Schedule a Free Financial Assessment with an experienced professional:

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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:

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DOWNLOAD more free guides:

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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:

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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:

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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:

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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:

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Leave your honest reviews and ratings in Apple Podcasts:

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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:

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DOWNLOAD more free guides:

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Leave your honest reviews and ratings in Apple Podcasts:

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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

Schedule a Free Financial Assessment with an experienced professional:

https://purefinancial.com/lp/free-assessment/?utm_source=captivate&utm_medium=podcast&utm_campaign=free-assessment&utm_content=ymyw-pod-ep592-description-free-assessment

Michael, K & J, and Tracy all need retirement spitballs and Roth conversion plans, but they didn't share one of the most important numbers in retirement planning: how much they actually want to spend. Today on Your Money, Your Wealth® podcast number 592, Joe Anderson, CFP® and Big Al Clopine, CPA reverse-engineer their spitballs to back into what might be the same numbers missing from your own plan. Plus, Sean wants to retire in two years at age 56 with $4.4M without handing half of it to the tax man, and Dallas and Leeloo are wondering if there's such a thing as too much Roth - they’re 48 and on track for $1M in theirs. Plus we’ll talk about some charitable giving strategies: what's the difference between a DAF and a CRUT?

Free Financial Resources in This Episode:

https://bit.ly/ymyw-592 (full show notes & episode transcript)

9th Annual YMYW Podcast Survey (password ymyw):

https://www.surveymonkey.com/r/ymywpodcast2026

Is There a Formula for Retirement? - YMYW TV:

https://purefinancial.com/ymyw/episodes/is-there-a-formula-for-retirement/?utm_source=captivate&utm_medium=podcast&utm_campaign=ymyw-tv&utm_content=ymyw-pod-ep592-description-tv-s10e09

Financial Blueprint (free, self-guided):

https://purefinancial.com/financialblueprint/?utm_source=captivate&utm_medium=podcast&utm_campaign=financial-blueprint&utm_content=ymyw-pod-ep592-description-blueprint

REQUEST your Retirement Spitball Analysis:

https://bit.ly/YMYWaskC

DOWNLOAD more free guides:

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Leave your honest reviews and ratings in Apple Podcasts:

https://podcasts.apple.com/us/podcast/your-money-your-wealth/id312900254

Chapters:

00:00 - The 9th Annual YMYW Podcast Survey is now open!

00:44 - Intro: This Week on the YMYW Podcast

01:39 - Working Until 70 With $6.5M Saved. Do I Need Roth Conversions? (Michael, Pittsburgh, PA)

09:25 - How Aggressively Should We Drain Our $2.6M IRA Before RMDs Hit? (K & J, the Cascades)

16:46 - Can I Retire Single at 63 With $1.5M? (Tracy, 63, CA)

20:15 - I'm 54, Single, With $4.4M. How Do I Retire at 56 Without Getting Crushed on Taxes? (Sean, Orlando, FL)

29:22 - How Much Roth is Too Much? We're 48, Heading for $1M in Roth. Did We Overshoot the Goal? (Dallas & Leeloo, 48, Brooklyn, NY)

36:15 - You Said CRTs Must Leave 10% to Charity. Let Me Correct the Record. (DG)

38:21 - DAF vs. CRUT: Which Charitable Tool is Better for $1M Company Stock That's Up 237%? (Fish Sean, 54, Winter Springs, FL)

44:22 - Outro: Next Week on the YMYW Podcast

Schedule a Free Financial Assessment with an experienced professional:

https://purefinancial.com/lp/free-assessment/?utm_source=captivate&utm_medium=podcast&utm_campaign=free-assessment&utm_content=ymyw-pod-ep591-description-free-assessment

B and S in Maryland are in their mid-40s with $425,000 and a couple of rental properties. Can they retire early at 62? Vee in Oregon came to the US as a refugee with nothing and built a three and three-quarter million dollar portfolio from the ground up. Is his Roth conversion plan solid? And finally, Chandler and Monica in Texas are sitting on $1.4 million and hope they can walk away from work in 3 years. Will Roth conversions keep the tax man from taking a giant bite on their way out? That’s all today on Your Money, Your Wealth® podcast 591 with Joe Anderson, CFP® and Big Al Clopine, CPA.

Free Financial Resources in This Episode:

https://bit.ly/ymyw-591 (full show notes & episode transcript)

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-ep591-description-whitepaper

The Number One Spending Mistake Ruining Retirements - YMYW TV

https://purefinancial.com/ymyw/episodes/number-one-spending-mistake-ruining-retirements/?utm_source=captivate&utm_medium=podcast&utm_campaign=ymyw-tv&utm_content=ymyw-pod-ep591-description-tv-s12e01

Financial Blueprint (free, self-guided):

https://bit.ly/YMYWblueprintC

REQUEST your Retirement Spitball Analysis:

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DOWNLOAD more free guides:

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Connect With Us:

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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

00:57 - Half a Million and Rental Properties in Our Mid-40s. Can We Retire Early? (B & S, Westminster, MD)

12:48 - Refugee to $3.75M: Is My Roth Conversion Plan Actually Solid? (Vee, OR)

25:55 - Can Friends with $1.4M and a Roth Conversion Puzzle Retire in 3 Years? (Chandler & Monica, TX)

33:05 - Outro: Next Week on YMYW Podcast

Schedule a Free Financial Assessment with an experienced professional:

https://bit.ly/YMYWassessC

Today on Your Money, Your Wealth® podcast 590, Joe Anderson, CFP® and Big Al Clopine, CPA spitball for people with a small fortune sitting in pre-tax accounts turning into a tax bomb. We’ll find out how Roth conversions and careful tax liability management can optimize their retirement income strategy. Eric in California is 72 with nearly four million dollars in pre-tax accounts. How much should he transfer in Roth conversions? Is borrowing against his own house to pay the tax bill brilliant or bonkers? Rick and Kiani hoping they can quit sooner than they think. Mike just hit full retirement age. Should he claim Social Security benefits now or wait until age 70? And finally, Jeff wants to walk away at 59 with a roadmap for aggressive Roth conversions, assuming the tax cliff doesn't get him first.

Free Financial Resources in This Episode:

https://bit.ly/ymyw-590 (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-ep590-description-whitepaper

Financial Blueprint (free, self-guided):

https://purefinancial.com/financialblueprint/?utm_source=captivate&utm_medium=podcast&utm_campaign=financial-blueprint&utm_content=ymyw-pod-ep590-description-blueprint

Retirement Checklist: Check Off These 7 Things Before You Retire - YMYW TV:

https://purefinancial.com/ymyw/episodes/retirement-checklist-check-off-these-7-things-before-you-retire/?utm_source=captivate&utm_medium=podcast&utm_campaign=ymyw-tv&utm_content=ymyw-pod-ep590-description-tv-s12e05

REQUEST your Retirement Spitball Analysis:

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Leave your honest reviews and ratings in Apple Podcasts:

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Chapters:

00:00 - Intro: This Week on the YMYW Podcast

01:01 - $3.9M Pre-Tax at 72: How Do We Minimize Taxes Before RMDs Hit? (Eric, CA)

11:13 - We’re on One Salary. Can We Retire at 62 With $1.7M and a $56K SS Benefit? (Rick & Kiani, Southern CA)

23:16 - Just Hit Full Retirement Age. Should I Delay Social Security or Start Now? (Mike, 66, NV)

31:04 - Retiring With $4M and a Roth Conversion Roadmap at Age 59. Does Our Plan Hold Up? (Jeff & Amber, 55, Orlando, FL)

44:54 - Outro: Next Week on the YMYW Podcast

Schedule a Free Financial Assessment with an experienced professional:

https://bit.ly/YMYWassessC

The margin loan debate continues today on Your Money, Your Wealth® podcast number 589. Jack and Jill recently moved from the UAE to Australia and want a sanity check on using margin loans (AKA pledge loans) to build and live off their portfolio. Joe and Big Al spitball whether borrowing against stocks and never paying tax on the gains, the Buy Borrow Die strategy, is smart, or a fast way to blow yourself up. They also recap the spicy comments on the episode 585 margin loan discussion. Then the fellas flip the script for Forest and Jenni in Virginia: does a reverse glide path, investing conservatively now and getting more aggressive as you age, actually hold up? And finally, Jack and Diane in New Jersey are retiring this year, selling the house, and moving to Florida, so Joe and Big Al stress-test their Roth conversion plan before they pull the trigger. We're making fun of finance over here on YMYW, the financial planning podcast that won't put you to sleep. Tell a friend.

Free Financial Resources in This Episode:

https://bit.ly/ymyw-589 (full show notes & episode transcript)

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-ep589-description-whitepaper

Retirement Sabotage! 12 Post-Retirement Money Mistakes to Avoid - YMYW TV: https://purefinancial.com/ymyw/episodes/retirement-sabotage-12-post-retirement-money-mistakes-to-avoid/?utm_source=captivate&utm_medium=podcast&utm_campaign=ymyw-tv&utm_content=ymyw-pod-ep589-description-tv-s10e08

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

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Connect With Us:

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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

01:53 - Margin Loans, Buy-Borrow-Die, and PFIC Risk: Sanity Check (Jack & Jill, Australia)

13:11 - Why I Love Margin: NYC Tax Math (Bones1999, YouTube)

14:29 - 8% Margin Loans to Buy Stocks: Bad Math! (Tom, YouTube)

19:39 - Reverse Glide Path at Retirement: Does Starting Conservative Make Sense for Us? (Forest & Jenni, VA)

35:43 - Retiring to Florida: SEP IRA Bridge, Home Sale Timing, and Roth Conversions (Jack & Diane, NJ)

43:18 - Outro: Next Week on the YMYW Podcast

Schedule a Free Financial Assessment with an experienced professional:

https://bit.ly/YMYWassessC

Joe Anderson, CFP® and Big Al Clopine, CPA spitball for three people planning for early retirement and wondering, can I really pull this off? How much risk can you take, and how much do you really need to? That’s today on Your Money, Your Wealth® podcast 588. Dr. Kickass Seabass and his wife are both 41 and they got a late start on savings. Can they still hit FIRE - that is, financial independence, retire early - by 55? Get your salt shakers ready. Aang and Katara have military pensions and a big thrift savings plan. Should they invest it aggressively or play it safe over the next decade? Finally, Steph has a mandatory retirement at 56 but wants out even sooner, at age 50… if his wife Ayesha doesn't kill him first for quitting seven years before her.

Free Financial Resources in This Episode:

https://bit.ly/ymyw-588 (full show notes & episode transcript)

Retirement Income Strategies Guide - free download:

https://purefinancial.com/white-papers/retirement-income-strategies/?utm_source=captivate&utm_medium=podcast&utm_campaign=whitepaper-retirement-income-strategies&utm_content=ymyw-pod-ep588-description-whitepaper

Financial Planning at Every Age: Retirement Planning for Millennials, Gen-X & Baby Boomers - YMYW TV:

https://purefinancial.com/ymyw/episodes/financial-planning-at-every-age-retirement-planning-millennials-gen-x-baby-boomers/?utm_source=captivate&utm_medium=podcast&utm_campaign=ymyw-tv&utm_content=ymyw-pod-ep588-description-tv-s10e7

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-ep588-description-whitepaper

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:

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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

01:00 - High-Earning Doc With a Late Start: Can I Actually FIRE at 55? (Kickass Seabass, NJ)

13:39 - Military Pension + TSP: How Aggressive Should We Stay for the Next Decade? (Aang & Katara, VA)

25:10 - Mandatory Retirement at 56, But Can I Punch at 50? (Steph & Ayesha, SF Bay Area)

46:54 - Outro: Next Week on the YMYW Podcast