Your Money, Your Wealth

Making fun of finance. A US News & World Report "Top 9 Personal Finance Podcast” (2025) and "Top 12 Retirement Podcast” (2023). One of the "10 Best Personal Finance YouTube Channels" (CardRates, 2023). “Best Retirement Podcast With Humor” (FIPhysician, 2020-2024). Learn strategies that can help you retire successfully. Financial advisor Joe Anderson, CFP® and certified public accountant Big Al Clopine, CPA answer your money questions and spitball on your 401k, IRA, Roth conversions and backdoor Roth IRA, how to pay less taxes, asset allocation, stocks and bonds, real estate, and other investments, Social Security benefits, capital gains tax, 1031 exchange, early retirement, expenses and withdrawals, and more money and wealth management strategies. YMYW is retirement planning, investing, and tax reduction made fun, presented by Pure Financial Advisors - a fee-only financial planning firm. Pure Financial adheres to the fiduciary standard of care, in which we are required by law to act in the best interest of our clients at all times. Access free financial resources and episode transcripts, Ask Joe & Big Al On Air to get your Retirement Plan Spitball Analysis: http://YourMoneyYourWealth.com

When Should You Take Social Security? (Don’t Screw This Up) - 574 03/24/2026

When Should You Take Social Security? (Don’t Screw This Up) - 574 Joe Anderson, CFP® and Big Al Clopine, CPA focus on Social Security claiming strategies as part of the retirement spitballs, today on Your Money, Your Wealth® podcast number 574. Bijou Plutus and her husband in Massachusetts are 62 and 64 with about a million dollars. Can she retire at 65, and should he claim Social Security early? Dr. Jekyll and Mrs. Hyde in the Twin Cities have about the same at 51 and 49, plus big pensions and high spending. Can they afford to retire early, and when should they claim Social Security? Diggler and Roller Girl in Tennessee are 57 and 58 with about $600K, and Diggler estimates his Social Security break-even is at age 77. Can he collect Social Security early and simply work recreationally? Free Financial Resources in This Episode: (full show notes & episode transcript) Social Security Handbook - free download: Tax-Free Retirement Guide - free download: How To Retire Tax-Free With A Smart Income Plan - 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: Subscribe on YouTube and join the conversation in the comments: Subscribe or follow YMYW in your favorite podcast app: Leave your honest reviews and ratings in Apple Podcasts: Chapters: 00:00 - Intro: This week on the YMYW Podcast 01:07 - 62 and 64 with About $1M. Can I Retire at 65? Should Hubby Claim Social Security Early? (Bijou Plutus, MA) 11:52 - Can We Retire in Our 50s With Pensions and High Spending? (Dr. Jekyll & Mrs. Hyde, Twin Cities, MN) 29:53 - Social Security Break-Even at 77. Claim Early and Work Recreationally? (Diggler & Rollergirl, 57 & 58, Tennessee) 42:52 - Outro: Next Week on the YMYY Podcast /episode/index/show/yourmoneyyourwealth/id/40539750

Could You Retire Tomorrow If You Had To? - 573 03/17/2026

Could You Retire Tomorrow If You Had To? - 573 Juan and Mary in Brooklyn are 49 and 48 with $2.2 million saved. Can Juan afford to retire early, or just walk away if he gets fired? And if they get divorced, yikes - but does the math still work? That's today on Your Money, Your Wealth® podcast number 573. But first, “Reuben Sailing Shoes” is 68, single, retired, and has $1.6 million saved, but he's never had a budget in his life. How much can he actually spend? “Leslie and Ben” are federal retirees in their seventies with great pensions and a mix of pre-tax and Roth savings, and “Mork and Mindy” in Delaware are retired with an annuity, a pension, Social Security, and $1.3 million in an IRA. Joe Anderson, CFP® and Big Al Clopine, CPA spitball on how Roth conversions and RMD timing can help both couples minimize taxes and make the most of what they've got. Free Financial Resources in This Episode: (full show notes & episode transcript) Complete Roth Papers Package - free download: Retirement Course: Can You Hit a Hole in One? With PGA Pro Chris Riley - 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: Subscribe on YouTube and join the conversation in the comments: Subscribe or follow YMYW in your favorite podcast app: Leave your honest reviews and ratings in Apple Podcasts: Chapters: 00:00 - Intro: This week on the YMYW Podcast 01:04 - How Much Can a Single 68-Year-Old Retiree With $1.6M(?) Spend Without Running Out of Money? (Reuben Sailing Shoes, Wyoming) 08:38 - 72 and 76 With $1.4M. Should We Keep Doing Roth Conversions After RMDs Start? (Leslie and Ben, Ohio) 17:12 - 71 and 73 With $1.73M. How to Balance Roth Conversions, RMDs, Widow Taxes, and Inheritance Goals? (Mork and Mindy, Delaware) 28:28 - 49 and 48 with $2.2M. If I Get Fired, Quit, or Get Divorced Tomorrow, Will We Be Fine? (Juan & Mary, Brooklyn, NY) 39:20 - Outro: Next Week on YMYW Podcast /episode/index/show/yourmoneyyourwealth/id/40422480

Could You Lose Half Your Retirement Income to Taxes? - 572 03/10/2026

Could You Lose Half Your Retirement Income to Taxes? - 572 “Carl and Jane” have eight million bucks, and their advisor is suggesting a 130/30 long-short investing strategy. Joe Anderson, CFP® and Big Al Clopine, CPA spitball on whether this is a smart tax move or unnecessary complexity - and whether they would do it themselves, today on Your Money, Your Wealth® podcast number 572. Plus, Tyrone and Tova think they may never even need their retirement accounts, so do they really need to bother with Roth conversions if the kids are going to inherit the money anyway, or could skipping the conversions mean losing half their retirement income to taxes? Mark in San Diego is juggling Roth conversions and Social Security timing without blowing up his tax bill, or the income-related monthly adjustment amount for Medicare, or net investment income tax. And “Boat Drinks” has a big non-qualified deferred compensation plan. How can he structure payouts before it turns into a tax nightmare - and before he potentially gets laid off? Free Financial Resources in This Episode: (full show notes & episode transcript) The Emotionless Investing Guide - free download The Ultimate Guide to Roth IRAs - free download 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: Subscribe on YouTube and join the conversation in the comments: Subscribe or follow YMYW in your favorite podcast app: Leave your honest reviews and ratings in Apple Podcasts: Chapters: 00:00 - Intro: This Week on the YMYW Podcast 01:12 - Should Investors with $8M Use a 130/30 Long-Short Investing Strategy? (Carl Sandburg and Jane Addams, California) 12:42 - We’ll Never Need Our Retirement Accounts. Should We Still Do Roth Conversions? (Tyrone and Tova) 27:18 - Roth Conversions vs. Social Security: Which Comes First? What About IRMAA and NIIT? (Mark, California) 38:16 - How to Structure Non-Qualified Deferred Compensation Payouts When a Layoff Might Be Coming? (Boat Drinks) 50:10 - Outro: Next Week on the YMYW Podcast /episode/index/show/yourmoneyyourwealth/id/40378400

Retire Early in Your 40s or 50s: Green Light or Reality Check? - 571 03/03/2026

Retire Early in Your 40s or 50s: Green Light or Reality Check? - 571 If you plan to punch the clock for the final time decades before “standard” retirement age, you need a financial strategy that goes beyond just saving. Joe Anderson, CFP® and Big Al Clopine, CPA spitball five different early retirement plans to see whose numbers are tight and who is ready to go for it, today on Your Money, Your Wealth® podcast 571. George in South Carolina wants to retire in 8 years at 53. Does he have enough in his brokerage account to bridge the gap to Social Security? Joe in Massachusetts is saving a staggering $200,000 a year, but will his high-spending lifestyle make a multi-million dollar nest egg look small? The fellas help 26-year-old Jonathan in Florida map out a path to retire in his 40s using his 457 plan, and they spitball on whether early exit strategies for both Kris and Rojo in California are a "green light" or a reality check. Plus, Joe explains why the "Rule of 55" and Roth conversions might be some of the most important tools in your early retirement toolbox. Free Financial Resources in This Episode: https://bit.ly/ymyw-571 (full show notes & episode transcript) Withdrawal Strategy Guide - free download: https://purefinancial.com/white-papers/withdrawal-strategy-guide/?utm_source=LibsynDestinations&utm_medium=podcast&utm_campaign=YMYW-571 Long-Term Care Planning Guide - free download: https://purefinancial.com/white-papers/long-term-care-planning-options/?utm_source=LibsynDestinations&utm_medium=podcast&utm_campaign=YMYW-571 The #1 Spending Mistake Ruining Retirements - YMYW TV: https://purefinancial.com/ymyw/episodes/number-one-spending-mistake-ruining-retirements/?utm_source=LibsynDestinations&utm_medium=podcast&utm_campaign=YMYW-571 Financial Blueprint (self-guided): https://bit.ly/PureFinancialBlueprint Financial Assessment (Meet with an experienced professional): https://bit.ly/PureFreeAssessment REQUEST your Retirement Spitball Analysis: https://bit.ly/AskJoeAndAl DOWNLOAD more free guides: https://bit.ly/PureGuides READ financial blogs: https://bit.ly/PureFinBlog WATCH educational videos: https://bit.ly/PureEdVideos SUBSCRIBE to the YMYW Newsletter: https://bit.ly/YMYWNewsletter Connect With Us: Subscribe on YouTube and join the conversation in the comments: https://bit.ly/YMYW-YT Subscribe or follow YMYW in your favorite podcast app: https://lnk.to/ymyw Leave your honest reviews and ratings in Apple Podcasts: https://podcasts.apple.com/us/podcast/your-money-your-wealth/id312900254 Chapters: 00:00 - Intro: This Week on the YMYW Podcast 01:06 - Is Retiring at 53 With No Pension a Smart Move or a Risky Bet? (George, South Carolina) 11:59 - High Income, High Spend, Early Retirement: Does the Math Still Work? (Joe, MA) 18:39 - At 26, Should I Go All In on a 457 to Retire Way Early? (Jonathan, Florida) 26:41 - Can I Retire Early and Still Cover Health Care and Long Term Care Costs? (Kris, California) 33:33 - I'm a Widowed Parent. Can I Retire at 57 and Still Fund College and Legacy Goals? (Rojo, California) 43:08 - Outro: Next Week on the YMYW Podcast /episode/index/show/yourmoneyyourwealth/id/40293415

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

Retirement Changes at These 5 Major Financial Crossroads - 569 02/17/2026

Retirement Changes at These 5 Major Financial Crossroads - 569 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: (full show notes & episode transcript) - free download - free download - YMYW TV (self-guided) (Meet with an experienced professional) REQUEST your DOWNLOAD READ WATCH SUBSCRIBE to the Connect With Us: : Subscribe and join the conversation in the comments : subscribe or follow YMYW in your favorite : 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 /episode/index/show/yourmoneyyourwealth/id/40121695

Tax-Smart Investing at Every Age: Starting Young or Catching Up - 568 02/10/2026

Tax-Smart Investing at Every Age: Starting Young or Catching Up - 568 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: (full show notes & episode transcript) - free guide - more free resources - YMYW TV (self-guided) (Meet with an experienced professional) REQUEST your DOWNLOAD READ WATCH SUBSCRIBE to the Connect With Us: : Subscribe and join the conversation in the comments : subscribe or follow YMYW in your favorite : 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 /episode/index/show/yourmoneyyourwealth/id/40040710

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

High Net Worth Pre-Retirees Share Their Biggest Fear (Here's How to Calm It) - 566 01/27/2026

High Net Worth Pre-Retirees Share Their Biggest Fear (Here's How to Calm It) - 566 "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: (full show notes & episode transcript) - free download (self-guided) (Meet with an experienced professional) WATCH on YMYW TV REQUEST your DOWNLOAD READ WATCH SUBSCRIBE to the Connect With Us: : Subscribe and join the conversation in the comments : subscribe or follow YMYW in your favorite : 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 /episode/index/show/yourmoneyyourwealth/id/39889820

48 and Worried About Early Retirement? This Changes the Math - 565 01/20/2026

48 and Worried About Early Retirement? This Changes the Math - 565 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: (full show notes & episode transcript) - YMYW TV Guides: Blogs: (self-guided) (Meet with an experienced professional) REQUEST your DOWNLOAD READ WATCH SUBSCRIBE to the Connect With Us: : Subscribe and join the conversation in the comments : subscribe or follow YMYW in your favorite : 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 /episode/index/show/yourmoneyyourwealth/id/39755685

Social Security Timing and When Family Wrecks Retirement - 564 01/13/2026

How to Beat the “Fire Hydrant” of Future Taxes: YMYW Best of 2025 - 563 01/06/2026

How to Beat the “Fire Hydrant” of Future Taxes: YMYW Best of 2025 - 563 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) - 3 free downloads in one! - YMYW TV (self-guided) (self-guided) (Meet with an experienced professional) LISTEN to the Best of the YMYW Podcast , , , LISTEN to the Top Funniest Moments from the YMYW Podcast , REQUEST your DOWNLOAD READ WATCH SUBSCRIBE to the Connect With Us: : Subscribe and join the conversation in the comments : subscribe or follow YMYW in your favorite : leave your honest reviews and ratings Chapters: 00:00 - Intro: This Week on the YMYW Podcast 00:54 - Roth IRA is “The Greatest Account Ever” Per Ed Slott. But Why? from : YMYW most listeners and plays in 2025 on , YMYW most downloaded in 2025 across 20:46 - Is There a Point Where Roth Conversions No Longer Make Sense? (Jerry, Phoenix, AZ) from : YMYW most views, watch time, and new subscribers in 2025 on , most engaged listeners in 2025 on 32:13 - Roth Conversions vs. Taking Advantage of Zero Percent Cap Gains (Skipper, CA) from : YMYW most consumed episode in 2025 on 43:06 - We're in Our Early 40s with $795K Saved. Can We Retire at 55? (Mr Buckeye, OH) from : YMYW longest average view duration in 2025 on 55:12 - Is My Husband Eligible for Spousal Social Security Benefits Now that WEP and GPO Are Gone? (Cherilyn, El Cajon, CA) from : YMYW most plays, most listeners, and most viewers in 2025 on 59:53 - Outro: 2025 Stats and Next Week on the YMYW Podcast /episode/index/show/yourmoneyyourwealth/id/39610045

I'm 42 and Burned Out with $2.25M. Can I Retire Early from My Toxic Job? - 562 12/30/2025

Retirement Finances Whether You're Married, Separated, or Single - 561 12/23/2025

The Truth About High Income Investments and Retirement Safety - 560 12/16/2025

Will Buying Your Dream Home Ruin Early Retirement? - 559 12/09/2025

Roth IRA vs. Traditional IRA: Which is Better for Retirement Savings? - 558 12/02/2025

Roth IRA vs. Traditional IRA: Which is Better for Retirement Savings? - 558 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) - limited time special offer, download yours before Friday, Dec 5, 2025! - free download - free download - YMYW TV (self-guided) (Meet with an experienced professional) REQUEST your DOWNLOAD READ WATCH SUBSCRIBE to the Connect With Us: : Subscribe and join the conversation in the comments : subscribe or follow YMYW in your favorite : 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 /episode/index/show/yourmoneyyourwealth/id/39162980

UGMA, 529, HSA, RMD, and Inherited IRA Tax Bombs Defused - 557 11/25/2025

UGMA, 529, HSA, RMD, and Inherited IRA Tax Bombs Defused - 557 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) - limited time Special Offer, download yours by Friday November 28, 2025! - YMYW TV (self-guided) (Meet with an experienced professional) REQUEST your DOWNLOAD READ WATCH SUBSCRIBE to the Connect With Us: : Subscribe and join the conversation in the comments : subscribe or follow YMYW in your favorite : 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 /episode/index/show/yourmoneyyourwealth/id/39146510

Roth Conversions vs. 0% Capital Gains Rate: a Retirement Tax Trap? - 556 11/18/2025

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

Change of Roth Plans for the New Senior Tax Bonus? Tax-Loss Wins? - 554 11/04/2025

Should You Convert to Roth Before or After You Retire? - 553 10/28/2025

Don’t Let Money Anxiety Ruin Your Retirement - 552 10/21/2025

Where Should You Take Retirement Money First If You’ve Saved $2M? - 551 10/14/2025

Where Should You Take Retirement Money First If You’ve Saved $2M? - 551 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: (full show notes & episode transcript) - all our financial resources! Ask Joe and Big Al, blogs, workshops, financial guides, and 11 seasons of YMYW TV! - YMYW TV (self-guided) (Meet with an experienced professional) REQUEST your DOWNLOAD READ WATCH SUBSCRIBE to the Connect With Us: : Subscribe and join the conversation in the comments : subscribe or follow YMYW in your favorite : leave your honest reviews and ratings Chapters: 00:00:00 - Intro: This Week on the YMYW Podcast 00:00:53 - How to Retire at 55 With $2.6M and Debt? First, How to Write a Good Spitball Request (Mackey, FL) 00:03:46 - Sequence of Retirement Withdrawals: IRA First or Taxable First? (G-Man and Nurse Ratched, PA) 00:12:10 - Roth Conversions vs Concentrated Stock: Which Comes First? (Mike & Carol, FL) 00:29:27 - What to Do With 90-Year-Old Mom’s $1.9M Annuity? (Mike, UT) 00:40:59 - Is Gifting Appreciated Assets to Parents Tax-Smart or Risky? (Doc McMuffin, MN) 00:48:27 - Outro: Next Week on the YMYW Podcast /episode/index/show/yourmoneyyourwealth/id/38535590

Is Your Roth Conversion Timing All Wrong? (Financial Blunders) - 550 10/07/2025

Is Your Roth Conversion Timing All Wrong? (Financial Blunders) - 550 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: (full show notes & episode transcript) - YMYW TV (self-guided) (Meet with an experienced professional) REQUEST your DOWNLOAD READ WATCH SUBSCRIBE to the Connect With Us: : Subscribe and join the conversation in the comments : subscribe or follow YMYW in your favorite : leave your honest reviews and ratings Chapters: 00:00:00 - Intro: This Week on the YMYW Podcast 00:00:55 - Should I Keep Converting $20K a Year in Retirement? (Barrie, NY) 00:07:17 - Can We Retire at 62 and Still Leave an Inheritance? Roth Conversion Strategies for Big Accounts (Jerry & Elaine, KS) 00:17:05 - I'm 31. Should I Convert $57K Now or Spread It Out? (Alex, PA) 00:29:12 - Roth Conversion Timing Before Retirement (Mike, Philly Suburbs) 00:36:49 - Confused About Roth Withdrawal Rules at 60 (Lisa, Omaha NE) 00:40:05 - Clarification on the Age + 20 Rule of Thumb for Contributions (Matt, YouTube) 00:45:40 - Can Rental Property Income Fund a Roth 401(k)? (Lisa, San Diego) 00:47:24 - Outro: Next Week on the YMYW Podcast /episode/index/show/yourmoneyyourwealth/id/38476625

What Retiring With $6 Million Really Looks Like - 549 09/30/2025

Is Financial Software Giving You False Retirement Confidence? - 548 09/23/2025

Is Financial Software Giving You False Retirement Confidence? - 548 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: (full show notes & episode transcript) Pay Off the Mortgage? - - DOWNLOAD WATCH on YMYW TV (free, self-guided) (free, meet with an experienced professional) REQUEST your DOWNLOAD READ WATCH SUBSCRIBE to the Connect With Us: : Subscribe and join the conversation in the comments : subscribe or follow YMYW in your favorite : 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 /episode/index/show/yourmoneyyourwealth/id/38302755

Roth Conversions: When to Make 'Em, When to Take 'Em - 547 09/16/2025

Roth Conversions: When to Make 'Em, When to Take 'Em - 547 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: (full show notes & episode transcript) (newly updated with One Big Beautiful Bill changes) - YMYW TV (self-guided) (Meet with an experienced professional) REQUEST your DOWNLOAD READ WATCH SUBSCRIBE to the Connect With Us: : Subscribe and join the conversation in the comments : subscribe or follow YMYW in your favorite : 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 /episode/index/show/yourmoneyyourwealth/id/38190740

How to Accomplish Your Retirement Goals - Even Without a Fat Wallet - 546 09/09/2025

What The New Law Means For Your Roth IRA! - 545 09/02/2025

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