Your Money, Your Wealth

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 LLC? How do you get the best tax breaks on rental real estate? How does real estate depreciation work? What do you need to think about when turning your primary residence into a rental property? Is a home equity line of credit (HECM, reverse mortgag...

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 on your Social Security benefits, does it make sense to claim early? If you apply for Social Security at age 70 but could've been taking spousal benefits, are you owed that money? How long was the recovery from the 1929 stock market crash, really? D...

How statistically and practically difficult is market timing? Plus, Backdoor Roth vs Roth conversions, rules, limits, and strategies for 401(k) and IRA contributions, moving retirement money between custodians like Vanguard and Fidelity, and negative but entertaining listener comments. But first, should a $100,000 inheritance be invested in tax deferred, taxable, or tax free accounts? Also, factor...

What are dollar-cost averaging and reverse dollar-cost averaging? Joe and Big Al explain as they answer questions about paying Medicare premiums with HSA funds, and ETFs vs mutual funds when dollar-cost averaging into small-cap value funds. Plus, why would you want to reduce the stock allocation in your emergency fund, and should a stable value fund be part of your portfolio? Is it possible to "re...

Should you use Roth contribution money to pay Roth conversion tax instead? Does the IRS really penalize ineligible Roth contributions? How will a mega backdoor Roth be taxed, and will the step transaction doctrine apply? Are family Social Security benefits affected if the spouse works? Plus, spitballing retirement pension options, and your comments. Show notes, free resources, Ask Joe & Al On Air:...

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 stacking rule, the foreign earned income exclusion, and taxes and working - or not - after you retire. Finally, at what point are you saving too much to pre-tax accounts, and is it a good idea to convert to that post-tax Roth before the tax brackets...

Covered calls, preferred stocks, interest on series I bonds, required minimum distributions (RMD) from your retirement accounts and when they must begin, using retirement savings at age 72 to buy a home, calculating the highest possible Social Security benefit, and how it may be taxed. Plus, listener comments about YMYW and Andi's record collection! Show notes, free resources, transcript, Ask Joe...

Should a trust be the beneficiary of your retirement accounts? Are withdrawal restrictions and required minimum distributions (RMD) reasons to transfer out of the thrift savings plan (TSP) at retirement? Plus, alternative minimum tax (AMT) explained, and strategies for health savings account (HSA) contributions and restricted stock units (RSU). Free financial resources, Ask Joe & Al On Air: https:...

Early retirement, backdoor and mega-backdoor Roth conversions, paying tax on a conversion, asset location... the important topics from our most popular podcast episodes and YouTube videos of 2021. Plus, "impactful" listener comments and the funniest Derails of 2021 (in real time!) Show notes, financial resources, Ask Joe & Al On Air: https://bit.ly/ymyw-362

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 earning and saving? Plus, a Roth conversion strategy when your income is too high. How to know if it pays for you to convert & how much, and should you contribute to a rollover IRA before or after leaving a job? Finally, should you purchase long-term care...

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 take as much investing risk as possible, or buy a condo? Plus, the tax-efficiency of robo-advisor brokerage account withdrawals, backdoor Roth conversions under the Build Back Better Act, using a charitable remainder trust to avoid inherited IRA tax und...

Learn how to get the biggest Social Security payment possible, whether you're married, divorced, or entitled to survivor benefits. Can you still file and suspend? What's a restricted application? What does "deemed" mean? Plus, the little-known family Social Security benefits. The first YMYW podcast of 2022 is a compilation of answers to all of your most recent spousal Social Security questions. Vi...

Spitballing Roth conversions: a conversion and pension lump sum strategy, converting vs. harvesting 0% long term capital gains, and how to avoid double taxed Roth conversions. Plus, how to allocate assets when using the Rule of 55? Do retirees regret not spending more in retirement? Will paying a thrift savings plan loan with real estate income avoid income tax? Will assets be better protected aga...

Does the 5-year Roth clock start with every Roth conversion? Plus, a Social Security, Medicare, IRMAA, Roth conversion spitball, a self-employed retirement savings and tax planning spitball, and Delaware Statutory Trusts, security-based loans, charitable remainder trusts, and other charitable giving strategies explained. Also, will your portfolio grow faster with the help of a financial advisor? V...

Should those in the 35% tax bracket contribute to traditional 401(k) or Roth 401(k)? Should a self-employed cryptocurrency investor do Roth conversions or tax gain harvesting? Also, a retirement spitball for a couple, age 35, wanting to retire with $5M at age 60. Plus, do the SECURE Act rules for required minimum distributions (RMDs) apply when inheriting an inherited IRA? Finally, comments on the...

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? How should a self-employed investor in Vanguard's Total Stock Market Index Fund (VTSAX) get retirement-ready? How to pay for new home construction and keep the earned income and child tax credits? Should Roth conversion funds come from retirement,...

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 requires moving your pension to an investment plan? Or maybe your only pension options are either 10-year period certain or joint with rights of survivorship? All of these pension spitball analyses are compiled into this single episode to help you choos...

How does the "Buy, Borrow, Die" strategy of the uber-wealthy work? Stacking capital gains vs. Roth conversions, contributing to a non-deductible IRA vs. a brokerage account, and minimizing tax when a trust is the TSP beneficiary. Also, why delay Social Security to age 70 if you don't need the money, and estimating benefits with a future salary of $0. Finally, can you "ghost" an advisor? Should you...

Can your investment portfolio be over diversified? How do dividends and net unrealized appreciation (NUA) work? How will ownership inequality in the stock market impact future returns for most investors? What do Joe & Big Al think of target date funds? Plus, the YMYW podcast is now on video! Watch the fellas spitball on annuities, bonds, long-term treasuries, risk tolerance, and the buckets of mon...

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 good way to liquidate property? Is there a point to Roth conversions when leaving your estate to charity? Should you name your trust as beneficiary on retirement accounts? When to draw from Social Security, pension, and annuity in retirement? Plus, Roth...

In what order you should contribute into which accounts for retirement? Joe & Al explain the reasoning behind the sequence of retirement savings and where a health savings account (HSA) fits. Following some retirement plan spitball analyses and Roth conversion strategizing, the fellas explain whether capital gains are taxed progressively, how required minimum distributions are taxed, & they revisi...

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 with unused 529 plan education savings funds, rules for 401(a) accounts, understanding the alternative minimum tax, the latest tax proposals, how to calculate employer solo 401(k) contributions - and that's just the tip of the iceberg. Visit the podcast...

How to calculate modified adjusted gross income (MAGI) for Medicare IRMAA, Social Security benefits when you're planning to FIRE (Financial Independence / Retire Early), family Social Security benefits for those with minor children, and a strategy to qualify for the Obamacare ACA subsidy. Plus, Roth conversions prior to early retirement, and untangling stock options, long-term incentives (LTI), an...

Asset allocation is the delicate balance of stocks, bonds, and other assets in an investment portfolio. What allocation is best for your retirement needs? What mix of domestic and international stocks is best? Is a 90/10 equities to fixed income mix crazy in a $10M portfolio? Should Dad be at 90/10 or 60/40? Can pension & Social Security count as a bond allocation? Plus, legacy tax planning: how t...

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 before selling your current home? Also: buying property in California with your kids, and should you pay the mortgage or save for retirement? Plus, what's the best way to pay credit card debt? Do corporations really pay no taxes? Can you contribute...