
Your Money, Your Wealth
by Joe Anderson, CFP® & Alan Clopine, CPA of Pure Financial Advisors
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Recent episodes
Roth Conversions vs. RMDs: Which Tax Bill Hurts More? - 587
Jun 23, 2026
Unknown duration
Roth Conversions: When to Pay Taxes NOW - 586
Jun 16, 2026
Unknown duration
Don't Overcomplicate Retirement: Margin Loans, Whole Life, Roth Mistakes - 585
Jun 8, 2026
Unknown duration
These Tax Strategies Let You Spend More in Retirement - 584
Jun 2, 2026
Unknown duration
$1.6M in One Stock? Here's How to Get Out Without Getting Crushed - 583
May 26, 2026
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| Date | Episode | Topics | Guests | Brands | Places | Keywords | Sponsor | Length | |
|---|---|---|---|---|---|---|---|---|---|
| 6/23/26 | ![]() Roth Conversions vs. RMDs: Which Tax Bill Hurts More? - 587 | Financial Assessment (Meet with an experienced professional):https://bit.ly/YMYWassessC11 rapid-fire spitballs today from Joe Anderson, CFP®, and Big Al Clopine, CPA, on Your Money, Your Wealth® podcast number 587, on everything from Roth conversions and RMDs to whether a guy named Wayne can finally treat himself to a seventy-five-thousand-dollar Audi. Aaron in Syracuse just hit a million bucks in his 401(k) and realizes he needs a spitball on keeping his RMDs low. Do new Roth conversions restart the 5-year clock? 72-year-old Mike in Texas wants to know. Marion inherited a not-yet-five-year-old Roth, and an IRMAA problem along with it. Lu and Stephen each argue that the fellas’ conversion and retirement spitball math might be misleading. Teachers Tony and his wife have pensions that cover everything, so should they even keep saving? John and Peggy need a retirement spitball, Rajesh wonders if he should pay off his mortgage or convert to Roth, and Mike in San Marcos asks about funding a Roth with pension money.Free Financial Resources in This Episode: https://bit.ly/ymyw-587 (full show notes & episode transcript)Retirement Accounts Guide - free download:https://purefinancial.com/white-papers/retirement-accounts-guide/?utm_source=captivate&utm_medium=podcast&utm_campaign=whitepaper-retirement-accounts-guide&utm_content=ymyw-pod-ep587-description-whitepaper401(k) vs. IRA vs. Equity Compensation: The Real Math - YMYW TV:https://purefinancial.com/ymyw/episodes/recipe-for-retirement-retirement-plans-explained/?utm_source=captivate&utm_medium=podcast&utm_campaign=ymyw-tv&utm_content=ymyw-pod-ep587-description-tv-s10e12Financial Blueprint (free, self-guided):https://purefinancial.com/financialblueprint/?utm_source=captivate&utm_medium=podcast&utm_campaign=financial-blueprint&utm_content=ymyw-pod-ep587-description-blueprintREQUEST your Retirement Spitball Analysis:https://bit.ly/YMYWaskCDOWNLOAD more free guides:https://bit.ly/YMYWguidesCREAD financial blogs:https://bit.ly/YMYWblogCWATCH educational videos:https://bit.ly/YMYWvidsCSUBSCRIBE to the YMYW Newsletter:https://bit.ly/YMYWnewsletterCConnect With Us:Subscribe on YouTube and join the conversation in the comments:https://bit.ly/YMYW-YTSubscribe or follow YMYW in your favorite podcast app:https://lnk.to/ymywLeave your honest reviews and ratings in Apple Podcasts:https://podcasts.apple.com/us/podcast/your-money-your-wealth/id312900254Chapters: 00:00 - Intro: This Week on the YMYW Podcast01:32 - $1.1 Million in My 401(k) at 56: Should I Do Roth Conversions Before RMDs Hit? (Aaron, Syracuse, NY04:51 - Can You Fund a Roth IRA With Pension Money? (Mike, San Marcos, CA)06:14 - Can You Roll an UTMA Into a 529 for Tax-Free Education Savings? (Bob the Builder, Westchester, NY)10:29 - I'm 72 With a 25-Year-Old Roth. Do New Conversions Trigger the 5-Year Clock for Roth Withdrawals? (Mike, TX)11:43 - Inherited a Roth Less Than 5 Years Old: Are the Earnings Taxable? Can IRMAA Be Avoided? (Marion)15:59 - You Ignore Future Income! How to Spitball Spending When a Pension and Social Security Are Coming (Stephen)21:02 - Are Your Roth Conversion Calculations Misleading? Why Future RMDs Need an Inflation Check (Lu)24:57 - We're Teachers With Pensions That Cover Everything. Should We Stop Saving and Fund the 529s? (Tony, NY28:23 - $4 Million and Ready to Exit the Rat Race at 61. Do the Numbers Work? (John and Peggy, San Jose, CA34:37 - $4 Million 401(k) and a 6.5% Rental Mortgage: Pay It Off or Convert to Roth? (Rajesh)38:42 - We're 62 With $1 Million. Can I Finally Buy the $75K Audi, or Should I Lease? (Wayne, Long Beach, NY)43:17 - Outro: Next Week on the YMYW Podcast | — | ||||||
| 6/16/26 | ![]() Roth Conversions: When to Pay Taxes NOW - 586 | Schedule a free financial assessment with an experienced professional at Pure Financial Advsiors: https://purefinancial.com/lp/free-assessment/?utm_source=captivate&utm_medium=podcast&utm_campaign=free-assessment&utm_content=ymyw-pod-ep586-description-free-assessment“Walter and Skyler” in Iowa ask if they’re on track to retire early, or if they’re just "cooking up overconfidence?" And how aggressively should they convert their retirement savings to tax-free Roth money before the pension and Social Security kick in? California Dreamin’ has it down to one decision: convert to the top of the 22 percent tax bracket, or push into the 24? “Mike and Carol” in Florida ask, when you're weighing a conversion, should you be looking at your tax bracket, or your actual effective tax rate? Finally, is it worth the cost for “Westley and Buttercup” to use the brand new option to turn a big employer contribution into Roth money? Joe Anderson, CFP® and Big Al Clopine, CPA from Pure Financial Advisors spitball on all of these questions, today on YMYW podcast 586.Free Financial Resources in This Episode: https://bit.ly/ymyw-586 (full show notes & episode transcript)10 Common Roth IRA Mistakes That Can Cost You $50,000 (or More!) - YMYW TV:https://purefinancial.com/white-papers/roth-ira-white-paper/?utm_source=captivate&utm_medium=podcast&utm_campaign=whitepaper-ultimate-guide-to-roth-iras&utm_content=ymyw-pod-ep586-description-whitepaperThe Ultimate Guide to Roth IRAs - free download:https://purefinancial.com/ymyw/episodes/10-common-roth-ira-mistakes-that-can-cost-you-50000-or-more/?utm_source=captivate&utm_medium=podcast&utm_campaign=ymyw-tv&utm_content=ymyw-pod-ep586-description-tv-s12e04Financial Blueprint (free, self-guided):https://bit.ly/YMYWblueprintCREQUEST your Retirement Spitball Analysis:https://bit.ly/YMYWaskCDOWNLOAD more free guides:https://bit.ly/YMYWguidesCREAD financial blogs:https://bit.ly/YMYWblogCWATCH educational videos:https://bit.ly/YMYWvidsCSUBSCRIBE to the YMYW Newsletter:https://bit.ly/YMYWnewsletterCConnect With Us:Subscribe on YouTube and join the conversation in the comments:https://bit.ly/YMYW-YTSubscribe or follow YMYW in your favorite podcast app:https://lnk.to/ymywLeave your honest reviews and ratings in Apple Podcasts:https://podcasts.apple.com/us/podcast/your-money-your-wealth/id312900254Chapters: 00:00 - Intro: This Week on the YMYW Podcast01:10 - Early Retirement Overconfidence? Aggressive Roth Conversions? (Walter & Skyler, Iowa)13:25 - Roth Conversion Bracket Call: 22% or 24%? (CA Dreamin', Central Coast)22:27 - Tax Bracket vs. Effective Rate: The Roth Math Most People Get Wrong (Mike & Carol, FL)32:16 - Should the NEC Go to the Roth? The 401(k) Decision (Westley & Buttercup, TX)42:28 - Outro: Next Week on the YMYW Podcast | — | ||||||
| 6/8/26 | ![]() Don't Overcomplicate Retirement: Margin Loans, Whole Life, Roth Mistakes - 585 | Financial Assessment (Meet with an experienced professional):https://bit.ly/YMYWassessCFree Financial Resources in This Episode: https://bit.ly/ymyw-585 (full show notes & episode transcript)Today on Your Money, Your Wealth® podcast number 585, Joe and Big Al spitball for folks who are already winning and thinking about getting fancy with it. Reno in Oregon is 50, and his pension is so big he's not sure how to invest or why he would need to convert to Roth. Michael is considering taking out a half-million-dollar margin loan to juice investment returns. What do the fellas think? Tune in for the surprising debate. Husker Fans just pocketed two million from selling their business here come the product pitches: should they buy annuities, set up a charitable trust, or just swallow the tax? What do the fellas think of whole life insurance? And finally, John and Lib on Waltons Mountain - or rather, the Catskills - aren’t sure if they’ve saved too little or too much. Can they bridge the gap until their pension?Emotionless Investing Guide - free download:https://purefinancial.com/white-papers/emotionless-investing-guide/?utm_source=captivate&utm_medium=podcast&utm_campaign=whitepaper-emotionless-investing-guide&utm_content=ymyw-pod-ep585-description-whitepaperFinancial Blueprint - free, self-guided:https://purefinancial.com/financialblueprint/?utm_source=captivate&utm_medium=podcast&utm_campaign=financial-blueprint&utm_content=ymyw-pod-ep585-description-blueprintRetirement Rebound: 5 Plays to Help You Score a Comeback - YMYW TV:https://purefinancial.com/ymyw/episodes/retirement-rebound-5-plays-help-score-comeback/?utm_source=captivate&utm_medium=podcast&utm_campaign=ymyw-tv&utm_content=ymyw-pod-ep585-description-tv-s10e11REQUEST your Retirement Spitball Analysis:https://bit.ly/YMYWaskCDOWNLOAD more free guides:https://bit.ly/YMYWguidesCREAD financial blogs:https://bit.ly/YMYWblogCWATCH educational videos:https://bit.ly/YMYWvidsCSUBSCRIBE to the YMYW Newsletter:https://bit.ly/YMYWnewsletterCConnect With Us:Subscribe on YouTube and join the conversation in the comments:https://bit.ly/YMYW-YTSubscribe or follow YMYW in your favorite podcast app:https://lnk.to/ymywLeave your honest reviews and ratings in Apple Podcasts:https://podcasts.apple.com/us/podcast/your-money-your-wealth/id312900254Chapters: 00:00 - Intro: This Week on the YMYW Podcast00:58 - How Should a Pension-Rich 50-Year-Old Invest? Should They Even Bother with Roth Conversions? (Reno, OR)10:30 - Should I Borrow $500K in a Margin Loan to Invest? (Michael, VA)23:01 - We're Getting $2M From Selling the Business. Annuity, Charitable Trust, or Bite the Tax? What About Whole Life Insurance? (Husker Fans, Nebraska)34:14 - Can a Frugal Mountain Couple Bridge the Gap to a $60K Pension? (John & Lib, NY Catskills)41:13 - Outro: Next Week on the YMYW Podcast | — | ||||||
| 6/2/26 | ![]() These Tax Strategies Let You Spend More in Retirement - 584 | Schedule a Free Financial Assessment with an experienced professional:https://bit.ly/YMYWassessCHeidi from the Space Coast of Florida found a money-saving tidbit in a past episode that completely changed how she thinks about her financial advisor's fee. Joe Anderson, CFP® and Big Al Clopine, CPA expand on the strategy, today on Your Money, Your Wealth® podcast number 584. Laverne and Shirley have four million bucks, Roth conversion questions, annuity questions, and a retirement plan so detailed it may require a diagram. Finally, Bess and George from Pure Michigan are already retired, already on Social Security, and already losing sleep over their investments. So why are they so stressed? Joe and Big Al’s a debate about a 1% advisory fee gets a little spicy in that one.Retirement Accounts Guide - free download:https://purefinancial.com/white-papers/retirement-accounts-guide/?utm_source=captivate&utm_medium=podcast&utm_campaign=whitepaper-retirement-accounts-guide&utm_content=ymyw-pod-ep584-description-whitepaperFinancial Blueprint - free, self-guided retirement plan check-in:https://purefinancial.com/financialblueprint/?utm_source=captivate&utm_medium=podcast&utm_campaign=financial-blueprint&utm_content=ymyw-pod-ep584-description-blueprintRetirement Course: Can You Hit a Hole in One? With PGA Pro Chris Riley - YMYW TV:https://purefinancial.com/ymyw/episodes/retirement-course-hole-in-one-pga-pro-chris-riley/?utm_source=captivate&utm_medium=podcast&utm_campaign=ymyw-tv&utm_content=ymyw-pod-ep584-description-tv-s11e02REQUEST your Retirement Spitball Analysis:https://bit.ly/YMYWaskCDOWNLOAD more free guides:https://bit.ly/YMYWguidesCREAD financial blogs:https://bit.ly/YMYWblogCWATCH educational videos:https://bit.ly/YMYWvidsCSUBSCRIBE to the YMYW Newsletter:https://bit.ly/YMYWnewsletterCConnect With Us:Subscribe on YouTube and join the conversation in the comments:https://bit.ly/YMYW-YTSubscribe or follow YMYW in your favorite podcast app:https://lnk.to/ymywLeave your honest reviews and ratings in Apple Podcasts:https://podcasts.apple.com/us/podcast/your-money-your-wealth/id312900254Chapters: 00:00 - Intro: This Week on the YMYW Podcast01:02 - Can Financial Advisor AUM Fees Come Out of Pre-Tax Money? (Heidi, Space Coast, FL)09:54 - Are We Converting Enough Before RMDs? What to Do With Annuities? (Laverne & Shirley, Cleveland, OH)30:23 - Target Date Funds and a Sad Brokerage: Good Enough? Can't See Ever Paying an Advisor (Bess & George, MI)45:37 - Outro: Next Week on the YMYW Podcast | — | ||||||
| 5/26/26 | ![]() $1.6M in One Stock? Here's How to Get Out Without Getting Crushed - 583 | Schedule a Free Financial Assessment with an experienced professional:https://bit.ly/YMYWassessCJoe Anderson, CFP® and Big Al Clopine, CPA spitball for people sitting on life-changing gains who are just one wrong move away from handing a third of it to the IRS. How should they diversify their concentrated stock positions? That’s today on Your Money, Your Wealth podcast number 583. First up, Walter's a software engineer who got lucky 15 years ago. Now he's got $1.6 million in company stock, and a retirement clock ticking down in six years. Richard from Staten Island listened to his son six years ago, went big on oil, saw a huge gain, and now 80% of his portfolio is in that one position. His custodian wants him to sell, but he’s not so sure. Finally, Doctors “Bones McCoy and Beverly Crusher” just discovered they’ll be inheriting millions still sitting in an old 401(k) loaded with company stock.Free Financial Resources in This Episode: https://bit.ly/ymyw-583 (full show notes & episode transcript)2026 Tax Planning Guide - free download:https://purefinancial.com/white-papers/tax-planning-guide/?utm_source=captivate&utm_medium=podcast&utm_campaign=whitepaper-tax-planning-guide&utm_content=ymyw-pod-ep583-description-whitepaper10 Steps to Improve Investing Success - free download:https://purefinancial.com/white-papers/10-steps-to-improve-investing-success/?utm_source=captivate&utm_medium=podcast&utm_campaign=whitepaper-10-steps-to-improve-investing-success&utm_content=ymyw-pod-ep583-description-whitepaperOnce Retirees See This Data, They Stop Worrying About Investing - YMYW TV:https://purefinancial.com/ymyw/episodes/once-retirees-see-this-data-they-stop-worrying-about-investing/?utm_source=captivate&utm_medium=podcast&utm_campaign=ymyw-tv&utm_content=ymyw-pod-ep583-description-tv-s12e03Strategies for Diversifying Concentrated Stock Positions - blog post:https://purefinancial.com/ask-pure/strategies-for-diversifying-concentrated-stock-positions/?utm_source=captivate&utm_medium=podcast&utm_campaign=learning-center&utm_content=ymyw-pod-ep583-description-learning-centerComic-Con 2014: https://www.youtube.com/watch?v=EQASw5viQPI2016: https://www.youtube.com/watch?v=WcSRFo7W5ZQFinancial Blueprint (free, self-guided):https://bit.ly/YMYWblueprintCREQUEST your Retirement Spitball Analysis:https://bit.ly/YMYWaskCDOWNLOAD more free guides:https://bit.ly/YMYWguidesCREAD financial blogs:https://bit.ly/YMYWblogCWATCH educational videos:https://bit.ly/YMYWvidsCSUBSCRIBE to the YMYW Newsletter:https://bit.ly/YMYWnewsletterCConnect With Us:Subscribe on YouTube and join the conversation in the comments:https://bit.ly/YMYW-YTSubscribe or follow YMYW in your favorite podcast app:https://lnk.to/ymywLeave your honest reviews and ratings in Apple Podcasts:https://podcasts.apple.com/us/podcast/your-money-your-wealth/id312900254Chapters:00:00 - Intro: This Week on the YMYW Podcast01:09 - How Do You Sell $1.6M in Company Stock Without Writing the IRS a Giant Check? (Walter & Jesse, NM)13:04 - One Oil Stock is 80% of My Portfolio. My Financial Advisors Want Me to Sell It. I Don't Trust Them. (Richard, Staten Island, NY)30:10 - We're Two Doctors About to Inherit a $1.35M Tax Bomb. What Now? (Bones & Beverly, MI)45:23 - Outro: Next Week on the YMYW Podcast | — | ||||||
| 5/19/26 | ![]() Safe Withdrawal Rate Debate: How Much Can You REALLY Spend in Early Retirement? - 582 | Schedule a Free Financial Assessment with an experienced professional:https://bit.ly/YMYWassessCToday on Your Money, Your Wealth® podcast number 582, Joe Anderson, CFP® and Big Al Clopine, CPA address something a not-insignificant portion of this audience has been complaining about for years: their so-called 'absurdly conservative' safe withdrawal rates for early retirement. Rand and Elayne from Ohio are here to gripe about it directly with a thought experiment: a million bucks at age 36 and a three-year sabbatical in France. When, if ever, would Joe and Big Al say they should cut it short and go back to work if the markets turned ugly? Mike2me17 piles on, with his own SWR take about AUM fees in his Apple Podcasts review. But first, a real world example: Ron and Harry from Florida are elite performers with a high-risk specialty job. Can they safely pull off moving to Portugal and living on $38,000 a year in their early 40s? If you’re one of the people yelling at your podcast app every time Joe or Al mentions a 2% withdrawal rate, today's your day, and we welcome you to leave more of your thoughts on the topic in Apple Podcasts, YouTube, on Reddit, in our inboxes - like everyone else has.Free Financial Resources in This Episode: https://bit.ly/ymyw-582 (full show notes & episode transcript)Withdrawal Strategy Guide - YMYW TV:https://purefinancial.com/white-papers/withdrawal-strategy-guide/?utm_source=captivate&utm_medium=podcast&utm_campaign=whitepaper-withdrawal-strategy-guide&utm_content=ymyw-pod-ep582-description-whitepaperFinancial Blueprint (free, self-guided):https://purefinancial.com/financialblueprint/?utm_source=captivate&utm_medium=podcast&utm_campaign=financial-blueprint&utm_content=ymyw-pod-ep582-description-blueprintRetirement Pop Quiz: 18 Questions to Get You Ready to Retire - YMYW TVhttps://purefinancial.com/ymyw/episodes/retirement-pop-quiz-18-questions-ready-to-retire/?utm_source=captivate&utm_medium=podcast&utm_campaign=ymyw-tv&utm_content=ymyw-pod-ep582-description-tv-s10e10REQUEST your Retirement Spitball Analysis:https://bit.ly/YMYWaskCDOWNLOAD more free guides:https://bit.ly/YMYWguidesCREAD financial blogs:https://bit.ly/YMYWblogCWATCH educational videos:https://bit.ly/YMYWvidsCSUBSCRIBE to the YMYW Newsletter:https://bit.ly/YMYWnewsletterCConnect With Us:Subscribe on YouTube and join the conversation in the comments:https://bit.ly/YMYW-YTSubscribe or follow YMYW in your favorite podcast app:https://lnk.to/ymywLeave your honest reviews and ratings in Apple Podcasts:https://podcasts.apple.com/us/podcast/your-money-your-wealth/id312900254Chapters: 00:00 - Intro: This Week on the YMYW Podcast01:14 - Elite Performers Semi-Retiring at 43 and Moving to Portugal. Can We Pull It Off? (Ron & Harry, FL)16:16 - YMYW Safe Withdrawal Rate Assumptions Are Absurd. At What Point Do You Go Back to Work If Markets Crash? (Rand & Elayne, ID)34:13 - YMW Safe Withdrawal Rates to Protect AUM Fee (Comment from mike2me17, Apple Podcasts)41:46 - Outro: Next Week on the YMYW Podcast | — | ||||||
| 5/12/26 | ![]() Roth Conversions, Pension Lump Sums & Annuities: Is Bigger Always Better? - 581 | Schedule a Free Financial Assessment with an experienced professional:https://bit.ly/YMYWassessCJune in Washington State is 62 with $2.5 million saved and a $350,000 pension on the table. Should she take the lump sum or the monthly check for life? Spoiler alert: there's a 3-to-1 vote in the studio, and Big Al is the one, today on Your Money, Your Wealth® podcast number 581 with Joe Anderson, CFP®, and Big Al Clopine, CPA. Plus, how aggressive should “Homer and Marge” get with Roth conversions, and is it smart to pay the conversion tax from an inherited IRA RMD? Pompous Assets drops his big, fat wallet on the YMYW table next: with millions in tax-deferred and taxable accounts, why is his financial advisor fighting him on a Roth conversion? Of course, Joe and Big Al have some thoughts on the subject. Finally, Johnny Mercer in Georgia is eyeing an immediate income annuity and a MYGA. The fellas break down why that 7.5% “rate of return” might not be what he thinks.Free Financial Resources in This Episode: https://bit.ly/ymyw-581 (full show notes & episode transcript)Ultimate Guide to Roth IRAs - free download:https://purefinancial.com/white-papers/roth-ira-white-paper/?utm_source=captivate&utm_medium=podcast&utm_campaign=whitepaper-ultimate-guide-to-roth-iras&utm_content=ymyw-pod-ep581-description-whitepaperFinancial Blueprint (free, self-guided):https://purefinancial.com/financialblueprint/?utm_source=captivate&utm_medium=podcast&utm_campaign=financial-blueprint&utm_content=ymyw-pod-ep581-description-blueprintYour 11 Step Path to Financial Freedom - YMYW TV:https://purefinancial.com/ymyw/episodes/your-11-step-path-to-financial-freedom/?utm_source=captivate&utm_medium=podcast&utm_campaign=ymyw-tv&utm_content=ymyw-pod-ep581-description-tv-s10e13REQUEST your Retirement Spitball Analysis:https://bit.ly/YMYWaskCDOWNLOAD more free guides:https://bit.ly/YMYWguidesCREAD financial blogs:https://bit.ly/YMYWblogCWATCH educational videos:https://bit.ly/YMYWvidsCSUBSCRIBE to the YMYW Newsletter:https://bit.ly/YMYWnewsletterCConnect With Us:Subscribe on YouTube and join the conversation in the comments:https://bit.ly/YMYW-YTSubscribe or follow YMYW in your favorite podcast app:https://lnk.to/ymywLeave your honest reviews and ratings in Apple Podcasts:https://podcasts.apple.com/us/podcast/your-money-your-wealth/id312900254Chapters: 00:00 - Intro: This Week on the YMYW Podcast01:08 - Should I Take the Pension Lump Sum or Monthly Income? (June, WA State)09:23 - How Much Should We Convert to Roth Each Year? (Homer & Marge)16:26 - Should I Convert My Entire IRA to a Roth? (Pompous Assets, Arkansas)23:00 - $5M All in Pre-Tax. Should I Buy an Annuity Before It's Too Late? (Johnny Mercer, GA)36:00 - Outro: Next Week on the YMYW Podcast | — | ||||||
| 5/5/26 | ![]() You Have Enough to Retire Before 60. Why Are You Still Working? - 580 | Schedule a Free Financial Assessment with an experienced professional:https://bit.ly/YMYWassessCToday on Your Money, Your Wealth® podcast number 580, Joe Anderson, CFP®, and Big Al Clopine, CPA, are spitballing for some folks who've done the work, hit the numbers, but aren’t sure if they can really walk away yet. Martha in DC is 44 and says her soul is being sucked out of her body by her employer. When can she stop working full-time and foster puppies instead? “Bandit” is bullish on his company stock in archeology instruments, but not so much on his work itself. “Kevin” is staring down a wall of deferred comp and needs a spitball on how aggressive his and “Winnie’s” Roth conversion strategy should be before RMDs hit. Can both “Bandit and Chilli” and “Kevin and Winnie” call it quits this year?Free Financial Resources in This Episode: https://bit.ly/ymyw-580 (full show notes & episode transcript)Tax-Free Retirement Guide - free download:https://purefinancial.com/white-papers/tax-free-retirement-guide/?utm_source=captivate&utm_medium=podcast&utm_campaign=whitepaper-tax-free-retirement-guide&utm_content=ymyw-pod-ep580-description-whitepaperRetirement Readiness Guide - free download:https://purefinancial.com/white-papers/retirement-readiness-guide/?utm_source=captivate&utm_medium=podcast&utm_campaign=whitepaper-retirement-readiness-guide&utm_content=ymyw-pod-ep580-description-whitepaper401(k) After Retirement? Here Are Your 4 Options (And The Costly Mistakes) - YMYW TV:https://purefinancial.com/ymyw/episodes/what-happens-to-your-401k-ira-at-retirement/?utm_source=libsyn&utm_medium=podcast&utm_campaign=ymyw-tv&utm_content=ymyw-pod-ep580-description-tv-s10e06Financial Blueprint (free, self-guided):https://bit.ly/YMYWblueprintCREQUEST your Retirement Spitball Analysis:https://bit.ly/YMYWaskCDOWNLOAD more free guides:https://bit.ly/YMYWguidesCREAD financial blogs:https://bit.ly/YMYWblogCWATCH educational videos:https://bit.ly/YMYWvidsCSUBSCRIBE to the YMYW Newsletter:https://bit.ly/YMYWnewsletterCConnect With Us:Subscribe on YouTube and join the conversation in the comments:https://bit.ly/YMYW-YTSubscribe or follow YMYW in your favorite podcast app:https://lnk.to/ymywLeave your honest reviews and ratings in Apple Podcasts:https://podcasts.apple.com/us/podcast/your-money-your-wealth/id312900254Chapters: 00:00 - Intro: This Week on the YMYW Podcast00:56 - Can We Exit the Rat Race in Our 40s With $6.5M? (Martha & George, DC)16:07 - Can I Retire at 51 Without Using Rule of 55? (Bandit & Chilli, CA)36:29 - Can I Retire Before My $3M Deferred Comp Pays Out? (Kevin & Winnie, Chicago)44:28 - Outro: Next Week on the YMYW Podcast | — | ||||||
| 4/28/26 | ![]() Too Much 401k Money? The $3M Roth Conversion Problem - 579✨ | Roth conversion401k strategies+4 | — | Pure Financial Advisors | New YorkUtah | Roth conversion401k+4 | — | 46m 21s | |
| 4/21/26 | ![]() The Retirement Question Every Couple Asks: Can We Afford It? - 578✨ | retirement planningfinancial security+4 | — | Pure Financial Advisors | — | retirementpensions+5 | — | 43m 33s | |
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| 4/14/26 | ![]() This Early Retirement Strategy Could Be a Huge Mistake✨ | early retirementfinancial planning+3 | — | — | WisconsinNorth Carolina+1 | early retirement72(t) tax election+3 | — | 45m 15s | |
| 4/14/26 | ![]() This Early Retirement Strategy Could Be a Huge Mistake - 577 | Joe Anderson, CFP® and Big Al Clopine, CPA spitball on whether a popular early retirement strategy could actually blow up your financial plan, today on Your Money, Your Wealth® podcast number 577. Red and Kitty from Wisconsin are burned out at 40 and wonder if retiring at 45 using the 72(t) tax election to take substantially equal periodic payments, or SEPP, is a smart bridge strategy. Jiminy Billy Bob in North Carolina is also considering a 72(t). How should he structure his withdrawal order, and does he need to shift into bonds before downshifting his career? Plus, Steve and Sharon in Minnesota have 8 million bucks. Steve is getting laid off at age 56. What should they do with their 401(k), stock options, incentives, and benefits before and after the layoff?Free Financial Resources in This Episode:https://bit.ly/ymyw-577 (full show notes & episode transcript)Recession Protection Guide - free downloadRetirement Readiness Guide - free download6 Ways Americans Accidentally Sabotage Their Retirement - YMYW TVFinancial Blueprint (self-guided):https://bit.ly/PureFinancialBlueprintFinancial Assessment (Meet with an experienced professional):https://bit.ly/PureFreeAssessmentREQUEST your Retirement Spitball Analysis:https://bit.ly/AskJoeAndAlDOWNLOAD more free guides:https://bit.ly/PureGuidesREAD financial blogs:https://bit.ly/PureFinBlogWATCH educational videos:https://bit.ly/PureEdVideosSUBSCRIBE to the YMYW Newsletter:https://bit.ly/YMYWNewsletterConnect With Us:Subscribe on YouTube and join the conversation in the comments:https://bit.ly/YMYW-YTSubscribe or follow YMYW in your favorite podcast app:https://lnk.to/ymywLeave your honest reviews and ratings in Apple Podcasts: https://podcasts.apple.com/us/podcast/your-money-your-wealth/id312900254Chapters:00:00 - Intro: This week on the YMYW Podcast01:06 - Why Retiring at 45 Using 72(t) SEPP Withdrawals is Risky (Red & Kitty, WI)13:28 - Early Retirement Strategy: Withdrawal Order, Bonds, and 72(t) (Jiminy Billy Bob, NC)22:49 - Laid Off at 56 With $7.9M: How to Handle Your Exit Strategy (Steve & Sharon, St. Paul, MN)43:51 - Outro: Next Week on the YMYW Podcast | — | ||||||
| 4/7/26 | ![]() When Roth Conversions Don't Make Sense (And When They're a No-Brainer) - 576✨ | Roth conversionscapital gains+3 | — | — | PANew England | Roth conversionscapital gains+3 | — | 43m 05s | |
| 3/31/26 | ![]() Die With Zero: Are You Giving Your Kids Too Much? - 575✨ | retirement planningfinancial support for children+3 | — | Pure Financial Advisors | Montgomery CountyMissouri+2 | retirementfinancial planning+4 | — | 44m 10s | |
| 3/24/26 | ![]() When Should You Take Social Security? (Don't Screw This Up) - 574✨ | Social Securityretirement planning+3 | — | — | MassachusettsTwin Cities+1 | Social Securityretirement+3 | — | 45m 04s | |
| 3/17/26 | ![]() Could You Retire Tomorrow If You Had To? - 573✨ | retirement planningfinancial independence+3 | — | Pure Financial Advisors | BrooklynDelaware | retirementfinancial planning+3 | — | 40m 06s | |
| 3/10/26 | ![]() Could You Lose Half Your Retirement Income to Taxes? - 572✨ | retirement incometax strategies+3 | — | Pure Financial Advisors | — | retirement incometaxes+5 | — | 51m 00s | |
| 3/3/26 | ![]() Retire Early in Your 40s or 50s: Green Light or Reality Check? - 571✨ | early retirementfinancial strategy+3 | — | — | South CarolinaMassachusetts+2 | early retirementfinancial strategy+3 | — | 45m 25s | |
| 2/24/26 | ![]() Retirement Planning for Aging Parents - and Can You Retire Early? - 570✨ | retirement planningfinancial safety net+4 | — | Your Money, Your Wealth | Texas | retirement planningfinancial safety net+6 | — | 45m 52s | |
| 2/17/26 | ![]() 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: https://bit.ly/ymyw-569 (full show notes & episode transcript) Growing Your Wealth Guide - free download Retirement Readiness Guide - free download Retire at 62: Great Idea or Huge Mistake? - YMYW TV Financial Blueprint (self-guided) Financial Assessment (Meet with an experienced professional) REQUEST your Retirement Spitball Analysis DOWNLOAD more free guides READ financial blogs WATCH educational videos SUBSCRIBE to the YMYW Newsletter Connect With Us: YouTube: Subscribe and join the conversation in the comments Podcast apps: subscribe or follow YMYW in your favorite Apple Podcasts: leave your honest reviews and ratings Chapters: 00:00 - Intro: This Week on the YMYW Podcast 01:09 - Should I Sell My Business or Wait? Is It Crazy to Spend More on My Vacation Home Than My Primary Residence? (Fine and Dandy, IL) 20:48 - Saving to Roth IRA vs Traditional IRA in the Final Year Before Retirement (BB and Shell) 23:50 - When to Take Your First RMD for the Maximum Tax Benefit (Joel, CA) 27:33 - Aging Alone in Retirement: How to Protect Assets Before Cognitive Decline (David, 68, Logan, NM) 35:37 - Why Some CPAs Cap Roth Conversions at $500K AGI (Shweta, CA) 37:05 - When Does It Make Sense for Retirees to Have an Emergency Fund - and How Much? (Brian, Albany, NY) 42:03 - Outro - Next Week on the YMYW Podcast | — | ||||||
| 2/10/26 | ![]() 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: https://bit.ly/ymyw-568 (full show notes & episode transcript) Why Asset Location Matters - free guide All About Asset Location - more free resources 15 Maneuvers to Duck an Unplanned Early Retirement Knockout - YMYW TV Financial Blueprint (self-guided) Financial Assessment (Meet with an experienced professional) REQUEST your Retirement Spitball Analysis DOWNLOAD more free guides READ financial blogs WATCH educational videos SUBSCRIBE to the YMYW Newsletter Connect With Us: YouTube: Subscribe and join the conversation in the comments Podcast apps: subscribe or follow YMYW in your favorite Apple Podcasts: leave your honest reviews and ratings Chapters: 00:00 - Intro: This Week on the YMYW Podcast 01:05 - After-Tax 401(k) Catch-Ups vs Taxable Investing (John Q Taxpayer) 06:16 - Forced Early Retirement: Social Security and Roth Conversion Timing? (Janine, Bothell, WA) 11:30 - Are 50-Year Mortgages Actually Affordable? (Semper Fi, Stevensville, MI) 17:59 - 401(k) Loan vs Mortgage Payoff (Pete, NC) 21:27 - Can You Manufacture a Step-Up in Basis? (Jonas Grumby, The Colony, TX) 25:03 - Inherited Gold Coins and Capital Gains Taxes (Dolly, 63, TN) 29:35 - Spitball for Young Investors Who Don't Have Millions (Young Financial Nerds, Omaha, NE) 42:13 - Outro: Next Week on the YMYW Podcast | — | ||||||
| 2/3/26 | ![]() Rising Costs and Retirement Unknowns? Here's What to Do - 567 | Should Al and Peggy in Illinois keep hammering pre-tax retirement savings or should they pivot to post-tax Roth for better tax diversification? Which pension option is best for their early retirement plans? Long-term care insurance premiums are going up endlessly for Eloise in Connecticut. Is she walking into an insurance industry trap? How do Eric and Tami in Baton Rouge help their kids with college without blowing up their own retirement, and when do student loans make sense? Finally, should Lana and Sterling harvest capital gains or prioritize Roth conversions before moving to a much higher-tax state? The basic question in all of these is the same: how do you protect your future from rising costs and unknowns that are out of your control? We'll find out what it takes, today on Your Money, Your Wealth podcast number 567. Free Financial Resources in This Episode: https://bit.ly/ymyw-567 (full show notes & episode transcript) Key Financial Data Guide - free download Retirement Panic Button: 7 Ways to Avoid Hitting It - YMYW TV Financial Blueprint (self-guided) Financial Assessment (Meet with an experienced professional) REQUEST your Retirement Spitball Analysis DOWNLOAD more free guides READ financial blogs WATCH educational videos SUBSCRIBE to the YMYW Newsletter Connect With Us: YouTube: Subscribe and join the conversation in the comments Podcast apps: subscribe or follow YMYW in your favorite Apple Podcasts: leave your honest reviews and ratings Chapters: 00:00 - Intro: This Week on the YMYW Podcast 00:55 - Pre-Tax vs. Late Roth Savings? Pension Lump Sum vs. Lifetime Income in Early Retirement? (Al & Peggy, Illinois) 14:14 - Should I Drop Long-Term Care Insurance Now at Age 70? (Eloise, Connecticut) 20:41 - College Costs vs Retirement Security for Parents (Tami & Eric, Baton Rouge, LA) 35:59 - Roth Conversions or Capital Gains Before Moving to a High Tax State? (Lana & Sterling, Nebraska) 48:14 - Next Week on the YMYW Podcast | — | ||||||
| 1/27/26 | ![]() 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: https://bit.ly/ymyw-566 (full show notes & episode transcript) Withdrawal Strategy Guide - free download Financial Blueprint (self-guided) Financial Assessment (Meet with an experienced professional) WATCH 6 Signs You Truly Have "Enough" For Retirement on YMYW TV REQUEST your Retirement Spitball Analysis DOWNLOAD more free guides READ financial blogs WATCH educational videos SUBSCRIBE to the YMYW Newsletter Connect With Us: YouTube: Subscribe and join the conversation in the comments Podcast apps: subscribe or follow YMYW in your favorite Apple Podcasts: leave your honest reviews and ratings Chapters: 00:00 - Intro: This Week on the YMYW Podcast 01:01 - 43 With $850K. Am I Too Late to Build Enough Roth Money? (Mr & Mrs Smith, Dallas, TX) 11:29 - Nearly $7M Saved at 58 and 64. Do We Have Enough for a High-Spend Retirement? (Lucy & Desi, Jersey Shore, NJ) 23:38 - 61 and 59 With $4.5M Saved. Can I Retire Now With a 50/50 Portfolio? (Tony & Carmela, San Ramon, CA) 32:09 - Mid-50s with $685K Saved. Can One Spouse Retire While the Other Works? (Jacques & Johana, Florida) 38:53 - Are Long-Short Direct Indexing Tax Strategies Worth the Fees? (Juicy Squeeze) 47:04 - Should I Work as an Employee or Contractor After 70 on Social Security? (Wendi) 52:04 - Outro: Next Week on the YMYW Podcast | — | ||||||
| 1/20/26 | ![]() 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: https://bit.ly/ymyw-565 (full show notes & episode transcript) The Last 5 Years Before Retirement Will Decide Your Lifestyle - Here's How - YMYW TV Guides: Growing Your Wealth Tax-Free Retirement One Big Beautiful Bill Act Blogs: A Market of Stocks Why AI May Not Be a Bubble Should You Own Gold Instead of Stocks? Financial Blueprint (self-guided) Financial Assessment (Meet with an experienced professional) REQUEST your Retirement Spitball Analysis DOWNLOAD more free guides READ financial blogs WATCH educational videos SUBSCRIBE to the YMYW Newsletter Connect With Us: YouTube: Subscribe and join the conversation in the comments Podcast apps: subscribe or follow YMYW in your favorite Apple Podcasts: leave your honest reviews and ratings Chapters: 00:00 - Intro: This Week on the YMYW Podcast 01:04 - Can I Retire at 50 with $5M and Bridge the Gap to Pensions and Social Security? (Lucky Lou) 10:51 - Which Retirement Accounts Should Young High Earners Max First? Can We Afford a House Downpayment? (Alexei & Anna, Cincinnati) 17:57 - Save to Roth 401(k) or Traditional If Our State Doesn't Tax Retirement Income? (Jay & Gloria, People's Republic of IL) 28:21 - Should a 28-Year-Old Buy a Home in an Expensive Market? (Sleepless in Seattle) 37:15 - How to Invest for Most Growth and Least Tax on an Inherited IRA? (Jennifer, TX) 41:04 - Outro: Next Week on the YMYW Podcast | — | ||||||
| 1/13/26 | ![]() Social Security Timing and When Family Wrecks Retirement - 564 | Hana's mom is 92. Mom's husband is 74, and after years of trying to help a family member, nearly a million dollars is gone. How do they stop the bleeding before it's too late, and how much can they spend each year from what's left? That's today on Your Money, Your Wealth® podcast number 564 with Joe Anderson, CFP® and Big Al Clopine, CPA. Plus, "Peter and Gwen" from Virginia have a pension, Roths, and a shrinking IRA. With the new tax law, IRMAA, and Social Security decisions all colliding, should they keep converting to Roth, and when should they actually collect Social Security? Also, does it make sense for "Mr. and Mrs. Scarecrow" to claim Social Security early and invest it? Finally, "Rosie and Astro" from Pennsylvania ask if they can retire in just three years with $1.3 million, and whether it's time to hire an advisor to help them get there. Free Financial Resources in This Episode: https://bit.ly/ymyw-564 (full show notes & episode transcript) Social Security Handbook Retirement Readiness Guide 6 Biggest Financial Pitfalls in America (Avoid These Traps!) - YMYW TV Financial Blueprint (self-guided) Financial Assessment (Meet with an experienced professional) REQUEST your Retirement Spitball Analysis DOWNLOAD more free guides READ financial blogs WATCH educational videos SUBSCRIBE to the YMYW Newsletter Connect With Us: YouTube: Subscribe and join the conversation in the comments Podcast apps: subscribe or follow YMYW in your favorite Apple Podcasts: leave your honest reviews and ratings Chapters: 00:00 - Intro: This Week on the YMYW Podcast 02:21 - Family Wrecking Retirement: How Much Can Benevolent Retirees Afford to Spend? (Hana) 10:30 - We Have a Pension. Should We Do Roth Conversions After the OBBBA? When to Claim Social Security? (Peter Parker & Gwen Stacy) 23:29 - Should We Claim Social Security Early and Invest It? (Mr & Mrs Scarecrow) 29:56 - We're 60 and 57 with $1.3M. Can We Retire in 3 Years? Should We Hire an Advisor? (Rosie & Astro, PA) 41:04 - Outro: Next Week on the YMYW Podcast | — | ||||||
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