Your Money, Your Wealth

Schedule a Free Financial Assessment with an experienced professional:
https://bit.ly/YMYWassessC
Joe Anderson, CFP® and Big Al Clopine, CPA are spitballing Roth conversions from every angle today on Your Money, Your Wealth® podcast number 597. John in Oklahoma is 75, sitting on a million dollars in traditional IRAs, and he's got a whole list of reasons NOT to convert to Roth. Is he right? Is it worth it as part of his retirement strategy? Jonathan and Jennifer in Phoenix have over six million dollars in tax-deferred accounts. How much should they convert, and where should they stop? J and C in Hawaii are both 38 and want to walk away from work at 55. How do they bridge the gap? And finally, are Bonnie and Clyde working for nothing if it all just turns into a giant tax bill?
Free Financial Resources in This Episode:
https://bit.ly/ymyw-597 (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-ep597-description-whitepaper
Ultimate Investing Guide - free download:
https://purefinancial.com/white-papers/the-ultimate-investing-guide/?utm_source=captivate&utm_medium=podcast&utm_campaign=whitepaper-ultimate-investing-guide&utm_content=ymyw-pod-ep597-description-whitepaper
Once 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-ep579-description-tv-s12e03
Financial Blueprint (free, self-guided):
https://bit.ly/YMYWblueprintC
REQUEST your Retirement Spitball Analysis:
https://bit.ly/YMYWaskC
DOWNLOAD more free guides:
https://bit.ly/YMYWguidesC
READ financial blogs:
https://bit.ly/YMYWblogC
WATCH educational videos:
https://bit.ly/YMYWvidsC
SUBSCRIBE to the YMYW Newsletter:
https://bit.ly/YMYWnewsletterC
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
00:55 - Roth at 75: Does the Math Actually Work? (John, OK)
10:03 - 12M and Still Worried About Taxes: Roth Conversion Spitball (Jonathan & Jennifer, Phoenix AZ)
16:47 - Retiring at 55 in Hawaii: When Do We Start the Taxable Account? (J & C, Hawaii)
27:26 - Am I Just Working to Create a Bigger Tax Problem? (Bonnie & Clyde)
34:20 - Outro: Next Week on the YMYW Podcast
36:53 - The Derails: Hart to Hart, Minutiae, and Levels of Fame

Schedule a Free Financial Assessment with an experienced professional:
https://bit.ly/YMYWassessC
Each of the questions Joe Anderson, CFP® and Big Al Clopine, CPA are spitballing today on Your Money, Your Wealth® podcast 596 has a real retirement risk attached to it. Philip and Elizabeth in DC have $7M. Philip's dying to quit a job he hates, but he's loading up on bonds to protect the nest egg. At 56, could playing it too safe be his real risk? Mr. Mojo Risin wants to retire in three years, but $1.7M of his nest egg is riding on one stock, and he needs a good CPA to help defuse it. BB and Shell got pitched a slick new AI crypto investment promising 15% a month. Too good to be true? And Huggy Bear in New Hampshire has $450K in cash value life insurance. Should he grab it now, or wait 20 years until he’s 80?
9th Annual YMYW Podcast Survey (password ymyw):
https://www.surveymonkey.com/r/ymywpodcast2026/
The Ultimate Investing Guide - free download:
https://purefinancial.com/white-papers/the-ultimate-investing-guide/?utm_source=captivate&utm_medium=podcast&utm_campaign=whitepaper-ultimate-investing-guide&utm_content=ymyw-pod-ep596-description-whitepaper
Retirement 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-ep596-description-whitepaper
Retire at 62: Great Idea or Huge Mistake? - YMYW TV:
https://purefinancial.com/ymyw/episodes/retire-at-62-great-idea-or-huge-mistake/?utm_source=captivate&utm_medium=podcast&utm_campaign=ymyw-tv&utm_content=ymyw-pod-ep596-description-tv-s11e14
Financial Blueprint (free, self-guided):
https://bit.ly/YMYWblueprintC
REQUEST your Retirement Spitball Analysis:
https://bit.ly/YMYWaskC
DOWNLOAD more free guides:
https://bit.ly/YMYWguidesC
READ financial blogs:
https://bit.ly/YMYWblogC
WATCH educational videos:
https://bit.ly/YMYWvidsC
SUBSCRIBE to the YMYW Newsletter:
https://bit.ly/YMYWnewsletterC
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
01:03 - We Have $7M and I Hate My Job. Why Am I Still Here? (Philip & Elizabeth, Washington DC)
10:20 - Retiring in 3 Years, $1.7M in One Stock. Where's the CPA for This? (Mr. Mojo Risin, GA)
19:33 - Is This AI Crypto Investment With 15% Monthly Return Too Good to Be True? (BB & Shell)
28:48 - Cash Out $450K in Life Insurance or Wait Until 80? (Huggy Bear, New Hampshire)
39:28 - Outro: Next Week on the YMYW Podcast
40:58 - The Derails: The Americans, Mr. Mojo Risin

Schedule a Free Financial Assessment with an experienced professional:
https://bit.ly/YMYWassessC
Today on Your Money, Your Wealth® podcast number 595, Joe Anderson, CFP® and Big Al Clopine, CPA spitball for Eeyore and Nurse Kathi: retired in Orlando, both 65, and they swear they've never heard this one on the show before: is a full Roth conversion strategy the way to go, or is there a point where you should stop? Harry and Sally in New York potentially moving to Florida, have been living off their brokerage for retirement account withdrawal for two years, and Sally is getting nervous. Is this a tax efficient retirement plan? When should they claim Social Security? And “When Can I Retire From 12 Hour Days” in Virginia is 62, single, and faced with the same decision: collect Social Security benefits at full retirement age, or hold out for the bigger check at 70?
Free Financial Resources in This Episode:
https://bit.ly/ymyw-595 (full show notes & episode transcript)
9th Annual YMYW Podcast Survey (password ymyw):
https://www.surveymonkey.com/r/ymywpodcast2026/

Social Security Handbook - free download:
https://purefinancial.com/white-papers/social-security-handbook/?utm_source=captivate&utm_medium=podcast&utm_campaign=whitepaper-social-security-handbook&utm_content=ymyw-pod-ep595-description-whitepaper

Claim Social Security at 62 or Wait Until 70? Here's What Actually Matters - YMYW TV:
https://purefinancial.com/ymyw/episodes/claim-social-security-62-wait-until-70-heres-what-actually-matters/?utm_source=captivate&utm_medium=podcast&utm_campaign=ymyw-tv&utm_content=ymyw-pod-ep595-description-tv-s12e06

Financial Blueprint (free, self-guided):
https://bit.ly/YMYWblueprintC
REQUEST your Retirement Spitball Analysis:
https://bit.ly/YMYWaskC
DOWNLOAD more free guides:
https://bit.ly/YMYWguidesC
READ financial blogs:
https://bit.ly/YMYWblogC
WATCH educational videos:
https://bit.ly/YMYWvidsC
SUBSCRIBE to the YMYW Newsletter:
https://bit.ly/YMYWnewsletterC
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
00:54 - Should We Convert All of Our Retirement to Roth? What About Selling Our Rental Property and Capital Gains? (Eeyore and Nurse Kathi, Orlando, FL)
14:56 - We've Lived Off Our Brokerage for 2 Years. Are We Crazy? When Should We Claim Social Security Benefits? (Harry & Sally, NY)
31:02 - Single, 62, $820K: Does My 2029 Retirement Plan Hold Up? When Should I Collect Social Security? (“When Can I Say Goodbye to 12 Hour Days?”, Virginia)
37:27 - Outro: Next Week on the YMYW Podcast
39:15 - The Derails: Winnie the Pooh and Eeyore, Smirnoff Ice, Childhood Stuffed Animals

Schedule a Free Financial Assessment with an experienced professional:
https://bit.ly/YMYWassessC
Today on Your Money, Your Wealth® podcast number 594, Joe Anderson, CFP® and Big Al Clopine, CPA spitball retirement planning for high net worth couples: Gary in Pennsylvania is 54 with $10 million, and get this, he still can't decide whether he can walk away or if he needs to grind out a few more years. What is up with that? But before we get to Gary, Frida and Diego are 54 and 52 in California with $5.3 million, itching to start their go-go years. Can they both retire right now? And is $200,000 a year of spending pushing it? Stanley and Stella in New York have a pension decision to make. Choosing the wrong option could leave one of them exposed for life.
Free Financial Resources in This Episode:
https://bit.ly/ymyw-594 (full show notes & episode transcript)

9th Annual YMYW Podcast Survey (password ymyw):
https://www.surveymonkey.com/r/ymywpodcast2026
Withdrawal Strategy Guide - free download:
https://purefinancial.com/white-papers/withdrawal-strategy-guide/?utm_source=captivate&utm_medium=podcast&utm_campaign=whitepaper-withdrawal-strategy-guide&utm_content=ymyw-pod-ep594-description-whitepaper
Retirement Spending: How Much is Too Much? - YMYW TV:
https://purefinancial.com/ymyw/episodes/retirement-spending-how-much-is-too-much/?utm_source=captivate&utm_medium=podcast&utm_campaign=ymyw-tv&utm_content=ymyw-pod-ep594-description-tv-s12e02
Financial Blueprint (free, self-guided):
https://bit.ly/YMYWblueprintC
REQUEST your Retirement Spitball Analysis:
https://bit.ly/YMYWaskC
DOWNLOAD more free guides:
https://bit.ly/YMYWguidesC
READ financial blogs:
https://bit.ly/YMYWblogC
WATCH educational videos:
https://bit.ly/YMYWvidsC
SUBSCRIBE to the YMYW Newsletter:
https://bit.ly/YMYWnewsletterC
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
00:56 - 54 and 52 with $5.3M. Can We Both Retire Now? (Frida & Diego, CA)
18:13 - Which Pension Option Protects Us Both? (Stanley & Stella, NY)
30:23 - Should We Retire at 54 with $10 Million? (Gary, PA)
40:51 - Outro: Next Week on the YMYW Podcast
42:14 - The Derails: Frida & Diego, Tesla, Kir Royale, Streetcar and Brando, Joe's pool remodel

Paul and Angela in Florida are 52 and 45. What's the earliest the two of them can walk away from work at the same time, so Paul can spend a whole lot more time in the boat? That’s today on Your Money, Your Wealth podcast number 593. Then the fellas spitball for Mike in Riverside. His mom inherited his dad's IRA at age 84. Can she still roll it into her own? Edward in Illinois is watching his bond funds lose value even while they pay him interest, and he's wondering if treasuries are the fix. "Blanche Devereaux" in California is 55 with $1.1M in pre-tax. Should she go all Roth for her last five working years? And "Mr and Mrs Smith" on the Carolina coast want to know if they can afford to retire at age 59.
Free Financial Resources in This Episode:
https://bit.ly/ymyw-593 (full show notes & episode transcript)
LIMITED TIME SPECIAL OFFER: The DIY Retirement Guide! Download yours before the Special Offer changes on Friday, August 7, 2026! https://purefinancial.com/ymyw/#specialoffer
9th Annual YMYW Podcast Survey (password ymyw):
https://www.surveymonkey.com/r/ymywpodcast2026
Your Favorite Money Influencer Might Be Wrong - YMYW TV:
https://purefinancial.com/ymyw/episodes/financial-advisors-expose-internets-worst-retirement-strategies/?utm_source=captivate&utm_medium=podcast&utm_campaign=ymyw-tv&utm_content=ymyw-pod-ep593-description-tv-s11e11
Financial Blueprint (free, self-guided):
https://bit.ly/YMYWblueprintC
REQUEST your Retirement Spitball Analysis:
https://bit.ly/YMYWaskC
DOWNLOAD more free guides:
https://bit.ly/YMYWguidesC
READ financial blogs:
https://bit.ly/YMYWblogC
WATCH educational videos:
https://bit.ly/YMYWvidsC
SUBSCRIBE to the YMYW Newsletter:
https://bit.ly/YMYWnewsletterC
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
00:58 - Nearly $3M at 52 and 45. When Can We Retire Together? (Paul & Angela, FL)
12:56 - Mom Inherited Dad's IRA at 84. Can She Still Roll It Into Her Own? (Mike, Riverside, CA)
18:13 - Bond Funds Keep Losing Value Despite Paying Interest. Treasuries Instead? (Edward, IL)
25:06 - $1.1M Pre-Tax: Roth for the Last 5 Years? (Blanche Devereaux, CA)
35:10 - How Much Will We Have by 2030? Is It Enough to Retire at 59? (Mr. & Mrs. Smith, Coastal NC)
39:26 - Comment: No NUA Step-Up at Death (Jeff)
42:20 - MYGA vs. Immediate Annuity. Is MYGA a CD in Disguise? (Holly, San Francisco)
44:18 - Outro: Next Week on the YMYW Podcast