How to Beat the “Fire Hydrant” of Future Taxes: YMYW Best of 2025 - 563
Release Date: 01/06/2026
The Retirement Question Every Couple Asks: Can We Afford It? - 578
Your Money, Your Wealth
“Chase and Ryder” are 56 and 55 with $5 million saved and huge pensions the day they retire. So why are they so nervous about pulling the trigger? That's today on Your Money, Your Wealth® podcast number 578 with Joe Anderson, CFP® and Big Al Clopine, CPA. “Andy and April” are 46 with $2.4 million saved and 10 years until they want to retire. Can they get there, and do they need a trust? “Burt and Sally” are in their late forties with solid pensions and a retirement dream, but is the math close enough to make it work? Finally, does “Dolly” have any options for squeezing more...
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This Early Retirement Strategy Could Be a Huge Mistake
Your Money, Your Wealth
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...
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When Roth Conversions Don't Make Sense (And When They're a No-Brainer) - 576
Your Money, Your Wealth
Are Roth conversions worth it? We’ll find out, today on Your Money, Your Wealth® podcast number 576. TJ in PA is gonna have huge capital gains. Joe and Big Al spitball on whether it’s worth it for him to convert. Rebels Without a Gauze in New England are over 70. Is it too late for them to convert? How much should Biking Barnsey convert from his tax-deferred accounts to Roth each year, and are there any single ladies in the YMYW audience that would like to help him spend his retirement money? Finally, the fellas spitball on whether Zisi and his wife are being too aggressive with...
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Die With Zero: Are You Giving Your Kids Too Much? - 575
Your Money, Your Wealth
Joe Anderson, CFP® and Big Al Clopine, CPA spitball on how to build your own retirement AND support your kids financially, today on Your Money, Your Wealth® podcast number 575. "Lloyd and Diane" in Montgomery County are 50 with $8.4 million. Can they retire early and still be generous with their kids? E and T in Missouri are 34 and 31 with $255K, and hopefully some big inheritances in the future. Can they fund the kids' college, and help them buy their first homes, AND retire early? Kent in Kansas City is 73 with 12 million bucks and $2 million in life insurance. Do Joe and Big Al back up...
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When Should You Take Social Security? (Don’t Screw This Up) - 574
Your Money, Your Wealth
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...
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Could You Retire Tomorrow If You Had To? - 573
Your Money, Your Wealth
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...
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Could You Lose Half Your Retirement Income to Taxes? - 572
Your Money, Your Wealth
“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...
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Retire Early in Your 40s or 50s: Green Light or Reality Check? - 571
Your Money, Your Wealth
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...
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Retirement Planning for Aging Parents - and Can You Retire Early? - 570
Your Money, Your Wealth
Joe and Big Al spitball two sides of the retirement equation, today on Your Money, Your Wealth® podcast number 570. Daniel in Texas is 40 and worrying about how to support Mom and Dad if their money runs out. Can he build some kind of financial safety net for them without ruining his own retirement? Jemma’s 82-year-old mom is drawing down her portfolio. Is locking in guaranteed income with an annuity a smart move, or could that create new problems down the road? Plus, “Cookie and Gerry” want to walk away from work before 50 with a big brokerage account and a pension. Are they positioned...
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Retirement Changes at These 5 Major Financial Crossroads - 569
Your Money, Your Wealth
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...
info_outlineYMYW 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
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Financial Assessment (Meet with an experienced professional)
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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 ep. 526: YMYW most listeners and plays in 2025 on Apple Podcasts, YMYW most downloaded in 2025 across all podcast platforms
- 20:46 - Is There a Point Where Roth Conversions No Longer Make Sense? (Jerry, Phoenix, AZ)
- from ep. 535: YMYW most views, watch time, and new subscribers in 2025 on YouTube, most engaged listeners in 2025 on Apple Podcasts
- 32:13 - Roth Conversions vs. Taking Advantage of Zero Percent Cap Gains (Skipper, CA)
- from ep. 517: YMYW most consumed episode in 2025 on Apple Podcasts
- 43:06 - We're in Our Early 40s with $795K Saved. Can We Retire at 55? (Mr Buckeye, OH)
- 55:12 - Is My Husband Eligible for Spousal Social Security Benefits Now that WEP and GPO Are Gone? (Cherilyn, El Cajon, CA)
- 59:53 - Outro: 2025 Stats and Next Week on the YMYW Podcast