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 ret

Low Mortgage Interest Rate vs. Future Gains: Is Trading Up Worth It? - 448

Low Mortgage Interest Rate vs. Future Gains: Is Trading Up Worth It?

Your Money, Your Wealth

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? (Sve

Can You Shorten Your Working Years?

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 IR

DIY Early Retirement Planning - 446

DIY Early Retirement Planning

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 p

Market Timing, Pension, & Roth Conversion Retirement Spitball - 445

Market Timing, Pension, & Roth Conversion Retirement Spitball

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 sal

What Are the Rules for Taking Money From a Roth IRA?

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 lo

Spitballing Retirement and Social Security for Worst Case Scenarios

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 

RSU, Mutual Funds, Bonds, and Annuities

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 J

Early Retirement Withdrawals & Capital Gains Tax Explained

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 Mu

Are Roth Conversions Really As Good as They Sound?

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 ab

$7M Tax-Free or $10M Retirement? Backdoor Roth or Lower Fees?

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

When Will You Be Able to Retire?

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 

Two Unspoken Assumptions About Collecting Social Security

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, Laur

Invest or Pay Off the Mortgage?

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 s

How to Maximize Your Inheritance: IRA Options and RMDs - 435

How to Maximize Your Inheritance: IRA Options and RMDs

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 

Ready to Retire? 5 Retirement Spitball Analyses - 434

Ready to Retire? 5 Retirement Spitball Analyses

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 Purc

Bonus Depreciation, Retirement Income, and Portfolio Diversification with Real Estate - 433

Bonus Depreciation, Retirement Income, and Portfolio Diversification with Real Estate

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 

Tax Jailbreak Early Retirement Strategy: Sense or Nonsense? - 432

Tax Jailbreak Early Retirement Strategy: Sense or Nonsense?

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 Fut

How to Calculate Your Retirement Needs in Future Dollars - 431

How to Calculate Your Retirement Needs in Future Dollars

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? (R

How to Consider Your Pension Options for Retirement - 430

How to Consider Your Pension Options for Retirement

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 benefi

HSA to Roth, RMD Investing, and Social Security Strategies - 429

HSA to Roth, RMD Investing, and Social Security Strategies

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 dist

What to Do With Inheritance Money? - 428

What to Do With Inheritance Money?

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 

Trust Issues, Death & Taxes: Estate Plan Spitball - 427

Trust Issues, Death & Taxes: Estate Plan Spitball

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 reti

Spitballing Retirement Real Estate and Tax Strategies - 426

Spitballing Retirement Real Estate and Tax Strategies

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 portf

Annuity? CD? Money Market? Where to Invest for Safety - 425

Annuity? CD? Money Market? Where to Invest for Safety

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 se

Investments vs. Retirement Withdrawal Strategy, FDIC Insurance - 424

Investments vs. Retirement Withdrawal Strategy, FDIC Insurance

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 spit

What to Do When There’s Too Much Money in Your Traditional IRA - 423

What to Do When There’s Too Much Money in Your Traditional IRA

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 exclusi

How to Reduce Taxes and Get Better Investing Returns? Asset Location - 422

How to Reduce Taxes and Get Better Investing Returns? Asset Location

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-Q

Roth Conversions & Retirement Spitball Analysis - 421

Roth Conversions & Retirement Spitball Analysis

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 Fun

Mutual Funds vs. ETFs, SECURE 2.0 & Capital Gains Strategies - 420

Mutual Funds vs. ETFs, SECURE 2.0 & Capital Gains Strategies

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 wha

How to Start Planning for Retirement - 419

How to Start Planning for Retirement

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

“Will I Ever Be Able to Retire?” - 418

“Will I Ever Be Able to Retire?”

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 allig

What to Do When You Get a Huge Pay Increase - 417

What to Do When You Get a Huge Pay Increase

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

Set-and-Forget Investing, Real Estate vs. Bonds, Pension, Social Security and Medicare - 416

Set-and-Forget Investing, Real Estate vs. Bonds, Pension, Social Security and Medicare

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, 

SECURE 2.0, FIRE, Tax Arbitrage & Roth Retirement Spitball - 415

SECURE 2.0, FIRE, Tax Arbitrage & Roth Retirement Spitball

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

Medicare IRMAA, Roth Pro-Rata, & Real Estate Strategies - 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 

Spitballing Diversified Portfolios for Retirement - 413

Spitballing Diversified Portfolios for Retirement

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 p

SECURE Act 2.0 & Retirement Rich, Cash Poor - 412

SECURE Act 2.0 & Retirement Rich, Cash Poor

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 - episo

Bear Market Survival & the 5W1H of Roth Conversions: YMYW Best of 2022 - 411

Bear Market Survival & the 5W1H of Roth Conversions: YMYW Best of 2022

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 wit

Retirement Planning, Investing, and Tax Reduction Made Fun: YMYW Trailer

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, analyz

Diversification Vs. Fees: What’s More Important for Retirement Investing? - 410

Diversification Vs. Fees: What’s More Important for Retirement Investing?

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 pa

Who to Trust? Second Opinion Retirement Spitball - 409

Who to Trust? Second Opinion Retirement Spitball

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, tra

Where to Save for Early Retirement? - 408

Where to Save for Early Retirement?

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 

Fixed Indexed Annuities, RMDs, and Early Social Security - 407

Fixed Indexed Annuities, RMDs, and Early Social Security

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 yo

How to Forecast Your Expenses in Retirement - 406

How to Forecast Your Expenses in Retirement

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 tha

Life Insurance, Muni Bonds, and Dividend Stocks in Retirement - 405

Life Insurance, Muni Bonds, and Dividend Stocks in Retirement

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 no

Roth IRA 5-Year Rules: How to Withdraw Money With No Taxes or Penalties - 404

Roth IRA 5-Year Rules: How to Withdraw Money With No Taxes or Penalties

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. S

Inflation Investing, Asset Location, and Real Estate Retirement Spitball - 403

Inflation Investing, Asset Location, and Real Estate Retirement Spitball

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 Sec

Will Your Retirement Savings Last Until You're 90 Years Old? - 402

Will Your Retirement Savings Last Until You're 90 Years Old?

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

Should Young People Save for Retirement? - 401

Should Young People Save for Retirement?

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 th

Anything Stupid or Overlooked in Your Retirement Plan Spitball? - 400

Anything Stupid or Overlooked in Your Retirement Plan Spitball?

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 

Survivor Social Security and Lowering Taxes in Retirement - 399

Survivor Social Security and Lowering Taxes in Retirement

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 experie

How to Manage Financial Market Stress? With the Help of a Caddie - 398

How to Manage Financial Market Stress? With the Help of a Caddie

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

Spitballing Retirement Planning in Your 40's & 50's - 397

Spitballing Retirement Planning in Your 40's & 50's

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 dis

Backdoor Roth, Investing, and Taxes - 396

Backdoor Roth, Investing, and Taxes

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 & 

Spitballing Early Retirement by the Ocean with Husband and Boyfriend - 395

Spitballing Early Retirement by the Ocean with Husband and Boyfriend

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 financ

How to Deal With Taxes When Income Goes Through the Roof - 394

How to Deal With Taxes When Income Goes Through the Roof

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

Is Now the Time for a Roth Conversion, or Wait Until Retirement? - 393

Is Now the Time for a Roth Conversion, or Wait Until Retirement?

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 

How to Spitball Retirement Taxes and the 4% Rule - 392

How to Spitball Retirement Taxes and the 4% Rule

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

Spitballing Retirement Planning in Your 30s - 391

Spitballing Retirement Planning in Your 30s

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

Working After Retirement and Wealth Gifting Strategies - 390

Working After Retirement and Wealth Gifting Strategies

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 fro

Save for a Home or Save for Retirement? - 389

Save for a Home or Save for Retirement?

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:

Pay Tax on This Move Now to Potentially Have More to Spend Later - 388

Pay Tax on This Move Now to Potentially Have More to Spend Later

Learn how to craft a retirement plan email question that’ll get you a model retirement spitball analysis. Plus, when should you contribute to Roth IRA, and when and how much of a Roth Conversion should you do? Is it hypocritical to prioritize investment returns over your conscience and values? Joe and Big Al talk ESG, or environmental, social, and governance investing, and they evaluate a strategy to keep taxes low while helping your kids buy a house. Finally, your comments about YMYW. Show note

A Model Retirement Plan Spitball Analysis - 387

A Model Retirement Plan Spitball Analysis

When the financial markets are down, should you postpone retirement? When inflation is up, should you change your investments and pile into things like value and commodities? Plus, the ever-popular retirement spitball analysis: an early retirement plan, Medicare, Social Security, TSP, and Roth conversions, and when and how business owners should convert $5.5M to Roth IRA. Also, if excess 2021 Roth contributions were returned, can you file last year’s taxes now without penalty? Finally, what’s th

Should We Hold Off on Retiring Until the Markets Recover? - 386

Should We Hold Off on Retiring Until the Markets Recover?

Inflation is high, interest rates are high, and the financial markets are volatile. Are bonds and series I bonds good investments or bad investments right now? How do bonds fit into your overall retirement portfolio? Plus, variable annuities, evaluating the long-term value of Roth contributions vs. Roth conversions, what if anything can be done about losses in an after-tax 401(k), helping adult kids buy a home, and drinks in the Derails. Show notes, free financial resources, Ask Joe & Big Al On 

Bonds and Series I Bonds, High Inflation, and High Interest Rates - 385

Bonds and Series I Bonds, High Inflation, and High Interest Rates

“Are we on track for retirement?” The ever-popular YMYW Retirement Spitball Analysis is all based on that simple question. Joe and Big Al spitball retirement for listeners planning to retire in just a few years, wondering if they should save to pre-tax or post-tax accounts, and strategizing around long-term capital gains, dividends, and Roth conversions. Show notes, free financial resources, Ask Joe & Big Al On Air: https://bit.ly/ymyw-384

Can We Retire Soon? Retirement Spitball Analysis - 384

Can We Retire Soon? Retirement Spitball Analysis

Equitable accumulators, cash management accounts, and Social Security: with today’s market volatility, how can you squeeze a few more dollars of income out of your retirement savings? Any reason not to use a robo-advisor for decumulation, in other words, spending down those savings? Plus, a pension retirement spitball follow-up, and is it possible to avoid tax liability on a lump sum withdrawal from a 401(k)? Finally, is Joe’s marriage the canary in the Coors Light Party Ball for YMYW? Show note

Where to Find Retirement Income When the Stock Market Freaks Out - 383

Where to Find Retirement Income When the Stock Market Freaks Out

If you own houses in your self-employed, self-directed solo 401(k), is converting a house a year to Roth to avoid required minimum distributions (RMDs) a good strategy? What’s an individual coverage health reimbursement arrangement (ICHRA) and is it a good healthcare option for those with C-corporations? When putting away retirement savings, should you contribute to a Roth IRA, a brokerage account, a 401(k), or your employee stock purchase plan (ESPP)? When it comes to step-up in basis, how do y

Where Should You Save for Retirement? Where Does Real Estate Fit? - 382

Where Should You Save for Retirement? Where Does Real Estate Fit?

Joe Anderson, CFP® and Big Al Clopine, CPA are all about having a plan for retirement. Using examples from past YMYW episodes, they cover five questions you need to answer before you retire - so you can stay retired. Show notes, free financial resources to help you answer each question, and Ask Joe & Al On Air: https://bit.ly/ymyw-381 1. Can We Afford to Retire? 2. When Should We Claim Social Security? 3. How Can We Reduce Taxes in Retirement? 4. Are We Prepared for Medical Costs? 5. How Will We

Don’t Retire Until You Can Answer These Five Practical Questions - 381

Don’t Retire Until You Can Answer These Five Practical Questions

Is there a way to get out of a bad SIMPLE IRA and stash cash in a tax-free Roth account? Can an owner of a company, that’s being sold to another company, load up a Roth account with company shares before the sale, and have a big chunk of cash happily growing tax-free? (What exactly are disqualified persons and prohibited transactions?) When designating beneficiaries of an annuity in a community property state like California, does state law or the annuity owner determine the beneficiary? Show no

How to Ditch a Bad SIMPLE IRA? What's a Prohibited Transaction? - 380

How to Ditch a Bad SIMPLE IRA? What's a Prohibited Transaction?

As bear market territory freaked out some investors, YMYW listeners were a bit more chill as Joe and Big Al spitballed on their specific strategies to manage the decline: does it make sense to move to cash inside your retirement account? How do down markets impact Roth Conversion decisions for older investors? What should your asset allocation be now, during market volatility, if you’re expecting a future windfall? How should you manage the relationship with your financial advisor if they buy hi