show episodes
 
On this retirement investing podcast, financial planner Joe Anderson, CFP® and certified public accountant Big Al Clopine answer your money questions about investing, portfolio diversification, how to reduce taxes, creating retirement income, collecting Social Security benefits, how much you can spend in retirement, Roth conversions, and more. Retirees and pre-retirees listen to this irreverent and informative personal finance podcast to laugh as they learn strategies that can help them reti ...
 
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show series
 
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, an…
 
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 don…
 
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…
 
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 id…
 
’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 bas…
 
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 …
 
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? A…
 
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? F…
 
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…
 
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 Hopkin…
 
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 o…
 
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 …
 
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 res…
 
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 Bogl…
 
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 $2…
 
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, spou…
 
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 includin…
 
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, Vangua…
 
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 l…
 
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. Wh…
 
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. Fil…
 
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 real estate investment properties fit in your retirement plan? How much Social Security is taxed, and will taking your pension lump sum before Social Security impact your taxes? Fill out the podcast surv…
 
Tax planning for Roth IRA conversions with itemized deductions, dividends, and long term capital gains, a Roth conversion vs. investing a 401(k) distribution in your Roth, separating pre-tax and post-tax money for a rollover, and gong baths. Plus, is a 3 year fixed annuity a safe place to earn more than 20 basis points? What should you do if you’re…
 
Investing strategies for dividend-paying stocks and how the pro-rata rule for Roth conversions work with dividends. Plus, Wealthfront, M1, Paul Merriman? Should young investors use a robo-advisor or pay for financial advice? Also, thoughts on a Vanguard retirement portfolio and ideas for self-employed small business owners to save money in retireme…
 
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 Congress. Plus, estate planning considerations when it comes to required minimum distributions (RMDs) for non-designated and designated beneficiaries. And, the 403(b) escape hatch, Social Security, records o…
 
Joe and Big Al spitball retirement plan considerations, including: - investing in brokerage and Roth instead of pre-tax - getting tax diversification - pension lump sum or annuity - paying for education - calculating a retirement number to put savings on autopilot Plus, what life insurance “investment” has a “guaranteed” 10% return? Do dividend pay…
 
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, why own bonds? Are Vanguard Roth accounts any better or worse than others? What’s the break even on taking Social Security early vs. late? Should you convert your 401(k) or retirement account to Rot…
 
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 paying the tax on a Roth conversion. Plus, stimulus package updates around paycheck protection program loans, required minimum distributions and Coronavirus-related distributions from retirement accoun…
 
What impact do ex-spouses, income, and early retirement have on collecting your Social Security benefits? Plus, indexed universal life insurance, estate planning with a step-up in basis on private placement real estate, and more on CRDs, RMDs, and stimulus checks. Joe and Big Al also submit their forecasts for whether Congress might tax Roth IRA gr…
 
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 kick the tires on an early retirement plan and they discuss equity allocations in a portfolio. And since no YMYW is complete without some Roth talk, how might Roth contributions for grandkids affect co…
 
Reducing real estate taxes, leveraging new rental income properties, coordinating Social Security benefits with Roth conversions, and bragging about your 401(k) balance. Also, 5-year Roth clocks, converting from your TSP, Roth conversion vs. Backdoor Roth conversion, and paying taxes on conversions. Plus, a chat about Social Security survivor benef…
 
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 you can, and if you should. Plus, more stimulus payment questions, charitable giving strategies from your required minimum distribution, selling stock for tax-free capital gains and an analysis of exc…
 
Roth IRA contributions and conversions come with plenty of rules: contribution rules, withdrawal rules, safe harbor rules, pro-rata and aggregation rules. In this episode, we explain these rules, and how they apply to both traditional retirement plans and accounts like SEP IRAs and thrift savings plans (TSP). Plus, understanding small-cap, mid-cap,…
 
Should market volatility and the economic downturn due to COVID-19 change where you save for retirement? Should contributions go to pre-tax accounts or to post-tax Roth accounts? Plus, Coronavirus related distributions, how to use a PPP loan to pay your self-employed self, backdoor Roth IRA conversions, and strategies for funding a Roth IRA for chi…
 
The windfall elimination provision (WEP), government pension offset (GPO) & spousal Social Security benefits. Also, Roth IRA conversions and Medicare, Roth conversions from a thrift savings plan (TSP), and conversions to buy real estate. Plus, asset location and other tax planning strategies beyond Roth IRA conversions, like life insurance and char…
 
Financial planning strategies around Coronavirus-Related Distributions from retirement accounts and required minimum distributions (RMDs). Plus, listener corrections on dependents and the CARES Act stimulus package. Also, two very different market volatility strategies: living off of cash and Social Security only, and leveraging a home equity line …
 
A mixed bag of questions on everything from spousal solo 401(k) contributions and inherited IRAs to house-buying strategies, to the fan-favorite, ripping on annuities, with a healthy dose of Roth conversion planning thrown in the middle. Sign up for the LIVE YMYW webinar on May 13, send in money questions, read the episode transcript and access fre…
 
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 episode, Joe and Big Al break down asset location and answer some of your tax planning questions. As always, the fellas also talk strategy when it comes to Roth IRA contributions and Roth conversions.…
 
In this jam-packed episode of the Your Money, Your Wealth® podcast, stimulus payments for self-employed, dependents, and those who message us on Facebook, plus, the paycheck protection program, round two of which started since this episode was recorded, coronavirus-related distributions, Roth and Backdoor Roth conversions, tax-loss harvesting, and …
 
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 stimulus payments for kids, retirement account distributions, and rethinking your retirement savings strategy. Also, SECURE Act stretch IRA rules, evaluating long term care insurance options, and why thrift…
 
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 state income tax impact on Roth conversions. Plus, earnings on a reversed excess IRA contribution, how dollar-cost averaging affects capital gains tax first in, first out (FIFO) rules, zero-coupon bonds, …
 
Recovery rebates, new rules for retirement account distributions, stimulus checks for those on Social Security & unemployment benefits. Plus, should a listener invest his forbearance, buy foreclosures, and capitalize on the financial crisis? We also get into the cash-on-cash math for rental real estate and potential property tax deduction changes f…
 
In these volatile financial markets, are you reconsidering your investing strategies? Joe and Big Al discuss cash, selling stocks in taxable accounts and repurchasing them in tax-deferred accounts, doing nothing and staying globally diversified, writing an investment policy statement, doing Roth conversions, and fixed indexed annuities (AKA equity-…
 
If you’re in the 22% tax bracket, does 22% of what you make go to the IRS? How does capital gains tax work with ordinary income tax? Joe & Big Al explain how tax brackets work and answer your Roth contribution and Roth conversion questions: like what's the point of a Roth conversion if you're just leaving the money to your kids? Plus some Mega Back…
 
Tax loss harvesting, Roth conversions and more: Joe and Big Al explain how bear markets like the one we're in now are the time to utilize these investing strategies in your retirement portfolio. And the fellas go over those Roth IRA 5-year withdrawal rules again. They’ll cover some Roth withdrawal mistakes and Roth rollover consequences, and they h…
 
How much of your money should you keep in cash? Should you buy VBK, the Vanguard Small-Cap Growth ETF? Plus, asset allocation and asset location, the pros and cons of the Roth 401(k), Medicare, spousal and survivor Social Security benefits, tax-saving charitable giving, small business strategies, who qualifies to be called Joe Anderson’s “peer,” an…
 
With volatility, should you time the market and change the asset allocation of your investment portfolio, your pension, or your Thrift Savings Plan (TSP)? Plus, asset location: should equities be in a brokerage account, Roth IRA or traditional IRA? And diversification vs. concentration, calculating how much you’ll have in retirement, how to get the…
 
How do you run the numbers to find a good, profitable rental property? Should you pay off the mortgage, buy more real estate, or save for retirement? Should you buy a home all cash? Can a property be considered a rental for tax purposes? Should you refinance your home to pay student loans? What can you do with unused education savings? And what do …
 
As Tax Day approaches, you've got taxes on your mind. When do you have to pay the tax on your Roth IRA conversion? Is converting beyond the current tax bracket ever recommended? Plus, answers to more of your SECURE Act retirement questions on IRA contributions and inherited IRAs and other assets, and Roth conversion and Backdoor Roth strategies for…
 
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