Your Money, Your Wealth

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 under the SECURE Act, and your comments. Show notes, free resources, Ask Joe & Al: https://bit.ly/ymyw-360

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. Visit the show notes, download free financial resources, and Ask Joe & Al On Air: https://bit.ly/ymyw-359

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 against litigation in a TSP or an IRA? Show notes, free resources, Ask Joe & Al On Air: https://bit.ly/ymyw-358

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? Visit the show notes for free financial resources and to Ask Joe & Al On Air: https://bit.ly/ymyw-357

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 latest Build Back Better Act. Show notes, financial resources, Ask Joe & Al On Air: https://bit.ly/ymyw-356

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, brokerage, or Social Security? Show notes, financial resources, Ask Joe & Al On Air: https://bit.ly/ymyw-355

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 choose between your own pension options. Show notes, free resources, Ask Joe & Al On Air: https://bit.ly/ymyw-354

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 hire a financial advisor near you? Show notes, free resources, Ask Joe & Al On Air: https://bit.ly/ymyw-353

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 money investing strategy. Show notes, video clips, free resources, Ask Joe & Al On Air: https://bit.ly/ymyw-352

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 conversions from a thrift savings plan. Show notes, resources, Ask Joe & Al On Air: https://bit.ly/ymyw-351

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 revisit indexed universal life insurance. Show notes, free resources, Ask Joe & Al On Air: https://bit.ly/ymyw-350

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 notes for free financial resources and to Ask Joe & Al your money questions: https://bit.ly/ymyw-349

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), and restricted share units (RSU). Show notes, free resources, Ask Joe & Al On Air: https://bit.ly/ymyw-348

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 to avoid confiscatory estate taxes? Show notes, free resources, Ask Joe & Al On Air: https://bit.ly/ymyw-347

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 to both Roth IRA and Roth 401(k)? Show notes, free resources, Ask Joe & Al On Air: https://bit.ly/ymyw-346

Retiring overseas and foreign earned income exclusion eligibility, using your tax refund for a back door Roth conversion, and working abroad and contributing to a health savings account (HSA). Plus, should you contribute to Roth, pre-tax accounts, or brokerage for early retirement? Are substantially equal periodic payments (SEPP) good to bridge the gap between retiring early and age 59.5? Is it ever a good time to time the market? Show notes, free resources, Ask Joe & Al On Air: https://bit.ly/ymyw-345

Joe & Big Al outline the House Ways and Means Committee's sweeping tax proposal that would impact Roth contributions, Roth conversions, RMDs, the backdoor Roth IRA and mega backdoor Roth (Megatron), marginal and capital gains tax rates, wash sale rules, and more. Plus, safe retirement income and withdrawal strategies, when NOT to do a Roth IRA conversion, and solo 401(k) retirement savings for self-employed small business owners. Show notes, free resources, Ask Joe & Al On Air: https://bit.ly/ymyw-344

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 condo, or keep investing for retirement? Next up Joe and Big Al spitball ideas on what to do with old whole life insurance policies. Plus, ABLE accounts for individuals with disabilities, and should you claim Social Security benefits before or after moving to a no income tax state? Free financial resources in the podcast show notes: https://bit.ly/ymyw-343

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 year Roth clock factor into a decision to leave money in an old Roth 401(k) or roll it to a new Roth IRA? Do reinvested dividends count as Roth contributions? Do capital gains count towards the capital gains income bracket? IRA contributions for minors and the unemployed, and how would you spend lottery winnings? Podcast show notes: https://bit.ly/ymyw-342

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, early retirement. Plus, the ever-popular Roth IRA conversions: how much to convert to Roth, when and how to pay tax on a Roth conversion, and why not pay tax on Roth conversions out of the retirement account you're converting from? Podcast survey (final day!), financial resources, Ask Joe & Big Al On Air in the podcast show notes: https://bit.ly/ymyw-341

Asset location: how to position assets to pay less tax without sacrificing investment growth? Should young folks contribute all of their retirement savings to Roth accounts? Also, conversations (not advice) on a self-employed defined benefit plan vs. pass-through profits, gifting tuition for education, Roth conversions with a special needs child in mind, a correction on inherited Roth IRAs, and listener comments. Podcast survey, free financial resources, Ask Joe & Al On Air: https://bit.ly/ymyw-340

Moving money from tax-deferred retirement accounts to accounts with lifetime tax-free investment growth: should you do Roth IRA conversions? Before marriage? From a 403(b)? When and how much to convert? Convert aggressive funds first? What about the ACA subsidy? Will paying Roth conversion tax ruin early retirement? And something completely different: Joe & Big Al's take on Ric Edelman's "pay off the mortgage" suggestion. Podcast survey, transcript, free resources, Ask Joe & Al: https://bit.ly/ymyw-339

Ways to diversify concentrated stock positions, like using a donor-advised fund. How does the IRS know if a required minimum distribution is a qualified charitable distribution? From which pool of money should you pull extra retirement income? Also, structured notes, & paying Grandma for daycare without impacting taxes on her pension - lump sum or monthly payments? Finally, thoughts on starting a career in financial planning. Podcast survey, transcript, resources, Ask Joe & Al: https://bit.ly/ymyw-338

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