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 questi...
Dec 01, 2020•45 min•Ep. 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://...
Nov 24, 2020•47 min•Ep. 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: http...
Nov 17, 2020•41 min•Ep. 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...
Nov 10, 2020•47 min•Ep. 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...
Nov 03, 2020•36 min•Ep. 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...
Oct 27, 2020•35 min•Ep. 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 fi...
Oct 20, 2020•41 min•Ep. 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.l...
Oct 13, 2020•46 min•Ep. 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: http...
Oct 06, 2020•48 min•Ep. 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/YM...
Sep 29, 2020•45 min•Ep. 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: h...
Sep 22, 2020•53 min•Ep. 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 ...
Sep 15, 2020•44 min•Ep. 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://b...
Sep 08, 2020•47 min•Ep. 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 resource...
Sep 01, 2020•48 min•Ep. 289
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 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...
Aug 25, 2020•44 min•Ep. 288
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 stuck in an annuity you don’t want? Send in questions, access free financial resources, and sign up for the August 26 YMYW live webinar: https://bit....
Aug 18, 2020•44 min•Ep. 287
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 retirement plans like SEP IRA, SIMPLE IRA, and Solo 401(k). Send in money questions and access the episode transcript and free financial resources: https://bi...
Aug 11, 2020•48 min•Ep. 286
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 of estimated tax payments, and assets on the FAFSA form. Send questions and access the transcript and free resources in the show notes: https://bit...
Aug 04, 2020•42 min•Ep. 285
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 paying stocks have a higher rate of return than VTSAX? Should individual stocks go in a taxable account? Send in money questions and access the episode t...
Jul 28, 2020•47 min•Ep. 284
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 Roth all at once? Send in money questions and access the episode transcript and free financial resources in the podcast show notes: https://bit.ly/YMYW-2...
Jul 21, 2020•51 min•Ep. 283
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 accounts. Send in money questions, access the episode transcript and free financial resources, and sign up for a free tax reduction analysis: https://bit.ly...
Jul 14, 2020•44 min•Ep. 282
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 growth in the future. Send in money questions and access the episode transcript and free financial resources in the podcast show notes: https://bit.ly/Y...
Jul 07, 2020•48 min•Ep. 281
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 college financial aid? Send in money questions and access the episode transcript and free financial resources in the podcast show notes: https://bit.ly/...
Jun 30, 2020•45 min•Ep. 280
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 benefits - and freezers. Send in money questions and access the episode transcript and free financial resources in the podcast show notes: https://bit.ly/Y...
Jun 23, 2020•42 min•Ep. 279
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 exchange traded funds vs. mutual funds. Send in money questions and access the transcript and free resources in the podcast show notes: https://bit.ly/YM...
Jun 16, 2020•48 min•Ep. 278
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, large-cap, value, and growth asset classes when it comes to investing. Sign up for the exclusive YMYW live webinar on June 10, send in money question...
Jun 09, 2020•53 min•Ep. 277
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 children. Sign up for the exclusive YMYW live webinar on June 10, send money questions and access the transcript and free financial resources: https://bi...
Jun 02, 2020•46 min•Ep. 276
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 charitable remainder trusts. Send in money questions and access the episode transcript and free financial resources in the podcast show notes: https:/...
May 26, 2020•49 min•Ep. 275
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 of credit (HELOC) to invest. Sign up for the LIVE YMYW webinar on May 27, send in money questions, access the transcript and free financial resources:...
May 19, 2020•45 min•Ep. 274
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 free financial resources: https://bit.ly/YMYW-273
May 12, 2020•43 min•Ep. 273
