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...

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? ...

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 o...

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? Fre...

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...

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...

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, fr...

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" sugge...

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. P...

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 resourc...

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 ques...

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. Finan...

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...

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...

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 ...

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-...

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 transcr...

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...

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....