Your Money, Your Wealth

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 an argument against Roth IRAs. Is it valid? Plus, what counts as contributions if you withdraw from Roth after 5 years? Why not pay the tax on a Roth conversion out of an IRA? Roth conversions vs. the medical insurance ACA subsidy, and what? Joe, arrogant?! Podcast survey, free resources, transcript, ask money questions: https://bit.ly/ymyw-337

Spitballing tax-efficient retirement withdrawals, savings, Social Security, and required minimum distributions (RMD). Plus, leveraging whole life insurance, and is investing 15% of an all-stock portfolio in preferred stocks too risky? First, Joe and Big Al break down the mechanics and safety of doing a 401(k) to IRA rollover. Visit the podcast show notes to access the transcript, free financial resources, and to ask your money questions: https://bit.ly/YMYW-336

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 market? Does it make a difference if you do a Roth conversion before or after moving states? Plus, is it better to do Roth conversions with ETFs or mutual funds? Is 0% long-term capital gains a hoax? Also, ABLE accounts for those with disabilities, and healthcare costs vs. taxes. Financial resources, transcript, Ask Joe & Big Al On Air: https://bit.ly/YMYW-335

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 tax arbitrage with pensions, Roth conversions, and Social Security? Can Mary switch to her ex-spouse's Social Security benefit? First, Tyler has questions about restricted stock units (RSUs) and net unrealized appreciation (NUA). Access the transcript and free financial resources, and Ask Joe & Big Al On Air in the podcast show notes: https://bit.ly/YMYW-334

Do you need a CERTIFIED FINANCIAL PLANNER™ professional? Is a financial advisor worth hiring? What does a fee-only fiduciary do, anyway? We get these questions frequently, and now you can listen to Joe & Big Al's answers from 2016 to the present, all in a single episode. Plus, how to measure CFP® performance, and when it's time to part ways with your financial planner. Access the transcript and free financial resources, and Ask Joe & Big Al On Air, all in the podcast show notes: https://bit.ly/YMYW-333

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 Monthly Adjustment Amount)? Also, a Roth conversion strategy to account for RMDs, those 5-year rules for withdrawing from your Roth depending on whether you're over or under age 59 and a half, and "how much should I have in a Roth to be in a low tax bracket in retirement?" Financial resources, transcript, Ask Joe & Big Al On Air: https://bit.ly/YMYW-332

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, happily retired)? Should you stop investing and start saving cash when approaching retirement? You're maxing retirement accounts, should you save to a deferred comp plan too? Is the employee stock purchase plan too many eggs in one basket? And finally, how to pay for long-term care insurance? Podcast show notes, Ask Joe & Big Al On Air: https://bit.ly/YMYW-331

Have Social Security payments ever been cut for those already receiving them? Plus, survivor benefits, the Windfall Elimination Provision (WEP), and CalPERS. Also: what retirement accounts should you save into in what order? How should you withdraw from a brokerage account in retirement? And paying the tax on a Roth conversion, overfunding a 529 plan for education, and mortgage refinancing and interest deduction. Access the transcript and financial resources, ask Joe & Big Al On Air: https://bit.ly/YMYW-330

Strategies to protect your portfolio from a stock market crash: put options, collars, non-correlated alternative investments, and tax-managed buy-and-hold. Also: how to measure financial advisor performance? How does tax-loss harvesting work? Are health savings accounts (HSA) tax-free? Is alternative minimum tax (AMT) a concern when moving Roth to an annuity? And how to get your MIL not to smoke in your car? YMYW podcast show notes, free financial resources, transcript, Ask Joe & Al: https://bit.ly/YMYW-329

Roth 401(k) contributions and "Megatron" (er, mega backdoor) Roth contributions for highly compensated employees, and the Roth conversion strategy of filling the tax bracket. Plus, moving a pension to an investment plan, owning real estate in a self-directed IRA, paying off the mortgage vs. refinancing your house, spousal vs. survivor Social Security benefits, and rolling a whole life insurance policy to a variable annuity. Access the YMYW podcast show notes and Ask Joe & Al on air: https://bit.ly/YMYW-328

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 your fixed income portfolio mix? Should you be more aggressive with Roth conversions? Is a 5% equities growth rate good for early retirement plans with inflation? Will a Spousal Lifetime Access Trust (SLAT) protect assets from a tax time bomb? Plus a SECURE Act 2.0 overview. Transcript, financial resources, ask your money questions at https://bit.ly/YMYW-327

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 rule on a mega backdoor Roth, and Roth IRA contributions when receiving restricted stock units (RSU) in retirement. Plus, moving money from solo 401(k) to IRA before age 59.5, suggestions for a CFP® to be, and matching your umbrella insurance policy to your net worth. Access the transcript & financial resources, ask your money questions: https://bit.ly/YMYW-326

"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 discussions, together in a single episode, to help you craft a tax-efficient strategy for managing dividends, Roth conversions, and paying less capital gains tax. Will your taxes be going up? Subscribe to the YMYW podcast and newsletter for the latest updates. Access the transcript and financial resources, ask your money questions: https://bit.ly/YMYW-325

Your latest investing strategy questions answered: are gold, real estate investment trusts (REITs), international and small-cap value funds good inflation hedges? Besides the S&P 500, what sectors or asset classes should you invest in for long-term portfolio diversification? Should you buy bonds? How should an 18-year-old invest the money in a Roth 401(k)? Also, how can you get out of a non-qualified annuity? Access the transcript and financial resources, ask your money questions: https://bit.ly/YMYW-324

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 to hire a financial advisor? Is it a good idea to do Roth IRA conversions to the top of your tax bracket each year? How can you move non-deductible IRA money to Roth IRA without paying taxes again? And a cautionary tale about Roth conversions and stimulus payments. Access the transcript and financial resources, ask your money questions: https://bit.ly/YMYW-323

Fielding emails on a wide range of personal finance topics: ex-spouse Social Security benefits, paying the mortgage or buying long-term care insurance, how the FIRE community uses the Roth conversion ladder, tax rules for sole proprietors hiring minors, using excess 529 plan education savings, paying taxes or paying back a Coronavirus Related Distribution, and when to file form 8606 to report IRA contributions. Access the transcript and financial resources, ask your money questions: https://bit.ly/YMYW-322

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. emerging markets: which has better risk-adjusted returns for market volatility? Are eREITs (non-traded real estate investment trusts) a good retirement investment? Is RPAR Risk Parity ETF a good inflation hedge? Should you do tax gain harvesting in declining financial markets? Access the transcript and resources, ask money questions: https://bit.ly/YMYW-321

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 investing and Roth IRA, Backdoor Roth conversions, and "Megatron" Roth contributions. Also, capital gains vs ordinary income, and are restricted stock units (RSU) ordinary income? Do they impact Social Security benefits? When can you collect spousal Social Security? Access the transcript and financial resources, ask your money questions: https://bit.ly/YMYW-320

Recharacterization of excess Roth IRA contributions, converting post-tax contributions to Roth 401(k), and the pro-rata rule. Plus, target date fund ladders? Also, investing 529 plan money, section 199A dividends from real estate investment trusts (REITs), and how Matt Stafford should save for retirement with his new $34M LA Rams contract (just in case you're expecting a football player's salary anytime soon.) Access the transcript and financial resources, ask your money questions: https://bit.ly/YMYW-319

Spitballing firefighters' retirement: deferred option retirement plans (DROP), HSA (health savings) vs. HYSA (high yield savings), and hear why YMYW always comes back to backdoor Roth IRA. Speaking of Roths, can you do a Roth conversion ladder with inherited IRA money? The fellas also break down required minimum distributions (RMDs) and they talk (or in Joe's case, rant) about variable annuities and indexed annuities. Access the transcript & financial resources, ask money questions: https://bit.ly/YMYW-318

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 fund or a QCD. Also, how to calculate multi-year Roth conversions, and do you lose compound interest when doing Roth conversions? Plus, thoughts on closed-end funds, a variable annuity rescue plan, and Social Security benefits when working vs. not working. Access the transcript and financial resources, ask your money questions: https://bit.ly/YMYW-317

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 donor-advised fund, 529 plans, and early retirement. Also, is growth on after-tax 401(k) contributions tax-free? How much of the portfolio should be in tax-free, taxable, and tax-deferred accounts? How does income from tax-deferred accounts impact Medicare premiums? Access the transcript and financial resources, ask your money questions: https://bit.ly/YMYW-316

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 universal life insurance plan purchased by an employer to replace a defined benefit plan? Plus, understanding qualified small business stock gain exclusion. Joe and Big Al also discuss the value of hiring a CERTIFIED FINANCIAL PLANNER™. Are they worth it? Access the transcript and financial resources, ask your money questions: https://bit.ly/YMYW-315

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 market value & rent it back to her? Can you max out Dad's Roth? Can you file 2020 taxes before receiving IRS form 1098? How should you diversify your portfolio into international investments? Plus, capital gains and ordinary income, and a correction on deemed Social Security. Access the transcript & financial resources, ask money questions: https://bit.ly/YMYW-314

A retirement plan spitball analysis for an engineer wondering if he can afford to retire, required minimum distribution questions answered, and discussion on when to stop contributing to tax-deferred accounts, when to start Roth conversions, and a conversion strategy for someone with no income. Plus, "conversation" - not advice - about Joe's possible wallet syndrome, and a limerick and music from Paul Lemire. Access the transcript and financial resources, ask your money questions: https://bit.ly/YMYW-313

Whether you call it a SERP, an individual supplemental executive retirement plan, a private pension, or the "Super Roth," the strategy is overfunding life insurance, and the question is, is it a good idea for retirement planning? Also: a Social Security, pension, retirement withdrawal, and Roth conversion strategy, portfolio modeling scenarios, the earned income tax credit, and other tax reduction strategies. Access the transcript and financial resources and ask your money questions: https://bit.ly/YMYW-312

Find out just how intertwined healthcare and retirement are, with answers to questions about Medicare as it relates to Social Security, Health Savings Accounts (HSA), and IRA required minimum distributions (RMDs). Also, strategies for Roth conversions and Social Security, saving for retirement in a brokerage account, and paying debt out of retirement funds or with a mortgage refinance - and a couple of corrections. Access the transcript & financial resources, ask money questions: https://bit.ly/YMYW-311

This week GameStop, AMC and Blackberry stocks went wild, with hedge funds shorting the stocks, and Redditors using the Robinhood investing app to put the squeeze on them - to the tune of billions of dollars. Is the stock market rigged? How do these investing plays affect you and your portfolio? Should you get in on the day-trading craze? Pure Financial Advisors' Executive Vice President and Director of Research Brian Perry, CFP®, CFA® joins Joe Anderson, CFP® to talk about it. Access the transcript and financial resources, ask your money questions: https://bit.ly/YMYW-310a "The markets can remain irrational longer than you can remain solvent." - John Maynard Keynes, Economist

Drilling down into the specifics of retirement distribution strategies: dollar cost averaging, pro-rata withdrawals, and buckets vs. the total return approach. Plus, a retirement withdrawal strategy with a side of pension and Social Security, another mortgage payoff question, the small business solo 401(k) trap, an LLC for a kayak side-hustle, and FIPhysician.com says nice things about YMYW. Access the podcast transcript and financial resources, and ask your money questions: https://bit.ly/YMYW-310

Answering questions from across the personal finance spectrum: inherited IRAs and late RMDs, contributing to non-qualified deferred compensation plans, making Roth contributions for grandkids, how a Roth impacts student loans, taxation on ESPPs and RSUs, paying off the mortgage, and retirement plan spitball analysis for a clergyman and his wife, and for a couple with a profitable side hustle. Access the transcript and financial resources, ask your money questions: https://bit.ly/YMYW-309

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 do you calculate Roth conversion taxes due to the pro-rata rule? Also, calculating a long retirement number or by age, a radical portfolio rebalance, why basis, gains, and losses are tracked, and donating stock upon death. Plus, does your financial advisor's location matter? Transcript, financial resources, ask your money questions: https://bit.ly/YMYW-308

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 analysis for John in TN who wants to retire early, a retirement withdrawal and 529 plan strategy for Ace in TX, and a breakdown of pension options for James in AZ - after Big Al figures out how to work his HP12C financial calculator. Access the transcript and financial resources, ask your money questions: https://bit.ly/YMYW-307

Wrapping up the longest year in history with means testing for Social Security, healthcare when one spouse is on Medicare, and how Roth IRA conversions affect Social Security & Medicare costs. Plus, can you avoid capital gains when selling rental real estate? Should you pay off the mortgage on your rental property or keep investing? Is it a good idea to put a home equity line of credit (HELOC) on an investment property? Access the transcript, financial resources, ask money questions: https://bit.ly/YMYW-306

'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 like best for retirement portfolio withdrawal? Plus, early retirement: calculating taxes correctly for it and dollar-cost averaging for it. Also, spreading SIPC risk, understanding the discrepancy in basis on a limited partnership, tax advantages of a health savings account (HSA), and some vehement listener comments on our discussion of paying off the mortgage from podcast #302. Access the transcript & financial resources, ask your money questions: https://bit.ly/YMYW-305

A final look at the CARES Act COVID-19 stimulus package, Coronavirus related distributions, and whether they affect your 2020 taxes. Plus, action items to pay less tax in 2020, like Roth conversions, tax gain and tax-loss harvesting, and charitable giving strategies. Also, when to do Roth contributions, how much of your portfolio should be in Roth accounts, and if you can lower your taxes from swing trading. Access the transcript & financial resources, ask your money questions: https://bit.ly/YMYW-304

There are taxable, tax-deferred, and tax-free accounts, and the proper balance of investments in each is called tax diversification. Are you tax diversified enough? Plus, how do capital gains and ordinary income work again? Should you contribute to traditional 401(k) or IRA, or to Roth? What can you do about excess contributions to your Roth IRA? And to mix it up, are municipal bonds a good idea for conservative investors? Access the transcript and financial resources, ask your money questions: https://bit.ly/YMYW-303

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 estate, how else can you save? (Hint: brokerage account.) Should self-employed small business owners contribute to a Solo 401(k) or Traditional IRA? Solo Roth 401(k), or Solo 401(k) to Roth conversion? Finally, Medicare, HSA, capital gains, and modified adjusted gross income (MAGI). Access transcript, financial resources, and send in your money questions: https://bit.ly/YMYW-302

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 will Social Security benefits affect taxes after a backdoor Roth IRA conversion? Should a highly compensated employee use the mega backdoor Roth strategy? Are the tax savings on a conversion worth it? Plus the fellas explain the pro-rata rule - again. Access the episode transcript and financial resources, and send in your money questions: https://bit.ly/YMYW-301

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 with just the funny stuff: great email intros, some of our funniest Derails, a couple never-before-heard outtakes, hilarious moments from our interviews with Dr. Daniel Crosby and Professor Jamie Hopkins, and the infamous story of Will and his free gasoline. Access the episode transcript and financial resources, and send in your money questions: https://bit.ly/YMYW-300

When does the real estate depreciation 121 exclusion happen and how do you account for rental property equity, or cap rates, to calculate retirement income? Plus, estate planning beneficiaries and charitable donations, stock market investing in an LLC, understanding the national debt, the differences between Roth 40(k) and traditional 401(k), and of course, Backdoor Roth and Roth IRA conversions. Access the episode transcript and financial resources, and send in your money questions: https://bit.ly/YMYW-299

Should retirement savings go in the older spouse's accounts first? Does Marion have a good VTSAX to VTWAX tax-loss harvesting and portfolio rebalancing strategy? Plus, making sense of fees from your financial advisor and on exchange-traded funds, or ETFs. Big Al provides pointers on selecting a good certified public accountant - other than him, of course, and finally, do 457 plans ever blow up? Access the episode transcript and financial resources and send in your money questions: https://bit.ly/YMYW-298

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 Social Security at 70 and RMDs at 72? Joe and Big Al also answer a question on the taxation of an overseas inheritance, and they discuss your comments. Access the episode transcript and financial resources and send in your money questions to be answered on the YMYW podcast: https://bit.ly/YMYW-297

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 money be going into Christy's pre-tax Roth accounts? Has Roger set up a good portfolio for his elderly relative? Plus, the Rule of 100 or 120 for investing in stocks and bonds, as touted by Jack Bogle and the Bogleheads. Also, should Tom take a Coronavirus-Related Distribution? And finally, when to take Social Security, and that Social Security file and suspend rule that affects people born in 1954. Access the transcript and financial resources, send in money questions: https://bit.ly/YMYW-296

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, and how capital gains work with Roth conversions. Also, strategizing for if and when the estate planning step up in basis tax laws change, whether a high yield savings account is good for investing $25K in cash, and listener comments on the show and the FIRE movement. Access transcript and financial resources, send in money questions: https://bit.ly/YMYW-295

Retirement portfolio rebalancing when the market goes down, accumulation, de-accumulation, dollar cost averaging, and IRR, ROR, and CAGR (not "kegger") as ways of calculating rates of return on investments. Plus step-up in basis, required minimum distributions or RMDs, capital accumulation life insurance plans, tax planning for new homebuyers, spousal Social Security benefits, and of course, backdoor Roth IRA conversions. Access transcript & financial resources, send in money questions: https://bit.ly/YMYW-294

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 IRA, and Joe and Big Al take a burning confession about Roth conversions and IRS form 8606. Also, more on Vanguard's VTSAX and dividend yield, and various options for investing for minor kids including Paul Merriman's suggestions, UTMA, and brokerage accounts. Access transcript and financial resources, and send in money questions: https://bit.ly/YMYW-293

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-tax retirement accounts? How long does money have to be in a traditional IRA before a backdoor Roth conversion? Can annuities be converted to Roth? And more on dividends, long term capital gains, Vanguard's Total Stock Market Index Fund, survivor Social Security benefits, and more. Access transcript and financial resources, send in money questions: https://bit.ly/YMYW-292

Answering questions across the financial and retirement spectrum, with topics like when your traditional IRA is growing faster than you can convert to Roth, consolidating retirement savings, annuities, the SECURE Act and inherited IRAs, undoing SEP-IRA contributions, Roth conversions after age 72, offsetting conversion gains against tax-harvested losses, tax diversification beyond conversions, and what to do if you think you blew up your Roth IRA. Access the transcript, resources, send in money questions, and your chance at a $100 Amazon e-gift card in the show notes: https://bit.ly/YMYW-291

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 loss harvesting, asset allocation, investing in bonds, the Windfall Elimination Provision (WEP) and Government Pension Offset (GPO) for spousal Social Security, and IRA vs. 529 plan for a newborn. Whew! Fill out the podcast survey for a chance to win a $100 Amazon e-gift card, send in money questions, and access free financial resources: https://bit.ly/YMYW-290

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 strategizing for your Coronavirus related distribution, stimulus (and possible future stimulus) tax planning, and your self-employed, small business retirement plans. And finally, listener comments. Fill out the podcast survey for a chance to win a $100 Amazon e-gift card, send in money questions, and access the transcript and free financial resources: https://bit.ly/YMYW-289