Your Money, Your Wealth

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...

Real Estate Investing: What Are Cash-on-Cash and Cap Rate? - 365

15 Feb 2022

Contributed by Lukas

What is a cap rate? What does cash-on-cash return mean? Joe and Big Al on rental real estate investing as an early retirement income source. Plus, the...

Covered Call Investing Strategies Explained, RMDs, and Social Security Taxation - 364

08 Feb 2022

Contributed by Lukas

Covered calls, preferred stocks, interest on series I bonds, required minimum distributions (RMD) from your retirement accounts and when they must beg...

Stock Acquisition, HSA, AMT, TSP, RSU, and Trust as Retirement Beneficiary - 363

01 Feb 2022

Contributed by Lukas

Should a trust be the beneficiary of your retirement accounts? Are withdrawal restrictions and required minimum distributions (RMD) reasons to transfe...

Early Retirement, Roth Conversion Tax: YMYW Best of 2021 - 362

25 Jan 2022

Contributed by Lukas

Early retirement, backdoor and mega-backdoor Roth conversions, paying tax on a conversion, asset location... the important topics from our most popula...

Financially Able But Afraid to Retire - 361

18 Jan 2022

Contributed by Lukas

The psychology of retirement: what if you've saved enough and you're financially ready to retire, but you're paralyzed by the idea of no longer earnin...

Should You Invest in the Stock Market or Buy Real Estate? - 360

11 Jan 2022

Contributed by Lukas

You've saved money for a house downpayment. Should you invest it in the stock market until you're ready to buy that property? Should a young saver tak...

Social Security Benefits for Spouses, Ex-Spouses, and Survivors - 359

04 Jan 2022

Contributed by Lukas

Learn how to get the biggest Social Security payment possible, whether you're married, divorced, or entitled to survivor benefits. Can you still file ...

Roth Conversions, the Rule of 55, and Retirement Withdrawal Regrets - 358

28 Dec 2021

Contributed by Lukas

Spitballing Roth conversions: a conversion and pension lump sum strategy, converting vs. harvesting 0% long term capital gains, and how to avoid doubl...

Does the 5 Year Rule Apply to Each Roth Conversion? - 357

21 Dec 2021

Contributed by Lukas

Does the 5-year Roth clock start with every Roth conversion? Plus, a Social Security, Medicare, IRMAA, Roth conversion spitball, a self-employed retir...

Spitballing Retirement and the Build Back Better Tax Proposal - 356

14 Dec 2021

Contributed by Lukas

Should those in the 35% tax bracket contribute to traditional 401(k) or Roth 401(k)? Should a self-employed cryptocurrency investor do Roth conversion...

Saving and Investing for Retirement with Company Stock, Bonds, and VTSAX? - 355

07 Dec 2021

Contributed by Lukas

How much company stock is too risky? Can I bonds be the "cash" in a portfolio? Would saving to a brokerage instead of 401(k) or 403(b) ever make sense...

Retirement Pension Lump Sum or Monthly Annuity Payment? - 354

30 Nov 2021

Contributed by Lukas

Should you take your pension all at once in a lump sum when you retire or spread it out over monthly annuity payments? What if the lump sum choice req...

Retirement Spitballing, Social Security, and Hiring & Ghosting Financial Advisors - 353

23 Nov 2021

Contributed by Lukas

How does the "Buy, Borrow, Die" strategy of the uber-wealthy work? Stacking capital gains vs. Roth conversions, contributing to a non-deductible IRA v...

Dividends, Asset Classes, and Diversification: How to Invest for Retirement? - 352

16 Nov 2021

Contributed by Lukas

Can your investment portfolio be over diversified? How do dividends and net unrealized appreciation (NUA) work? How will ownership inequality in the s...

Estate Planning, Social Security, and TSP to Roth Conversions - 351

09 Nov 2021

Contributed by Lukas

Is there a step up in basis on (and advantage to) a joint tenants with rights of survivorship brokerage account? Is a charitable remainder trust a goo...

Spitballing the Sequence of Retirement Savings - 350

02 Nov 2021

Contributed by Lukas

In what order you should contribute into which accounts for retirement? Joe & Al explain the reasoning behind the sequence of retirement savings and w...

How to Pay the Tax on a Roth Conversion - 349

26 Oct 2021

Contributed by Lukas

Learn the basics of Roth IRA conversions, how to calculate the tax on a Roth conversion, when to pay the tax, and more. Plus, ideas for what to do wit...

Medicare, Social Security, and FIRE Early Retirement - 348

19 Oct 2021

Contributed by Lukas

How to calculate modified adjusted gross income (MAGI) for Medicare IRMAA, Social Security benefits when you're planning to FIRE (Financial Independen...

What's the Right Mix of Stocks and Bonds for Your Investment Portfolio? - 347

12 Oct 2021

Contributed by Lukas

Asset allocation is the delicate balance of stocks, bonds, and other assets in an investment portfolio. What allocation is best for your retirement ne...

Buying and Selling Your House or Real Estate - 346

05 Oct 2021

Contributed by Lukas

How do you estimate net investment income tax when selling your primary residence? Is the all-in-one mortgage a temporary solution when buying a house...

Working or Retiring Abroad and Early Retirement Spitball - 345

28 Sep 2021

Contributed by Lukas

Retiring overseas and foreign earned income exclusion eligibility, using your tax refund for a back door Roth conversion, and working abroad and contr...

It Could Be Over for the Mega Backdoor Roth IRA - 344

21 Sep 2021

Contributed by Lukas

Joe & Big Al outline the House Ways and Means Committee's sweeping tax proposal that would impact Roth contributions, Roth conversions, RMDs, the back...

HELOC, All-in-One Mortgages, and What to Do With Old Life Insurance Policies - 343

14 Sep 2021

Contributed by Lukas

What is a home equity line of credit? Is a HELOC better than a traditional mortgage? What are all-in-one mortgage loans? Does it make sense to buy a c...

Roth 401(k), Conversions, RMDs, and Cap Gains - 342

07 Sep 2021

Contributed by Lukas

How to calculate Roth conversions to reduce taxes at required minimum distribution age? What are the rules for RMDs from Roth 401(k)? How does the 5 y...

Early Retirement Spitball Analysis - 341

31 Aug 2021

Contributed by Lukas

Some YMYW listeners have had enough of the 9 to 5 and are ready to punch early. Joe & Big Al spitball on whether they're financially ready for a long,...

Where to Locate Assets for Tax Efficiency Without Compromising Growth? - 340

24 Aug 2021

Contributed by Lukas

Asset location: how to position assets to pay less tax without sacrificing investment growth? Should young folks contribute all of their retirement sa...

Should We Do a Roth Conversion? - 339

17 Aug 2021

Contributed by Lukas

Moving money from tax-deferred retirement accounts to accounts with lifetime tax-free investment growth: should you do Roth IRA conversions? Before ma...

What to Do When You Own Too Much of One Stock - 338

10 Aug 2021

Contributed by Lukas

Ways to diversify concentrated stock positions, like using a donor-advised fund. How does the IRS know if a required minimum distribution is a qualifi...

Is It Crazy to Be Happy Paying Tax on Massive Stock Market Gains? - 337

03 Aug 2021

Contributed by Lukas

Is it better to pay tax on $5 million than on $1M? Also, an asset location strategy to lower RMDs and taxes but still maintain portfolio growth, and a...

How to Spitball Your Most Tax-Efficient Retirement Withdrawal Strategy - 336

27 Jul 2021

Contributed by Lukas

Spitballing tax-efficient retirement withdrawals, savings, Social Security, and required minimum distributions (RMD). Plus, leveraging whole life insu...

Which States Are the Most Tax-Friendly in Retirement? - 335

20 Jul 2021

Contributed by Lukas

Which states are best for retirement taxes? When moving to a state with a lower cost of living, is it wise to take on mortgage debt to invest in the m...

Are We On Track for Retirement? Financial Plan Spitball Analysis - 334

13 Jul 2021

Contributed by Lukas

Spitballing retirement readiness for Sean and for Little Al who has UK retirement funds and is desperate to quit work now. Plus, how can Doug do some ...

Are Financial Advisors Really Worth the Money? - 333

06 Jul 2021

Contributed by Lukas

Do you need a CERTIFIED FINANCIAL PLANNER™ professional? Is a financial advisor worth hiring? What does a fee-only fiduciary do, anyway? We get thes...

Roth Conversions, Medicare, and Required Minimum Distributions - 332

29 Jun 2021

Contributed by Lukas

Do Roth IRA conversions increase Medicare premiums? How can you convert to Roth and stay below the IRMAA threshold (that is, Medicare's Income-Related...

What is the Best Age to Retire, Financially Speaking? - 331

22 Jun 2021

Contributed by Lukas

Financially, what's the ideal retirement age? Are Roth conversions to the 37% tax bracket a good idea when you've achieved FAHR (financial abundance, ...

Has the Government Ever Reduced Social Security Benefits? - 330

15 Jun 2021

Contributed by Lukas

Have Social Security payments ever been cut for those already receiving them? Plus, survivor benefits, the Windfall Elimination Provision (WEP), and C...

How to Protect Investments Against a Stock Market Crash? - 329

08 Jun 2021

Contributed by Lukas

Strategies to protect your portfolio from a stock market crash: put options, collars, non-correlated alternative investments, and tax-managed buy-and-...

Should People in High Tax Brackets Save in Roth Retirement Accounts? - 328

01 Jun 2021

Contributed by Lukas

Roth 401(k) contributions and "Megatron" (er, mega backdoor) Roth contributions for highly compensated employees, and the Roth conversion strategy of ...

How to Avoid a Tax Time Bomb: Retirement Plan Spitball Analysis - 327

25 May 2021

Contributed by Lukas

Maxing out Roth IRA, 457, and HSA - check. Pension - check. What else do you need for retirement planning? How do pension and Social Security fit into...

How to Get Tax-Free Growth on Investments for Life - 326

18 May 2021

Contributed by Lukas

Learn to rack up tax-free Roth retirement income: Roth IRA vs. Roth 401(k), paying the tax on a Roth conversion, avoid violating the 60-day rollover r...

Capital Gains Tax Vs. Ordinary Income Tax Explained - 325

11 May 2021

Contributed by Lukas

"Can you explain how long-term capital gains are 'stacked on top' of ordinary income?" Here are all the YMYW capital gains tax vs. ordinary income tax...

Which Asset Classes Are Good Investments to Hedge Against Inflation? - 324

04 May 2021

Contributed by Lukas

Your latest investing strategy questions answered: are gold, real estate investment trusts (REITs), international and small-cap value funds good infla...

Real Estate: Should We Sell Rental Property to Buy a Primary Residence? - 323

27 Apr 2021

Contributed by Lukas

Spitballing a real estate strategy: sell investment rental properties to buy a home, use restricted stock units (RSU), or both? Plus, is it worth it t...

Pay Down the Mortgage or Buy Long Term Care Insurance? - 322

20 Apr 2021

Contributed by Lukas

Fielding emails on a wide range of personal finance topics: ex-spouse Social Security benefits, paying the mortgage or buying long-term care insurance...

Inflation, Variable Annuities, Real Estate: How to Invest Against Risk - 321

13 Apr 2021

Contributed by Lukas

Is selling rental property to buy a variable annuity a good risk management strategy against sequence of return and interest rate risks? Small-cap vs....

Early Retirement: Can You Afford to Retire Now? - 320

06 Apr 2021

Contributed by Lukas

William has investing experience, money in the bank, and a retirement plan. Is he ready for early retirement at age 59.5? Plus, BRRR real estate inves...

Roth IRA Excess Contributions and the Pro-Rata Rule - 319

30 Mar 2021

Contributed by Lukas

Recharacterization of excess Roth IRA contributions, converting post-tax contributions to Roth 401(k), and the pro-rata rule. Plus, target date fund l...

Firefighters' Retirement Plan Spitballing, Annuities, and RMDs - 318

23 Mar 2021

Contributed by Lukas

Spitballing firefighters' retirement: deferred option retirement plans (DROP), HSA (health savings) vs. HYSA (high yield savings), and hear why YMYW a...

Charitable Giving and Roth Conversion Retirement Tax Strategies - 317

16 Mar 2021

Contributed by Lukas

How to make the most of a retirement strategy that involves a thrift savings plan, Roth IRA conversions, and charitable giving from a donor-advised fu...

Monthly Retirement Pension Vs. Lump Sum Payment: How to Choose -316

09 Mar 2021

Contributed by Lukas

Choosing the pension lump sum or monthly payment: let it ride, roll it, or annuitize it? Plus, spitball analyses involving the 72(t) tax election, a d...

Are These Three Investment Products Too Good To Be True? - 315

02 Mar 2021

Contributed by Lukas

Should you invest in a real estate investment trust (REIT)? What about a fixed indexed annuity or structured notes? What can be done about an indexed ...

Is the Backdoor Roth IRA a Good Strategy For You? - 314

23 Feb 2021

Contributed by Lukas

Are you eligible for a backdoor Roth IRA conversion? Is it taxed? How does a Roth 401k differ from a Roth IRA? Can you buy Mom's condo for below marke...

Are You Financially Ready for Retirement? - 313

16 Feb 2021

Contributed by Lukas

A retirement plan spitball analysis for an engineer wondering if he can afford to retire, required minimum distribution questions answered, and discus...

"Super Roth": Should You Overfund Supplemental Executive Retirement Plan Insurance? -312

09 Feb 2021

Contributed by Lukas

Whether you call it a SERP, an individual supplemental executive retirement plan, a private pension, or the "Super Roth," the strategy is overfunding ...

Social Security, Medicare, HSA and Roth Conversions - 311

02 Feb 2021

Contributed by Lukas

Find out just how intertwined healthcare and retirement are, with answers to questions about Medicare as it relates to Social Security, Health Savings...

[SPECIAL] GameStop: Stocks Gone Wild! Should You Join the Day Trading Craze? - 310a

29 Jan 2021

Contributed by Lukas

This week GameStop, AMC and Blackberry stocks went wild, with hedge funds shorting the stocks, and Redditors using the Robinhood investing app to put ...

What's the Best Way to Take Retirement Distributions? - 310

26 Jan 2021

Contributed by Lukas

Drilling down into the specifics of retirement distribution strategies: dollar cost averaging, pro-rata withdrawals, and buckets vs. the total return ...

Retirement Plan Spitball Analyses for Side Hustles, Clergy & Grandkids - 309

19 Jan 2021

Contributed by Lukas

Answering questions from across the personal finance spectrum: inherited IRAs and late RMDs, contributing to non-qualified deferred compensation plans...

How to Do the Mega Backdoor Roth IRA - 308

12 Jan 2021

Contributed by Lukas

Backdoor Roth IRA withdrawal rules and the mechanics of the mega backdoor (dump truck!) Roth. Can you still contribute to a Roth after a rollover? How...

How to Choose Your Pension Options and Retirement Withdrawal Strategy - 307

05 Jan 2021

Contributed by Lukas

In this first YMYW episode of 2021, Joe and Big Al go over estate planning strategies for CFP® candidate/Redditor Nate in SC, they do a spitball anal...

Social Security, Medicare and Real Estate - 306

29 Dec 2020

Contributed by Lukas

Wrapping up the longest year in history with means testing for Social Security, healthcare when one spouse is on Medicare, and how Roth IRA conversion...

What's the Best Retirement Withdrawal Strategy? - 305

22 Dec 2020

Contributed by Lukas

'Twas the Tuesday before Christmas and all through YMYW, Joe and Big Al's stockings were stuffed with your money questions: which strategy do they lik...

5 Last Minute Ways to Cut Your 2020 Taxes - 304

15 Dec 2020

Contributed by Lukas

A final look at the CARES Act COVID-19 stimulus package, Coronavirus related distributions, and whether they affect your 2020 taxes. Plus, action item...

How to Use Tax Diversification in Your Retirement Portfolio - 303

08 Dec 2020

Contributed by Lukas

There are taxable, tax-deferred, and tax-free accounts, and the proper balance of investments in each is called tax diversification. Are you tax diver...

Should You Pay Off the Mortgage? First Consider Your Tax Strategy - 302

01 Dec 2020

Contributed by Lukas

Paying off your mortgage? First, think of your investing and tax strategy. And, if you max out retirement and health savings accounts and own real est...

Borrow Money to Pay Tax on a Roth IRA Conversion? - 301

24 Nov 2020

Contributed by Lukas

Should you borrow money to pay the tax on a Roth IRA conversion? Should you do a Roth conversion or capture non-qualified long term capital gains? How...

Top Funniest Moments From the Your Money Your Wealth Podcast - 300

17 Nov 2020

Contributed by Lukas

Joe and Big Al have been making retirement planning, investing, and tax reduction fun for years on the YMYW podcast. We're celebrating 300 episodes wi...

Rental Real Estate Property: How to Calculate Cap Rates and Depreciation - 299

10 Nov 2020

Contributed by Lukas

When does the real estate depreciation 121 exclusion happen and how do you account for rental property equity, or cap rates, to calculate retirement i...

Retirement Portfolio Strategies and Making Sense of Fees - 298

03 Nov 2020

Contributed by Lukas

Should retirement savings go in the older spouse's accounts first? Does Marion have a good VTSAX to VTWAX tax-loss harvesting and portfolio rebalancin...

The Barn Door, Garage Door, Mega Backdoor Roth IRA Conversion - 297

27 Oct 2020

Contributed by Lukas

What is the MEGA backdoor Roth IRA conversion and should you do one? How do you create retirement income for the gap between retiring at 66 and taking...

YMYW Spitball Analysis 3: Tax Diversification and Asset Allocation - 296

20 Oct 2020

Contributed by Lukas

On round 3 of the YMYW Retirement Plan Spitball Analysis, Joe and Big Al focus on your tax diversification and asset allocation questions: should more...

All About the Backdoor Roth IRA Strategy - 295

13 Oct 2020

Contributed by Lukas

Should you wait until retirement to do a backdoor Roth IRA conversion? Plus, the pro-rata rule, self-employed modified adjusted gross income vs. AGI, ...

Rebalancing Your Retirement Portfolio in Market Downturns - 294

06 Oct 2020

Contributed by Lukas

Retirement portfolio rebalancing when the market goes down, accumulation, de-accumulation, dollar cost averaging, and IRR, ROR, and CAGR (not "kegger"...