Recent Podcasts
Should Suzanne in Michigan do Roth conversions in 2025 and 2026 since she’s widowed and won’t be married filing jointly? How should she pay the tax on her conversions? Jennifer in Washington state is 55 and her husband is 70. Should she retire now and do aggressive Roth conversions before...
More Podcasts
Are real estate investment trust (REIT) ETFs a good way for Leon to begin investing in real estate? Can AI Seth stay retired at age 52, and should he do Roth conversions? Jenn in Ohio wants the fellas to be brutally honest about whether she should move with work, take a break, or retire now. And “George and Weezy” are in their mid-50s – can they “move on up” to a deluxe retirement lifestyle in 2026, or even earlier?
Hawkeye and Elle are age 61 and in the 32% tax bracket. How should they get money into their Roth accounts for tax-free retirement income? Clark and Ellen are 69 and 68, expenses will pretty much be covered by their fixed income, but they’d like to leave Roth money to their kids. Should they keep converting to Roth, or use required minimum distributions for their living expenses? Tom and his wife are 73, and fixed income will cover their retirement spending too. Is it advantageous to them to make three huge Roth conversions beyond their marginal tax bracket to reduce future RMDs? Should they keep things simple by leaving their money in an S&P 500 Index Fund?
Should David in Ohio use 457 funds to do an in-plan Roth conversion in his 403(b) plan, and should he hire a financial advisor? Chris in DC needs a retirement and Roth conversion spitball analysis, and he needs help getting out of a variable annuity. Kim is anxious that she made a mess of her finances and she wonders how much she should convert to Roth. Plus, what’s the best way for Alissa in Cedar Rapids, Iowa to make tax-efficient retirement withdrawals from an inherited IRA?
Joe and Big Al spitball on three different listeners’ strategies for paying the tax on a Roth conversion now, to have lifetime tax-free growth on that money in the future: should “Neo” convert to Roth at the beginning or end of the year in his plan to make quarterly estimated tax payments on his conversion? Is it a good strategy for Tim to use reimbursements from his health savings account to pay Roth conversion taxes? What do Joe and Big Al think of Samantha’s plan to convert to Roth and pay the tax with her IRA money? Plus, the fellas answer questions from our YouTube and Spotify followers on required minimum distributions from Roth accounts, reasons to put retirement withdrawals in a brokerage account instead of a Roth, choosing pension options, the difference between commercial annuities and pension annuities, and their thoughts on single premium immediate annuities (SPIA).
TJ in Louisiana has been sitting on the sidelines, but now it’s time to get into the market. Should he dollar cost average, or just go all in? Does Margaret in CA’s idea of selling a stock at a loss and buying a put option on that stock that expires after the 30-day waiting period work as a tax loss harvesting strategy? When is it worth it for Brian in Charlotte, NC to diversify beyond a basic three-fund portfolio? Should Christine in San Diego convert her variable annuity to a fixed indexed annuity? How should Dean in Columbus, GA invest inherited retirement money? Are Jen and John in CA on track for retirement, and how should they fund their home remodel? Are there any negative consequences for Steve in PA if he finds a new financial advisor just a few months after hiring his current advisor? The fellas also talk through how Chris can give money to charity from his required minimum distributions (RMDs), and finally, Terry calls in with a follow-up question about whether a solo 401(k) is an option to avoid unrelated business income tax (UBIT).
Can Alanis retire early at age 60? With Barney and Betty’s spending patterns, can they retire ASAP? Daisy and Donald need retirement income for 40 years. Can they retire now? Plus, we review the results of the 7th Annual YMYW Podcast Survey (congratulations to jemart for winning the Amazon e-gift card!) And Joe and Big Al take on some critical YouTube comments from Keith, following their interview with Ed Slott, CPA.
What is an exchange fund and is it a good thing if you have a lot of capital gains, like Bryan in New York? What should be the timing and ordering of Billy Joe and Bobby Sue’s Roth conversion strategy to help them achieve 33 years of retirement income? Is Boston overspending or underspending in retirement? Should Andy keep life insurance policies for her kids with ADHD? How does the 5-year rule for Roth withdrawals apply to inherited Roth IRAs for Karen?
What do Joe and Big Al think about alternative investments? Andrew in Ohio wants to know. Are real estate syndication deals for real, and a YMYW listener just chose poorly? And Stewart in Serra Mesa is curious whether Joe has changed his position on annuities lately, as rates have “normalized” in the past couple of years? Plus, when should Steve in Las Vegas’ friend quit her casino job and collect Social Security and child benefits? And how is D in the Midwest’s plan for creating income in retirement?
Can Claire and her husband retire early at age 60? Joe and Big Al spitball for them and explain how to calculate how much you’ll need in retirement. Plus, should Jeff invest his pension money more aggressively, and should he save to his thrift savings plan or his Roth? Should Paula save to her brokerage account or her 401(k)? When and how much should Ken and “Fume Guzzler” each convert to Roth? The IRS charged Lex late fees for not paying estimated taxes throughout the year on her Roth conversion – find out how to avoid that yourself. Finally, how can Ken get out of an annuity? And is it harmful for Sarah to advise co-workers with little financial experience?
The single biggest retirement planning mistake to avoid, the problem with tax professionals, and answers to some of the most frequently asked retirement questions we get on YMYW: should you name a trust as beneficiary on your retirement accounts? What’s the break-even point on a Roth conversion? What if you don’t have the money to pay the tax when you convert to Roth? Plus, find out the eye-opening amount of money good tax planning can save you! Someone has to be very knowledgeable, entertaining, and special to make it as a guest on YMYW these days. Today “the IRA guru” Ed Slott, CPA from IRAHelp.com joins Joe Anderson, CFP® and Big Al Clopine, CPA to discuss all of these topics, along with changes to stretch IRAs and required minimum distributions from the SECURE Act and SECURE 2.0 Act. Finally, don’t miss your chance to get a free copy of Ed Slott’s latest book, The Retirement Savings Time Bomb Ticks Louder.
Is timing the market when withdrawing money from retirement accounts or doing Roth conversions an effective strategy for YMYW listener Robert to minimize tax and maximize returns? Should Doug change his 60/40 asset allocation, and should he start a solo 401(k)? Jefe plans to withdraw from his retirement accounts beyond the top of the 24% tax bracket for the first few years of retirement. Is there any reason to put it in a brokerage account rather than converting it to Roth? The fellas also spitball on Roth conversion methods and strategies for Srinivas, Todd, Debbie, and JZ in California, and they spitball on JZ in New York’s “bucketing” strategy for early retirement withdrawals.