Your Money, Your Wealth
Joe Anderson, CFP® & Alan Clopine, CPA of Pure Financial Advisors
Recent Episodes
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
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READ financial blogs
WATCH educational videos
SUBSCRIBE to the YMYW Newsletter
Connect With Us:
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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)
One Big Beautiful Bill Act Guide
Retirement Income Strategies Guide
Retirement Rebound: 5 Plays to Help You Score a Comeback - YMYW TV
Financial Blueprint (self-guided)
Financial Assessment (Meet with an experienced professional)
REQUEST your Retirement Spitball Analysis
DOWNLOAD more free guides
READ financial blogs
WATCH educational videos
SUBSCRIBE to the YMYW Newsletter
Connect With Us:
YouTube: Subscribe and join the conversation in the comments
Podcast apps: subscribe or follow YMYW in your favorite
Apple Podcasts: leave your honest reviews and ratings
Chapters:
00:00:00 - Intro
00:00:56 - Should We Stop Roth Conversions for the New $6,000 Senior Bonus Tax Deduction? (Chris, Maple Grove, MN)
00:07:44 - Lost Cost Basis After Moving Funds to Vanguard. Now What? (Windy Chicago, Chino Hills, CA)
00:10:21 - Tax Loss Harvesting: When Is It Too Much? (Teri, Salt Lake City)
00:18:49 - Can We Retire with Rising Health Costs and Care Needs? (Larry & Sally Morgan, voice)
00:33:34 - Outro: Next Week on the YMYW Podcast