Your Money, Your Wealth

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 ev...

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 sel...

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 m...

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 minor...

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 (f...

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 li...

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...

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...

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, arro...

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 re...

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, an...

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 transcrip...

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 fr...

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...

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 finall...

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 int...

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 i...

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 po...

Maxing out Roth IRA, 457, and HSA - check. Pension - check. What else do you need for retirement planning? How do pension and Social Security fit into your fixed income portfolio mix? Should you be more aggressive with Roth conversions? Is a 5% equities growth rate good for early retirement plans with inflation? Will a Spousal Lifetime Access Trust (SLAT) protect assets from a tax time bomb? Plus...

Learn to rack up tax-free Roth retirement income: Roth IRA vs. Roth 401(k), paying the tax on a Roth conversion, avoid violating the 60-day rollover rule on a mega backdoor Roth, and Roth IRA contributions when receiving restricted stock units (RSU) in retirement. Plus, moving money from solo 401(k) to IRA before age 59.5, suggestions for a CFP® to be, and matching your umbrella insurance policy t...

"Can you explain how long-term capital gains are 'stacked on top' of ordinary income?" Here are all the YMYW capital gains tax vs. ordinary income tax discussions, together in a single episode, to help you craft a tax-efficient strategy for managing dividends, Roth conversions, and paying less capital gains tax. Will your taxes be going up? Subscribe to the YMYW podcast and newsletter for the late...

Your latest investing strategy questions answered: are gold, real estate investment trusts (REITs), international and small-cap value funds good inflation hedges? Besides the S&P 500, what sectors or asset classes should you invest in for long-term portfolio diversification? Should you buy bonds? How should an 18-year-old invest the money in a Roth 401(k)? Also, how can you get out of a non-qualif...

Spitballing a real estate strategy: sell investment rental properties to buy a home, use restricted stock units (RSU), or both? Plus, is it worth it to hire a financial advisor? Is it a good idea to do Roth IRA conversions to the top of your tax bracket each year? How can you move non-deductible IRA money to Roth IRA without paying taxes again? And a cautionary tale about Roth conversions and stim...

Fielding emails on a wide range of personal finance topics: ex-spouse Social Security benefits, paying the mortgage or buying long-term care insurance, how the FIRE community uses the Roth conversion ladder, tax rules for sole proprietors hiring minors, using excess 529 plan education savings, paying taxes or paying back a Coronavirus Related Distribution, and when to file form 8606 to report IRA...

Is selling rental property to buy a variable annuity a good risk management strategy against sequence of return and interest rate risks? Small-cap vs. emerging markets: which has better risk-adjusted returns for market volatility? Are eREITs (non-traded real estate investment trusts) a good retirement investment? Is RPAR Risk Parity ETF a good inflation hedge? Should you do tax gain harvesting in...