Your Money, Your Wealth

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