Your Money, Your Wealth

Tax Strategies, Backdoor Roth, Buy vs. Rent - 464

16 Jan 2024

Contributed by Lukas

It's a voice message extravaganza as Joe and Big Al talk about tax gain harvesting on Dante in New York's daughter's custodial account, and the tax im...

Retirement Investing, Roth Conversion Pros & Cons: YMYW Best of 2023 - 463

09 Jan 2024

Contributed by Lukas

We're revisiting your favorite Your Money, Your Wealth topics and Derails of 2023 in this Roth and retirement investing mega-episode. Safe investing w...

Can You Retire Early at Age 50 or 60? - 462

02 Jan 2024

Contributed by Lukas

Can Clark Kent's dad in Hutchinson, Kansas retire at age 50? Will Devin in South Carolina be fat and happy or cutting calories if he retires at 59 and...

Roth & Retirement Spitball, Insurance, and the Origins of YMYW - 461

26 Dec 2023

Contributed by Lukas

Spitballing on early retirement and Roth conversions to finish 2023. How can Jack and Diane (no, the other, other Jack and Diane, these are the ones i...

How to Invest: Bonds, CDs, and Roth Conversions - 460

19 Dec 2023

Contributed by Lukas

Joe and Big Al spitball on investing in index funds, bonds, CDs, treasuries, annuities, net unrealized appreciation on company stock, and where to par...

Advisor Touts 8% Returns, But Says I Can Only Withdraw 4%?! - 459

12 Dec 2023

Contributed by Lukas

Do financial advisors have some secret blood handshake that they'll all  claim they can get you 8 percent returns, but then tell their clients they c...

Retirement Spending and Timing Your Mortgage Payoff - 458

05 Dec 2023

Contributed by Lukas

Should Brian in Binghamton, New York pay off his mortgage for a guaranteed 6% return? How bad did Steve in Pittsburgh screw up his retirement, and can...

How to Cut Your Taxes Before Year-End - 457

28 Nov 2023

Contributed by Lukas

Last-minute tax questions answered: should Brad in Wahoo, NE save to his regular 401(k) instead of his Roth 401(k) so he can claim the American Opport...

How to Bridge the Gap to Retirement Income: Pension Spitball - 456

21 Nov 2023

Contributed by Lukas

Planning to retire early? Joe and Big Al spitball on bridging the gap to your retirement income when there's a pension in the mix, today on Your Money...

Can High Earners Fund a Roth IRA Without Paying More Tax? - 455

14 Nov 2023

Contributed by Lukas

Steve & Sharon in Minnesota are high earners - can they get more money into their Roth IRA without paying more tax? Should Fred in western New York do...

Is Our Retirement Savings Enough to Ever Retire? - 454

07 Nov 2023

Contributed by Lukas

Will Ron and Candy in Connecticut ever be able to retire, and are Bruce and Selina in Philly saving enough to retire? That's today on Your Money, Your...

No Retirement Advice or Recommendations, Just Spitballing - 453

31 Oct 2023

Contributed by Lukas

Can Jessie and Becky in Iowa retire now at age 52? Should Robert and his wife file their taxes separately, to pay less tax on their required minimum d...

Why Would a Tax Advisor Discourage 529 Plan College Savings? - 452

24 Oct 2023

Contributed by Lukas

Why does Becca in Florida's advisor "poo-poo" her strategy for funding 529 plans for education? Keith, commenting on Spotify, wants to know about reim...

Mega Backdoor Roth Conversion 5-Year Rule and Bond Investing - 451

17 Oct 2023

Contributed by Lukas

Should Jim in New Jersey do the YMYW-infamous Megatron (the Mega Backdoor Roth IRA) or use his Roth 401(k) - and how can he keep bonds out of his Roth...

Retirement Withdrawals: What's a Safe Distribution Rate? - 450

10 Oct 2023

Contributed by Lukas

How much can you safely spend in retirement? Is the four percent rule outdated? Joe and Big Al spitball on a safe retirement distribution rate for tho...

What To Do With Your Employer-Sponsored Retirement Plan? - 449

03 Oct 2023

Contributed by Lukas

What should Martin do about his outrageously fee-heavy 403(b) plan? Should EF hedge his pre-tax non-qualified 415 excess plan? What should Max do with...

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

26 Sep 2023

Contributed by Lukas

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 wor...

Can You Shorten Your Working Years? - 447

19 Sep 2023

Contributed by Lukas

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 mai...

DIY Early Retirement Planning - 446

12 Sep 2023

Contributed by Lukas

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-yea...

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

05 Sep 2023

Contributed by Lukas

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...

What Are the Rules for Taking Money From a Roth IRA? - 444

29 Aug 2023

Contributed by Lukas

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 with...

Spitballing Retirement and Social Security for Worst Case Scenarios - 443

22 Aug 2023

Contributed by Lukas

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 de...

RSU, Mutual Funds, Bonds, and Annuities - 442

15 Aug 2023

Contributed by Lukas

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,...

Early Retirement Withdrawals & Capital Gains Tax Explained - 441

08 Aug 2023

Contributed by Lukas

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 independ...

Are Roth Conversions Really As Good as They Sound? - 440

01 Aug 2023

Contributed by Lukas

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, annu...

$7M Tax-Free or $10M Retirement? Backdoor Roth or Lower Fees? - 439

25 Jul 2023

Contributed by Lukas

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-divers...

When Will You Be Able to Retire? - 438

18 Jul 2023

Contributed by Lukas

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 f...

Two Unspoken Assumptions About Collecting Social Security - 437

11 Jul 2023

Contributed by Lukas

YMYW listener Alan feels that there are two unspoken assumptions that many different podcasters make when it comes to claiming Social Security benefit...

Invest or Pay Off the Mortgage? - 436

04 Jul 2023

Contributed by Lukas

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. Moneyb...

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

27 Jun 2023

Contributed by Lukas

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 distributio...

Ready to Retire? 5 Retirement Spitball Analyses - 434

20 Jun 2023

Contributed by Lukas

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 retirem...

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

13 Jun 2023

Contributed by Lukas

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 ta...

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

06 Jun 2023

Contributed by Lukas

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 ...

How to Calculate Your Retirement Needs in Future Dollars - 431

30 May 2023

Contributed by Lukas

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 R...

How to Consider Your Pension Options for Retirement - 430

23 May 2023

Contributed by Lukas

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 payme...

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

16 May 2023

Contributed by Lukas

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...

What to Do With Inheritance Money? - 428

09 May 2023

Contributed by Lukas

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. ...

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

02 May 2023

Contributed by Lukas

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...

Spitballing Retirement Real Estate and Tax Strategies - 426

25 Apr 2023

Contributed by Lukas

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 ...

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

18 Apr 2023

Contributed by Lukas

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 choosi...

Investments vs. Retirement Withdrawal Strategy, FDIC Insurance - 424

11 Apr 2023

Contributed by Lukas

Should retirement living expenses be drawn from your stable value fund, your CD or money market, brokerage account, or FDIC insured bank accounts? Can...

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

04 Apr 2023

Contributed by Lukas

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 ret...

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

28 Mar 2023

Contributed by Lukas

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 alph...

Roth Conversions & Retirement Spitball Analysis - 421

21 Mar 2023

Contributed by Lukas

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 C...

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

14 Mar 2023

Contributed by Lukas

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,...

How to Start Planning for Retirement - 419

07 Mar 2023

Contributed by Lukas

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 plannin...

"Will I Ever Be Able to Retire?" - 418

28 Feb 2023

Contributed by Lukas

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 h...

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

21 Feb 2023

Contributed by Lukas

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 ne...

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

14 Feb 2023

Contributed by Lukas

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 por...

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

07 Feb 2023

Contributed by Lukas

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 an...

Medicare IRMAA, Roth Pro-Rata, & Real Estate Strategies - 414

31 Jan 2023

Contributed by Lukas

Modified adjusted income for Medicare and IRMAA and the pro-rata and aggregation rules for Roth conversions explained... clearly? Will a combat zone T...

Spitballing Diversified Portfolios for Retirement - 413

24 Jan 2023

Contributed by Lukas

How should young savers invest pensions and estimate their retirement income needs? Is going into your employee stock purchase plan a good portfolio d...

SECURE Act 2.0 & Retirement Rich, Cash Poor - 412

17 Jan 2023

Contributed by Lukas

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 mak...

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

10 Jan 2023

Contributed by Lukas

IRA withdrawal strategies when you retire in a down market, Roth contributions vs. Roth conversions, converting now or waiting to convert to Roth in r...

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

03 Jan 2023

Contributed by Lukas

Welcome to Your Money, Your Wealth® podcast, with CERTIFIED FINANCIAL PLANNER™ professional Joe Anderson and Certified Public Accountant Alan "Big ...

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

27 Dec 2022

Contributed by Lukas

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 fluctuatio...

Who to Trust? Second Opinion Retirement Spitball - 409

20 Dec 2022

Contributed by Lukas

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 r...

Where to Save for Early Retirement? - 408

13 Dec 2022

Contributed by Lukas

Asset location strategies, liquidity, and building up tax-free Roth IRA money when retiring early, how growth is taxed in taxable accounts, the pros a...

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

06 Dec 2022

Contributed by Lukas

We're hearing more about fixed-indexed annuities with these volatile financial markets. Is it time to reconsider? Plus, clarification on required mini...

How to Forecast Your Expenses in Retirement - 406

29 Nov 2022

Contributed by Lukas

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 ...

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

22 Nov 2022

Contributed by Lukas

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...

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

15 Nov 2022

Contributed by Lukas

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...

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

08 Nov 2022

Contributed by Lukas

Following the Fed's fourth consecutive interest rate hike last week, should you be changing your investing strategy to time this inflationary market, ...

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

01 Nov 2022

Contributed by Lukas

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? B...

Should Young People Save for Retirement? - 401

25 Oct 2022

Contributed by Lukas

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...

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

18 Oct 2022

Contributed by Lukas

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 loa...

Survivor Social Security and Lowering Taxes in Retirement - 399

11 Oct 2022

Contributed by Lukas

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 Secur...

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

04 Oct 2022

Contributed by Lukas

As the financial markets fall and then surge, Joe and Big Al talk about market timing, reallocating retirement contributions, and portfolio rebalancin...

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

27 Sep 2022

Contributed by Lukas

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 ret...

Backdoor Roth, Investing, and Taxes - 396

20 Sep 2022

Contributed by Lukas

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 pos...

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

13 Sep 2022

Contributed by Lukas

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 Flow...

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

06 Sep 2022

Contributed by Lukas

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 str...

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

30 Aug 2022

Contributed by Lukas

Should you convert money from your pre-tax retirement accounts to Roth now, or wait until retirement, or until required minimum distributions kick in?...

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

23 Aug 2022

Contributed by Lukas

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 retire...

Spitballing Retirement Planning in Your 30s - 391

16 Aug 2022

Contributed by Lukas

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 ...

Working After Retirement and Wealth Gifting Strategies - 390

09 Aug 2022

Contributed by Lukas

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 retiremen...

Save for a Home or Save for Retirement? - 389

02 Aug 2022

Contributed by Lukas

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 ...

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

26 Jul 2022

Contributed by Lukas

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 retirem...

A Model Retirement Plan Spitball Analysis - 387

19 Jul 2022

Contributed by Lukas

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...

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

12 Jul 2022

Contributed by Lukas

When the financial markets are down, should you postpone retirement? When inflation is up, should you change your investments and pile into things lik...

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

05 Jul 2022

Contributed by Lukas

Inflation is high, interest rates are high, and the financial markets are volatile. Are bonds and series I bonds good investments or bad investments r...

Can We Retire Soon? Retirement Spitball Analysis - 384

28 Jun 2022

Contributed by Lukas

"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 ret...

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

21 Jun 2022

Contributed by Lukas

Equitable accumulators, cash management accounts, and Social Security: with today's market volatility, how can you squeeze a few more dollars of incom...

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

14 Jun 2022

Contributed by Lukas

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...

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

07 Jun 2022

Contributed by Lukas

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 questi...

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

31 May 2022

Contributed by Lukas

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 compa...

6 Money Strategies for Down Markets Depending on Your Goals - 379

24 May 2022

Contributed by Lukas

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...

Is My BF BSing Me on RMDs? Required Minimum Distributions Explained - 378

17 May 2022

Contributed by Lukas

Required minimum distributions: how do they work, when do you have to take them, and do Roth IRAs have RMDs too? Plus, were the fellas being misleadin...

Roth IRA, 457, TSP, and Retire Early Spitball - 377

10 May 2022

Contributed by Lukas

Joe & Big Al talk strategy for converting to Roth and paying tax from the IRA when you have limited funds, eliminating required minimum distributions ...

Self-Employed Retirement, Fixed Index Annuities, and Investment Property - 376

03 May 2022

Contributed by Lukas

How does Social Security work for self-employed small business owners? Is there a solo 401(k) that allows after-tax contributions? How much cold, hard...

Roth Conversion Retirement Spitball Analysis - 375

26 Apr 2022

Contributed by Lukas

Does it make sense to do larger "Calvin Johnson" (megatron, aka mega backdoor) Roth conversions when the financial markets are way down? Should you co...

Annuities, Social Security, and Real Estate Taxes - 374

19 Apr 2022

Contributed by Lukas

When is it appropriate to buy an annuity? Joe and Big Al run a retirement annuity spitball analysis. When might it make sense to take Social Security ...

Can We Retire Early? Investing and Retirement "Rothification" - 373

12 Apr 2022

Contributed by Lukas

Will the Senate pass the SECURE Act 2.0, and will it require a Roth option for retirement savings? Plus, "pandemic unemployment" from the CARES Act an...

Retirement Spitball: Social Security, Pension, and Self-Employed - 372

05 Apr 2022

Contributed by Lukas

Spitballing retirement for a police officer turning teacher, a self-employed small business owner, an early retiree with an employee stock ownership p...

When Must You Pay Roth Conversion Taxes? - 371

29 Mar 2022

Contributed by Lukas

When do you have pay the taxes on a Roth IRA conversion to avoid any IRS penalties? Was it a mistake to convert to Roth IRA? What percentage of your a...

Taxes and Real Estate Investing Explained - 370

22 Mar 2022

Contributed by Lukas

Can multiple rental property losses be written off against other properties or income? What are the pros and cons of putting investment property in an...

Should You Claim Social Security Early? - 369

15 Mar 2022

Contributed by Lukas

What part do taxes play in deciding to claim Social Security early? If Social Security creates too much provisional income so that you have to pay tax...

Why Is It So Difficult to Time the Market? - 368

08 Mar 2022

Contributed by Lukas

How statistically and practically difficult is market timing? Plus, Backdoor Roth vs Roth conversions, rules, limits, and strategies for 401(k) and IR...

Dollar-Cost Averaging, Small Cap, and Stable Value Funds - 367

01 Mar 2022

Contributed by Lukas

What are dollar-cost averaging and reverse dollar-cost averaging? Joe and Big Al explain as they answer questions about paying Medicare premiums with ...

Roth Conversions vs. Roth Contributions - 366

22 Feb 2022

Contributed by Lukas

Should you use Roth contribution money to pay Roth conversion tax instead? Does the IRS really penalize ineligible Roth contributions? How will a mega...