Your Money, Your Wealth

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

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

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

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

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

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

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