going Solo Guide for free WATCH: Going Solo: Navigating Your Financial Future Single 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 01:01 - Financially Speaking, Should Old Bear Marry His Honey? (Northern Kentucky, near Cincinnati, OH) 08:41 - Navigating Finances When Separating from Your Spouse (Sebastian, VA) 15:13 - Watch Going Solo: Navigating Your Financial Future Single on YMYW TV, Download the Going Solo Guide for free 15:42 - How Much is Enough for Retirement? When Can We Take Our Foot Off the Gas? (JC Penney & Laura Ingalls Wilder, Kansas City, MO) 28:31 - How to Bridge the Long Gap Between Retirement and Social Security (Paul with the Big Wallet) 38:50 - Calculate your free Financial Blueprint 39:20 - Can I Retire at Age 58? Where to Save? Should I Do a Roth Conversion Ladder in Retirement? (Aspiring Adventurer, OR) 51:00 - YMYW Podcast Outro

Today on Your Money, Your Wealth® podcast 560, Joe Anderson, CFP® and Big Al Clopine, CPA spitball business development company (BDC) funds for Edward in Illinois before diving into buckets of cash, T-bills, decumulation, and Roth conversion timing for Pebbles and Bam Bam. Plus, the fellas help 34 year old Keith in Connecticut figure out if he's actually on track, whether he's taking too much risk, or just worrying too much. They also spitball on the six-figure annuity gain that Gus in Philly's 95 year old dad has amassed. Finally, why yelling "never pay an advisor" on the internet doesn't necessarily magically turn MYGAs into the perfect investment for everyone. (While Joe and Big Al enjoy a little seasonal downtime and Andi recovers from surgery, enjoy this encore presentation of these questions from a January 2025 episode.) Free Financial Resources in This Episode: https://bit.ly/ymyw-560 (full show notes & episode transcript) 10 Steps to Improve Investing Success - free download Tax-Smart Charitable Giving Guide 6 Secrets to Bigger Tax Deductions from Your Non-Profit Donations - 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 01:03 - What's the Risk With Business Company Development (BDC) Funds? (Edward, IL) 03:58 - T-Bills, Decumulation, IRAs, and Investing Strategies (Pebbles & Bam Bam, Kentuckystone) 12:02 - I'm 34. Are My Investments Appropriate for My Time Horizon? (Keith, CT) 17:59 - MYGA Retirement Withdrawal Strategy for Dad (Gus in Philly) 23:00 - Just Buy Multi-Year Guaranteed Annuities (MYGAs) and Bonds (comment from Ken, YouTube) 28:04 - YouTube comments: State Taxes, Pro-Rated Sale of Primary Residence, Bonds vs. Pension, and PERMA 35:27 - YMYW Podcast Outro

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 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 - 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

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

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

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

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

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) 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 - Intro 00:56 - Should We Stop Roth Conversions for the New $6,000 Senior Bonus Tax Deduction? (Chris, Maple Grove, MN) 07:44 - Lost Cost Basis After Moving Funds to Vanguard. Now What? (Windy Chicago, Chino Hills, CA) 10:21 - Tax Loss Harvesting: When Is It Too Much? (Teri, Salt Lake City) 18:49 - Can We Retire with Rising Health Costs and Care Needs? (Larry & Sally Morgan, voice) 33:34 - Outro: Next Week on the YMYW Podcast

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) 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 - Intro: This Week on the YMYW Podcast 00:56 - 457(b) vs. Brokerage: Are High Fees Worth the Tax Break? (James, TX) 06:43 - Roth Conversions in Retirement: Hitting the Road and the 12% Bracket ("Lois & Clark", FL) 19:54 - Early Retirement Pivot: Quit at 55 and Convert to Roth? ("Ray Charles", Chicago, IL) 33:28 - Should We Borrow From 401(k) For Home Repairs? (Gun & Rose, LA) 38:54 - Outro: Next Week on the YMYW Podcast

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

We’re playing “which comes first” today on Your Money, Your Wealth® podcast number 551 with Joe Anderson, CFP® and Big Al Clopine, CPA. “Retired G-Man and Nurse Ratched” from Pennsylvania have saved $2 million. Should they withdraw money first from their IRA or their taxable accounts in retirement? “Mike and Carol in Florida” want to know when and how much to convert to Roth, but they’re also sitting on a mountain of company stock. Should they deal with that first? Mackey in Florida is 55 and wonders if he can retire now with $2.6 million and some lingering debt - but there’s an important first he’s missing too! Plus, Mike in Utah asks Joe and Big Al to spitball on a plan for his 90-year-old mom’s $1.9 million annuity, and Doc McMuffin in Minnesota asks for the fellas’ take on her plan to gift appreciated assets to her parents. Free Financial Resources in This Episode: https://bit.ly/ymyw-551 (full show notes & episode transcript) YourMoneyYourWealth.com - all our financial resources! Ask Joe and Big Al, blogs, workshops, financial guides, and 11 seasons of YMYW TV! 10 Big Retirement Regrets to Avoid (Before It’s Too Late) - 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 - How to Retire at 55 With $2.6M and Debt? First, How to Write a Good Spitball Request (Mackey, FL) 03:46 - Sequence of Retirement Withdrawals: IRA First or Taxable First? (G-Man and Nurse Ratched, PA) 12:10 - Roth Conversions vs Concentrated Stock: Which Comes First? (Mike & Carol, FL) 29:27 - What to Do With 90-Year-Old Mom’s $1.9M Annuity? (Mike, UT) 40:59 - Is Gifting Appreciated Assets to Parents Tax-Smart or Risky? (Doc McMuffin, MN) 48:27 - Outro: Next Week on the YMYW Podcast

Joe and Big Al spitball on how to avoid screwing up the timing of your Roth conversions, today on Your Money, Your Wealth® podcast number 550. Barrie from New York is 62 and single, and she’s been diligently converting pre-tax money each year for lifetime tax-free Roth growth. Should she continue after she retires next year? “Jerry and Elaine” want to retire in the next six years and still leave the kids an inheritance. When should they start Roth conversions? Alex in Pennsylvania is a 31-year-old software engineer. Should he convert his IRA to Roth all at once? Plus, how can he transition into a career as a financial planner? A clarification on the age plus 20 rule of thumb for retirement contributions from one of our YouTube viewers is very un-clarified for Joe, and the fellas let Lisa in San Diego know whether she can use her rental real estate income to fund a Roth 401(k). Free Financial Resources in This Episode: https://bit.ly/ymyw-550 (full show notes & episode transcript) Ultimate Guide to Roth IRAs 6 Signs You Truly Have “Enough” for 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 00:55 - Should I Keep Converting $20K a Year in Retirement? (Barrie, NY) 07:17 - Can We Retire at 62 and Still Leave an Inheritance? Roth Conversion Strategies for Big Accounts (Jerry & Elaine, KS) 17:05 - I'm 31. Should I Convert $57K Now or Spread It Out? (Alex, PA) 29:12 - Roth Conversion Timing Before Retirement (Mike, Philly Suburbs) 36:49 - Confused About Roth Withdrawal Rules at 60 (Lisa, Omaha NE) 40:05 - Clarification on the Age + 20 Rule of Thumb for Contributions (Matt, YouTube) 45:40 - Can Rental Property Income Fund a Roth 401(k)? (Lisa, San Diego) 47:24 - Outro: Next Week on the YMYW Podcast

Today on Your Money, Your Wealth® podcast number 549 with Joe Anderson, CFP® and Big Al Clopine, CPA, a comment on one of our YouTube videos sparks a dialogue between Joe and Big Al on the 4% rule vs. the "guardrails" withdrawal strategy. Joe at the Beach is managing his ~$6M portfolio on his own, but wants the fellas’ take on his upper limit for yearly spending, so he can keep drinking his old-fashioneds. Can Joe Ko in Virginia afford to bridge the gap between retiring at 67 and taking Social Security at 70? Plus, "Harold and Maude" have nearly $7M saved. Should they accelerate Roth conversions into high-tax brackets before moving from low-tax Colorado to high-tax California? And how much more than their current annual spend can they afford for family vacations and travel? Free Financial Resources in This Episode: https://bit.ly/ymyw-549 (full show notes & episode transcript) Withdrawal Strategy Guide Cruising Into Retirement Checklist and Guide (limited time offer, download by this Friday!) How to Cruise Into Your 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 00:50 - What About the Guardrails Withdrawal Strategy? (Bill, YouTube) 04:13 - I’m 69 with $5.7 Million Saved. What’s the Max I Can Spend in Retirement? (Joe at the Beach) 15:12 - 63 and 58 With $1.85M Saved. How Much Can We Spend from 67 Until Social Security at 70? (Joe Ko, VA) 21:30 - We’re 61 and 69 with $7.6 million. Can We Increase Our Retirement Spending? How Should We Do Roth Conversions? (“Harold and Maude”, Durango, CO) 33:49 - Outro: Next Week on the YMYW Podcast

Wendy and Joe in Colorado ran the numbers, and their financial planning software says they'll have over $10 million when they pass. Wendy's wondering if they should continue converting to Roth while working, despite their high tax bracket. But has the software lulled them into a false sense of security? That’s today on Your Money, Your Wealth® podcast number 548 with Joe Anderson, CFP® and Big Al Clopine, CPA. Plus, which is smarter for "Kurt and Courtney" in New York: aggressively paying down their mortgage, or putting their extra money to work in the market before Kurt retires early in 20 years? Finally, when does it stop making sense for high-earners "Tim and Faith" in Boston to contribute to their Roth? The fellas duke it out on this one (and we figure out, based on our earliest musical interests, which era we’re each children of.) Free Financial Resources in This Episode: https://bit.ly/ymyw-548 (full show notes & episode transcript) Pay Off the Mortgage? - YouTube playlist - Spotify playlist DOWNLOAD The Retirement Readiness Guide WATCH 4 Hard Truths About Retirement You Need to Face on YMYW TV Financial Blueprint (free, self-guided) Financial Assessment (free, 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 01:11 - Financial Software Says We’ll Have $10M. Should We Continue Converting to Roth While Working, Despite Our High Tax Bracket? (Wendy, Loveland, CO) 16:35 - Watch 4 Hard Truths About Retirement You Need to Face on YMYW TV, Download the Retirement Readiness Guide 17:37 - What Are the Pros and Cons of Paying Off Our Home Before I Retire Early? (Kurt & Courtney, NY) 31:54 - Pay Off the Mortgage: YMYW Podcast Playlists on YouTube and Spotify, Calculate your free Financial Blueprint 32:51 - We're Late 40s With $3M + $2M RSUs. Continue Contributing to Tax-Deferred? Are We On Track for Retirement at 55 or 60? (Tim & Faith, MA) 46:15 - Next Week on the YMYW Podcast 46:37 - YMYW Podcast Outro

A YMYW listener from Missouri and his wife are retired at 69 and 67, with less than $2 million dollars. Should they continue converting retirement savings to Roth for the tax-free growth? What should they do about long term care insurance? More importantly, is our listener’s name (Cousy) pronounced "Cuzzy" or "Koozy"? Speaking of Roth conversions, must “Peggy Hill” wait five years to withdraw her conversion money, or only its earnings? That’s today on Your Money, Your Wealth® podcast number 547 with Joe Anderson, CFP® and Big Al Clopine, CPA. Plus, is Skipper’s retirement payout plan the killer deal he thinks it is? How can Jeff in Dallas pay less capital gains tax on his 3 million dollar single stock, million dollar 401(k), and potential eBay income? Is selling on eBay still a thing? Does Dolly in Tennessee need to empty her inherited IRA within the next 10 years due to the SECURE Act? And finally, HSA vs. HRA: how should Larry in Rhode Island navigate switching from his current employer’s health savings account to his future employer’s health reimbursement arrangement? Free Financial Resources in This Episode: https://bit.ly/ymyw-547 (full show notes & episode transcript) 5 Year Rules for Roth IRA Withdrawals 2025 Key Financial Data Guide (newly updated with One Big Beautiful Bill changes) 10 Steps to Improve Investing Success What to Do When the Stock Market Gets Crazy - 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 01:11 - Should We Continue Roth Conversions in Retirement? What About Long-Term Care? (Cousy, MO) 13:03 - Must I Wait 5 Years to Withdraw My Roth Conversion, Or Only Its Earnings? ("Peggy Hill", MN) 21:50 - Is My Retirement Plan Payout the Killer Deal I Think It Is? (Skipper) 28:07 - How to Minimize My Capital Gains Tax? (Jeff, Dallas, TX) 33:37 - Must I Empty My Inherited IRA Within 10 Years With The SECURE Act? (Dolly, Bristol, TN) 37:50 - HSA and HRA: Health Savings Account vs. Health Reimbursement Arrangement (Larry, RI) 40:48 - Outro: Next Week on the YMYW Podcast

We heard your feedback, and today on Your Money, Your Wealth® podcast number 546, Joe Anderson, CFP® and Big Al Clopine, CPA are spitballing retirement for the not-so-fat wallets: Joe and Masako in Washington state and Reid in Indiana have less than a million saved. Can they still accomplish their retirement goals in their 60s? Mr Buckeye in Ohio and Old Macdonald in Maine have less than a million saved, and Curt in Pennsylvania has less than $1.5 million saved. Can they retire early - in their 40s and 50s? Free financial resources & episode transcript: https://bit.ly/ymyw-546 DOWNLOAD The Going Solo Guide WATCH Going Solo: Navigating Your Financial Future Single on YMYW TV CALCULATE your free Financial Blueprint SCHEDULE your Free Financial Assessment ASK Joe & Big Al for your Retirement Spitball Analysis LEAVE YOUR HONEST RATINGS AND REVIEWS on Apple Podcasts SUBSCRIBE or FOLLOW on your favorite podcast app JOIN THE CONVERSATION on YouTube DOWNLOAD more free guides READ financial blogs WATCH educational videos SUBSCRIBE to the YMYW Newsletter Timestamps: 00:00 - Intro: This Week on the YMYW Podcast 00:36 - We’re 59 and 65 with Less than $1M. Can We Still Accomplish Our Retirement Goals? (Joe and Masako, WA state) 08:18 - We’re 33 with $200K. Can We Retire at 65 and Spend $159K/Year? (Reid, IN) 15:58 - Calculate your Free Financial Blueprint 16:32 - We're Early 40s With $795K. Can We Retire at 55? (Mr Buckeye, OH) 28:38 - Watch Going Solo: Navigating Your Financial Future Single YMYW TV, Download the Going Solo Guide 29:25 - I'm 43 With $50K and a Paid Off House. Can I Retire ASAP? (Old MacDonald, Limington, Maine) 37:35 - I'm 35 With $1.4M. Can I Retire at 45 and Spend $75K/year? (Conshohocken Curt, PA) 49:04 - Next Week on the YMYW Podcast 49:23 - YMYW Podcast Outro

One Big Beautiful Bill is now law. How does it impact your Roth conversion strategies and other financial decisions? Plus, you may have seen or heard other advisors talking about their strategies for getting your retirement savings into tax-free Roth accounts. How are these different from a good ol’ Roth conversion, and what do Joe and Big Al think of them? Find out today on Your Money, Your Wealth® podcast number 545 with Joe Anderson, CFP® and Big Al Clopine, CPA. Also, why is Ed Slott, CPA, the man known to many as "the IRA guru," such a fan of permanent cash value life insurance? Finally, an attempted correction from a YMYW YouTube viewer turns into a rousing game of death trivia, and we’ll share some of your opinions from the 8th Annual YMYW Podcast Survey, which just closed. (Congratulations Larry, for being the randomly-chosen winner of the $100 Amazon e-gift card, just for completing the survey!) Free financial resources & episode transcript: https://bit.ly/ymyw-545 DOWNLOAD The Ultimate Guide to Roth IRAs WATCH Your 11 Step Path to Financial Freedom on YMYW TV CALCULATE your free Financial Blueprint SCHEDULE your Free Financial Assessment ASK Joe & Big Al for your Retirement Spitball Analysis LEAVE YOUR HONEST RATINGS AND REVIEWS on Apple Podcasts SUBSCRIBE or FOLLOW on your favorite podcast app JOIN THE CONVERSATION on YouTube DOWNLOAD more free guides READ financial blogs WATCH educational videos SUBSCRIBE to the YMYW Newsletter

You’ve heard Joe and Big Al talk about the benefits of tax diversification in retirement. That is, having money in tax-deferred, tax-free, and taxable accounts. But what should you do if this tax triangle of yours is lopsided? Joe and our special guest co-host, Marc Horner, CFP®, spitball on this quandary for Rae and Roy in Central California, today on Your Money, Your Wealth® podcast number 544. Plus, do Rae or Roy need to get a part-time job? Also, "Elwood Blues" in Illinois would like to retire in two years, but is willing to go for 3 more to make his retirement plan work. Joe and Marc spitball on when "Elwood" can really put down that harmonica. Free financial resources & episode transcript: https://bit.ly/ymyw-544 Complete the 8th Annual YMYW Podcast Survey by 5pm Pacific on August 31, 2025, for your chance at a $100 Amazon e-gift card! (secret password: ymyw) WATCH 15 Maneuvers to Duck an Unplanned Early Retirement Knockout on YMYW TV CALCULATE your free Financial Blueprint ASK Joe & Big Al for your Retirement Spitball Analysis SCHEDULE your Free Financial Assessment LEAVE YOUR HONEST RATINGS AND REVIEWS on Apple Podcasts SUBSCRIBE or FOLLOW on your favorite podcast app JOIN THE CONVERSATION on YouTube DOWNLOAD more free guides READ financial blogs WATCH educational videos SUBSCRIBE to the YMYW Newsletter Timestamps: 00:00 - Intro: This Week on the YMYW Podcast with Joe Anderson, CFP® and Marc Horner, CFP® 00:49 - Our Tax Triangle is Lopsided. Should One of Us Get a Part-Time Job? (Rae and Roy, Central CA) 12:03 - Watch 15 Maneuvers to Duck an Unplanned Early Retirement Knockout, Calculate your Financial Blueprint, Schedule a Financial Assessment 13:11 - I'd Like to Retire in 2 Years. Willing to Work 3 More to Make it Work (Elwood Blues, IL) 27:10 - Next Week on YMYW Podcast: The One Big Beautiful Bill + More 27:40 - YMYW Podcast Outro