Your Money, Your Wealth

Market declines just before you retire, or early in your retirement, can really screw up your retirement income strategy. If you're in the middle of the expensive kid years, how do you avoid this sequence of returns risk when making your retirement plans? That's "Jaclyn Smith's" question, today on Your Money, Your Wealth® podcast 485 with Joe Anderson, CFP® and Big Al Clopine, CPA. Plus, can Vern's wife collect Social Security at age 63, then switch to spousal benefits at age 70? Matt wants to know if 2026 catch-up Roth contributions will be subject to the pro-rata rule, and Tom and Amy are trying to figure out how to avoid Medicare's monthly income-related adjustment amount, or IRMAA, in their plan for Roth conversions. Free financial resources and transcript: https://bit.ly/ymyw-485 How to Build a Recession-Proof Portfolio - YMYW TV Recession Protection Guide - free download The Election is Coming: Should You Sell? - read the blog Investment Vehicle Selection: SMA vs. ETF vs. Mutual Fund – Which One Best Fits You? - read the blog Is Roth IRA Money Taxed Twice? Watch the latest YMYW Extra Schedule a free financial assessment Ask Joe & Big Al for your Retirement Spitball Analysis Timestamps: 00:00 - Intro 00:49 - How to Minimize Sequence of Returns Risk When Spitballing Retirement in the Expensive Kid Years? (Jaclyn Smith) 17:18 - Collect Social Security Early at Age 63, Then Switch to Spousal Benefits at Age 70? (Vern, Beautiful Portland Oregon) 23:30 - Will 2026 Catch-Up Contributions to Roth Be Subject to Pro-Rata Rule? (Matt, TX) 23:47 - Should We Do Roth Conversions? What About Medicare IRMAA? (Tom & Amy, Northern MN) 31:51 - The Derails

Should Mike in Virginia keep using his IRA money to pay the tax on his Roth conversions? How do you do a Roth conversion when you don't have the money to pay the tax? That's PeterLemonJello's question, but is it the question he should be asking? Spitballing Roth IRA conversion strategies to reduce your taxable required minimum distributions (RMD) in retirement - that's today on Your Money, Your Wealth® podcast 484 with Joe Anderson, CFP® and Big Al Clopine, CPA. Plus, Susan and Mike in Ohio are retired, in the 24% tax bracket, and considering converting $50k or $75k to Roth - should they do it? How is D-Rock and Matilda's strategy for selling rental properties and doing Roth conversions as they bridge the gap to early retirement? And finally, how do required minimum distributions work on inherited Roth accounts? Free financial resources and transcript: https://bit.ly/ymyw-484 Navigating Your Financial Future Single - YMYW TV Going Solo Guide - free download Asset Location & Roth Conversion Retirement Spitball - YMYW Extra Ep. 1 Ask for your own Retirement Spitball Analysis Schedule a Free Financial Assessment Timestamps: 00:00 - Intro 00:54 - How to Pay the Tax on a Roth Conversion: Are You Asking the Right Question? (Peter LemonJello, FL) 05:45 - Should I Keep Doing Roth Conversions and Paying Tax from the IRA? (Mike, VA) 14:24 - Retired, in the 24% Tax Bracket. Should We Convert $50-$75K to Roth in 2024? (Susan, OH) 18:28 - Roth Conversions and Selling Rental Property to Bridge to Early Retirement (D-Rock & Matilda, New York) 28:11 - Required Minimum Distributions for Inherited Roth IRAs Explained (Elisa, Fremont) 34:12 - The Derails

Sunshine in Orange County has been waiting patiently since January for a full Retirement Spitball Analysis: how are her assumptions for rates of return and inflation, her plans for Roth conversions, her asset allocation and asset location, her tax planning, her retirement income and retirement spending plans, and so much more? What missed opportunities is she overlooking? So many excellent Retirement Spitball requests have come in that Your Money, Your Wealth® hosts, Joe Anderson CFP®, and Big Al Clopine CPA can't handle them all. On these bonus episodes, called YMYW Extra, producer Andi Last enlists the help of the experienced professionals on Joe and Big Al's team at Pure Financial Advisors. In today's YMYW Extra number 1, thanks to David Cook, CFP® from Pure Financial's San Diego headquarters, Sunshine finally gets her Retirement Spitball Analysis. Free financial resources and transcript: https://bit.ly/ymywe-1 Request your own Retirement Spitball Analysis EASIretirement.com - free retirement calculator Why Asset Location Matters - download the free guide More Guides | Blogs | Educational Videos | YMYW Newsletter Schedule a free financial assessment Timestamps: 00:00 - Intro 02:35 - Rate Assumptions 05:58 - Retirement Spending 06:54 - Retirement Income Strategy 12:08 - Retirement Planning: Asset Allocation vs. Asset Location 15:50 - Sequence of Returns Risk 17:53 - Social Security Tax Torpedo 20:01 - Goals & Questions 22:50 - Other Strategies: Qualified Charitable Distributions 24:23 - IRMAA & Tax Optimization 26:37 - Likelihood of Success & DIY Tools

Are women better investors and financial planners? Today on Your Money, Your Wealth® podcast 483 with Joe Anderson, CFP® and Big Al Clopine, CPA, three different husbands want to retire, while their wives feel they need to work longer. Can Jack and Diane, Mark and Belle, and Mike and his wife hit the slopes now, or do they need to keep wearing their suits? Joe and Big Al spitball on who's right. Plus, should Ellie take her pension in a lump sum or in monthly annuity payments? The fellas also consider a solo 401(k) strategy for self-employed types from our buddy Will. Free financial resources and transcript: https://bit.ly/ymyw-483 Withdrawal Trap Doors: How to Avoid Them - Watch YMYW TV Withdrawal Strategy Guide - free download Subscribe to YMYW on YouTube - comments are now open! Ask Joe & Big Al On Air for a Retirement Spitball Analysis Schedule a Free Financial Assessment Timestamps: 00:00 - Intro 00:40 - Can We Retire Now or Do We Need to Wait a Few Years? (Jack & Diane, Houston - voice) 09:35 - How to Bridge the Gap in Early Retirement? (Mark & Belle, VA) 19:44 - Help Me Convince My Wife to Retire This Summer! (Michael, MN) 26:28 - Should I Take the Pension Lump Sum or Monthly Annuity Payments? (Ellie, PA) 31:52 - How's My Solo 401(k) Contribution Strategy? (Will) 36:51 - The Derails

Will building a new home delay Janelle's early retirement? Can Mike and his wife retire early at ages 50 and 55, and how much should they convert to Roth? Maria and her partner keep their finances separate - can Maria cover her own expenses in early retirement? That's today on Your Money, Your Wealth® podcast 482 with Joe Anderson, CFP® and Big Al Clopine, CPA. Plus, the fellas explain the difference between FDIC insurance and SIPC insurance for Edward, who wonders if he should spread his assets between banks for protection. Fajita Willy needs a spitball on his MYGA retirement strategy, that is, multi-year guaranteed annuities. Nancy wants to know if mandatory seismic retrofit expenses are tax-deductible. And how should Lee manage Roth contributions and IRMAA now that his Social Security disability has finally been approved and he's received 5 years of back pay? Free financial resources and transcript: https://bit.ly/ymyw-482 Retirement Readiness Guide - free download EASIretirement.com - free retirement calculator Financial Planning at Every Age: Retirement Planning for Millennials, Gen-X, and Baby Boomers - YMYW TV Ask Joe & Big Al On Air for your Retirement Spitball Analysis Schedule a free financial assessment Timestamps: 00:00 - Intro 01:02 - Will Building a New Home Delay My Early Retirement? (Janelle, CO - voice) 07:35 - Should I Spread Assets Between Banks for FDIC Insurance? (Edward, IL) 13:16 - Multi-Year Guaranteed Annuity (MYGA) Retirement Spitball (Fajita Willy, TX) 21:09 - Is the Mandatory Seismic Retrofit Expense Tax-Deductible? (Nancy, Tarzana, CA) 22:47 - My SSDI Was Approved and I've Received 5 Years of Back Pay. How to Manage Roth IRA Contributions and Medicare IRMAA? (Lee, Jacksonville, FL) 28:33 - Can We Retire Early Next Year at Ages 55 and 50? How Much Should We Convert to Roth? (Mike, NY) 34:57 - My Partner and I Maintain Separate Finances. Can I Cover My Own Expenses in Early Retirement? (Maria, Chicago suburbs, IL) 42:06 - The Derails

Should 70-year-old Bob live off of capital gains and dividends from his mutual funds plus Social Security, or should he sell poor-performing mutual funds for living expenses and reinvest the cap gains and dividends? Which account should Neal's 76-year-old Mother use for living expenses? Should Neal and his wife fund their Roth 403(b) until retirement, or contribute to the regular 403(b) and then do Roth conversions after they retire? That's today on Your Money, Your Wealth® podcast 481 with Joe Anderson, CFP® and Big Al Clopine, CPA. Plus, the fellas spitball on whether IndyGuy can retire at 64 and Die With Zero, and Rod doesn't want a spitball, but he'd like a dart on the wall as to whether his retirement savings will last until age 88. Free financial resources and transcript: https://bit.ly/ymyw-481 Cruising Into Retirement Checklist & Guide - LIMITED TIME OFFER - download by Friday, May 17! How to Cruise Into Your Retirement - YMYW TV 10 Gruesome Estate Planning Mistakes to Avoid - register for the free webinar, May 22, 12pm PDT/3pm EDT Timestamps: 00:00 - Intro 00:48 - Living Expenses: Cap Gains, Dividends & Social Security or Poor Performers? (Bob, Jupiter, FL) 10:02 - From Which Account Should 76yo Mom Withdraw Living Expenses? (Neal, Dallas, TX) 18:11 - Dart on the Wall for Our Retirement to Age 88? (Rod) 26:08 - Can We Retire at 64 and Die With Zero? (IndyGuy) 35:50 - Save to Roth 403(b) or Traditional Until Roth Conversions at Retirement? (Neal, Dallas, TX) 42:54 - The Derails

Kyle and his fiancée are in their 30s, have done a great job saving, and are in a high tax bracket. Would it make more sense for them to contribute to their 401(k)s or Roth 401(k)s for retirement? Mick's wife Pam has both W-2 and sole proprietor income - where should she save for retirement? That's today on Your Money, Your Wealth® podcast 480 with Joe Anderson, CFP® and Big Al Clopine, CPA. Plus, the fellas spitball for Janet on where junk bonds belong in a portfolio, they untangle the pro-rata and aggregation rules concerning 401(k) to Roth conversions for Nancy, and they spitball on whether Cary and Mark should retire now or work for two more years when pensions will provide them an extra $50K a year. Free financial resources and transcript: https://bit.ly/ymyw-480 2024 Key Financial Data Guide - free download Timeless Wisdom from Warren Buffet and Charlie Munger, Berkshire Hathaway's Dynamic Duo - read the blog Understanding Stock Market Indexes - read the blog Free retirement calculator - EASIretirement.com Ask Joe & Big Al On Air for your Retirement Spitball Analysis Timestamps: 00:00 - Intro 00:57 - We're in Our 30s and in a High Tax Bracket. Where Should We Save for Retirement? (Kyle, WI) 07:34 - Junk Bonds Explained (Janet, the Bronx) 13:19 - Does Pro-Rata Rule Apply When Converting 401(k) to Roth 401(k)? (Nancy, SE Wisconsin) 20:37 - We Have $4M. Should We Retire Now or in Two Years When Pensions Provide an Extra $50K/Year? (Cary & Mark, Los Angeles) 27:50 - How to Save for Retirement with Sole Proprietor and W-2 Work? (Mick, Davis, CA) 36:47 - The Derails

Linda is retired and financially independent. Her advisor suggests she have a separately managed account specifically for tax loss harvesting. Today on Your Money, Your Wealth® podcast 479, Joe Anderson, CFP® and Big Al Clopine, CPA spitball on how to save as much tax as possible on retirement withdrawals. Plus, Brian wants to know if it ever makes sense to put IRA money into a brokerage account, rather than doing Roth conversions, so the fellas explain the benefits of tax gain harvesting. Also, why is Robert and Jane's financial advisor constantly trading in Jane's professionally managed account? Pete wants to know if flat-fee financial advisors are worth their fee, and Daniel needs financial guidance for his 34-year-old daughter. He's also considering a free assessment, but he doesn't really know what he's getting himself into, so Joe and Al explain. Free Financial Resources & Transcript: https://bit.ly/ymyw-479 What Happens to Your 401(k) & IRA at Retirement? - YMYW TV Retirement Readiness Guide - free download Free Financial Assessment - schedule now Ask Joe & Big Al On Air for your Retirement Spitball Analysis Timestamps: 00:00 - Intro 00:55 - Separately Managed Account for Tax Loss Harvesting To Optimize Retirement Withdrawals? (Linda, MD) 11:54 - Why is Our Advisor Constantly Trading in Our Professionally Managed Account? (Robert, GA) 18:00 - Are Flat-Fee Advisors Worth the Fee? (Pete, Knoxville, TN) 27:03 - Financial Planning for 34-Year-Old Daughter and Pure's Free Assessment (Daniel, Whittier) 35:17 - Does Moving from IRA to Brokerage instead of Roth Ever Make Sense for Tax Gain Harvesting? (Brian, Albany, NY) 42:12 - The Derails

So you won the lottery - congratulations! After you celebrate, should you rip off the band-aid and convert the entire lump sum payment to a Roth IRA? That's today on Your Money, Your Wealth® podcast 478 with Joe Anderson, CFP® and Big Al Clopine, CPA. Also, Bucky in WA is required to have the same asset allocation in his traditional and Roth 401(k). Joe and Big Al spitball on his options, along with the pros and cons of consolidating retirement accounts for Scott in NC, and they explain the spousal Roth IRA for Rock Rochester in Manistique, MI. Plus, should Scott in Jackson, MS sign up for the state public employees' retirement system or a traditional retirement plan? Can Driving Fast, Loving Life in TX speed away in her Porsche from RSU capital gains? And should she and her hubbs retire abroad? Finally, can Sean in Reno, NV buy a million dollar vacation home in 10 years, and can Jennifer in La Mirada, CA afford to retire after being forced out of a 21-year career? Access this week's free financial resources and the episode transcript in the podcast show notes, and Ask Joe & Big Al On Air for your Retirement Spitball Analysis, at https://bit.ly/ymyw-478 Timestamps: 00:00 - Intro 01:06 - Should We Convert $1.75M Lottery Winnings To Roth? 09:31 - Free Financial Assessment - schedule now 10:38 - Asset Allocation Must Be the Same in 401(k) and Roth 401(k). What to Do? (Bucky, Washington state) 18:08 - Pros and Cons of Consolidating Retirement Accounts (Scott, NC) 23:28 - Spousal Roth IRA Explained (Rock Rochester, Manistique, MI) 27:07 - Traditional Retirement or PERS State Retirement? (Scott, Jackson, MS) 31:00 - Avoiding RSU Concentrated Position and Capital Gains and Retiring Abroad (Driving Fast, Loving Life in TX) 38:43 - Restricted Stock Units (RSU) - read the blog Employee Stock Purchase Plans (ESPP) - read the blog 39:19 - Should We Buy a $1M Vacation Home in 10 Years? We'll Have $12M. (Sean, Reno, NV) 43:11 - Can I Afford to Retire After Being Forced Out of a 21-Year Career? (Jennifer, La Mirada, CA) 49:24 - The Derails

Are there ever times when going all Roth isn't the best strategy? How do you determine the break-even point on doing Roth conversions? That's today on Your Money, Your Wealth® podcast number 477, as Joe Anderson, CFP® and Big Al Clopine, CPA spitball on marginal vs. effective tax rates for Joseph Allen, saving to after-tax brokerage or pre-tax 403(b) for Gigi in Illinois, the arithmetic of Roth conversions for Carl Spackler in Florida, and the mega backdoor Roth for Jefe in Texas. For something completely different, we'll wrap it up with a discussion of tax forms that need to be filed for your solo 401(k) depending on the account balance, for Smitty in The Villages. Access this week's free financial resources and the episode transcript in the podcast show notes, and Ask Joe & Big Al On Air for your Retirement Spitball Analysis, at https://bit.ly/ymyw-477 Timestamps: 00:44 - Marginal Vs. Effective Tax Rate: Going All Roth Isn't the Best Strategy? (Joseph Allen, Wichita, KS) 14:32 - Free retirement calculator EASIretirement.com 15:37 - I'm 43 and Will Have $2.4M in Retirement. Should I Save to After Tax Brokerage or Pre-Tax 403(b)? (Gigi, IL) 23:17 - Is There a Break-Even Calculation for Roth Conversions? (Carl Spackler, FL) 29:30 - Retirement Income Strategies Guide - free download How to Create a Steady Stream of Retirement Income - YMYW TV 30:38 - Mega Backdoor Roth: Must I Convert Traditional IRA When I Roll After-Tax Money? (Jefe, TX) 36:29 - Must I File Form 5500-EZ If Solo 401(k) Had No Balance at Year-End? (Smitty, The Villages) 42:18 - The Derails

What is private credit and where does it fit in your investment portfolio? At age 60, Hope is tired of working and she's hoping to retire in 2-3 years. Should she factor home equity into her retirement spending plan with a reverse mortgage? Which mortgage option for a Houston dream home is best for Nisa in San Jose's early retirement goals? That's today on Your Money, Your Wealth® podcast number 476 with Joe Anderson, CFP® and Big Al Clopine, CPA. Plus, Wayne in Phoenix needs to know how the section 121 tax exclusion works on a vacation home, and Jack and Jill in the UAE have questions about tax gain harvesting and the foreign earned income exclusion. Finally, are Joe and Big Al off their strategy game? A Spotify listener takes the fellas to task about the Affordable Care Act subsidy discussed in episode 472, and challenges their spitball for Duke and Daisy's retirement spending plan in episode 475. Access this week's free financial resources and the episode transcript in the podcast show notes, and Ask Joe & Big Al On Air for your Retirement Spitball Analysis, at https://bit.ly/ymyw-476 Timestamps: • 00:00 - Intro • 01:03 - What Is Private Credit? (Janine, La Jolla, CA) • 08:07 - Is a Reverse Mortgage Right for Me? (Hope) • 14:21 - Using Reverse Mortgages To Secure Retirement with Dr. Wade Pfau - YMYW Podcast 117 • How Your Home Can Create Retirement Income - YMYW TV • 14:59 - Which Mortgage Option is Best for Me in Early Retirement? (Nisa, San Jose, CA) • 24:04 - Section 121 Tax Exclusion on a Vacation Home? (Wayne, Phoenix, AZ) • 26:48 - What You Need to Know Before Filing Your Taxes in 2024 webinar • 2024 Tax Planning Guide • 27:39 - Foreign Earned Income Exclusion: Can I Harvest Long-Term Capital Gains? (Jack & Jill, UAE) • 37:06 - ACA Subsidy & Retirement Spitball: Are Joe and Big Al Off Their Strategy Game? (Spotify commenter) • 45:02 - The Derails

Will Duke and Daisy's retirement spending plan work? If you're a fan of hearing Joe Anderson, CFP® and Big Al Clopine, CPA debate, you're in luck today on Your Money, Your Wealth® podcast 475, as they disagree on assumptions when it comes to retirement planning. The EASIretirement.com calculator says Chuck in South Carolina could convert even more to Roth, and the fellas spitball on the pros and cons. Plus, what should Chuck's asset allocation be for his daughters, and how should Scott in Kansas City's parents allocate their assets? Can Rothaholic undo his Roth conversion? Brian Fantana and his wife are in their 30s and want to retire at 60. Are they on track? Ricky in Alabama wants to avoid Medicare's IRMAA, or income related monthly adjustment amount. Should he spend from his IRA or from his Roth? Daniel in Whittier wants to know what exactly counts for IRMAA income, anyway? And finally, Elisa in Fremont wants to know, with the new SECURE Act 2.0 rules, when can you transfer 529 college savings funds to Roth? Access this week's free financial resources and the episode transcript in the podcast show notes, and Ask Joe & Big Al On Air for your Retirement Spitball Analysis, at https://bit.ly/ymyw-475 Timestamps: 00:00 - Intro 01:07 - Will Our Withdrawal Rate Be Too High If We Retire in 3 Years? (Duke and Daisy, Charlotte, NC) 10:50 - Withdrawal Strategy Guide Retirement calculator 11:28 - EASIretirement.com Says I Should Convert More to Roth. Asset Allocation for Daughters? (Chuck, SC) 22:13 - Can I Undo My Roth Conversion? (Roth Aholic) 27:55 - In Our 30s, Want to Retire at 60. How Are We Doing? (Brian Fantana, WA) 30:36 - What's the Right Asset Allocation for Aging Parents? (Scott, Kansas City, MO) 32:00 - Free financial resources: Choosing a Financial Advisor blog Small Business Tax Filing Guide 2024 Tax Planning Webinar Retirement Lifestyles Guide 32:51 - IRA vs. Roth for Living Expenses? (Ricky, Birmingham, AL) 35:50 - What Counts for Medicare IRMAA? (Daniel, Whittier, CA) 39:49 - SECURE Act 2.0: When Can We Transfer 529 College Savings to Roth? (Elisa, Fremont) 44:44 - The Derails

Jimmy in Wisconsin will have a pension, Social Security, and a seven year retirement shortfall. How should he cover it? Skipper in Texas has some unusual pension options, which makes the most sense for his retirement needs? That's today on Your Money, Your Wealth® podcast 474 with Joe Anderson, CFP® and Big Al Clopine, CPA. Should Mike and Carol in Virginia wait to do Roth conversions if they'll be in a lower tax bracket in retirement? Where should Duncan in Texas invest in the 10 years before he retires early? Would it be stupid for Jay Z in Minnesota to miss out on free Roth opportunities? Can Ben in San Francisco's "friend" use the rule of 55 on a rollover retirement plan? And finally, YMYW is fun, but of limited value, according to a recent review. Access this week's free financial resources and the episode transcript in the podcast show notes, and Ask Joe & Big Al On Air for your Retirement Spitball Analysis, at https://bit.ly/ymyw-474 Timestamps: 00:51 - Pension & Social Security: How Should We Cover Our 7 Year Retirement Shortfall? (Jimmy, WI) 08:17 - 2:1 Matched Company Money vs. My Contribution: What to Do With My Pension? (Skipper, TX) 15:46 - EASIretirement.com free retirement calculator 16:47 - Should We Wait on Conversions If We'll Be in a Lower Bracket in Retirement? (Mike & Carol, Falls Church, VA) 24:22 - Where Should I Invest My Early Retirement Savings for the Next 10 Years? (Duncan, TX) 30:18 - Is It Stupid to Miss Free Roth Opportunities? (Jay Z, MN) 37:46 - Complete Roth Papers Package - free download 38:33 - Rule of 55 on a Rollover Retirement Plan? (Ben, San Francisco) 44:34 - Comment: Fun but limited value (Wemby2024) 50:41 - The Derails

Why would a financial advisor suggest that Frank in Lake Wobegon sell a piece of inherited property, pay 25% tax, and invest the lump sum? Mark in Florida is 72 and invested in CDs. Should he go back to his financial advisor, or just buy more CDs? That's today on Your Money, Your Wealth® podcast 473 with Joe Anderson, CFP® and Big Al Clopine, CPA. Plus, Adam in Tennessee will have deferred income in 5 years. Should his asset allocation be more conservative? And in order to retire early at age 55, should Lewis in Arkansas delay starting Roth conversions? But first, if Mike's wife outlives him, how can he keep her in a similar tax bracket? Access this week's free financial resources and the episode transcript in the podcast show notes, and Ask Joe & Big Al On Air for your Retirement Spitball Analysis, at https://bit.ly/ymyw-473 Timestamps: 00:00 - Intro 00:48 - If My Wife Outlives Me, How Do We Keep Her in a Similar Tax Bracket? (Mike) 06:49 - Long Term Capital Gains: Retirement and Real Estate Spitball (Frank, Lake Wobegon) 15:58 - 10 Tax-Cutting Moves to Make Now - YMYW TV Top 10 Tax Tips - free download (for a limited time only!) 2024 Tax Planning webinar 17:04 - I'm 72. Should I Go Back to an Advisor or Just Buy More CDs? (Mark, FL) 21:32 - Should My Deferred Income Asset Allocation Be More Conservative? (Adam, Franklin, TN) 30:16 - Investing Basics Guide - free download 31:13 - Should We Delay Starting Roth Conversions to Retire Early by Age 55? (Lewis, AR) 41:11 - The Derails

Rob and his wife in North Carolina are 51 and 44 and would like to retire in the next 3-5 years. Are they on track, and what should they consider as far as Roth conversions are concerned once the tax brackets go back up, which they're slated to do when that provision in the Tax Cuts and Jobs Act sunsets at the end of 2025? Is Mark in West Virginia on track to retire at 59 and a half, and do Joe and Big Al have any pointers on how he can find the love of his life? Mike and Gina in Rhode Island are optimistic about retiring early at 61 and 58, but is their optimism delusional? Jake in rural Michigan is self employed. Can he do Roth conversions to retire at age 60 and hang with Big Al in Hawaii? Retirement readiness and Roth conversions, today on Your Money, Your Wealth® podcast 472 with Joe Anderson, CFP® and Big Al Clopine, CPA. But first, the fellas spitball on a retirement and real estate strategy for (50 Shades of) Grey and Elena in Massachusetts. Access this week's free financial resources and the episode transcript in the podcast show notes, and Ask Joe & Big Al On Air for your Retirement Spitball Analysis, at https://bit.ly/ymyw-472 Timestamps: 01:04 - Real Estate Puts Us in High Bracket. Max Retirement & Roth, Save to Brokerage? (Grey & Elena, MA) 11:57 - Social Security Basics You Need to Know: Common Questions Answered - YMYW TV Social Security Handbook - free download 12:48 - Roth Conversions After 2025? Are We on Track for Our Retirement Goals in 3-5 Years? (Rob, NC) 19:34 - On Track for Retirement at 59.5? How to Find the Love of My Life? (Mark, West Virginia) 24:24 - Is Our Early Retirement Optimism Delusional? (Mike, RI) 31:16 - EASIretirement.com - free retirement calculator 32:19 - Self-Employed: Roth Conversions to Retire Early and Hang with Big Al in Hawaii at 60? (Jake, rural Michigan) 45:19 - The Derails

Big Tex, Paul in Maryland, and Nick in Alabama all need to know how much money they should convert to Roth to pay as little tax as possible, today on Your Money, Your Wealth® podcast 471 with Joe Anderson, CFP® and Big Al Clopine, CPA. Johnny and June forgot to convert their backdoor Roth money - are they in trouble? Darren in Nevada has no plans at all to do Roth conversions, but surprisingly still listens to YMYW, and still wants a spitball on his retirement and real estate investment strategies. Plus, can Lolly Pop in New Jersey be less miserly and back off on saving for retirement? Can John in South Carolina use this year's lower income to reduce his Medicare premiums? And finally, if Ordinary Guy in Boston meets an untimely demise, should that change his plans to retire early? Access this week's free financial resources and the episode transcript in the podcast show notes, and Ask Joe & Big Al On Air for your Retirement Spitball Analysis, at https://bit.ly/ymyw-471 Timestamps: 00:00 - Intro 00:58 - Can I Use This Year's Lower Income to Reduce My Medicare Premiums? (John, South Carolina - voice) 04:39 - Forgot to Convert our Backdoor Roths. Are We in Trouble? (Johnny and June, Oakland, CA - voice) 07:47 - Is Retiring This Year Doable? Should We Convert to Roth? $1.8M Saved, Spend $140K/Year (Big Tex - voice) 13:55 - DIY Retirement Guide - limited time offer - download by Friday, March 8, 2024! 15:05 - Should I Convert My Entire SEP-IRA If I'm Staying in the Highest Tax Bracket? (Paul, Baltimore, MD) 20:51 - $11M+ at Age 46. How Much Roth Conversion and When to Retire? (Nick, AL) 24:42 - Can I Back Off on Retirement Saving So I Can Be Less Miserly? (Lolly Pop, NJ) 30:43 - Financial Markets Master Class webinar - watch on demand 31:24 - Spitball on My Retirement and Real Estate Investment Strategies (Darren, NV) 38:28 - Should My Untimely Demise Change Our Early Retirement Plans? (Ordinary Guy, Boston, MA) 48:10 - The Derails

Barney and Betty in Maryland hit the jackpot. How's Barney's strategy for net unrealized appreciation, retirement withdrawals, and asset location for his $5 million employee stock ownership plan? Nick in the PNW will have $8 million when he retires early at 53. Should he contribute to his 401(k) or do the good ol' mega backdoor Roth until then? Those are just a couple of the fat wallets Joe Anderson, CFP® and Big Al Clopine, CPA spitball on, today on Your Money, Your Wealth® podcast number 470. Plus, should Allen in New Braunfels' recently widowed sister contribute to her traditional IRA and do some Roth conversions? Should Alicia in Denver take Social Security early to pay off her rental property, and how can Vern in Wickenburg Arizona buy a new home before or during the sale of his current home? Finally, Bryan in Washington needs to know the best investment strategy for his thrift savings plan, and Lyse in Georgia wonders when in a market downturn you should start spending your cash. Access this week's free financial resources and the episode transcript in the podcast show notes, and Ask Joe & Big Al On Air for your Retirement Spitball Analysis, at https://bit.ly/ymyw-470 Timestamps: 01:06 - Retirement Spitball Analysis for My Widowed Sister (Allen, sunny New Braunfels, TX) 06:52 - $5M ESOP Strategy: Net Unrealized Appreciation, Retirement Withdrawals, and Tax Location (Barney & Betty, MD) 18:07 Why Asset Location Matters - free download Are You Ready to Retire? Review Your Retirement Readiness - YMYW TV 19:00 - Should I Take Social Security Early to Pay Off My Rental Property? (Alicia, Denver, CO) 23:22 - How to Buy a Home Before or During the Sale of My Existing Home? (Vern, Wickenburg, AZ) 26:50 - Should I Buy a Qualified Longevity Annuity Contract as a Long Term Care Insurance Alternative? (Ron, IL) 31:08 - I'll Have $8M When I Retire at 53. Should I Contribute to 401(k) or Do the Mega Backdoor Roth Until Then? (Nick, PNW) 37:05 - EASIretirement.com - free retirement calculator 38:06 - What's the Best Thrift Savings Plan Investment Strategy? (Bryan, WA) 40:21 - When in a Market Downturn Should You Start Spending Cash? (Lyse, GA) 46:00 - The Derails

Erik in MN is divorced, and the OC Birdman of South OC is getting divorced. Should Erik contribute to pre-tax retirement accounts or Roth? How should the Birdman and his soon-be-ex time the sale of their house and the filing of their taxes? That's today on Your Money, Your Wealth® podcast 469 with Joe Anderson, CFP® and Big Al Clopine, CPA. Plus, Don has questions about the 401(k) rule of 55 and excess 529 plan college savings. Valerie in Portland wants to know what to do with her old 401(k), and how to invest her new retirement accounts. An advisor tells K-Dog in IN to save cash or open a Roth, then live on those funds and get free ACA "Obamacare" healthcare in early retirement. Is that really possible? Also, what should be Laura in WA's sequence of retirement withdrawals, and is there any benefit to her doing Roth conversions? Should RJ in CA convert his or his wife's rollover IRA to the top of the giant 24% tax bracket? Access this week's free financial resources and the episode transcript in the podcast show notes, and Ask Joe & Big Al On Air for your Retirement Spitball Analysis, at https://bit.ly/ymyw-469 Timestamps: 00:00 - Intro 01:06 - 401(k) Rule of 55 and Excess 529 Plan Funds (Don, Everywhere, USA) 06:03 - What to Do With Old 401(k) and How to Invest New Retirement Accounts? (Valerie, Portland, OR) 10:33 - 10 Steps to Improve Investing Success - free download Protecting Your Retirement Income - YMYW TV 11:39 - Is My Early Retirement Spending & Free Healthcare Plan Really Possible? (K-dog, Northern IN) 22:13 - Should I Contribute to Pre-Tax or Roth Post-Divorce? (Erik, Minneapolis) 28:27 - How to Sell House and File Taxes While Finalizing Divorce (OC Birdman in South OC) 32:27 - Q1 2024 Financial Markets Update Webinar, Feb 28, 2024, 12pm Pacific - register now 33:07 - What's the Sequence of Retirement Withdrawals? I Don't See the Benefit of Roth Conversions (Laura, Seattle - Olympic Peninsula) 40:42 - Roth Conversion to the Top of the Giant 24% Bracket? Which Rollover to Convert First? (RJ, Anaheim) 49:09 - The Derails

Are there general guidelines on what percentages of your investment portfolio should be in tax-free accounts like your Roth, tax-deferred accounts like your 401(k), and taxable accounts like your brokerage? Joe Anderson, CFP® and Big Al Clopine, CPA spitball on tax diversification today on Your Money, Your Wealth® podcast 468 for Brian in Naperville, IL. William in NH also wants to be tax-diversified. Is his Roth conversion strategy a mistake? Should he be converting much more to Roth? The fellas also do a retirement spitball analysis for Tom in Spokane, WA, and for Claire in CO, who wants to retire next year. Plus, how does Matthew in CT calculate excess Roth contributions, and how should Thomas in IA reallocate assets he over-contributed to his brokerage account? But first a couple of voice messages: Now that Sean in FL no longer has a traditional IRA, can he use the backdoor Roth strategy? We kick things off with a question from Joe in Dallas on how to account for taxes on the money you'll be spending in retirement. Access this week's free financial resources and the episode transcript in the podcast show notes, and Ask Joe & Big Al On Air for your Retirement Spitball Analysis, at https://bit.ly/ymyw-468 Timestamps: 01:06 - How to Account for Taxes on What I'll Spend in Retirement? (Joe, Dallas, TX (voice) 06:13 - Now That I Don't Have a Traditional IRA, Can I Do a Backdoor Roth? (Sean, FL - voice) 10:29 - 2024 Key Financial Data Guide - free download 11:35 - Spitball Our Financial Status and How to Reach Our Retirement Goals (Tom, Spokane, WA) 17:42 - Tax Diversification General Guidelines? (Brian, Naperville, IL) 23:23 - Goal: Tax Diversification. Is My Roth Conversion Strategy a Mistake? Should I Convert Much More? (William, NH) 29:12 - Retirement Pop Quiz and Free Financial Assessment 30:04 - Spitball If I Can Retire in 2025 (Claire, CO) 34:39 - How to Calculate Excess Roth Contributions? (Matthew, CT 38:23 - Over-contributed to Brokerage. How Should I Reallocate Assets? (Thomas, Iowa) 42:55 - The Derails

What does retirement at age 60 look like for Allison in Northern Virginia? The EASIretirement.com calculator says Jimmy and Rosalynn in Georgia are on track to reach their retirement goals, even though they're late starters - but are they being realistic? Ingrid used the free EASIretirement.com calculator too, but is she able to contribute more than her annual income to her 403(b) and her Roth? That's today on Your Money, Your Wealth® podcast number 467 with Joe Anderson, CFP® and Big Al Clopine, CPA. Plus, Perry and his wife in Winston-Salem also have 403(b) plans and they wonder if they should take the lifetime annuity or the managed payout in retirement? Finally, should Brad in Sarasota, Florida reserve his health savings account money for long term care insurance? Access this week's free financial resources and the episode transcript in the podcast show notes, and Ask Joe & Big Al On Air for your Retirement Spitball Analysis, at https://bit.ly/ymyw-467 Timestamps: 00:00 - Intro 00:48 - What Does Retirement at 60 Look Like for Me? (Allison from Northern Virginia) 09:19 - Retirement Rescue Plan - YMYW TV Retirement Rescue Guide - free download for a limited time only! Get it by this Friday 09:59 - Late Starters. EASIretirement.com Says We're OK. Are We Being Realistic About Retirement? (Jimmy & Rosalynn, GA) 16:07 - Earnings vs. Contributions When Using EASIretirement.com (Ingrid) 21:36 - EASIretirement.com - free retirement calculator 22:37 - Lifetime Annuities or Managed Payouts from Our 403(b)s in Retirement? (Perry, Winston-Salem, NC) 28:54 - Should I Reserve Health Savings Account (HSA) Money for Long Term Care? (Brad, Sarasota, FL) 34:11 - The Derails

Should Peter LemonJello, who has high income, and his wife, who is retired with zero income, file their taxes as married filing separately so they can start Roth conversions? What are the tax implications of Roth conversions for Randy in Chi-town, an early retiree in the 32% tax bracket? Caity with a C in SLC is self-employed and over the income max to contribute to a Roth, so now what? And Ben in Oceanside, CA wants to know what impact Roth conversions will have on required minimum distributions after age 73? Joe Anderson, CFP® and Big Al Clopine, CPA spitball on all these Roth conversion tax reduction strategies, today on Your Money, Your Wealth® podcast 466. Plus, does the math make sense on a company-matched Kai-Zen indexed universal life insurance policy for Kickass Seabass in New Jersey? Ed in Virginia wants to know the earnings limits for family Social Security benefits. But first, can JJ in Florida's retirement portfolio handle withdrawals of $150,000 per year? And from the banks of the Mighty Mississippi, what should midwestfabs' post-employment asset allocation be? Access this week's free financial resources and the episode transcript in the podcast show notes, and Ask Joe & Big Al On Air for your Retirement Spitball Analysis, at https://bit.ly/ymyw-466 Timestamps: 00:00 - Intro 01:12 - Can Our Retirement Portfolio Handle $150K Annual Withdrawals? (JJ, FL) 04:08 - What Should My Asset Allocation Be, Post-Employment? (Midwestfabs) 11:43 - 2024 Financial Market Outlook: read the blog by Brian Perry, CFP®, CFA, Pure Financial Advisors' Executive Vice President and Chief Investment Officer 12:39 - Tax Spitball: Married Filing Separate and Start Roth Conversions? (Peter LemonJello, FL) 14:58 - Roth Conversion Tax Implications for an Early Retiree in the 32% Bracket (Randy, Chicago) 21:34 - Self-Employed and Over the Max to Contribute to Roth – Now What? (Caity, Salt Lake City) 25:07 - Impact of Roth Conversions After Age 73 on RMDs (Ben, Oceanside, CA) 28:12 - Mile Markers to Retirement - YMYW TV Retirement Readiness Guide - free download 28:52 - Does the Math Make Sense on a Company-Matched Kai-Zen IUL Policy? (Kickass Seabass, NJ) 34:53 - Social Security Family Benefits Earnings Limits (Ed, VA) 42:42 - The Derails

How and what should we teach teenagers about money, to make the next generation financially literate? That's what CJ in Philadelphia and Teresa want to know, today on Your Money, Your Wealth® podcast 465 with Joe Anderson, CFP® and Big Al Clopine, CPA. Plus, Hap and Bee have a military pension and VA disability - Joe and Big Al spitball on when they'll be able to retire, and what they need to do to get there. And they spitball on whether Grace in Seattle is on track to retire early at age 55. David and Victoria in Grand Rapids, Michigan are killing the game - in their early 30s with $400,000 income and over a million saved. When should they start funding the traditional retirement accounts instead of the Roth accounts? And, find out how the first annual Anderson Household Financial Summit went! Access this week's free financial resources and the episode transcript in the podcast show notes, and Ask Joe & Big Al On Air for your Retirement Spitball Analysis, at https://bit.ly/ymyw-465 Timestamps: 00:00 - Intro 00:53 - Financial Guidance for Teenagers (CJ, Philadelphia - voice) 07:43 - How to Start a Finance 101 High School Course? (Teresa) 13:12 - EASIretirement.com - free retirement calculator 14:18 - Military Spitball: When Will I Be Able to Retire (Hap & Bee, CA) 22:56 - Anderson Family Financial Summit 26:03 - Spitball If I Can Retire Early at Age 55 (Grace, Seattle) 33:02 - 10 Will & Trust Mistakes to Avoid | Estate Planning - YMYW TV Estate Plan Organizer and Survivor's Guide - free download 33:51 - Killing it at 34, When to Consider Contributing to Traditional IRA? (David & Victoria, Grand Rapids, MI) 44:43 - The Derails

It's a voice message extravaganza as Joe and Big Al talk about tax gain harvesting on Dante in New York's daughter's custodial account, and the tax impacts of Leon in Chicago investing in his brokerage account. The fellas also spitball on whether Michelle in San Diego, en route to San Francisco, should buy or rent in her 60's, the mega backdoor Roth and the pro rata rule for Sean and his cichlids in Winter Springs, Florida, and whether Jason in NOLA can do the backdoor after recharacterizing his contribution. Plus, should Kevin in Ohio make like the Steve Miller Band and "take the (pension) money and run"? Can Scott in Colorado make like Johnny Paycheck and "take his job and shove it" when it's time for the rule of 55? And should Suzi and Peter consider long term care insurance and protecting their assets with an irrevocable trust? Access this week's free financial resources and the episode transcript in the podcast show notes at https://bit.ly/ymyw-464 Timestamps: 01:07 - Custodial Account Tax Gain Harvesting: Reported on My Daughter's Taxes or Mine? (Dante, NY - voice) 05:17 - Tax Impacts of Investing in a Brokerage Account? (Leon, Chicago - voice) 10:50 - Three (okay, four) ways you make YMYW the show that it is Ask Joe & Big Al On Air for your Retirement Spitball Analysis 12:28 - Is it Better to Buy or Rent in My 60s? (Michelle, San Diego - voice) 19:50 - Mega Backdoor Roth & the Pro-Rata Rule (Sean, Winter Springs, FL - voice) 26:56 - Should I Take the (Pension) Money and Run? (Kevin, OH - voice) 32:13 - Money Makeover Guide - limited time special offer - download by this Friday! Complete Money Makeover - How to Do a Financial Facelift - YMYW TV 33:08 - Should We Consider Long Term Care Insurance and Protecting Our Assets with an Irrevocable Trust? (Suzi & Peter, San Diego) 39:23 - Can I Do a Backdoor Roth After a Re-characterization? (Jason, NOLA) 43:42 - Spitball My Early Retirement Plan & the Rule of 55 (Scott, CO) 52:29 - The Derails

We're revisiting your favorite Your Money, Your Wealth topics and Derails of 2023 in this Roth and retirement investing mega-episode. Safe investing when you're risk averse, mutual funds vs. ETFs, stable value funds, and estimating retirement income needs when you're a young saver with a pension made the YMYW best of 2023 on the investing side. On the Roth side, what to do when there's too much money in your traditional IRA, whether Roth conversions are really as good as they sound, and who's right about the Roth conversion strategy, our listener or his advisor? Timestamps: 01:05 - How to Safely Invest and Protect $400K When You're Risk Averse (Tyler, OH – voice - from episode 425, among YMYW most popular 2023 episodes on YouTube) 07:43 - Stable Value Fund Vs. Brokerage Account for Living Expenses? (Sharon, Waukesha - voice - from episode 424, among YMYW most popular 2023 episodes on Apple Podcasts) 17:02 - Mutual Funds vs. ETFs in a Tax-Advantaged Account? (Midwestfabs, St Paul, MN from episode 420, among YMYW most popular 2023 episodes on Spotify) 23:40 - How Should Young Savers Invest Pensions and Estimate Retirement Income Needs? (Adam, Oregon - from episode 413, among YMYW most popular 2023 episodes on Spotify) 29:43 - I'm Not Sure Roth Conversions Are as Good as They Sound! (Christine, Seattle - from episode 440, among YMYW most popular 2023 episodes on Apple Podcasts) 39:31 - Who's Right About My Roth Conversion Strategy, Me or My Financial Advisor? (Brad, Sarasota, FL - from episode 409, published at the end of 2022, but one of our 2023 top viewed on YouTube) 49:17 - We Have Too Much in Traditional IRA. How's Our Roth Conversion Plan? (Kelly, Idaho - from episode 423, among YMYW most popular 2023 episodes on YouTube) 01:00:59 - The Best YMYW Derails of 2023 Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-463 Emotional Investing - YMYW TV Emotionless Investing Guide - our special offer for a limited time, download it by this Friday! Ultimate Guide to Roth IRAs - free download Episode Transcript & YMYW Best-Of 2023 Lists! Ask Joe & Big Al On Air for your Retirement Spitball Analysis

Can Clark Kent's dad in Hutchinson, Kansas retire at age 50? Will Devin in South Carolina be fat and happy or cutting calories if he retires at 59 and a half? Can Scott Magic in Idaho retire to a good and simple life at age 60? Gina and her wife are 52 and 58. Can they retire in four years, and how much should they be putting in their Roth accounts? Plus, Frenchie in Maine needs a spitball on a Roth conversion strategy with Canadian retirement funds, and Andi shares what she knows about target date funds. Timestamps: 00:49 - Can Superman's Dad Retire at Age 50? (Martha Kent, Hutchinson, KS) 07:23 - Can We Retire to a Good Simple Life at Age 60? (Scott Magic, ID) 14:12 - Fat & Happy in Retirement or Cutting Calories at Age 59 and a Half? (Devin, SC) 20:56 - We're 52 and 58. Can We Retire in 4 Years? How Much Should We Put in Roth? (Gina, WA) 28:06 - Canadian Retirement Roth Conversion Strategy? Target Date Funds? (Frenchie, Maine) 37:06 - The Derails Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-462 EASIretirement.com free retirement calculator Episode Transcript Ask Joe & Big Al On Air for your Retirement Spitball Analysis

Spitballing on early retirement and Roth conversions to finish 2023. How can Jack and Diane (no, the other, other Jack and Diane, these are the ones in Rochester, MN) bridge the gap to retirement at age 61? Can Michael in San Diego do a Roth conversion without it impacting his taxes? Plus, what should "the Flintstones" do with their whole life insurance policies? What spitballs of wisdom do the fellas have for Michael, who is "benefit-less" in Kansas City, MO? Then, we wrap up the final episode of the year with the YMYW origin story. Timestamps: 00:48 - How to Bridge the Gap to Retirement at Age 61? (Jack & Diane, Rochester, MN) 06:04 - Can I Convert to Roth Without Impacting My Taxes? (Michael, San Diego) 10:22 - What to Do with Whole Life Insurance Policies? (Wilma & Fred Flintstone) 16:55 - Financial Strategies for the "Benefitless" (Michael, Kansas City, MO) 23:46 - The Origins of YMYW 36:14 - The Derails Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-461 The Complete Roth Papers Package Financial New Year's Resolutions: Tips for Getting Your Finances in Order The Economy, Currencies, Stocks, and 2024: End of Year Market Update webinar Episode Transcript Ask Joe & Big Al On Air for your Retirement Spitball Analysis

Joe and Big Al spitball on investing in index funds, bonds, CDs, treasuries, annuities, net unrealized appreciation on company stock, and where to park cash right now. Plus, how do taxes, Roth conversions or the Mega Backdoor Roth, and donor advised funds factor into those investing strategies? Will and Debbie in Gettysburg are investing an inheritance, LJ in Philly and Jane want the fellas' take on the pros and cons of various safe investments, Roger and Jessica in Cowtown Ft. Worth need four different financial spitballs, and should M.E. in Atlanta do a Roth conversion and put money in a donor-advised fund in the same year? But first, Dianna in Spotsylvania needs an investing plan for her 86-year-old Mom. Timestamps: 00:57 - Investment Spitball for 86yo Mom: Index Funds? Roth IRA and Conversions? (Dianna from Spotsylvania, Virginia) 05:57 - How Should I Invest My Inheritance? (Will and Debbie, Gettysburg, PA) 14:12 - How's My Laddered CD Investing Strategy? (LJ, Philly) 17:07 - Tax on Treasuries vs. CDs vs. Annuity: Where to Park Cash Right Now? (Jane) 22:27 - NUA Company Stock, De-Risking With Bonds, & Mega Backdoor Roth (Roger & Jessica, Ft. Worth) 34:13 - Donor Advised Fund and Roth Conversion in the Same Year? (M.E., Atlanta) 40:54 - The Derails Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-460 Top 10 Tax Tips Guide (limited time offer - download by this Friday!) 10 Tax-Cutting Moves to Make Now - YMYW TV Investing Basics Guide 10 Steps to Improve Investing Success Episode Transcript Ask Joe & Big Al On Air for your Retirement Spitball Analysis

Do financial advisors have some secret blood handshake that they'll all claim they can get you 8 percent returns, but then tell their clients they can only withdraw 4 percent in retirement? That's Mark in Minnesota's question today on YMYW. Plus, should Matthew in Seattle quit the DIY approach to his finances and hire a fee-based financial planner? What do Joe and Big Al think about Steven in Connecticut's "opposite of sequence of returns risk" strategy for retirement withdrawals and "bonuses"? Can listener Joe have an active and comfortable retirement at age 62? Elle in Los Angeles needs some spitballing on contributing to traditional or Roth 401k, student loans, and the potential tax benefits for paying mother in law for babysitting. The fellas also answer some more last-minute year-end tax questions for George, and for Chuck in Idaho. But first, Mike in CO gets priority with his voice message about tax loss harvesting. Timestamps: 01:08 - Any Reason Not to Do Tax Loss Harvesting? (Mike, Steamboat Springs, Colorado - voice) 05:46 - Should I Switch from DIY to a Fee-Based Financial Planner? (Matthew, Seattle, WA) 16:00 - If Advisor Touts 8% Returns, Why Can I Only Withdraw 4%? (Mark, MN) 24:49 - 3% Retirement Withdrawals + Bonuses = Opposite of Sequence of Returns Risk? (Steven, CT) 31:05 - Can I Have an Active and Comfortable Retirement at Age 62? (Joe) 36:35 - 401k Vs Roth 401k Contributions, Student Loans, and Babysitting Tax Benefit (Elle, Los Angeles) 41:16 - When to Pay Taxes on a 2023 Roth Conversion? (George) 43:26 - Cost Basis: First In First Out to Minimize Taxes? (Chuck, ID) 47:27 - The Derails Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-459 EASI Retirement Spitball Analysis: YMYW TV EASIretirement.com Free Retirement Calculator 6 Secrets to Bigger Tax Savings from Your Nonprofit Donations: YMYW TV Tax-Smart Charitable Giving Guide Episode Transcript Ask Joe & Big Al On Air for your Retirement Spitball Analysis

Should Brian in Binghamton, New York pay off his mortgage for a guaranteed 6% return? How bad did Steve in Pittsburgh screw up his retirement, and can he afford to buy a new house away from his a-hole neighbors? Can Susan and her husband in Cape Canaveral Florida retire in a year and a half and should they pay off their mortgage? And how can Edith and Archie in Kansas maximize Roth Conversions and factor paying off the mortgage into their retirement spending strategy? Plus, Steve and Marcia in Indiana and Florida wonder about their retirement spending and whether they should collect Social Security now or wait until age 70, and should Sunny D in Arizona keep potential withdrawals in cash or sell investments as needed to satisfy required minimum distributions (RMDs)? We kick things off with Shelly's voicemail about investing the proceeds from the sale of a business. Timestamps: 00:58 - How to Invest $1M From the Sale of a Business? (Shelly - voice) 06:55 - RMDs: Keep Potential Withdrawals in Cash or Sell Investments as Needed? (Sunny D, AZ) 10:00 - Pay Off Mortgage for Guaranteed 6% Return? (Brian, Binghamton, NY) 15:52 - How Bad Did I Screw Up My Retirement? Can I Afford to Buy a New House? (Steve, Pittsburgh) 21:40 - Can We Retire in 1.5 Years? Should We Pay Off the Mortgage (Susan, Cape Canaveral, FL) 32:14 - How to Maximize Roth Conversions While Spending From Our Portfolio and Paying Off the Mortgage (Archie & Edith, KS) 39:39 - Retirement Spending and Collecting Social Security Now or Wait to Age 70? (Steve & Marcia, Indiana & Florida) 47:56 - The Derails Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-458 Withdrawal Strategies Guide Free Financial Assessment Episode Transcript Ask Joe & Big Al On Air for your Retirement Spitball Analysis

Last-minute tax questions answered: should Brad in Wahoo, NE save to his regular 401(k) instead of his Roth 401(k) so he can claim the American Opportunity Tax Credit? Should Jennifer and Zeke in NY set up a Roth IRA and file taxes for their 13-year-old that's got some earned income? Does Cindy in San Diego have to report her Medicare Advantage over-the-counter medication benefit on her taxes? And should our buddy Carl Spackler wait until the new year to deposit his rollover check? Plus, Em in FL needs ideas for moving her Mom from a low-cost-of-living area to a high-cost-of-living area, Wannabe Landlord wonders about creating an LLC for his real estate, and can CJ in FL and IN report pro-rated real estate expenses on schedule E? Finally, the 5-year rule on Roth withdrawals once again, this time for Brutus Buckeye, and Bruce from Joisey is back, this time he wants to pay cash for a car. Timestamps: 01:08 - American Opportunity Tax Credit and Other Tax Strategies (Brad, Wahoo, NE) 05:07 - Tax Filing for 13-Year-Old With Earned Income (Jennifer & Zeke, NY state) 09:47 - HSA: The Last Month Rule for Health Savings Accounts (JZ, New York) 13:01 - Income Tax and Sales Tax Explained (Cindy, San Diego - North County) 16:23 - Deposit Rollover Check After New Year to Avoid the Pro-Rata Rule? (Carl Spackler, FL) 21:12 - Strategies for Mom to Move from LCOL to HCOL Area (Em, FL) 26:28 - LLC For Real Estate Investment Properties? (Wannabe Landlord) 28:28 - How to Report Pro-Rated Real Estate Expenses on Taxes (CJ, Florida & Indiana) 32:22 - 5-Year Roth IRA Withdrawal Rule - Sigh (Brutus Buckeye, Columbus, OH) 37:41 - Should I Pay Cash for a Car? (Bruce, Joisey) 43:15 - The Derails Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-457 Reduce Your 2023 Taxes With These End-of-Year Tax Planning Strategies (free on-demand webinar) End-of-Year Tax Strategies Guide DIY Retirement Guide (LIMITED TIME OFFER! Download by Friday, Dec. 1, 2023!) Episode Transcript Ask Joe & Big Al On Air for your Retirement Spitball Analysis

Planning to retire early? Joe and Big Al spitball on bridging the gap to your retirement income when there's a pension in the mix, today on Your Money, Your Wealth® podcast 456. Manley and his wife are in their early 50s and have teacher's pensions. Can they retire in 2 and a half, or even one and a half years? Can Bucky in the Midwest retire in 2024, and can Henry Karl Kittensburg III retire in about 3 years, with all the milk his heart desires? How should Paul in Houston choose his pension options for early retirement? Is Greg in Southern California's CalSTRS teacher's pension enough for his retirement? Keaton Money in Colorado needs the fellas to help him decide between his pension's fringe benefits and brokerage account returns, and big Paw in a mid-Atlantic state asks for a spitball on how to reduce taxes on an impending headcount reduction lump sum payout. Timestamps: 00:58 - Early 50s, Teacher's Pensions. Can We Retire Early in 1.5 or 2.5 Years? (Manley, Nashville) 08:17 - How to Choose Pension Options for Early Retirement (Paul, Houston, TX) 18:25 - Is CalSTRS Teacher's Pension Enough in Retirement? (Greg, Southern California) 22:02 - Am I In Good Shape to Retire in 2024? (Bucky from the Midwest) 23:32 - Pension Fringe Benefits vs. Brokerage Account Returns (Keaton Money, CO) 32:00 - Can We Retire at Age 59? (Henry Karl Kittensburg III, Western OH) 40:42 - How to Reduce Taxes On a Headcount Reduction Retirement Lump Sum Payout? (Big Paw, mid-Atlantic state) 50:50 - The Derails Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-456 Retirement Income Strategies Guide EASIretirement.com free retirement calculator Episode Transcript Ask Joe & Big Al On Air for your Retirement Spitball Analysis

Steve & Sharon in Minnesota are high earners - can they get more money into their Roth IRA without paying more tax? Should Fred in western New York do Roth conversions before required minimum distributions kick in? If Mike in Utah saves on healthcare premiums now, will that mean large RMDs and tax bills for him later? Should Mark in Maryland do a backdoor Roth after maxing out his 401(k)? And should Joseph in Kansas contribute to his new employer's traditional or Roth 401(k)? Timestamps: 00:49 - Should We Do Roth Conversions Before RMDs Kick In? (Fred, western NY) 10:22 - Will Saving on Healthcare Premiums Now Mean Large RMDs and Tax Bills Later? (Mike, UT) 19:36 - Where to Invest After Maxing Out 401(k)? Backdoor Roth? (Mark, MD) 28:04 - How to Get More into Roth Without Paying More Tax? (Steve & Sharon, Roseville, MN) 39:24 - Roth 401(k) or Traditional 401(k) With New Employer? (Joseph from Wichita, KS) 47:08 - The Derails Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-455 End-of-Year Tax Planning Webinar - live and free, tomorrow Nov 15, 2023, 12pm Pacific, 3pm Eastern - register now! How to Build a Recession-Proof Portfolio - YMYW TV Recession Protection Guide - free download Episode Transcript Ask Joe & Big Al On Air for your Retirement Spitball Analysis

Will Ron and Candy in Connecticut ever be able to retire, and are Bruce and Selina in Philly saving enough to retire? That's today on Your Money, Your Wealth® podcast 454 with Joe Anderson, CFP® and Big Al Clopine, CPA. Plus, are Pebbles and Bam Bam in Kentuckystone missing anything when it comes to using their brokerage account to pay Roth Conversion taxes? And Susan in San Diego is 55, spends about $36K a year, and has almost a million saved - can she retire yet? And finally, our buddy Will knows he shouldn't time the market, but…. Timestamps: 00:50 - Will We Ever Be Able to Retire? (Ron, CT) 09:54 - Are We Saving Enough to Retire? (Bruce and Selina, Philadelphia) 17:36 - What Am I Missing? Brokerage Account Spitball (Pebbles & Bam Bam, Kentuckystone) 27:05 - Nearly $1M at 55, Spending $36k/Year: Can I Retire Early? (Susan, San Diego) 31:36 - I Know We Shouldn't Time the Market, But… (Will) 40:46 - The Derails Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-454 How to Cruise Into Your Retirement - YMYW TV Cruising Into Retirement Checklist - download by this Friday! EASIretirement.com free retirement calculator Episode Transcript Ask Joe & Big Al On Air for your Retirement Spitball Analysis

Can Jessie and Becky in Iowa retire now at age 52? Should Robert and his wife file their taxes separately, to pay less tax on their required minimum distributions? Can Joe and Al validate Mike in Minnesota's retirement plan, and does a backdoor Roth make sense for him? How in the world will Mike in New York be able to retire at a reasonable age? And what will retirement income look like for Marty in San Diego? Just spitballs here, no retirement advice! Timestamps: 00:49 - Can We Retire Now at Age 52? (Jessie and Becky, IA) 10:09 - Should We File Taxes Separately to Minimize Taxes on RMDs? (Robert) 19:56 - Validate Our Retirement Plan: Does a Backdoor Roth Make Sense? (Mike, MN) 25:11 - How in the World Am I Going to Retire at a Reasonable Age? (Mike, Utica, NY) 29:19 - What Will Our Retirement Income Look Like? (Marty, San Diego) 35:06 - The Derails Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-453 Retirement Readiness Guide - free download Retirement Pop Quiz - how well do you know retirement? EASIRetirement.com - free retirement calculator Episode Transcript Ask Joe & Big Al On Air for your Retirement Spitball Analysis

Why does Becca in Florida's advisor "poo-poo" her strategy for funding 529 plans for education? Keith, commenting on Spotify, wants to know about reimbursing yourself from a 529 plan for the scholarship amount used for education without penalty, and Wendy way up in New York wants to know if she should use retirement funds to pay for college and home renovations. Plus, what are the pros and cons of starting Roth conversions for Renee in Wisconsin, and is she on track for retirement? Will the IRS penalize Dan in Michigan for not paying Roth conversion tax in January? With the 5-year Roth clock, how does compounding interest work when Aaron in Ohio changes custodians? And Kirk in Iowa wonders how the Affordable Care Act tax credit works with dependents. Timestamps: 00:55 - Why Doesn't My Financial Advisor Want Me to Fund 529 Plans? (Becca, FL) 08:19 - Is 529 Plan Self-Reimbursement for Scholarships Okay? (Keith) 10:22 - Should We Use Retirement Funds to Pay for College and Home Renovations? (Wendy, way up in north NY) 18:11 - Pros and Cons of Starting Roth Conversions: Are We On Track for Retirement? (Renee, WI) 28:58 - Is the IRS Going to Penalize Me For Not Paying Roth Conversion Tax in January? (Dan, Milford, MI) 30:38 - Roth 5-Year Clock: Compounding Interest on Rolled Over Retirement Accounts (Aaron, OH) 32:19 - How Does the Affordable Care Act Tax Credit Work with Dependents? (Kirk, IA) 37:11 - The Derails Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-452 ABCs of College Funding - free download Money Saving Tips fro Funding College - YMYW TV How to Save for Education; 529 Plan, Coverdell, Prepaid Tuition and More - on-demand webinar Episode Transcript Ask Joe & Big Al On Air for your Retirement Spitball Analysis

Should Jim in New Jersey do the YMYW-infamous Megatron (the Mega Backdoor Roth IRA) or use his Roth 401(k) - and how can he keep bonds out of his Roth accounts? Joe and Big Al discuss the January first start date when it comes to the 5-year rule on Roth conversions for Nancy in Wisconsin, and they spitball on those Roth clocks for withdrawals and tax-efficient investments for Johnny Mercer in Savannah, GA, who also wants to know the pros and cons of bonds vs. bond funds vs. CDs. Plus, should Brad in St. Louis incorporate bonds into his investment portfolio, given the fact that he will have pensions and Social Security providing 5 streams of fixed income in retirement? Timestamps: 00:58 - The Megatron: Mega Backdoor Roth IRA vs. Roth 401(k) (Jim, NJ) 14:42 - 5-Year Rule on Roth Conversions: How Does January First Default Start Date Apply? (Nancy, WI) 19:43 - 5-Year Rule on Roth Conversions vs. Tax-Efficient Investments, Bond Funds Vs. Bonds Vs. CDs (Johnny Mercer, Savannah, GA) 32:42 - What's the Best Strategy for Incorporating Bonds into Our Retirement Portfolio? (Brad, St. Louis) 40:09 - The Derails Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-451 Complete Roth Papers Package - includes the Roth Basics Guide, the 5-Year Rules for Roth IRA Withdrawals, and the Ultimate Guide to Roth IRAs 10 Steps to Improve Investing Success Investing Basics Guide Episode Transcript Ask Joe & Big Al On Air for your Retirement Spitball Analysis

How much can you safely spend in retirement? Is the four percent rule outdated? Joe and Big Al spitball on a safe retirement distribution rate for those in the 55-60 age range for Clay in Ohio. They also spitball on withdrawal rates when there's a pension in the mix for Jonny and June in the Bay Area of California, and for William in Maryland, who is concerned he might be exposing himself to sequence of returns risk by spending too much in early retirement. Plus, when does Dan have to take required minimum distributions from the IRA he inherited from his Dad in 2021? Finally, Wayne in San Diego wants to know how to protect his bank accounts from FedNow, the Federal Reserve's new peer-to-peer payment system. Timestamps: 00:53 - What's a Safe Retirement Distribution Rate? (Clay, OH) 07:57 - Can We Retire at Ages 50 and 48? (Johnny & June, East Bay, CA) 19:01 - Spitball My Retirement Withdrawal Rate (William, MD) 24:50 - When Am I Required to Take Money From My Inherited IRA? (Dan) 28:54 - How to Protect Money From FedNow? (Wayne, San Diego) 32:37 - The Derails Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-450 Withdrawal Strategy Guide - free download Withdrawal Trap Doors: How to Avoid Them! YMYW TV Episode Transcript Ask Joe & Big Al On Air for your Retirement Spitball Analysis

What should Martin do about his outrageously fee-heavy 403(b) plan? Should EF hedge his pre-tax non-qualified 415 excess plan? What should Max do with his old TIAA plan, and what are the pros and cons of a cash balance defined benefit plan for self-employed people like Brent Money? Plus, Mike needs Joe and Big Al's spitball on the highly compensated employee rule and excess 401(k) contributions, and the fellas explain how employee stock purchase plans are taxed for Big Cheese Bob the Tomato. Timestamps: 00:55 - What to Do About My Outrageous Fee-Heavy 403(b)? (Martin, Miami, FL) 05:56 - Should I Hedge My Pre-Tax Non-Qualified 415 Excess Plan? (EF, Kansas) 14:25 - What to Do With My Old TIAA Retirement Plan? (Max, Seattle) 24:29 - Highly Compensated Employee Rule and Excess 401(k) Contributions (Mike, Castleton, NY) 29:16 - How Are Employee Stock Purchase Plans (ESPP) Taxed? (Big Cheese/Bob the Tomato) 32:26 - Cash Balance Plans Pros and Cons for Self-Employed (Brent Money, Bennington, NE) 40:52 - The Derails Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-449 Investing Basics Guide - free download Financial Boot Camp: Investing Basics - new from YMYW TV Episode Transcript Ask Joe & Big Al On Air for your Retirement Spitball Analysis

Coach Dobber and his wife in Edina, Minnesota have a low mortgage interest rate and a decent amount of home equity. Should they put that equity to work and take the risk on buying a higher value home at a reduced price, even if it means a much higher interest rate and higher monthly payments too? Plus, Joe and Big Al spitball for Adam, in the birthplace of aviation, on the taxation of passive rental income, and capital gains from his portfolio and the sale of his business, prior to his early retirement. They also spitball for Charles in Idaho, on taxes on the sale of his mother-in-law's house. And should Dan's wife and business co-owner retire from the business and take Social Security Disability? And will Social Security be reduced for everyone? Steve in Vegas has a cautionary tale to tell. Timestamps: 00:55 - Stay With a Low Mortgage Rate, or Buy Up at a Reduced Price? (Coach Dobber, Edina, MN) 16:10 - Early Retirement Taxes on Rental Income and Capital Gains? (Adam, Dayton, OH) 24:55 - How to Figure Taxes on Sale of Mom's House (Charles, ID) 29:47 - Should Spouse and Business Co-Owner with Alzheimer's Retire and Take Social Security Disability? (Dan, Midwest USA) 36:04 - Will Social Security Be Reduced for Everyone? A Cautionary Tale (Steve, Las Vegas) 44:17 - The Derails Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-448 2023 Key Financial Data Guide EASIRetirement.com - new free retirement calculator! Social Security Handbook Episode Transcript Ask Joe & Big Al On Air for your Retirement Spitball Analysis

Can Sven and Olga in Minnesota shorten their working years? Should PJ in Michigan take his pension lump sum or the annuity payments, and should he maintain an aggressive asset allocation in retirement? Plus, the fellas spitball early retirement strategies for Joe in Massachusetts and Nick in California, and they discuss how to tell the difference between post-tax contributions and pre-tax funds converted to Roth at tax time for Victor. Timestamps: 00:45 - Can We Shorten Our Working Years? (Sven & Olga, MN) 07:50 - Pension Lump Sum or Annuity? Aggressive Asset Allocation in Retirement? (PJ, Michigan) 23:31 - Can We Retire at Ages 55 and 52? (Joe, MA) 29:54 - Help Me Spitball Some Retirement Goals (Nick, CA) 35:07 - Post-Tax Contributions and Pre-Tax Funds Converted: How to Tell the Difference? (Victor) 39:40 - The Derails Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-447 Retirement Income Strategies Guide Register for the Investing 101 webinar, Wednesday, Sept 27, 12pm PT Episode Transcript Ask Joe & Big Al On Air for your Retirement Spitball Analysis

Should Jackson and Elsa from Wyoming fire their financial advisors and shop for lower fees, or switch to do-it-yourself financial planning? Can 34-year-old Bob in Texas retire early at 50, and what's the best way for him to put an extra $30K to work? How much should 35-year-old Matthew in the middle of nowhere Wisconsin be saving for retirement in pre-tax accounts vs. post-tax accounts? And finally, should Michelle in Minnesota leave excess education savings in a 529 plan or move it to a Roth IRA? Timestamps: 00:58 - Should We Fire Our Advisors and Go DIY or Shop for Lower Fees? (Jackson & Elsa, WY) 11:51 - Can We Retire at Age 50? Best Way to Put Extra $30K to Work? (Bob, TX) 19:51 - How Much Should We Save for Retirement Pre-Tax vs. Post-Tax? (Matthew, Middle of Nowhere, WI) 28:27 - Excess 529 Plan College Savings: Leave it or Move it to Roth? (Michelle, MN) 35:34 - The Derails Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-446 DIY Retirement Guide - limited time offer, download by Friday 9/15/23! EASIRetirement.com - free retirement calculator Episode Transcript Ask Joe & Big Al On Air for your Retirement Spitball Analysis

How will a diet COLA on a pension affect retirement plans for Joe and Barb in Tulsa? Percy in South Carolina has a pension too. He's timing the market, but should he change his investing strategy as he approaches retirement? Plus, Michael in Virginia needs ideas to fund a custodial Roth IRA for his 3-year-old and 2-month-old kids, and Rocco in NYC catches Big Al on capital gains exclusions. But first, will scary future events mean Michelle in San Diego will have to pay more tax and the highest possible Medicare premiums? Timestamps: 00:44 - Will Scary Future Events Mean Paying More Tax and Highest Medicare Premiums? (Michelle, San Diego) 10:46 - Market Timing, Pension & Roth Retirement Spitball (Percy, North Myrtle Beach, SC) 18:34 - FERS & Military Pension Diet COLA Retirement Spitball (Joe and Barb, Tulsa, OK) 26:49 - Can I Employ My 3-Year-Old and 2-Month-Old Kids to Fund a Custodial Roth IRA? (Michael, VA) 29:38 - Capital Gains Exclusion: Both Members of a Married Couple Need to Be on Title? (Rocco, NYC) 35:16 - COMMENT: Semi-Retired at 65 (Jetta Jay from Raleigh) 39:00 - The Derails Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-445 EASIRetirement.com - new free retirement calculator! Retirement Rescue Plan - Your Money, Your Wealth TV Retirement Rescue Guide - limited-time offer, download by Friday 9/8/23 Episode Transcript Ask Joe & Big Al On Air

Charles has had it with Joe and Big Al stumbling through the Roth 5-year rules, so he explains to Joe and Big Al, once and for all, the rules for withdrawing money from a Roth IRA. Plus, is Shane missing any retirement risks before he retires early at age 55? Nick wants to know if employers are required to adopt all of the provisions in the SECURE Act 2.0, or if they can pick and choose which to implement, like they can with the rule of 55? Plus, how can Stew offset huge capital gains on the sale of an inherited house, and we revisit whether George can move investments in-kind from an inherited trust to a brokerage account. Timestamps: 01:57 - Roth IRA 5-Year Rules for Withdrawals Explained (Charles) 10:39 - Any Retirement Risks I'm Missing Before I Retire at Age 55? (Shane, Chester County, PA) 16:42 - Do Employers Have to Adopt All of SECURE 2.0? (Nick, OH) 21:10 - How to Offset Huge Capital Gains Taxes on the Sale of an Inherited House? (Stew, Clairemont) 25:49 - Can I Move Investments In-Kind From Inherited Trust to Brokerage Account? (George, KS - from ep. 433) 34:02 - The Derails Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-444 EASIRetirement.com - new free retirement calculator! 5-Year Rules for Roth IRA Withdrawals Guide - free download SECURE Act 2.0 Guide - free download 6th Annual YMYW Podcast Survey - one randomly-chosen participant will win a $100 Amazon e-gift card! Episode Transcript Ask Joe & Big Al On Air for your Retirement Spitball Analysis

Harsh realities of life can very quickly change your retirement plans and your entire financial future. In this episode, Joe and Big Al spitball on dealing with these realities. What financial strategies can they suggest for William and his 33-year-old wife, who has metastatic breast cancer? Debbie and Emily each experienced the unexpected sudden passing of their partners. Is it possible to minimize the capital gains tax on Debbie's son's inheritance, and can Emily retire in a year? Josie has lousy longevity in her family and wants to plan for the worst case scenario of dying before her husband. Alfred is 81 and concerned that he's going to run out of money before he runs out of time, and Richard has a sobering story that changed his thoughts about when to collect Social Security. Finally, Irene is subject to the Government Pension Offset (GPO) - can she withdraw the money she paid into Social Security? Timestamps: 01:03 - Financial Strategies for the Young and Disabled (William, TX) 08:16 - How to Minimize Son's Capital Gains Tax on Inheritance (Debbie, HI) 14:37 - Can I Quit Work in a Year? Should I Do Roth Conversions? (Emily, Rochester, MN) 20:22 - Worst Case Scenario Retirement Spitball Analysis (Josie, Atlanta) 28:45 - Are We Going to Run Out of Money? How Much Can We Safely Withdraw? (Alfred Pennyworth) 32:35 - Life Lesson on When to Take Social Security (Richard) 40:15 - Can I Withdraw the $17,000 I Paid into Social Security? (Irene, Bremerton, WA) 46:00 - The Derails Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-443: Estate Planning Organizer - free download Social Security Handbook - free download 6th Annual YMYW Podcast Survey - one randomly-chosen participant will win a $100 Amazon e-gift card! Episode Transcript Ask Joe & Big Al On Air for your Retirement Spitball Analysis

What's the best strategy for E-Dog's restricted stock units with his employer, how are RSUs taxed, and how do Roth conversions fit into the mix? Plus, should Jay in Raleigh liquidate his annuities or follow "Stan the Annuity Man's" advice and take the annual payments? Elisa wants to know how a mutual fund portfolio would work in retirement, and what's a good way for listener Joe to invest in bonds in a taxable account to bring his portfolio back into proper balance? Finally, the fellas spitball on Medicare savings vs. Roth conversions for David, and an unrealized gain strategy on an UTMA education savings account for Jay in California. Timestamps: 00:50 - Restricted Stock Units: RSU Spitball Analysis (E-Dog, Boulder, CO) 14:44 - Annuity Retirement Spitball Analysis (Jay, Raleigh, NC) 26:36 - How Would a Mutual Fund Portfolio Work in Retirement? (Elisa) 31:13 - Asset Location: How to Invest in Bonds in a Taxable Account to Rebalance? (Joe) 35:09 - Medicare Savings Vs. Roth Conversions (David, Logan, NM) 40:04 - UTMA College Savings Unrealized Gain Strategy (Jay, CA) 47:05 - The Derails Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-442 Why Asset Location Matters - free guide 6th Annual YMYW Podcast Survey - one randomly-chosen participant will win a $100 Amazon e-gift card! Episode Transcript Ask Joe & Big Al On Air for your Retirement Spitball Analysis

Does the math work for Chris' early retirement plan? What's a safe retirement withdrawal rate for Luke, who wants to be part of the financial independence / retire early or FIRE movement - and what does Joe have against FIRE? Plus, Jake is about to change jobs, can Joe and Big Al uncover any tax planning opportunities for him? The fellas also explain capital gains tax for our buddy Carl Spackler, and they spitball on those capital gains when it comes to selling a house for Olga and for LJ, and Jim wonders about the impact of selling a house on Affordable Care Act subsidies. Timestamps: 00:54 - Early Retirement Spitball: Does the Math Work? (Chris, Philadelphia) 04:27 - FIRE Withdrawal Rate for Long-Term Capital Preservation? (Luke, Ft. Collins, CO) 14:26 - We're 38 and 33. Any Tax Planning Opportunities Before I Change Jobs? (Jake, VA) 20:48 - Capital Gains Tax Explained (Carl Spackler, FL) 23:55 - House Sale Tax Strategy (Olga, Chula Vista) 26:32 - Do I Need to Worry About Investment Property Sale Proceeds? (LJ, Philadelphia) 30:46 - How Will Selling a Home Impact ACA Subsidies? (Jim, Santa Cruz) 35:52 - New One Star and Five Star Reviews 38:10 - The Derails Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-441 Guide to Cracking the Financial Code at Any Age FIRE interviews on YMYW Spitballing Retirement Planning in Your 30s (YMYW podcast 391) 6th Annual YMYW Podcast Survey - one randomly-chosen participant will win a $100 Amazon e-gift card! Episode Transcript Ask Joe & Big Al On Air for your Retirement Spitball Analysis

Christine isn't sure that Roth conversions are all they're cracked up to be. Erick needs a retirement spitball analysis for his Roth conversions, annuities, and the real estate in his self-directed IRA, Billy the disgruntled attorney wants to know if he can retire now, and Zach wonders just how bad is it to rely on the lottery for retirement? But first, Joe and Big Al spitball military retirement strategies. Timestamps: 01:16 - I'm 22, Military. Should I Be Spending More Instead of Saving So Much? (Cole - voice) 06:19 - I'm 27. How Should I Max Out Military and Second Job Retirement Contributions? (Adam) 09:08 - Retiring With Pensions at Ages 59 & 63. Is Our Retirement Plan Sound? (Scott, AL) 16:55 - I'm Not Sure Roth Conversions Are as Good as They Sound! (Christine, Seattle) 26:44 - Roth Conversion, Annuities, Real Estate in Self-Directed IRA Strategy? (Erick, CA) 37:23 - Can a Disgruntled Attorney Quit and Retire Now? (Billy, Joplin, MO) 39:53 - Just How Bad an Idea Is Relying on the Lottery for Retirement? (Zach, Tuscaloosa, AL) 47:18 - The Derails Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-440: 6th Annual YMYW Podcast Survey - one randomly-chosen participant will win a $100 Amazon e-gift card! Financial benefits for military families 2023 Key Financial Data Guide Episode Transcript Ask Joe & Big Al On Air

Should Carl Spackler stick with his backdoor Roth strategy, or go for lower fees? Should Kevin go all Roth, or stick with his current three tax-diversified buckets strategy? (That depends - would he rather have $7 million tax-free, or $10 million in tax-deferred retirement accounts?) Can Lily claim all the extra allowances she can, to jam as much money as possible into her Roth? Can Dave retire now and ride his motorcycle into the Bavarian Alpine sunset, and does Peggy Lee need to be feverish about the tax underpayment penalty with her Roth strategy? Timestamps: 00:53 - Do I Need to Worry About a Tax Underpayment Penalty with My Roth Strategy? (Peggy Lee, North Dakota) 07:17 - What Am I Doing Wrong? Can I Retire Now? What About Taxes? (Dave, Germany) 15:28 - Back Door Roth vs. Lower Fees: Which Would You Choose? (Carl Spackler, FL) 21:40 - Should We Go All Roth or Three Tax-Diversified Buckets? (Kevin, NJ ) 28:53 - Can I Claim Extra Allowances to Contribute More to Roth IRA? (Lily, San Diego) 33:46 - Should I Split Money Between Multiple Brokerage Firms to Avoid Hacking? (Wesley from Unincorporated Gwinnett County, GA) 40:18 - The Derails Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-439 Register for the Q3 Financial Market Outlook live webinar, July 26, 2023, 12pm PT / 3pm ET The Ultimate Guide to Roth IRAs YMYW in US News and World Report's Best Personal Finance Podcasts to Listen to in 2023 Episode Transcript Big Al's Island Studio (photo) Ask Joe & Big Al On Air for your Retirement Spitball Analysis

Steven has got "one more year" syndrome. Can he retire at age 65? Today on Your Money, Your Wealth® podcast 438, Joe and Big Al spitball retirement for him, and for MB - can she and her husband live comfortably if she retires at age 59½? And for Johnny - does he have enough to fill the gap until retirement, and should his dad do Roth conversions before Johnny inherits his wealth? Is Austin maximizing his future gains by saving to his 401(k) at age 29, rather than his Roth IRA? But first, how can Mike and his wife leave their kids a lower tax bill when they pass? Timestamps: 00:45 - How to Leave the Kids a Lower Tax Bill When We Pass? (Mike, Boerne, TX - voice) 04:24 - I Have "One More Year" Syndrome. Can I Retire at 65? (Steven, Exton, PA) 08:30 - Can We Live Comfortably If I Retire at 59½? (MB, Louisville, KY) 12:49 - Do I Have Enough to Fill the Gap Until Retirement? Should Dad Convert My Inheritance to Roth? (Johnny, El Dorado, CA) 21:49 - Am I Maximizing Future Gains By Saving to Pre-Tax 401(k)? (Austin, Naples, FL) 29:42 - The Derails Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-438 Retirement Lifestyles Guide Register for the Q3 Financial Markets Outlook live webinar, July 26, 2023, 12pm PT / 3pm ET Episode Transcript Ask Joe & Big Al On Air

YMYW listener Alan feels that there are two unspoken assumptions that many different podcasters make when it comes to claiming Social Security benefits. Joe and Big Al spitball on those assumptions, along with safe retirement withdrawal rates before and after Social Security and pension for Rick and Jen, and a thrift savings plan (TSP) and Social Security retirement strategy for Theresa. Plus, Mark and his wife are semi-retired at 51 and 44. Are they going to run out of money? Where should Mary be saving for retirement, and how should she handle large Roth conversions before required minimum distributions (RMDs) kick in? Timestamps: 00:45 - Unspoken Assumptions About Collecting Social Security? (Alan, Daufuskie Island, SC) 09:38 - Safe Withdrawal Rates Before and After Social Security & Pension (Rick & Jen, Atwater, OH) 19:25 - Thrift Savings Plan and Social Security Retirement Strategy ("Theresa") 29:28 - Retirement Spitball: Will We Run Out of Money? (Mark, St. George, UT) 37:37 - Where to Save for Retirement and Roth Conversions Prior to RMDs? (Mary, small town Indiana) 47:54 - The Derails Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-437 Social Security Handbook Episode Transcript Ask Joe & Big Al On Air for your Retirement Spitball Analysis