Your Money, Your Wealth

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"...

Backdoor Roth Conversions and Investing for Kids - 293

29 Sep 2020

Contributed by Lukas

Are you screwing up your Backdoor Roth IRA conversion? Find out. Plus, tax on mega-Backdoor Roth conversions, Medicaid spend-down rules and your Roth ...

Will Estate Tax Law Changes Affect Your Family Financial Plan? - 292

22 Sep 2020

Contributed by Lukas

How might Joe Biden's or Donald Trump's changes to the lifetime estate tax exemption impact your estate plan? Plus, is there any reason to have pre-ta...

Roth Conversions, Annuities and Inherited IRAs - 291

15 Sep 2020

Contributed by Lukas

Answering questions across the financial and retirement spectrum, with topics like when your traditional IRA is growing faster than you can convert to...

Market Timing and Day Trading in a Roth IRA? - 290

08 Sep 2020

Contributed by Lukas

Is timing the market and day trading in your Roth IRA in retirement a good idea? How are you taxed if you collect dividends vs. reinvesting? Plus, tax...

Backdoor Roth IRA Conversions, Stimulus and Self-Employed Retirement -289

01 Sep 2020

Contributed by Lukas

How do you report a backdoor Roth IRA conversion over two tax years, and is there a point at which the backdoor Roth doesn't make sense? Plus, more st...

YMYW Spitball Analysis 2: Retirement and Social Security - 288

25 Aug 2020

Contributed by Lukas

The YMYW Retirement Plan Spitball Analysis was so popular that it's time for part 2! Where do Roth IRA conversions, primary residences, and rental rea...

Roth Conversion Tax Planning Strategies and Annuities - 287

18 Aug 2020

Contributed by Lukas

Tax planning for Roth IRA conversions with itemized deductions, dividends, and long term capital gains, a Roth conversion vs. investing a 401(k) distr...

Dividend-Paying Stocks and Investing Strategies at All Ages - 286

11 Aug 2020

Contributed by Lukas

Investing strategies for dividend-paying stocks and how the pro-rata rule for Roth conversions work with dividends. Plus, Wealthfront, M1, Paul Merrim...

New Stimulus Check & Coronavirus Relief Package On the Way? - 285

04 Aug 2020

Contributed by Lukas

With CARES Act provisions expiring, Joe & Big Al recap the two new stimulus bills - the HEALS Act and the HEROES Act - now being negotiated in Congres...

What Is Your Retirement Number? YMYW Spitball Retirement Analysis - 284

28 Jul 2020

Contributed by Lukas

Joe and Big Al spitball retirement plan considerations, including: - investing in brokerage and Roth instead of pre-tax - getting tax diversification ...

Tax Gain Harvesting, Active vs. Passive Investments… and Roth Conversions - 283

21 Jul 2020

Contributed by Lukas

Should you tax gain harvest or do a Roth IRA conversion? Should active or passive investments go in retirement accounts? If you're on the younger side...

How to Do a Roth Conversion and Pay Taxes On It - 282

14 Jul 2020

Contributed by Lukas

Do you have to transfer from a 401(k) to a traditional IRA before you do a Roth IRA conversion? Does the pro-rata rule apply? Also, the logistics of p...

Will These Three Things Affect Your Social Security? - 281

07 Jul 2020

Contributed by Lukas

What impact do ex-spouses, income, and early retirement have on collecting your Social Security benefits? Plus, indexed universal life insurance, esta...

Are These Retirement Investment Strategies On Track? - 280

30 Jun 2020

Contributed by Lukas

Joe and Big Al take a look at an investing strategy a listener set up for his parents, and they run the numbers on their variable annuity. They also k...

Real Estate, Roth Conversions, and Social Security - 279

23 Jun 2020

Contributed by Lukas

Reducing real estate taxes, leveraging new rental income properties, coordinating Social Security benefits with Roth conversions, and bragging about y...

Can You Do a Coronavirus-Related Distribution to Roth Conversion? - 278

16 Jun 2020

Contributed by Lukas

Is it possible to do a Roth IRA conversion with a Coronavirus-Related Distribution from your retirement accounts? Joe and Big Al will explain whether ...

Roth IRA Conversion and Contribution Rules - 277

09 Jun 2020

Contributed by Lukas

Roth IRA contributions and conversions come with plenty of rules: contribution rules, withdrawal rules, safe harbor rules, pro-rata and aggregation ru...

Pre-Tax or Roth Contributions for Retirement Savings? - 276

02 Jun 2020

Contributed by Lukas

Should market volatility and the economic downturn due to COVID-19 change where you save for retirement? Should contributions go to pre-tax accounts o...

Social Security WEP, GPO & Roth IRA Conversion Strategies - 275

26 May 2020

Contributed by Lukas

The windfall elimination provision (WEP), government pension offset (GPO) & spousal Social Security benefits. Also, Roth IRA conversions and Medicare,...

CARES Act: Distributions, RMDs & Dependents - 274

19 May 2020

Contributed by Lukas

Financial planning strategies around Coronavirus-Related Distributions from retirement accounts and required minimum distributions (RMDs). Plus, liste...

Real Estate, Roth Conversions & Annuities - 273

12 May 2020

Contributed by Lukas

A mixed bag of questions on everything from spousal solo 401(k) contributions and inherited IRAs to house-buying strategies, to the fan-favorite, ripp...

Asset Location: Where Should You Hold Retirement Investments? - 272

05 May 2020

Contributed by Lukas

What types of investments you keep in your taxable, tax-deferred and tax-free accounts can play a big part in how much tax you pay over time. In this ...

4 Financial Strategies from the Stimulus Package - 271

28 Apr 2020

Contributed by Lukas

In this jam-packed episode of the Your Money, Your Wealth® podcast, stimulus payments for self-employed, dependents, and those who message us on Face...

In Market Volatility, Beware of Annuity Pitches - 270

21 Apr 2020

Contributed by Lukas

In these volatile markets, pitches for fixed indexed annuities will be on the upswing. Here's how to analyze them for yourself. Plus, CARES Act stimul...

Revisiting Roth IRA Conversion Strategies - 269

14 Apr 2020

Contributed by Lukas

Roth IRA conversion pro-rata rule considerations with RMDs on an inherited IRA, tax bracket planning to account for the loss of a spouse, and the stat...

CARES Act: What's in the Coronavirus Stimulus Package - 268

07 Apr 2020

Contributed by Lukas

Recovery rebates, new rules for retirement account distributions, stimulus checks for those on Social Security & unemployment benefits. Plus, should a...

Analyzing 5 Investing Strategies for Volatile Markets - 267

31 Mar 2020

Contributed by Lukas

In these volatile financial markets, are you reconsidering your investing strategies? Joe and Big Al discuss cash, selling stocks in taxable accounts ...