Your Money, Your Wealth

Are you behind on your retirement savings? What do you need to do to catch up? If you retire in just a few years, will your money last until age 90? Based on the 5-year Roth withdrawal rules, do you need to open a new Roth IRA for each Roth conversion? Plus, Joe and Big Al spitball a health insurance, capital gains, and real estate strategy to save more money and have more wealth in retirement. Finally, they revisit the SECURE Act rules for withdrawing money from an inherited IRA, and Social Security income limits. Show notes, free financial resources, transcript, Ask Joe & Big Al On Air: https://bit.ly/ymyw-402

New research says some young people shouldn't save for retirement. Find out what Joe and Big Al think about that. Plus, is it tax fraud if you re-file taxes to take advantage of new student loan forgiveness? Should you invest in CDs instead of bonds, since both stocks and bonds are getting crushed right now? How can you consolidate your stock portfolio to minimize capital gains tax? Also, charitably inclined YMYW listeners want to know how to use donor-advised funds when spitballing tax planning around an IPO, and whether to do more Roth conversions or more qualified charitable distributions. Show notes, free financial resources, transcript, Ask Joe & Big Al On Air: https://bit.ly/ymyw-401

Are there any holes in a 5-year plan to retire from the Air Force, buy a house and a plane, and become a commercial pilot? Can you claim an unpaid loan to a start-up as a tax loss, do a Roth conversion, and pay no tax? Are Roth conversions a good idea in a low-earnings year? Does it matter if you convert to Roth before or after changing custodians? What retirement savings options do independent contractors have besides the Solo 401(k)? Does it make sense to cash out a 529 college savings plan that's losing money? Plus, Joe and Big Al spitball a real estate strategy, and they discuss a state retirement account held at an insurance company. Show notes, free financial resources, transcript, Ask Joe & Big Al On Air: https://bit.ly/ymyw-400

Joe and Big Al explain when and how to claim Social Security survivor benefits and how earning income impacts your benefit if you collect Social Security before full retirement age. Plus, how much should you withdraw in retirement from tax-free, taxable, and tax-deferred accounts? Also, RMDs, deciding whether to keep a life insurance policy, and of course, Roth Conversion strategies - is the backdoor Roth better for long term portfolio growth? Show notes, free financial resources, Ask Joe & Big Al On Air: https://bit.ly/ymyw-399

As the financial markets fall and then surge, Joe and Big Al talk about market timing, reallocating retirement contributions, and portfolio rebalancing. Plus, your questions answered on estimated taxes, Roth conversions, and the logistics of inheriting IRAs and passing assets on. Finally, how is a financial advisor like a golf caddie when markets get volatile? Joe and his Pebble Beach golf caddie buddy, Big G from the Real Life Caddie Podcast, discuss how their professional knowledge and experience can help the rest of us avoid big mistakes. Show notes, free financial resources, transcript, Ask Joe & Big Al On Air: https://bit.ly/ymyw-398

A compilation of some of Joe and Big Al's retirement plan spitballing specifically for those in their 40s and 50s - a critical time on the path to retirement. Is your financial plan set up so you pay as little tax as possible? Does it take volatile markets and potential future tax increases into account? Have you got a strategy nailed down for Roth conversions, or backdoor Roth, or pension options? Maybe you're making big decisions about what to do with your money between now and when you retire, like buying a house vs. saving for retirement? Are you comfortable with the retirement lifestyle you're creating? Do you know what you'll do with your time once you're permanently off the clock? Visit the podcast show notes to access free financial resources, transcript, and to Ask Joe & Big Al On Air: https://bit.ly/ymyw-397

Joe & Big Al answer your questions on, of course, backdoor Roth strategies. Y'know, to get as much lifetime tax-free growth on your investments as possible. Plus, investing strategies: does it make sense to buy a property now and rent it out until retirement? How much of a single stock in your investment portfolio can you sell and pay no capital gains tax? The fellas also explain capital loss carryovers, inherited IRAs, spousal Social Security and delayed retirement credits, required minimum distributions, and they spitball on an appropriate allocation of bonds, domestic stocks, and international stocks. Show notes, free financial resources, Ask Joe & Big Al On Air: https://bit.ly/ymyw-396

What's the next move for a 22-year-old who wants to retire early at 50? Can another YMYW listener afford to retire by the ocean in 10 months? Can Flowergirl and her husband AND her boyfriend retire next year? Joe and Big Al also check extensive retirement spitball math sent in PDF format. Plus, what are the fellas' philosophies on single vs. married tax rates when one spouse passes, and how does high state income tax impact a retirement strategy? Show notes, free financial resources, Ask Joe & Big Al On Air: https://bit.ly/ymyw-395

If a fortunate equity event or liquidity event should cause your income to skyrocket, what will that do to your taxes? Joe and Big Al spitball tax strategies to help you manage this good problem to have. Plus, Backdoor Roth, contributions, conversions, and income limits explained, converting twelve and a half million bucks to Roth, and what happens to retirement accounts when you pass - will there be a tax bill due? Kicking it off with the 7-twelve portfolio - what is it? Show notes, free financial resources, Ask Joe & Big Al On Air: https://bit.ly/ymyw-394

Should you convert money from your pre-tax retirement accounts to Roth now, or wait until retirement, or until required minimum distributions kick in? Should a mid-30s couple do Roth Conversions or Backdoor Roth? Should a 93-year-old open his first ever Roth and start converting? What's a good retirement savings mix between pre-tax and post-tax? And the fellas do a worst-case scenario retirement spitball analysis. Show notes, free financial resources, Ask Joe & Big Al On Air: https://bit.ly/ymyw-393

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 retirement well enough to convince his wife that they can afford a new luxury truck? Can another YMYW listener take advantage of what seems to be a big opportunity to sell company stock, pay no capital gains tax, and do Roth conversions? Can Big Al's high school friend do a 1031 exchange to buy a rental property, make it his primary residence in 5 or 10 years, and pay no tax when selling? Is earned income from stock trading still taxable for Social Security if your LLC is in a trust? Finally, a compliment comes in, and Joe and Big Al assume it's for them. Show notes, free financial resources, the YMYW podcast survey, and Ask Joe & Big Al On Air: https://bit.ly/ymyw-392

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 Joe and Big Al's financial spitballing over the last couple of years specifically for savers and investors in their 30s and even 20s, some of whom want to retire early. Show notes, free financial resources, the YMYW podcast survey, and Ask Joe & Big Al On Air: https://bit.ly/ymyw-391

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 retirement? Should you do Roth conversions before or after you quit working? Plus, find out what Joe and Big Al think about a 529 and series I bond gifting strategy, and using whole life insurance to transfer wealth to the kids. Show notes, free financial resources, the YMYW podcast survey, and Ask Joe & Big Al On Air: https://bit.ly/ymyw-390

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 it after 20 years, and how does a 1031 exchange work? Also, opening a Roth IRA with the Backdoor Roth strategy, and the 5 year Roth withdrawal rules explained. Plus, a couple retirement spitball analyses: are you saving too aggressively for retirement? Can you avoid the Medicare IRMAA, or income related monthly adjustment amount, and high taxes from required minimum distributions? Show notes with annual podcast survey, free financial resources, and Ask Joe & Big Al On Air: https://bit.ly/ymyw-389

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 retirement. How does that work with long-term capital gains and dividends, and how much should you convert to Roth, and when, and how? Plus, deciding how to invest 529 plan college savings, whether to save to pre-tax or post-tax retirement accounts, and the ever-popular Backdoor Roth strategy. Show notes, free financial resources, Ask Joe & Big Al On Air: https://bit.ly/ymyw-388

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, and when and how much of a Roth Conversion should you do? Is it hypocritical to prioritize investment returns over your conscience and values? Joe and Big Al talk ESG, or environmental, social, and governance investing, and they evaluate a strategy to keep taxes low while helping your kids buy a house. Finally, your comments about YMYW. Show notes, free financial resources, Ask Joe & Big Al On Air: https://bit.ly/ymyw-387

When the financial markets are down, should you postpone retirement? When inflation is up, should you change your investments and pile into things like value and commodities? Plus, the ever-popular retirement spitball analysis: an early retirement plan, Medicare, Social Security, TSP, and Roth conversions, and when and how business owners should convert $5.5M to Roth IRA. Also, if excess 2021 Roth contributions were returned, can you file last year's taxes now without penalty? Finally, what's the difference between a collective investment trust and regular mutual funds? Show notes, free financial resources, Ask Joe & Big Al On Air: https://bit.ly/ymyw-386

Inflation is high, interest rates are high, and the financial markets are volatile. Are bonds and series I bonds good investments or bad investments right now? How do bonds fit into your overall retirement portfolio? Plus, variable annuities, evaluating the long-term value of Roth contributions vs. Roth conversions, what if anything can be done about losses in an after-tax 401(k), helping adult kids buy a home, and drinks in the Derails. Show notes, free financial resources, Ask Joe & Big Al On Air: https://bit.ly/ymyw-385

"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 retirement for listeners planning to retire in just a few years, wondering if they should save to pre-tax or post-tax accounts, and strategizing around long-term capital gains, dividends, and Roth conversions. Show notes, free financial resources, Ask Joe & Big Al On Air: https://bit.ly/ymyw-384

Equitable accumulators, cash management accounts, and Social Security: with today's market volatility, how can you squeeze a few more dollars of income out of your retirement savings? Any reason not to use a robo-advisor for decumulation, in other words, spending down those savings? Plus, a pension retirement spitball follow-up, and is it possible to avoid tax liability on a lump sum withdrawal from a 401(k)? Finally, is Joe's marriage the canary in the Coors Light Party Ball for YMYW? Show notes, free financial resources, Ask Joe & Big Al On Air: https://bit.ly/ymyw-383

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) a good strategy? What's an individual coverage health reimbursement arrangement (ICHRA) and is it a good healthcare option for those with C-corporations? When putting away retirement savings, should you contribute to a Roth IRA, a brokerage account, a 401(k), or your employee stock purchase plan (ESPP)? When it comes to step-up in basis, how do you determine the past fair market value of a home? And finally, what happens if you retire before your construction loan becomes a permanent mortgage? Show notes, free financial resources, Ask Joe & Al On Air: https://bit.ly/ymyw-382

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 questions you need to answer before you retire - so you can stay retired. Show notes, free financial resources to help you answer each question, and Ask Joe & Al On Air: https://bit.ly/ymyw-381 1. Can We Afford to Retire? 2. When Should We Claim Social Security? 3. How Can We Reduce Taxes in Retirement? 4. Are We Prepared for Medical Costs? 5. How Will We Fill Our Time?

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 company, load up a Roth account with company shares before the sale, and have a big chunk of cash happily growing tax-free? (What exactly are disqualified persons and prohibited transactions?) When designating beneficiaries of an annuity in a community property state like California, does state law or the annuity owner determine the beneficiary? Show notes, free financial resources, Ask Joe & Al On Air: https://bit.ly/ymyw-380

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 manage the decline: does it make sense to move to cash inside your retirement account? How do down markets impact Roth Conversion decisions for older investors? What should your asset allocation be now, during market volatility, if you're expecting a future windfall? How should you manage the relationship with your financial advisor if they buy high and sell low in your investment portfolio? Should you leave a partially vested pension to grow, or withdraw the money now and convert to Roth? What's the best way to withdraw from an IRA in a down market? Show notes, free financial resources, Ask Joe & Al On Air: https://bit.ly/ymyw-379

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 misleading when they talked about claiming Social Security early vs. late if you save and invest the benefits? Listen for their rebuttal. When you change 401(k) custodians, is it a transfer, or a whole new plan? Can you convert your entire 401(k) to Roth, and should you? Finally, If you're worried about high tax brackets in retirement, should all your contributions now go to Roth? Show notes, free financial resources, Ask Joe & Al On Air: https://bit.ly/ymyw-378

Joe & Big Al talk strategy for converting to Roth and paying tax from the IRA when you have limited funds, eliminating required minimum distributions (RMD) on a Roth 457 and avoiding the 5-year Roth clock, and Roth 457, Roth IRA, and Roth TSP. Plus, the fellas spitball pension options, retiring early, and an intricate and potentially risky deferred compensation strategy. Show notes, free financial resources, Ask Joe & Al On Air: https://bit.ly/ymyw-377

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 cash should you keep on hand? Why do advisors suggest buying a fixed indexed annuity, and how do qualified charitable distributions work? Finally, is it a good idea to pre-pay the mortgage on a real estate investment, and how do you calculate the tax on a home you inherited? Show notes, free financial resources, Ask Joe & Al On Air: https://bit.ly/ymyw-376

Does it make sense to do larger "Calvin Johnson" (megatron, aka mega backdoor) Roth conversions when the financial markets are way down? Should you convert to Roth now, or in retirement? How do you spitball the right amount to have in 529 plans for education savings? And are the rules for doing a backdoor Roth the same if you're married filing separately? Show notes, free financial resources, Ask Joe & Al On Air: https://bit.ly/ymyw-375

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 early, and what are the rules for collecting survivor Social Security benefits? Finally, how does net investment income tax (NIIT or the Medicare surtax) on long term capital gains impact a house sale? Is it possible to do a 1031 exchange from rental real estate in Utah for investment property in California? Show notes, free financial resources, Ask Joe & Al On Air: https://bit.ly/ymyw-374

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 and the earned income tax credit. Next, are you eligible to make Roth contributions, and should you contribute only to Roth for retirement? Then, the pros and cons of consolidating retirement accounts, and some early retirement spitball analyses. When you plan to retire early, should you invest in dividend paying stocks or real estate? And finally, is the bucket investing strategy really that complicated? Podcast show notes, free financial resources, Ask Joe & Al On Air: https://bit.ly/ymyw-373

Spitballing retirement for a police officer turning teacher, a self-employed small business owner, an early retiree with an employee stock ownership plan (ESOP) wanting to do Roth conversions and withdraw 5 or 6% in retirement, and a pension and Social Security analysis. Plus, how many months of expenses should you save in your emergency fund? Also, you may know where Ric Edelman and Dave Ramsey stand on 15 vs. 30 year mortgages and using cash vs. credit, but what does YMYW think? Show notes, free financial resources, Ask Joe & Al On Air: https://bit.ly/ymyw-372

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 assets should be in tax-free, tax-deferred, and taxable accounts to give maximum flexibility in retirement? And finally, do Roth conversions count as income toward your eligibility to contribute to a Roth, and how will a pension be taxed? Podcast show notes, episode transcript, free financial resources, Ask Joe & Al On Air: https://bit.ly/ymyw-371

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 mortgage) a good idea? Also: a complicated property inheritance and self-funding long term care insurance. Financial resources, Ask Joe & Al On Air: https://bit.ly/ymyw-370

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? Do higher yield investments early in retirement offset sequence of returns risk? Plus, a listener takes issue with YMYW's dollar-cost averaging discussion, and Joe's big news in the Derails. Transcript, free financial resources, Ask Joe & Al On Air: https://bit.ly/ymyw-369

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, factors to consider when choosing large cap value funds. Show notes, financial resources, Ask Joe & Al On Air: https://bit.ly/ymyw-368

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-identify" an inherited IRA as a spousal IRA to change the RMD calculation? Is the section 162 executive bonus plan just whole life insurance? And finally, Joe's past comes back to haunt him with 9 cats, a neurotic beagle, and 200 IRAs. Show notes, free resources, Ask Joe & Al On Air: https://bit.ly/ymyw-367

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: https://bit.ly/ymyw-366

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 change? Financial resources, transcript, Ask Joe & Al On Air: https://bit.ly/ymyw-365

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 & Al On Air: https://bit.ly/ymyw-363

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://bizlink.to/ymyw-363

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 insurance or self-insure? Show notes, free financial resources, Ask Joe & Al On Air: https://bit.ly/ymyw-361

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