Roth Conversions: When to Make 'Em, When to Take 'Em - 547

A YMYW listener from Missouri and his wife are retired at 69 and 67, with less than $2 million dollars. Should they continue converting retirement savings to Roth for the tax-free growth? What should they do about long term care insurance? More importantly, is our listener’s name (Cousy) pronounced "Cuzzy" or "Koozy"? Speaking of Roth conversions, must “Peggy Hill” wait five years to withdraw her conversion money, or only its earnings? That’s today on Your Money, Your Wealth® podcast number 547 with Joe Anderson, CFP® and Big Al Clopine, CPA. Plus, is Skipper’s retirement payout plan the killer deal he thinks it is? How can Jeff in Dallas pay less capital gains tax on his 3 million dollar single stock, million dollar 401(k), and potential eBay income? Is selling on eBay still a thing? Does Dolly in Tennessee need to empty her inherited IRA within the next 10 years due to the SECURE Act? And finally, HSA vs. HRA: how should Larry in Rhode Island navigate switching from his current employer’s health savings account to his future employer’s health reimbursement arrangement? Free Financial Resources in This Episode:  https://bit.ly/ymyw-547 (full show notes & episode transcript) 5 Year Rules for Roth IRA Withdrawals 2025 Key Financial Data Guide (newly updated with One Big Beautiful Bill changes) 10 Steps to Improve Investing Success What to Do When the Stock Market Gets Crazy - 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 01:11 - Should We Continue Roth Conversions in Retirement? What About Long-Term Care? (Cousy, MO) 13:03 - Must I Wait 5 Years to Withdraw My Roth Conversion, Or Only Its Earnings? ("Peggy Hill", MN) 21:50 - Is My Retirement Plan Payout the Killer Deal I Think It Is? (Skipper) 28:07 - How to Minimize My Capital Gains Tax? (Jeff, Dallas, TX) 33:37 - Must I Empty My Inherited IRA Within 10 Years With The SECURE Act? (Dolly, Bristol, TN) 37:50 - HSA and HRA: Health Savings Account vs. Health Reimbursement Arrangement (Larry, RI) 40:48 - Outro: Next Week on the YMYW Podcast

We heard your feedback, and today on Your Money, Your Wealth® podcast number 546, Joe Anderson, CFP® and Big Al Clopine, CPA are spitballing retirement for the not-so-fat wallets: Joe and Masako in Washington state and Reid in Indiana have less than a million saved. Can they still accomplish their retirement goals in their 60s? Mr Buckeye in Ohio and Old Macdonald in Maine have less than a million saved, and Curt in Pennsylvania has less than $1.5 million saved. Can they retire early - in their 40s and 50s?    Free financial resources & episode transcript: https://bit.ly/ymyw-546 DOWNLOAD The Going Solo Guide WATCH Going Solo: Navigating Your Financial Future Single on YMYW TV CALCULATE your free Financial Blueprint SCHEDULE your Free Financial Assessment ASK Joe & Big Al for your Retirement Spitball Analysis LEAVE YOUR HONEST RATINGS AND REVIEWS on Apple Podcasts SUBSCRIBE or FOLLOW on your favorite podcast app JOIN THE CONVERSATION on YouTube DOWNLOAD more free guides READ financial blogs WATCH educational videos SUBSCRIBE to the YMYW Newsletter Timestamps: 00:00 - Intro: This Week on the YMYW Podcast 00:36 - We’re 59 and 65 with Less than $1M. Can We Still Accomplish Our Retirement Goals? (Joe and Masako, WA state) 08:18 - We’re 33 with $200K. Can We Retire at 65 and Spend $159K/Year? (Reid, IN) 15:58 - Calculate your Free Financial Blueprint 16:32 - We're Early 40s With $795K. Can We Retire at 55? (Mr Buckeye, OH) 28:38 - Watch Going Solo: Navigating Your Financial Future Single YMYW TV, Download the Going Solo Guide 29:25 - I'm 43 With $50K and a Paid Off House. Can I Retire ASAP? (Old MacDonald, Limington, Maine) 37:35 - I'm 35 With $1.4M. Can I Retire at 45 and Spend $75K/year? (Conshohocken Curt, PA) 49:04 - Next Week on the YMYW Podcast 49:23 - YMYW Podcast Outro

One Big Beautiful Bill is now law. How does it impact your Roth conversion strategies and other financial decisions? Plus, you may have seen or heard other advisors talking about their strategies for getting your retirement savings into tax-free Roth accounts. How are these different from a good ol’ Roth conversion, and what do Joe and Big Al think of them? Find out today on Your Money, Your Wealth® podcast number 545 with Joe Anderson, CFP® and Big Al Clopine, CPA. Also, why is Ed Slott, CPA, the man known to many as "the IRA guru," such a fan of permanent cash value life insurance? Finally, an attempted correction from a YMYW YouTube viewer turns into a rousing game of death trivia, and we’ll share some of your opinions from the 8th Annual YMYW Podcast Survey, which just closed. (Congratulations Larry, for being the randomly-chosen winner of the $100 Amazon e-gift card, just for completing the survey!) Free financial resources & episode transcript: https://bit.ly/ymyw-545 DOWNLOAD The Ultimate Guide to Roth IRAs WATCH Your 11 Step Path to Financial Freedom on YMYW TV CALCULATE your free Financial Blueprint SCHEDULE your Free Financial Assessment ASK Joe & Big Al for your Retirement Spitball Analysis LEAVE YOUR HONEST RATINGS AND REVIEWS on Apple Podcasts SUBSCRIBE or FOLLOW on your favorite podcast app JOIN THE CONVERSATION on YouTube DOWNLOAD more free guides READ financial blogs WATCH educational videos SUBSCRIBE to the YMYW Newsletter

You’ve heard Joe and Big Al talk about the benefits of tax diversification in retirement. That is, having money in tax-deferred, tax-free, and taxable accounts. But what should you do if this tax triangle of yours is lopsided? Joe and our special guest co-host, Marc Horner, CFP®, spitball on this quandary for Rae and Roy in Central California, today on Your Money, Your Wealth® podcast number 544. Plus, do Rae or Roy need to get a part-time job? Also, "Elwood Blues" in Illinois would like to retire in two years, but is willing to go for 3 more to make his retirement plan work. Joe and Marc spitball on when "Elwood" can really put down that harmonica. Free financial resources & episode transcript: https://bit.ly/ymyw-544 Complete the 8th Annual YMYW Podcast Survey by 5pm Pacific on August 31, 2025, for your chance at a $100 Amazon e-gift card! (secret password: ymyw) WATCH 15 Maneuvers to Duck an Unplanned Early Retirement Knockout on YMYW TV CALCULATE your free Financial Blueprint ASK Joe & Big Al for your Retirement Spitball Analysis SCHEDULE your Free Financial Assessment LEAVE YOUR HONEST RATINGS AND REVIEWS on Apple Podcasts SUBSCRIBE or FOLLOW on your favorite podcast app JOIN THE CONVERSATION on YouTube DOWNLOAD more free guides READ financial blogs WATCH educational videos SUBSCRIBE to the YMYW Newsletter Timestamps: 00:00 - Intro: This Week on the YMYW Podcast with Joe Anderson, CFP® and Marc Horner, CFP® 00:49 - Our Tax Triangle is Lopsided. Should One of Us Get a Part-Time Job? (Rae and Roy, Central CA) 12:03 - Watch 15 Maneuvers to Duck an Unplanned Early Retirement Knockout, Calculate your Financial Blueprint, Schedule a Financial Assessment 13:11 - I'd Like to Retire in 2 Years. Willing to Work 3 More to Make it Work (Elwood Blues, IL) 27:10 - Next Week on YMYW Podcast: The One Big Beautiful Bill + More 27:40 - YMYW Podcast Outro

Is it possible, common even, to spend a lot early in retirement to celebrate your financial freedom? How do Roth conversions and withdrawals work if you do plan to call it quits around age 57, and spend big early on? Should you convert retirement funds to tax-free Roth after you stop working? Joe Anderson CFP® and our special guest co-host, Marc Horner, CFP® spitball on these topics for "Beavis and Daria" in Texas and "Clark Kent" in Pennsylvania, today on Your Money, Your Wealth® podcast number 543. Plus, the sooner 56-year-old "Tony Soprano" in New Jersey can retire, the better. What tips do Joe and Marc have for him? By the way, Marc is one of the newest principals here at Pure Financial Advisors. He’s the founder of Fairhaven Wealth Management, which has just become the newest Pure Financial Advisors Chicagoland office in Wheaton, Illinois - so help us welcome him for his YMYW debut. Free financial resources & episode transcript: https://bit.ly/ymyw-543 Complete the 8th Annual YMYW Podcast Survey for your chance at a $100 Amazon e-gift card! (secret password: ymyw) DOWNLOAD the Withdrawal Strategy Guide for free WATCH Withdrawal Trap Doors on YMYW TV ASK Joe & Big Al for your Retirement Spitball Analysis SCHEDULE your Free Financial Assessment LEAVE YOUR HONEST RATINGS AND REVIEWS on Apple Podcasts SUBSCRIBE or FOLLOW on your favorite podcast app JOIN THE CONVERSATION on YouTube DOWNLOAD more free guides READ financial blogs WATCH educational videos SUBSCRIBE to the YMYW Newsletter Timestamps: 00:00 - Intro: This Week on the YMYW Podcast 01:00 - Spending Higher Earlier in Retirement to Celebrate? How to Convert? Where to Withdraw? (Beavis & Daria, TX) 12:30 - Watch Withdrawal Trap Doors on YMYW TV and Download the Withdrawal Strategy Guide for free 13:36 - Can I Retire at 57 Even With a High Draw Down Rate? Should I Convert After Retirement? Should I Consider an Annuity? (Clark Kent, PA) 28:23 - Complete the 8th Annual YMYW Podcast Survey for your chance at a $100 Amazon e-gift card! (secret password: ymyw) 29:09 - When Can I Retire? The Sooner the Better. (Tony Soprano, NJ) 37:43 - Next Week on the YMYW Podcast 38:01 - YMYW Podcast Outro

"Rubble and Skye" in Minnesota want to spend $65,000 a year in retirement, and they’ll have $67K in annual fixed income. Are they cutting it too close? "Atouk and Tala" in New Jersey will have retirement money, Social Security, and “Lumpy,” their lump sum pension - will they be okay? We’ll find out today on Your Money, Your Wealth® podcast number 542 with Joe Anderson, CFP® and Big Al Clopine, CPA. Plus, should David in Redondo Beach California use his Roth money to buy a home? And what do the fellas think about "Charlie Pepper" in Colorado using a home equity line of credit (HELOC) for retirement spending, instead of living off of pre-tax money? Free financial resources & episode transcript: https://bit.ly/ymyw-542 DOWNLOAD the Investing Basics Guide WATCH Financial Boot Camp on YMYW TV COMPLETE the 8th Annual YMYW Podcast Survey for your chance at a $100 Amazon e-gift card! (secret password: ymyw) ASK Joe & Big Al for your Retirement Spitball Analysis SCHEDULE your Free Financial Assessment LEAVE YOUR HONEST RATINGS AND REVIEWS on Apple Podcasts SUBSCRIBE or FOLLOW on your favorite podcast app JOIN THE CONVERSATION on YouTube DOWNLOAD more free guides READ financial blogs WATCH educational videos SUBSCRIBE to the YMYW Newsletter Timestamps: 00:00 - Intro: This Week on the YMYW Podcast 00:43 - $250K Saved, $67K Fixed Income, $65K Spending. Are We Cutting Retirement Too Close? (Rubble & Sky, MN) 05:20 - We Have a $700K Pension, $335K Retirement, Plus Social Security. Will We Be OK? (Atouk and Tala, NJ) 13:14 - Watch Financial Boot Camp on YMYW TV, Download the Investing Basics Guide 14:03 - Should I Use My Roth Money for a Home Purchase? (David, Redondo Beach, CA) 21:03 - Complete the 8th Annual YMYW Podcast Survey for your chance at a $100 Amazon e-gift card! (secret password: ymyw) 22:01 - HELOC vs. Pre-Tax Account for Retirement Spending (Charlie Pepper, CO) 34:23 - Next Week on YMYW Podcast: Guest Co-Host Marc Horner, CFP® 34:53 - YMYW Podcast Outro

Pam and Jim in Phoenix are 38 and 41 and want to retire at 59 and 62. Matt and his wife in Pennsylvania are both 39 and want to retire at 57. Are these millennials on the right financial path, or have they brunched and YOLO’d away their retirement dreams? That’s today on Your Money, Your Wealth® podcast number 541 with Joe Anderson, CFP® and Big Al Clopine, CPA. Plus, do Roth conversions make sense for Will and Jane in New York, given their high income and high tax bracket? Which pension option is best for their circumstances? Finally, the fellas spitball for Juan’s mother in Florida on how long-term capital gains on the installment sale of her company will be taxed. Free financial resources & episode transcript: https://bit.ly/ymyw-541 Complete the 8th Annual YMYW Podcast Survey for your chance at a $100 Amazon e-gift card! (secret password: ymyw) LIMITED TIME OFFER: Download The Money Makeover Guide before this Friday, August 8, 2025! WATCH Complete Money Makeover on YMYW TV ASK Joe & Big Al for your Retirement Spitball Analysis SCHEDULE your Free Financial Assessment LEAVE YOUR HONEST RATINGS AND REVIEWS on Apple Podcasts SUBSCRIBE or FOLLOW on your favorite podcast app JOIN THE CONVERSATION on YouTube DOWNLOAD more free guides READ financial blogs WATCH educational videos SUBSCRIBE to the YMYW Newsletter   Timestamps:  00:00 - Intro: This Week on the YMYW Podcast 00:44 - We’re Millennials. Have We Brunched and YOLO'd Away Our Retirement Dreams? (Pam & Jim, Phoenix, AZ) 12:10 - We're 39 With $840K. Can We Retire at Age 57? (Matt, PA) 22:57 - Complete the 8th Annual YMYW Podcast Survey for your chance at a $100 Amazon e-gift card! 23:53 - Do Roth Conversions Make Sense Given Our High Income and Tax Bracket? What Pension Option is Best? (Will and Jane, NY - voice) 37:04 - Watch Complete Money Makeover on YMYW TV, Download the Complete Money Makeover Guide before Friday, August 8, 2025! 37:46 - How Will Long Term Capital Gains on the Installment Sale of My Company Be Taxed? (Juan's Mother, FL) 47:50 - YMYW Podcast Outro  

Can Beth and Rip retire early, spend more, and Die with Zero? When should they claim Social Security? Forrest and Jenny have 10 rental properties at age 31. Can they retire at age 50? (And what makes you a real estate professional from a tax perspective?) Plus, what are the rules for spousal IRA contributions and required minimum distributions? Memphis wants to know. Joe Anderson, CFP® and Big Al Clopine, CPA spitball for YMYW audience members who are definitely not fictional characters, today on Your Money, Your Wealth® podcast number 540. Free financial resources & episode transcript: https://bit.ly/ymyw-540 Complete the 8th Annual YMYW Podcast Survey for your chance at a $100 Amazon e-gift card! (secret password: ymyw) Watch Retirement Panic Button: 7 Ways to Avoid Hitting It on YMYW TV CALCULATE your free Financial Blueprint ASK Joe & Big Al for your Retirement Spitball Analysis SCHEDULE your Free Financial Assessment LEAVE YOUR HONEST RATINGS AND REVIEWS on Apple Podcasts SUBSCRIBE or FOLLOW on your favorite podcast app JOIN THE CONVERSATION on YouTube DOWNLOAD more free guides READ financial blogs WATCH educational videos SUBSCRIBE to the YMYW Newsletter   Timestamps: 00:00 - Complete the 8th Annual YMYW Podcast Survey for your chance at a $100 Amazon e-gift card! 00:35 - Intro: This Week on the YMYW Podcast 01:13 - Can We Retire Early, Spend More, and Die With Zero? When Should We Collect Social Security? (Beth and Rip, FL - voice) 12:06 - Watch Retirement Panic Button: 7 Ways to Avoid Hitting It on YMYW TV Calculate your Financial Blueprint Schedule a Free Assessment 13:41 - We Have 10 Rental Properties at Age 31. Are We on Track to Retire at Age 50? (Forrest and Jenny, Cherry Hill, NJ - voice) 20:04 - Spousal IRA Contributions and RMD Rules (Memphis) 32:23 - YMYW Podcast Outro

Roger in Canton, Ohio, is burnt out. Can he and his wife Jane pre-retire next year in their mid-50s with $2.8 million? Joe and Big Al spitball on whether they’ll still have enough money for their Go-Go years, Joe’s favorite, today on Your Money, Your Wealth® podcast number 539. Roger also has an employee stock purchase plan. For the best asset location strategy, should he max out the ESPP at a 15% discount, convert to Roth IRA, build his brokerage account, or a little of all the above? Speaking of asset location, some of our YouTube viewers object to the idea of putting higher performing assets in your Roth account. They say you can’t write off the losses and you’ll be exposed to sequence of returns risk. Stick around for Joe and Al’s response. Free financial resources & episode transcript: https://bit.ly/ymyw-539  DOWNLOAD Why Asset Location Matters for Free CALCULATE Your Free Financial Blueprint WATCH Recipe for Retirement | Retirement Plans Explained on YMYW TV ASK Joe & Big Al for your Retirement Spitball Analysis SCHEDULE your Free Financial Assessment LEAVE YOUR HONEST RATINGS AND REVIEWS on Apple Podcasts SUBSCRIBE or FOLLOW on your favorite podcast app JOIN THE CONVERSATION on YouTube DOWNLOAD more free guides READ financial blogs WATCH educational videos SUBSCRIBE to the YMYW Newsletter Timestamps: 00:00 - Intro: This Week on the YMYW Podcast 02:03 - I’m Burned Out. Can I Pre-Retire Next Year? (Roger & Jane, Canton, OH) 11:46 - Watch Recipe for Retirement | Retirement Plans Explained on YMYW TV and Calculate Your Free Financial Blueprint 12:50 - Would You Rather for Asset Location: Roth vs. Brokerage? Roth vs. ESPP with 15% Discount? (Roger & Jane, Canton, OH, cont'd) 21:08 - Higher Performing Assets in Roth Exposes You To Sequence of Returns Risk and You Can't Write Off  The Losses (YouTube comment) 24:54 - Next Week on the YMYYW Podcast 25:27 - Download Why Asset Location Matters for Free

George and Weezy in the land of Lincoln will have deferred compensation and wonder if they can retire in mid-2026, or even earlier. Will they have enough? Should Jenn in Ohio move with work, take a break, or just retire? She asks Joe Anderson, CFP® and Big Al Clopine, CPA for a brutally honest spitball, today on Your Money, Your Wealth® podcast 538. Plus, Seth isn’t sure if he can afford to stay retired at age 52, and whether he should convert his retirement savings to Roth, so he uses an AI voice to ask the fellas for his spitball. And Leon uses his real voice to ask whether REIT ETFs are a good way to get into real estate investing. Free financial resources & episode transcript: https://bit.ly/ymyw-538  Test your knowledge: take our Retirement Pop Quiz Watch Retirement Pop Quiz: 18 Questions To Get You Ready to Retire on YMYW TV Download the Retirement Readiness Guide for free Email Us and Request a Free Copy of The Best of Jonathan Clements: Classic Columns on Money and Life on Kindle!  Watch or Listen to “The Payoff is Huge”: Jonathan Clements’ Final Initiative to Empower Lifelong Savers ASK Joe & Big Al for your Retirement Spitball Analysis SCHEDULE your Free Financial Assessment LEAVE YOUR HONEST RATINGS AND REVIEWS on Apple Podcasts SUBSCRIBE or FOLLOW on your favorite podcast app JOIN THE CONVERSATION on YouTube DOWNLOAD more free guides READ financial blogs WATCH educational videos SUBSCRIBE to the YMYW Newsletter   Timestamps: 00:00 - Intro: This Week on the YMYW Podcast 01:03 - Can “George and Weezy” Retire in 2026 or Earlier With Deferred Compensation? (IL) 12:17 - Pop Quiz, Retirement Readines Guide 13:02 - Should I Move With Work, Take a Break, or Retire Now? Be Brutally Honest (Jenn, OH) 17:43 - Can I Stay Retired at Age 52? Should I Convert Retirement Savings to Tax-Free Roth? (Seth, Montana, AI voice) 24:34 - Ask Joe & Big Al for your Retirement Spitball Analysis, Schedule a Free Financial Assessment 25:30 - Are REIT ETFs a Good Way to Get Into Real Estate Investing? (Leon, Chicago - voice) 33:56 - Request a Free Kindle Copy of The Best of Jonathan Clements,  Watch or Listen to “The Payoff is Huge”: Jonathan Clements’ Final Initiative to Empower Lifelong Savers