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
Aug 16, 2022•44 min•Ep. 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...
Aug 09, 2022•38 min•Ep. 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 fro...
Aug 02, 2022•45 min•Ep. 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 ...
Jul 26, 2022•41 min•Ep. 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 note...
Jul 19, 2022•46 min•Ep. 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 th...
Jul 12, 2022•41 min•Ep. 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...
Jul 05, 2022•44 min•Ep. 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...
Jun 28, 2022•38 min•Ep. 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 note...
Jun 21, 2022•29 min•Ep. 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 y...
Jun 14, 2022•36 min•Ep. 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 Wil...
Jun 07, 2022•46 min•Ep. 381
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 no...
May 31, 2022•30 min•Ep. 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 hi...
May 24, 2022•49 min•Ep. 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 contr...
May 17, 2022•42 min•Ep. 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...
May 10, 2022•45 min•Ep. 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://bi...
May 03, 2022•44 min•Ep. 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...
Apr 26, 2022•44 min•Ep. 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, As...
Apr 19, 2022•32 min•Ep. 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, i...
Apr 12, 2022•38 min•Ep. 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, fr...
Apr 05, 2022•1 hr•Ep. 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-3...
Mar 29, 2022•35 min•Ep. 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. ...
Mar 22, 2022•27 min•Ep. 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 tak...
Mar 15, 2022•31 min•Ep. 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...
Mar 08, 2022•40 min•Ep. 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 execu...
Mar 01, 2022•41 min•Ep. 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
Feb 22, 2022•50 min•Ep. 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...
Feb 15, 2022•42 min•Ep. 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...
Feb 08, 2022•42 min•Ep. 364
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
Feb 01, 2022•49 min•Ep. 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
Jan 25, 2022•47 min•Ep. 362
