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