Your Money, Your Wealth

It's a common question: should you pay off your mortgage when you have extra cash, or invest for retirement? Joe and Big Al spitball on how Ms. Moneybags and her wife-to-be should use their upcoming windfall. Plus, what should Bob's asset allocation be as he nears retirement? Should Harley and Harlene do Roth conversions after tax rates increase, and should they take advantage of net unrealized appreciation (NUA) on Harlene's company stock? Pete needs a 13 year retirement plan sanity check, Lauren wants to know if she can retire early or at least go part time, and Michael and Carol want the fellas to spitball whether they're on track for retirement. Timestamps: 00:57 - Should We Pay Off the Mortgage or Invest Our Windfall On the Way? (Ms. Money Bags) 09:00 - What Should My Asset Allocation Be When Nearing Retirement? (Bob in New York) 17:21 - Should We Convert to Roth After Tax Rates Go Up? Should We Leverage NUA? (Harley) 29:04 - 10-13 Year Retirement Plan Spitball Sanity Check (Pete, AL) 38:15 - Can I Retire Early or Go Part Time and Stop Contributing to 401(k)? (Lauren, IL) 43:17 - Retirement Spitball: Are We On Track? (Michael & Carol, Las Vegas) 48:24 - The Derails Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw_436 Portfolio Tracker: How to Manage Your Assets at Any Age Episode Transcript Ask Joe & Big Al On Air

A little ditty about Jack and Diane, who will eventually inherit about $4.5M from Diane's parents. How do they manage the required minimum distributions? Which of three options should Matt take with his inherited IRA? Making the most of your inheritance today on YMYW 435. Plus, Clay wants to know if it's a good idea to take money off the table and rebalance to safer or more aggressive investments, depending on your risk tolerance? Can Elizabeth offset pre-tax IRA losses with the gains from the sale of rental real estate? Is it true that you can make one time contributions from your IRA to your HSA that is, your health savings account? And finally, can Cory gift stock to his daughters and avoid paying the kiddie tax as a way to pay for college? And can Rich supercharge a 529 college savings plan with himself as beneficiary? Timestamps: 00:58 - How Do We Manage RMDs on a Pending Inheritance? (Jack & Diane) 11:31 - Which of 3 Options Should I Take With This Inherited IRA? (Matt, San Diego) 18:57 - Should I Take Money Off the Table and Rebalance to Safety? (Clay, Westerville (Columbus), OH) 23:50 - Can I Offset Pre-Tax IRA Losses With Gains from the Sale of Rental Real Estate? (Elizabeth, Lake Forest) 26:43 - Is It True We Can Make One Time Contributions From IRA to HSA? (Scott, NC) 32:06 - How to Pay for College: Gifting Stock and Avoiding the Kiddie Tax? (Cory, Bethesda, MD) 36:16 - Should I Supercharge a 529 Plan With Myself as Beneficiary? (Rich, NY) 41:17 - The Derails Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-435 Estate Planning Organizer Emotional Investing - YMYW TV Emotionless Investing Guide Episode Transcript Ask Joe & Big Al On Air

Joe and Big Al spitball five different retirement plans: is Jaybird on track to retire with a decent nest egg? Should Ted and his wife use the retirement smile spending pattern and spend more early in retirement? Is it safe for Aaron to retire at age 59 and a half? How much can Karla convert to Roth for the most tax-efficient retirement withdrawal plan? LEO Jay has Roth TSP retirement strategy questions, and Lynn suggests a super-easy Roth conversion calculator - but Big Al's got an even easier idea. Timestamps: 00:44 - Are We On Track to Retire With a Decent Nest Egg? (Jaybird, Penciltucky - PA) 08:57 - Retirement "Smile": Should We Spend More Early in Retirement? (Ted) 16:57 - Is it Safe to Retire at Age 59 and a Half? (Aaron, suburb of Philadelphia) 25:42 - Spitball My Tax-Efficient Withdrawal Plan: How Much Roth Conversion? ("Karla", New York City) 34:21 - Should I Max Roth TSP and Retire at 50? When Can I Withdraw from Roth TSP? (Jay, San Diego) 37:00 - Super Easy Roth IRA Conversion Calculator (Lynn) 42:51 - The Derails Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-434 Retirement Pop Quiz: test your retirement knowledge Retirement Readiness Guide Episode Transcript Ask Joe & Big Al On Air - get your own Retirement Spitball Analysis

How does bonus accelerated depreciation work when it comes to commercial real estate? Is real estate a good source of retirement income, and can it take the place of safe assets like bonds in your investment portfolio? Plus, can investments be transferred in-kind from an inherited trust to a brokerage account? And what tips do the fellas have for ace-ing the CFP exam and launching a career as a financial advisor? Timestamps: 00:43 - Bonus Accelerated Depreciation on Commercial Real Estate Purchase (Papa Joe, Naples, FL) 07:04 - Is Real Estate a Good Investment for Retirement Income? (Doctor Jerry, Waco, TX - from episode 426) 13:00 - Is Real Estate a Substitute for Bonds in a Diversified Investment Portfolio? (Don, VA - from episode 416) 17:08 - Can I Move Investments In-Kind From Inherited Trust to Brokerage Account? (George, KS) 24:15 - Tips for Taking the CFP Exam and Building a Career as a Financial Advisor (Craig, St. Clairsville, OH) Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-433 Real Estate Retirement Income Webinar - Wednesday June 21, 2023, 12pm PT/3pm ET - register now 10 Tips for Real Estate Investors Guide Episode Transcript Ask Joe & Big Al On Air for your Retirement Spitball Analysis

Can you retire early - before age 55 - simply by contributing to your 401(k) only up to the company match and then saving to a brokerage account? Joe and Big Al spitball on using this so-called tax "jailbreak" strategy to retire early. Plus, is Christine on track to have $150,000 present value to live on in retirement? Is John stuck just watching his money grow and turn into big required minimum distributions (RMDs)? Can Jackie contribute to a SEP IRA and convert it all to Roth? And what do the fellas think of Lee's I-Bond emergency fund? Timestamps: 00:49 - Is the Tax "Jailbreak" Early Retirement Strategy Nonsense? (William) 04:31 - Retirement Spitball: Can I Spend $150K Present Value in Retirement? (Christine, Seattle) 13:18 - Am I Stuck Watching My Money Grow and Being Saddled With Big RMDs? (John, TX - voice) 18:10 - Can I Contribute to SEP IRA and Convert it All to Roth, or Roll it to 401(k)? (Jackie, Bethesda, MD) 23:19 - How is My I-Bond Emergency Fund Strategy? (Lee, Jacksonville, FL) 28:12 - The Derails: One of YMYW's Most Brutal One-Star Reviews Ever Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-432 How to Build a Recession-Proof Portfolio - The latest episode of YMYW TV Recession Protection Guide SECURE Act 2.0 webinar (on demand) and companion guide Episode Transcript Ask Joe & Big Al On Air

How much will money will you need in retirement, adjusted for inflation? Joe and Big Al spitball on your future dollars, how to calculate the tax on Roth conversions, and the benefits of converting to Roth when financial markets are down. Plus, should retirement savings contributions be half pre-tax and half post-tax? And finally, saving to a 529 plan for your kids, or sending them to Hollywood stunt training camp - which would you do!? Timestamps: 00:49 - How Much Will I Need to Retire in Future (Inflated) Dollars? (Jared, Clifton Park, NY) 05:51 - Can We Retire Early With $400K Savings and $80K Pensions? That Depends on the Inflation Factor (Marcus, Queens, NYC - from episode 373) 15:22 - How to Calculate Tax on Roth Conversions & the Benefits of Converting in Down Markets (Robin) 20:00 - Should I Save Half Pre-Tax and Half-Post Tax for Retirement? (John Brown, NV) 28:26 - Hollywood Stunt Training Camp vs. Saving to 529 Plan (Mike, Utica, NY) 33:40 - The Derails Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-431 Big Al's Quick Retirement Calculation Guide 10 Steps to Improve Investing Success Episode Transcript Ask Joe & Big Al On Air

When should you take your pension, what types of things should you think about when it comes to deciding between a lump sum or a monthly annuity payment - risk protection, for example - and how do you work your pension into your overall retirement plan? Spitballing on retirement pension options, and saving to a taxable account when you're concerned about required minimum distributions or RMDs, on today's show. Timestamps: 00:42 - When to Collect My Pensions: Now, Early Retirement, or Age 70? (Rose, CA) 12:16 - I'm Concerned About RMDs. Should I Save to a Taxable Account for Retirement? (John Doe, Seattle, WA) 17:33 - Pension Retirement Spitball: Are We On Track to Retire in 2032 Without Saving Any More? (Jennifer & Zeke, NY State) 25:32 - Roth 457 vs. Roth IRA and Pension Options Retirement Spitball (Clay, Westerville, OH - from episode 377) 35:39 - COMMENT: Pension Vs. Lump Sum Risk Protection (Stephen) 38:53 - The Derails Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-430 Key Financial Data Guide Surviving Retirement Without a Pension - YMYW TV S4E17 Register for a free webinar: Navigating Retirement Solo, tomorrow, Wed. May 24, 2023, 12pm PT/3pm ET Episode Transcript Ask Joe & Big Al On Air

Can you convert your health savings account (HSA) to Roth, and do the five-year Roth withdrawal clocks apply? What should you do with money you'd been putting to your student loan debt if you're part of the student loan forgiveness program? What's the best way to invest your RMDs, or required minimum distributions? How does IRMAA, the income-related monthly adjustment amount for Medicare, apply to zero-coupon municipal bonds? And finally, strategies for collecting survivor Social Security benefits. Timestamps: 00:49 - Can I Convert a Health Savings Account HSA to Roth IRA and Do the 5-Year Rules Apply? (Philip) 07:49 - My Student Loans Were Forgiven. Now Should We Contribute to Roth 403(b)? (Pete, Winston-Salem, NC) 15:37 - How Should I Invest Required Minimum Distributions? (Judy, San Diego) 22:17 - How is IRMAA for Medicare Applied to Zero Coupon Municipal Bonds? (Jimmy) 26:40 - 62 and Widowed: Claim Survivor Social Security Benefits Until Age 67? (Mark, Burke, VA) 30:11 - Is Signing Up for Social Security Just Pretty Much Straight Forward? (Michael) 32:09 - The Derails Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-429 Debt Ceiling and the US Dollar - new educational video Talking About Recessions - new blog post Medicare Check-Up Guide Episode Transcript Ask Joe & Big Al On Air

So you're about to receive a large inheritance - what should you do with it? Joe and Big Al spitball on suddenly becoming $85 million dollars richer. Plus, is it nuts to semi-retire early? Should retirement contributions be split between Roth and traditional accounts? Can you do conversions to your kids' custodial Roth accounts? The fellas also spitball tax bracket-based Roth conversion strategies to help you pay the least amount of tax possible, long term, and they discuss required minimum distributions on inherited assets, and whether to pay off a 401(k) loan if it's "paying" you 8% per year. Timestamps: 00:48 - I'm Inheriting Millions of Dollars. What Should I Do With It? (Michael, Binghamton, NY) 07:04 - Should I Split Retirement Contributions Between Roth and Traditional 457? (Kevin, Folsom, CA - voice) 11:34 - Should I Do 100% Roth TSP Contributions? Am I Nuts to Semi-Retire Early? (Derek, Seattle) 16:30 - Should We Do Roth Conversions to the Top of the 22% or 24% Tax Bracket? (Bill, Maryland) 23:53 - Is My CPA Correct That I Can Convert $24K to Roth Tax-Free? (Sam, Newark, NJ) 26:52 - Can I Convert 457 Money to My Kids' Custodial Roth Accounts? (Brian, Binghamton, NY) 32:50 - RMD Rules for Inherited Roth IRA and Traditional IRA (Dan, Brick, NJ) 38:48 - Should I Pay Off My 401(k) Loan That's "Paying" Me Over 8% Per Year? (Anon, Denver, CO) 42:59 - Comments on Keeping Employer IRA Money Separated 44:46 - The Derails Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-428 Complete Roth Papers Package Episode Transcript Ask Joe & Big Al On Air

If you knew exactly when you were gonna die, so many financial decisions would be simple. But generally, we don't, so today Joe and Big Al spitball on death, taxes, and trust issues of the estate planning variety. Fair warning, it's "the dark show" today on YMYW, as the fellas discuss cancer trust funds, making your trust the beneficiary on your retirement accounts, when and how to take Social Security benefits and pension options, Roth conversion strategies taking into account the 5-year rules for withdrawals, and potentially donating required minimum distributions to charity rather than doing conversions. Timestamps: 00:49 - Pension Plan Options Retirement Spitball: Lump Sum, Annuity, or Hybrid? (Dave, CO) 07:37 - Should We Have a Cancer Trust Fund? (Melinda, Milwaukee) 12:02 - Why Not Make Our Trust the Beneficiary on Retirement Accounts? (Ms. Merry, MD) 21:40 - Is There a 5-Year Rule on Taking Dividends from a Roth IRA After Age 59½? (Douglas, Bonita, CA) 23:34 - I'm 60, My Ex is 74. Am I Eligible for Spousal Social Security Benefits? (Salwa) 24:39 - How Much If Any Roth Conversion Should We Do? (Paul, NJ/SC) 28:53 - Why Do a Roth Conversion Instead of Donating to Charity? (Kevin, Raleigh) 32:57 - Why Separate and Never Add Money to a Profit-Sharing Plan Rolled to IRA? (Nancy, Foxboro, MA) 35:46 - Retirement Pension at 57 or 60? Social Security at 62 or 70? (midwestfabs) 45:56 - The Derails Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-427 Estate Planning Organizer Inflation, Interest Rates, Recession? Financial Markets Update Webinar Replay Going Solo: Navigating Your Financial Future Single - YMYW TV & companion guide Episode Transcript Ask Joe & Big Al On Air

Gidget wants to find her very own Moon Doggie so she can get married and reap that sweet, sweet capital gain exclusion when she sells her house. What do Joe and Big Al think, and can they help her find a man? Plus, is real estate a good investment for retirement income? Is taking out a TSP (thrift savings plan) loan to pay off your mortgage a good idea? Also, the fellas spitball a tax and ACA (Affordable Care Act) strategy, a FIRE strategy - well, financial independence, but not necessarily retire early - and they discuss capital gains taxes on RSUs (restricted stock units.) Timestamps: 00:45 - How's My Marriage Strategy for Extra Capital Gain Exclusion on the Sale of My Primary Residence? (Gidget, San Diego) 10:46 - Is Real Estate a Good Investment for Retirement Income? (Doctor Jerry, Waco, TX) 16:14 - Should I Pay Off My Mortgage with a Thrift Savings Plan Loan? (Jake - voice message) 19:35 - Spitball Our Retirement, Tax Planning, and ACA Strategy? (John from LA - Lower Anderson, SC) 26:31 - Do I Need to Pay Quarterly Capital Gains Taxes When I Sell RSUs? (Jerry, Redmond, WA) 31:43 - FIRE Retirement Spitball Analysis: How to Structure Our Investments? (Jim, Washington State) Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-426 10 Tips for Real Estate Investors Alternative Retirement Income Sources: Real Estate and Beyond webinar Real Estate Investing: What Are Cash-on-Cash and Cap Rate? YMYW podcast episode 365 Episode Transcript Ask Joe & Big Al On Air

How do you protect your nest egg when you're really risk-averse and want safe, low-risk investments - should you invest in annuities, CDs? When choosing a money market fund, should you just invest in the one with the highest post-tax return? How do you go about replenishing cash, or rebalancing your portfolio, when the stock market is up? Plus, the widow's penalty in relation to Roth conversions, and switching from survivor Social Security benefits to your own. Also - withdrawing from your portfolio before RMD age? One listener says nobody should ever need to do it! Timestamps: 00:51 - How to Safely Invest and Protect $400K When You're Risk Averse (Tyler, OH - voice) 07:31 - Rebalancing: How to "Replenish Cash" When Stocks Are Up? (Elisa, Fremont, CA) 13:27 - Money Market Funds: Don't I Want the Highest Post-Tax Return? (Michael, CO) 18:42 - The Widow's Penalty and Roth IRA Conversions (KBH, San Antonio) 27:46 - Can I Switch from Survivor Social Security Benefits to My Own at Age 70? (Sara, Tucson, AZ) 30:43 - COMMENT: Come On People, You've Had a Lifetime to Set Up Your Retirement (April, Tinley Park, IL) 36:46 - The Derails Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-425 Withdrawal Trap Doors - YMYW TV episode and free companion guide Register for the Q1 2023 Market Update / Q2 2023 Financial Market Outlook Webinar, April 26, 12pm PT / 3pm ET with Pure Financial Advisors' EVP and Chief Investment Officer, Brian Perry, CFP®, CFA. Episode Transcript Ask Joe & Big Al On Air

Should retirement living expenses be drawn from your stable value fund, your CD or money market, brokerage account, or FDIC insured bank accounts? Can you even trust the banks after the recent bank failures? What about sequence of returns risk? Which investments are best for long-term retirement savings when you're early in your career? Joe and Big Al explain why your strategy for retirement savings and withdrawals should be your first step - before you consider investments, asset classes, or sectors. Timestamps: 00:49 - Stable Value Fund Vs. Brokerage Account for Living Expenses? (Sharon, Waukesha - voice) 09:08 - Sequence of Returns Risk: Should I Save for 5 Years in CD, Money Market or Brokerage Account? (Carlos, Tampa Bay) 15:46 - High Income and Tax-Deferred Savings, Low Tax Rate: Where Should I Save? (Josh, Boston, MA) 21:40 - Am I Overcomplicating My Investments at Age 35? (Mike, VA) 29:44 - I'm 28. Should I Max Out Pre-Tax or Post-Tax 457 Plan Retirement Savings? (Michael) 33:55 - How Does FDIC Insurance Work? SVB and Signature Bank Failures (Jon, Powhatan, VA) 39:46 - Should We Roll 401(k) to Several FDIC-Insured IRA Accounts to Live Off Of? (Joan, Long Island, NY) Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-424: YMYW Guide to Growing Your Wealth Register for the Q1 2023 Market Update / Q2 2023 Financial Market Outlook Webinar, April 26, 12pm PT / 3pm ET with Pure Financial Advisors' EVP and Chief Investment Officer, Brian Perry, CFP®, CFA. Episode Transcript Ask Joe & Big Al On Air

How can you reduce taxes, IRMAA, net investment income tax, and required minimum distributions when you've got too much money in your tax-deferred retirement account - and just how much Roth conversion should you do? Plus, can you contribute to a Roth by transferring stocks "in kind"? If the check you send off to pay your estimated taxes isn't cashed before the deadline is it late? How does SECURE 2.0 impact 529 plans, and is 529 better than Roth IRA for college savings? Finally, the fellas spitball a 401(k) in-plan Roth conversion and retirement account consolidation strategy. Timestamps: 00:48 - We Have Too Much in Traditional IRA. How's Our Roth Conversion Plan? (Kelly, Idaho) 10:54 - Can I Make a Roth IRA Contribution by Transferring Stocks "In Kind"? (GDO, Delco) 14:36 - How to Pay Estimated Taxes: If My Check Isn't Cashed Immediately, Is It Late? (Judi, San Diego) 16:51 - 529 Plan vs. Roth IRA: Does SECURE 2.0 Affect 529 College Savings? (George) 20:49 - 401(k) In-Plan Roth Conversion and Retirement Account Consolidation (Steve, Maine) 27:07 - The Derails Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-423: Tax Takedown: brand new YMYW TV and companion guide 2023 Tax Planning Guide Episode Transcript Ask Joe & Big Al On Air

Which investments should go in your traditional IRA vs your Roth IRA, and does that asset location depend on your age? Learn how to generate "tax alpha" to get better returns on your investments. Plus, Joe and Big Al spitball whether to roll a TIAA 403(b) to an IRA or take the annuity, and they spitball retirement and Roth conversion and Roth contribution strategies for an overseas officer with a military pension, and for Americans working abroad who qualify for the foreign earned income exclusion. Timestamps: 00:51 - Best Assets to Hold in Traditional IRA and Roth IRA? (Michael, Colorado - voice) 7:40 - Is Investment Asset Location Dependent on Age? (Glen) 11:35 - TIAA 403(b): Take the Annuity or Roll to an IRA? (Brad, Northeast TN) 19:34 - Military Pension Spitball: Overseas Officer with Fluctuating Income & Taxes (US Grant, Alexandria, VA... usually) 24:29 - Foreign Earned Income Exclusion & Roth 401(k) Rules (Jeff, Singapore via North Dakota) 31:32 - The Derails Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-422: Why Asset Location Matters Guide Register for our free 2023 tax planning webinar, March 29, 12pm PT/3pm ET Schedule a free financial assessment Episode Transcript Ask Joe & Big Al On Air

Should Edith and Archie live off their non-qualified accounts and pay Roth conversion taxes from their 401(k)? How can Johnny from Knoxville do Roth Conversions and stay in a low tax bracket Plus, at age 31, are Shad and his wife saving enough for retirement? What should Tech Chick do with her severance package after being laid off from her tech industry job? Finally, listener comments on retirement plan education, Roth conversions, and the 5-year Roth clocks. Timestamps: 00:39 - Live Off Non-Qualified Accounts, Pay Roth Conversion Tax From 401(k)? (Edith & Archie, TX) 11:35 - How to Do Roth Conversions and Stay in a Low Tax Bracket + Estimating Taxes (John, Knoxville, TN) 19:11 - Retirement Spitball Analysis: Are We Saving Enough at Age 31? (Shad, Smith's Grove, KY) 27:11 - Laid Off From the Tech Industry. What Should I Do With My Severance Package? (Tech Chick, Mile High Rocky Mountains) 39:55 - Comment: No Financial People Ever Mentioned Roth Conversions to Me Before! (Donna, Valencia) 40:55 - Comment: Thanks for Letting Me Educate You on Retirement Plans (Debra, St Louis, MO) 42:41 - Comment: You Got the Roth 5 Year Clock Wrong (David, Michigan) 48:06 - The Derails Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-421 Register for our free 2023 tax planning webinar, March 29, 12pm PT 2023 Key Financial Data Guide Complete Roth Papers Package, Including: the Ultimate Guide to Roth IRAs, the Guide to the 5-Year Rules for Roth IRA Withdrawals, and the Roth IRA Basics Guide Episode Transcript Ask Joe & Big Al On Air

Are low-cost mutual funds or ETFs better investments in a tax-advantaged account? Also, more strategizing from that SECURE Act 2.0 529 plan provision, the pros and cons of selling a rental house now or holding it until you pass, and an easy-breezy self-employed retirement account that's better than a SEP IRA. Plus, will municipal bond income bump you into a higher tax bracket? Can you avoid capital gains tax by investing less aggressively over time? Timestamps: 00:00 - Intro 00:46 - Mutual Funds vs. ETFs in a Tax-Advantaged Account? (Midwestfabs, St Paul, MN) 08:06 - SECURE Act 2.0 529 Plan Strategy (Chris, Atlanta) 14:51 - Will Municipal Bond Income Bump Me Into a Higher Tax Bracket? (Bobby, Philadelphia) 26:31 - Can I Avoid Capital Gains By Investing Less Aggressively Over Time? (Joe, Aston, PA) 33:12 - Pros and Cons of Selling a Rental House Right Now (Joe, Chula Vista) 34:48 - An Easy Breezy Self-Employed Retirement Account Better than the SEP IRA? (Steve, Las Vegas) 39:58 - The Derails Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-420 The SECURE 2.0 Circus: brand new YMYW TV and companion guide Blog post: Self-Employed Tax Filing & Small Business Retirement Plans The Ultimate Guide to IRAs Episode Transcript Ask Joe & Big Al On Air (plus, cute dog photo alert! We've got Midwestfabs' dog, "Jake-from-State-Farm"!)

In order to retire comfortably at age 60, what should you be doing with your finances when you're in your 20s? A framework for getting started planning for retirement on today's episode of YMYW. Plus, if you're a small business with a SIMPLE IRA plan, is it stupid to save for retirement in a brokerage account rather than a traditional IRA? If you inherited money and promised to donate to charity, should you do Roth conversions? What's the most efficient way to pay financial advisor fees, and what's a good strategy for making pre-tax and post-tax retirement contributions? Timestamps: 00:51 - A Framework for Getting Started in Planning for Retirement (Anonymous) 05:36 - I'm 24. What Should I Do to Retire Comfortably at 60? Michael, 24 (Binghamton, NY) 12:14 - I'm 32. Opened a SIMPLE IRA. Is It Stupid to Fund Brokerage Instead of Traditional IRA? (Ron Burgundy) 17:42 - I Inherited $450K, Promised to Donate to Charity. Should I Do Roth Conversions? (Allison, Northern Virginia) 23:02 - What's the Most Efficient Way to Pay Advisor Fees? (Nick, OH) 26:06 - Strategy for Pre-Tax and Post-Tax Retirement Contributions? (Dave) 29:56 - The Derails Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-419 Cracking the Code - Succeeding Financially at Every Age: YMYW TV & Companion Guide Spitballing Retirement Planning in Your 30's (and even in your 20's!) - YMYW podcast 391 Top 10 Most Popular Your Money Your Wealth Podcast Episodes - Spotify playlist Schedule a free financial assessment with Pure Financial Advisors Episode Transcript Ask Joe & Big Al On Air (plus a photo of YMYW listener Nick's cute dogs!)

If you've got some retirement savings but can't contribute any more, will you ever be able to retire? Joe and Big Al have three simple strategies to help you get there. Plus, how long does it take to get off of Medicare's income-related monthly adjustment amount, or IRMAA, after your income decreases at retirement, and how do you take unknown future IRMAA income limits into account when setting up your financial plan? Can you "re-do" Social Security and stop taking benefits after claiming Social Security early? Do spousal benefits change after one spouse files for Social Security? And finally, the fellas address a few corrections they've received recently regarding Medicare and safe harbor 401(k) plans. What exactly is "top-heavy" anyway? Timestamps: 00:00 - Intro 01:02 - Will I Ever Be Able to Retire? I Have Some Savings But Can't Contribute More (Patty, NY) 06:38 - Retired, Income Dropped, Enrolled in Medicare. How Long to Get Off IRMAA? (Randy, Hb, Ca) 08:05 - How to Plan for Unknown Future Medicare IRMAA Income Limits? 10:53 - "Re-Doing" Social Security: Can You Stop Taking Benefits After Claiming Early? (Lauris, Volcano, Hawaii) 12:39 - Will Spousal Social Security Benefit Amounts Change When One Spouse Files? (Philip, Los Angeles) 15:09 - SECURE 2.0: When Must You Pay Taxes on Company Match Retirement Contributions? (Jim, Dallas, TX) 19:47 - CORRECTION: ACP Test for Safe Harbor 401(k) Plans, After-Tax Contributions (Debra, St Louis) 25:08 - CORRECTION - Medicare Test: Creditable Drug Coverage (Steve, Las Vegas) 28:56 - DUKE's Medicare Enrollment Experience (DUKE (John Wayne), Knoxville, TN) 32:54 - The Derails Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-418: Retirement Readiness Guide NAPA-net: 401(k) After-Tax Contributions Are 'Testy' Turbocharge Your Wealth! YMYW TV & Companion Guide Episode Transcript Ask Joe & Big Al On Air (Plus, YMYW Producer Andi Last video interview on the Audience Growth Podcast)

How should your financial strategy change when your income increases dramatically? We're talking like $450K one year to a million and a quarter the next? (If you guessed Roth conversions might be in the answer you'd be correct!) Joe and Big Al also spitball strategies for when your income is too high to make Roth contributions, and can you use capital gains to contribute to Roth? Can "Alligator Joe" afford to retire early, or does he need to keep gutting it out at his current job wrestling alligators? Should Catherine contribute to her 401(k) or buy company stock before she quits her day job to start a business? The fellas also spitball retirement planning involving structured settlements, inherited assets, and ACA credits, and they discuss transferring annuities to a CD vs. deferring the interest into another annuity. Timestamps: 00:58 - Income Increased Dramatically. Should Our Retirement Tax Strategies Change? (Cookie Baron, Texas) 08:59 - Can I Use Capital Gains to Make Roth Contributions? (Aaron) 12:12 - Early Retirement Spitball: Should I Keep Gutting it Out at My Current Job? ("Alligator Joe Frazier", The Sunshine State FL) 18:11 - Contribute to 401(k) or Buy Company Stock Before Quitting to Start a Business? (Catherine, TX) 20:32 - Retirement Spitball: Income is Too High for Roth Contributions (Kelly, Owensboro, KY) 25:10 - Retirement Spitball: Structured Settlement, ACA Credits, & Inherited Assets (Kara from PA) 29:42 - Should We Transfer Annuities to CD, or Defer Interest Into Another Annuity? (Norma, Chula Vista) 34:00 - The Derails Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-417: The Complete Roth Papers Package 10 Ways the SECURE Act 2.0 Changes Your Taxes and Retirement Planning (webinar) Episode Transcript Ask Joe & Big Al On Air

Joe and Big Al spitball on set-and-forget brokerage investments for 30-something investors, real estate as a substitute for bonds in a diversified portfolio, and options for taking a state pension with or without sick time pay. The fellas also discuss how to bridge the retirement gap until collecting Social Security, strategies for claiming spousal Social Security benefits, and whether you need to sign up for Medicare if you'd rather keep the healthcare you already have. Timestamps: 00:49 - Set-It-and-Forget-It Brokerage Investments for a 30-Something Investor? (Chris, Scottsdale) 07:56 - Is Real Estate a Substitute for Bonds in a Diversified Investment Portfolio? (Don, VA) 12:42 - State Pension Options: $21K at Age 55 Plus $13K Sick Time, or $30K at Age 62? (Rich, NY/NC - voice message) 19:35 - Which Funds Should We Use to Bridge the Gap Until Collecting Social Security? (Jeff, San Diego) 25:29 - When Will I Receive Spousal Social Security Benefits? (Sharon) 28:37 - Spitballing a Spousal Social Security Claiming Strategy (G, Philly) 33:50 - Do We Have to Register for Medicare If We Aren't Going to Use it? (Jim Santa Cruz) 39:03 - The Derails Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-416: 10 Ways the SECURE Act 2.0 Changes Your Taxes and Retirement Planning Portfolio Tracker: How to Manage Your Assets at Any Age Social Security Handbook Medicare Checkup Guide Episode Transcript Ask Joe & Big Al On Air

With the new SECURE Act 2.0 rules regarding retirement savings contributions, should your company match go into the traditional or Roth 401(k)? Joe and Big Al also discuss whether you can or should do Roth conversions when your company fails non-discrimination testing for highly compensated employees (HCEs), the mega backdoor Roth vs. the employee stock purchase plan, and they spitball a tax arbitrage strategy. Plus, a retirement spitball for a 37-year-old couple wanting to retire in their 60s, and another couple wanting to FIRE (financial independence/ retire early) - but are they screwing up and creating a huge future tax bill? Show notes, free financial resources, transcript, Ask Joe & Big Al On Air: https://bit.ly/ymyw-415

Modified adjusted income for Medicare and IRMAA and the pro-rata and aggregation rules for Roth conversions explained... clearly? Will a combat zone TSP transfer be subject to those rules? Plus, joint tenants with rights of survivorship vs. transfer on death for a brokerage account, reducing taxes on the sale of a timeshare, how much to spend on home improvements, and using a reverse mortgage instead of long-term care insurance. And wait 'til you hear Joe and Big Al's thoughts on the best way to pay the least amount of tax when you cash out your retirement savings to buy gold and silver. Show notes, many new free financial resources, transcript, Ask Joe & Big Al On Air: https://bit.ly/ymyw-414

How should young savers invest pensions and estimate their retirement income needs? Is going into your employee stock purchase plan a good portfolio diversification strategy? What do Joe and Big Al think of multi-year guaranteed annuities (MYGA), and dividend-paying stocks vs. ETFs? Plus, a $10.6M retirement spitball analysis, making extra mortgage payments vs. saving to a brokerage account, and contributing to Roth 401(k) vs. traditional 401(k). Also, will a 403(b) held by an insurance company be subject to separation costs or surrender fees when rolled to an IRA? And the specifics on when to file tax form 5500. Show notes, Why Asset Location Matters Guide and other free financial resources, transcript, Ask Joe & Big Al On Air: https://bit.ly/ymyw-413

Joe and Big Al are back with a SECURE Act 2.0 recap and a proposed backdoor 529 plan strategy from the new law. Plus, is there a scenario where it makes sense to not max retirement accounts, to avoid being retirement rich and cash poor? Also, the fellas' thoughts on a break-even point for Social Security, required minimum distributions (RMD) from inherited IRAs, and of course, Roth IRA strategies: as in, the 5-year rules for Roth withdrawals, preserving Roth money and avoiding early withdrawal penalties, and Roth conversions to offset brokerage account losses. Show notes, transcript, free financial resources - including the free guide to the SECURE 2.0 Act - and to Ask Joe & Big Al On Air for your Retirement Spitball Analysis: https://bit.ly/ymyw-412

IRA withdrawal strategies when you retire in a down market, Roth contributions vs. Roth conversions, converting now or waiting to convert to Roth in retirement, and why you'd want to lose today's tax savings and contribute to Roth in the first place, today on the best of the YMYW podcast 2022. Plus, how to know if your financial plan is on track and the funniest Derails of the year. Visit the podcast show notes for more financial resources - including the free guide to the SECURE Act 2.0 - episode transcript, and Ask Joe & Big Al On Air for a retirement plan spitball analysis of your own: https://bit.ly/ymyw-411

Welcome to Your Money, Your Wealth® podcast, with CERTIFIED FINANCIAL PLANNER™ professional Joe Anderson and Certified Public Accountant Alan "Big Al" Clopine. Your Money, Your Wealth® is retirement planning, investing, and tax reduction made fun! Follow YMYW on your favorite podcast app and share this trailer. Visit YourMoneyYourWealth.com and click Ask Joe and Big Al On Air to get a Retirement Spitball Analysis of your own. And hey, thanks for listening, because the show wouldn't be a show without you. Your Money, Your Wealth® is presented by Pure Financial Advisors, a registered investment advisor. This show does not intend to provide personalized investment advice through this broadcast and does not represent that the securities or services discussed are suitable for any investor. Investors are advised not to rely on any information contained in the broadcast in the process of making a full and informed investment decision.

Is it better to choose low-cost index funds or to diversify investments, even if it means paying higher fees? What causes mutual fund price fluctuation? Are mid-cap funds necessary in a balanced portfolio? Joe and Big Al also talk about real estate funds vs. real estate investment trusts (REITs), and TIAA annuities vs. bonds in a retirement portfolio. Finally, we revisit some investing strategy questions that are still relevant in today's volatile markets on moving to cash in tough times, analyzing your asset allocation, and rebalancing your retirement portfolio. Show notes, free financial resources, transcript, Ask Joe & Big Al On Air: https://bit.ly/ymyw-410

Can you trust the opinion of just one advisor when planning for your entire financial future? Joe and Big Al spitball their second opinions for some retirement plan and Roth conversion strategies, they illustrate one way some financial advisors may be acting in their own best interests, and they explain how to determine if you're on track for a successful retirement. Plus, can you take penalty-free withdrawals from a Roth TSP to Roth IRA rollover in order to bridge the gap until age 59½? Will paying for a home remodel with Roth conversion funds avoid tax? And, should you use Roth conversion money for these purposes? Show notes, free financial resources, transcript, Ask Joe & Big Al On Air: https://bit.ly/ymyw-409

Asset location strategies, liquidity, and building up tax-free Roth IRA money when retiring early, how growth is taxed in taxable accounts, the pros and cons of rolling an employer retirement plan into a traditional IRA, how stock futures are determined and why stock price matters, and buying 8-week treasuries. And, if you're planning to make a killing on eBay or at your next garage sale, the fellas get into the weeds on how to maximize your tax savings. Show notes, free financial resources, transcript, Ask Joe & Big Al On Air: https://bit.ly/ymyw-408

We're hearing more about fixed-indexed annuities with these volatile financial markets. Is it time to reconsider? Plus, clarification on required minimum distributions (RMDs) being waived for non-spouse IRA beneficiaries in 2021 and 2022, taxation on trusts, and suggestions for a 40-year-old considering an early mini-retirement. Also, can a 62-year-old immediately withdraw Roth conversion money? Finally, a strategy to claim Social Security early while working and invest the difference in a Roth IRA, and Joe and Big Al attempt to explain family Social Security benefits without phoning it in. Show notes, free financial resources, transcript, Ask Joe & Big Al On Air: https://bit.ly/ymyw-407

What will you actually need to spend in retirement? Joe and Big Al explain how to really think about and calculate your retirement expenses. Plus, if you want to reduce your tax-deferred account balances, does it make more sense to do Roth conversions or reinvest? What about doing Roth conversions to a higher tax bracket than the one you'll be in during retirement? Also, the fellas explain the alternative minimum tax, how Social Security spousal benefits work, and when in the year you turn 72 you must take required minimum distributions from your retirement accounts. And finally, what should someone with no credit history who hasn't paid taxes do with a sudden $100,000 windfall? Show notes, free financial resources, transcript, Ask Joe & Big Al On Air: https://bit.ly/ymyw-406

Joe and Big Al discuss LIRPs, or life insurance retirement plans, they spitball whether to take full pension survivor benefits or buy a life insurance policy, and whether to sell losing stocks for even bigger losers to take advantage of the 0% capital gains tax bracket. Plus, zero coupon municipal bonds and the de minimis rule, and target date funds as part of Paul Merriman's Two Funds for Life strategy. Finally, how do dividends figure into the 4% rule for retirement withdrawals, and should that 4% come from stocks or bonds? Show notes, free financial resources, transcript, Ask Joe & Big Al On Air: https://bit.ly/ymyw-405

Joe and Big Al clarify once and for all those 5-year clocks for withdrawing money from your Roth accounts. How do the 5-year Roth IRA rules impact the taxation of dividend income? Do the 5-year rules for Roth withdrawals impact thrift savings plan (TSP) to Roth conversions as well? Plus, why contribute to a Roth in the first place and lose today's tax savings? Joe and Big Al rise to that challenge and they discuss Roth conversions and required minimum distributions from an inherited IRA. Show notes, free financial resources, transcript, Ask Joe & Big Al On Air: https://bit.ly/ymyw-404

Following the Fed's fourth consecutive interest rate hike last week, should you be changing your investing strategy to time this inflationary market, moving from bonds to 3-year annuity CDs? Plus, Joe and Big Al spitball on asset location and Roth conversions for the in-laws, and a net unrealized appreciation (NUA) strategy for company stock in a 401(k). They also discuss whether extra home mortgage payments are part of an investment portfolio, and what real estate expenses are tax deductible. Show notes, free financial resources, transcript, Ask Joe & Big Al On Air: https://bit.ly/ymyw-403

Are you behind on your retirement savings? What do you need to do to catch up? If you retire in just a few years, will your money last until age 90? Based on the 5-year Roth withdrawal rules, do you need to open a new Roth IRA for each Roth conversion? Plus, Joe and Big Al spitball a health insurance, capital gains, and real estate strategy to save more money and have more wealth in retirement. Finally, they revisit the SECURE Act rules for withdrawing money from an inherited IRA, and Social Security income limits. Show notes, free financial resources, transcript, Ask Joe & Big Al On Air: https://bit.ly/ymyw-402

New research says some young people shouldn't save for retirement. Find out what Joe and Big Al think about that. Plus, is it tax fraud if you re-file taxes to take advantage of new student loan forgiveness? Should you invest in CDs instead of bonds, since both stocks and bonds are getting crushed right now? How can you consolidate your stock portfolio to minimize capital gains tax? Also, charitably inclined YMYW listeners want to know how to use donor-advised funds when spitballing tax planning around an IPO, and whether to do more Roth conversions or more qualified charitable distributions. Show notes, free financial resources, transcript, Ask Joe & Big Al On Air: https://bit.ly/ymyw-401

Are there any holes in a 5-year plan to retire from the Air Force, buy a house and a plane, and become a commercial pilot? Can you claim an unpaid loan to a start-up as a tax loss, do a Roth conversion, and pay no tax? Are Roth conversions a good idea in a low-earnings year? Does it matter if you convert to Roth before or after changing custodians? What retirement savings options do independent contractors have besides the Solo 401(k)? Does it make sense to cash out a 529 college savings plan that's losing money? Plus, Joe and Big Al spitball a real estate strategy, and they discuss a state retirement account held at an insurance company. Show notes, free financial resources, transcript, Ask Joe & Big Al On Air: https://bit.ly/ymyw-400

Joe and Big Al explain when and how to claim Social Security survivor benefits and how earning income impacts your benefit if you collect Social Security before full retirement age. Plus, how much should you withdraw in retirement from tax-free, taxable, and tax-deferred accounts? Also, RMDs, deciding whether to keep a life insurance policy, and of course, Roth Conversion strategies - is the backdoor Roth better for long term portfolio growth? Show notes, free financial resources, Ask Joe & Big Al On Air: https://bit.ly/ymyw-399

As the financial markets fall and then surge, Joe and Big Al talk about market timing, reallocating retirement contributions, and portfolio rebalancing. Plus, your questions answered on estimated taxes, Roth conversions, and the logistics of inheriting IRAs and passing assets on. Finally, how is a financial advisor like a golf caddie when markets get volatile? Joe and his Pebble Beach golf caddie buddy, Big G from the Real Life Caddie Podcast, discuss how their professional knowledge and experience can help the rest of us avoid big mistakes. Show notes, free financial resources, transcript, Ask Joe & Big Al On Air: https://bit.ly/ymyw-398

A compilation of some of Joe and Big Al's retirement plan spitballing specifically for those in their 40s and 50s - a critical time on the path to retirement. Is your financial plan set up so you pay as little tax as possible? Does it take volatile markets and potential future tax increases into account? Have you got a strategy nailed down for Roth conversions, or backdoor Roth, or pension options? Maybe you're making big decisions about what to do with your money between now and when you retire, like buying a house vs. saving for retirement? Are you comfortable with the retirement lifestyle you're creating? Do you know what you'll do with your time once you're permanently off the clock? Visit the podcast show notes to access free financial resources, transcript, and to Ask Joe & Big Al On Air: https://bit.ly/ymyw-397

Joe & Big Al answer your questions on, of course, backdoor Roth strategies. Y'know, to get as much lifetime tax-free growth on your investments as possible. Plus, investing strategies: does it make sense to buy a property now and rent it out until retirement? How much of a single stock in your investment portfolio can you sell and pay no capital gains tax? The fellas also explain capital loss carryovers, inherited IRAs, spousal Social Security and delayed retirement credits, required minimum distributions, and they spitball on an appropriate allocation of bonds, domestic stocks, and international stocks. Show notes, free financial resources, Ask Joe & Big Al On Air: https://bit.ly/ymyw-396

What's the next move for a 22-year-old who wants to retire early at 50? Can another YMYW listener afford to retire by the ocean in 10 months? Can Flowergirl and her husband AND her boyfriend retire next year? Joe and Big Al also check extensive retirement spitball math sent in PDF format. Plus, what are the fellas' philosophies on single vs. married tax rates when one spouse passes, and how does high state income tax impact a retirement strategy? Show notes, free financial resources, Ask Joe & Big Al On Air: https://bit.ly/ymyw-395

If a fortunate equity event or liquidity event should cause your income to skyrocket, what will that do to your taxes? Joe and Big Al spitball tax strategies to help you manage this good problem to have. Plus, Backdoor Roth, contributions, conversions, and income limits explained, converting twelve and a half million bucks to Roth, and what happens to retirement accounts when you pass - will there be a tax bill due? Kicking it off with the 7-twelve portfolio - what is it? Show notes, free financial resources, Ask Joe & Big Al On Air: https://bit.ly/ymyw-394

Should you convert money from your pre-tax retirement accounts to Roth now, or wait until retirement, or until required minimum distributions kick in? Should a mid-30s couple do Roth Conversions or Backdoor Roth? Should a 93-year-old open his first ever Roth and start converting? What's a good retirement savings mix between pre-tax and post-tax? And the fellas do a worst-case scenario retirement spitball analysis. Show notes, free financial resources, Ask Joe & Big Al On Air: https://bit.ly/ymyw-393

How do you determine how much you need in retirement when you factor in taxes, and how does the 4% rule apply? Has one YMYW listener spitballed retirement well enough to convince his wife that they can afford a new luxury truck? Can another YMYW listener take advantage of what seems to be a big opportunity to sell company stock, pay no capital gains tax, and do Roth conversions? Can Big Al's high school friend do a 1031 exchange to buy a rental property, make it his primary residence in 5 or 10 years, and pay no tax when selling? Is earned income from stock trading still taxable for Social Security if your LLC is in a trust? Finally, a compliment comes in, and Joe and Big Al assume it's for them. Show notes, free financial resources, the YMYW podcast survey, and Ask Joe & Big Al On Air: https://bit.ly/ymyw-392

Setting up your saving and investing strategies when you're in your 30s can put you on a good path to meeting your retirement goals. We're revisiting Joe and Big Al's financial spitballing over the last couple of years specifically for savers and investors in their 30s and even 20s, some of whom want to retire early. Show notes, free financial resources, the YMYW podcast survey, and Ask Joe & Big Al On Air: https://bit.ly/ymyw-391

When you retire and when you actually stop working may be two different things. How can you get a raise when you're working for a startup in retirement? Should you do Roth conversions before or after you quit working? Plus, find out what Joe and Big Al think about a 529 and series I bond gifting strategy, and using whole life insurance to transfer wealth to the kids. Show notes, free financial resources, the YMYW podcast survey, and Ask Joe & Big Al On Air: https://bit.ly/ymyw-390

Should you save for a house down payment or invest for retirement? How much long term capital gains tax do you pay on a rental property when you sell it after 20 years, and how does a 1031 exchange work? Also, opening a Roth IRA with the Backdoor Roth strategy, and the 5 year Roth withdrawal rules explained. Plus, a couple retirement spitball analyses: are you saving too aggressively for retirement? Can you avoid the Medicare IRMAA, or income related monthly adjustment amount, and high taxes from required minimum distributions? Show notes with annual podcast survey, free financial resources, and Ask Joe & Big Al On Air: https://bit.ly/ymyw-389

The time may be right for a giant Roth IRA conversion, especially now while the market is down, to potentially give you more money to spend in retirement. How does that work with long-term capital gains and dividends, and how much should you convert to Roth, and when, and how? Plus, deciding how to invest 529 plan college savings, whether to save to pre-tax or post-tax retirement accounts, and the ever-popular Backdoor Roth strategy. Show notes, free financial resources, Ask Joe & Big Al On Air: https://bit.ly/ymyw-388