Schedule a Free Financial Assessment with an experienced professional:

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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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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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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:

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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

01:53 - 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:

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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

01:00 - 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

Financial Assessment (Meet with an experienced professional):

https://bit.ly/YMYWassessC

11 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-whitepaper

401(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-s10e12

Financial Blueprint (free, self-guided):

https://purefinancial.com/financialblueprint/?utm_source=captivate&utm_medium=podcast&utm_campaign=financial-blueprint&utm_content=ymyw-pod-ep587-description-blueprint

REQUEST your Retirement Spitball Analysis:

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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

01:32 - $1.1 Million in My 401(k) at 56: Should I Do Roth Conversions Before RMDs Hit? (Aaron, Syracuse, NY

04:51 - 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, NY

28:23 - $4 Million and Ready to Exit the Rat Race at 61. Do the Numbers Work? (John and Peggy, San Jose, CA

34:37 - $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

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-whitepaper

The 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-s12e04

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

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https://bit.ly/YMYWnewsletterC

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

01:10 - 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

Financial Assessment (Meet with an experienced professional):

https://bit.ly/YMYWassessC

Free 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-whitepaper

Financial Blueprint - free, self-guided:

https://purefinancial.com/financialblueprint/?utm_source=captivate&utm_medium=podcast&utm_campaign=financial-blueprint&utm_content=ymyw-pod-ep585-description-blueprint

Retirement 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-s10e11

REQUEST your Retirement Spitball Analysis:

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https://bit.ly/YMYWvidsC

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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 - 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

Schedule a Free Financial Assessment with an experienced professional:

https://bit.ly/YMYWassessC

Heidi 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-whitepaper

Financial 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-blueprint

Retirement 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-s11e02

REQUEST your Retirement Spitball Analysis:

https://bit.ly/YMYWaskC

DOWNLOAD more free guides:

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https://bit.ly/YMYWblogC

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https://bit.ly/YMYWvidsC

SUBSCRIBE to the YMYW Newsletter:

https://bit.ly/YMYWnewsletterC

Connect With Us:

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Chapters:

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

01:02 - 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

Schedule a Free Financial Assessment with an experienced professional:

https://bit.ly/YMYWassessC

Joe 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-whitepaper

10 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-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-ep583-description-tv-s12e03

Strategies 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-center

Comic-Con 2014: https://www.youtube.com/watch?v=EQASw5viQPI

2016: https://www.youtube.com/watch?v=WcSRFo7W5ZQ

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:

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WATCH educational videos:

https://bit.ly/YMYWvidsC

SUBSCRIBE to the YMYW Newsletter:

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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

01:09 - 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

Schedule a Free Financial Assessment with an experienced professional:

https://bit.ly/YMYWassessC

Today 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-whitepaper

Financial Blueprint (free, self-guided):

https://purefinancial.com/financialblueprint/?utm_source=captivate&utm_medium=podcast&utm_campaign=financial-blueprint&utm_content=ymyw-pod-ep582-description-blueprint

Retirement Pop Quiz: 18 Questions to Get You Ready to Retire - YMYW TV

https://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-s10e10

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

01:14 - 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