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When to HOLD OFF on Doing Roth Conversions

John in Boston is in the 32% tax bracket. Should he do Roth conversions? Flight Deck Dad and Irish Girl in Pensacola have a lot of tax-free pension income. Should they do Roth conversions? Bert and Ernie in New Jersey wonder if they should convert to Roth or take advantage of zero percent capital gains tax rates. Joe Anderson, CFP® and Big Al Clopine, CPA spitball for all of them today. Plus, Michael and his wife in Bellevue are 34, in the 24% tax bracket and wonder if they should contribute to tax-free or tax-deferred accounts, and if they should slow down on retirement savings and start a bridging account for the years between when they want to punch the clock in their early to mid-50s, and when they can access their retirement savings. Then, for something completely different, Frenchie from Maine writes back in: What are the disadvantages to paying off her mortgage ASAP, and what’s the tax efficiency of a money market compared to bond funds?

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13
MAY
2025
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Defusing a Future Tax Bomb With Roth Conversions

Does it make sense for Alex and his wife in Massachusetts to do Roth conversions now to the top of their eventual tax bracket? Steve in San Diego got serious about saving for retirement after Joe and Big Al gave him some tough love 5 years ago. Is he good to retire now, and should he convert to Roth? Can Barbara in New Jersey’s grandson move excess 529 funds to a Roth and withdraw the money after 5 years? P. Ware has a cunning plan to gift appreciated stock to avoid capital gains tax, but will it work? Should Mike create a limited liability company (LLC) for his rental properties? Qualified charitable distributions (QCD) don’t make sense to GetSmart Paul. Sherri in California wonders if her kids can inherit her savings account without any tax penalty, and whether there’s a safe, high-yielding investment she should put it in. Finally, Houry in New York wonders if her IRA can fund a charitable remainder unitrust (CRUT).

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31
DEC
2024
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Exchange Funds Explained, Roth Conversion Timing

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?

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27
AUG
2024
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Which Account Should Fund Living Expenses in Retirement?

Should 70-year-old Bob live off of capital gains and dividends from his mutual funds plus Social Security, or should he sell poor-performing mutual funds for living expenses and reinvest the cap gains and dividends? Which account should Neal’s 76-year-old Mother use for living expenses? Should Neal and his wife fund their Roth 403(b) until retirement, or contribute to the regular 403(b) and then do Roth conversions after they retire? Plus, Joe and Big Al spitball on whether IndyGuy can retire at 64 and Die With Zero, and Rod doesn’t want a spitball, but he’d like a dart on the wall as to whether his retirement savings will last until age 88. 

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14
MAY
2024
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How to Manage Taxes When You Win the Lottery

So you won the lottery – congratulations! After you celebrate, should you rip off the band-aid and convert the entire lump sum payment to a Roth IRA? Also, Bucky in WA is required to have the same asset allocation in his traditional and Roth 401(k). Joe and Big Al spitball on his options, along with the pros and cons of consolidating retirement accounts for Scott in NC, and they explain the spousal Roth IRA for Rock Rochester in Manistique, MI. Plus, should Scott in Jackson, MS sign up for the state public employees’ retirement system or a traditional retirement plan? Can Driving Fast, Loving Life in TX speed away in her Porsche from RSU capital gains? And should she and her hubbs retire abroad? Finally, can Sean in Reno, NV buy a million-dollar vacation home in 10 years, and can Jennifer in La Mirada, CA afford to retire after being forced out of a 21-year career? 

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23
APR
2024
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Does Your Financial Advisor Just Want to Collect Fees?

Why would a financial advisor suggest that Frank in Lake Wobegon sell a piece of inherited property, pay 25% tax, and invest the lump sum? Mark in Florida is 72 and invested in CDs. Should he go back to his financial advisor, or just buy more CDs? Plus, Adam in Tennessee will have deferred income in 5 years. Should his asset allocation be more conservative? And in order to retire early at age 55, should Lewis in Arkansas delay starting Roth conversions? But first, if Mike’s wife outlives him, how can he keep her in a similar tax bracket?

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19
MAR
2024
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Market Timing, Pension & Roth Conversion Retirement Spitball

How will a diet COLA on a pension affect retirement plans for Joe and Barb in Tulsa? Percy in South Carolina has a pension too. He’s timing the market, but should he change his investing strategy as he approaches retirement? Plus, Michael in Virginia needs ideas to fund a custodial Roth IRA for his 3-year-old and 2-month-old kids, and Rocco in NYC catches Big Al on capital gains exclusions. But first, will scary future events mean Michelle in San Diego will have to pay more tax and the highest possible Medicare premiums?

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05
SEP
2023
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Early Retirement Withdrawals & Capital Gains Tax Explained

Does the math work for Chris’ early retirement plan? What’s a safe retirement withdrawal rate for Luke, who wants to be part of the financial independence / retire early or FIRE movement? Plus, Jake is about to change jobs, can Joe and Big Al uncover any tax planning opportunities for him? The fellas also explain capital gains tax for our buddy Carl Spackler, they spitball on those capital gains when it comes to selling a house for Olga and for LJ, and Jim wonders about the impact of selling a house on Affordable Care Act subsidies.

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08
AUG
2023
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Capital Gains vs Dividends: What’s the Difference? | Financial Tip

Pure’s Senior Financial Planner, Richard Alexander, CFP®, AIF®, explains the difference between capital gains and dividends. Capital gains are profits from selling investments at a higher price, while dividends are income paid out by corporations to stockholders. FREE GUIDE | 10 Tips for Real Estate Investors Transcript Capital Gains vs Dividends. Both are sources of […]

02
JUN
2023
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Mutual Funds vs. ETFs, SECURE 2.0, & Capital Gains Strategies

Are low-cost mutual funds or ETFs better investments in a tax-advantaged account? Also, more strategizing from that SECURE Act 2.0 529 plan provision, the pros and cons of selling a rental house now or holding it until you pass, and an easy-breezy self-employed retirement account that’s better than a SEP IRA. Plus, will municipal bond income bump you into a higher tax bracket? Can you avoid capital gains tax by investing less aggressively over time?

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14
MAR
2023
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How to Forecast Your Expenses in Retirement

What will you actually need to spend in retirement? Joe and Big Al explain how to really think about and calculate your retirement expenses. Plus, if you want to reduce your tax-deferred account balances, does it make more sense to do Roth conversions or reinvest? What about doing Roth conversions to a higher tax bracket than the one you’ll be in during retirement? Also, the fellas explain the alternative minimum tax, how Social Security spousal benefits work, and when in the year you turn 72 you must take required minimum distributions from your retirement accounts. And finally, what should someone with no credit history, who hasn’t paid taxes, do with a sudden $100,000 windfall?

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29
NOV
2022
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Life Insurance, Muni Bonds, and Dividend Stocks in Retirement

Joe and Big Al discuss LIRPs, or life insurance retirement plans, they spitball whether to take full pension survivor benefits or buy a life insurance policy, and whether to sell losing stocks for even bigger losers to take advantage of the 0% capital gains tax bracket. Plus, zero coupon municipal bonds and the de minimis rule, and target date funds as part of Paul Merriman’s Two Funds for Life strategy. Finally, how do dividends figure into the 4% rule for retirement withdrawals, and should that 4% come from stocks or bonds?

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22
NOV
2022
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Will Your Retirement Savings Last Until You’re 90 Years Old?

Are you behind on your retirement savings? What do you need to do to catch up? If you retire in just a few years, will your money last until age 90? Based on the 5-year Roth withdrawal rules, do you need to open a new Roth IRA for each Roth conversion? Plus, Joe and Big Al spitball a health insurance, capital gains, and real estate strategy to save more money and have more wealth in retirement. Finally, they revisit the SECURE Act rules for withdrawing money from an inherited IRA, and Social Security income limits. 

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01
NOV
2022
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Should Young People Save for Retirement?

New research says some young people shouldn’t save for retirement. Find out what Joe and Big Al think about that. Plus, is it tax fraud if you re-file your taxes to take advantage of new student loan forgiveness? Should you invest in CDs instead of bonds, since both stocks and bonds are getting crushed right now? How can you consolidate your stock portfolio to minimize capital gains tax? Also, charitably inclined YMYW listeners want to know how to use donor-advised funds when spitballing tax planning around an IPO, and whether to do more Roth conversions or more qualified charitable distributions. 

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25
OCT
2022
LISTEN NOW

Backdoor Roth, Investing, and Taxes

Answers to your questions on, of course, backdoor Roth strategies. Y’know, to get as much lifetime tax-free growth on your investments as possible. Plus, investing strategies: does it make sense to buy a property now and rent it out until retirement? How much of a single stock in your investment portfolio can you sell and pay no capital gains tax? The fellas also explain capital loss carryovers, inherited IRAs, spousal Social Security and delayed retirement credits, required minimum distributions, and they spitball on an appropriate allocation of bonds, domestic stocks, and international stocks.

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20
SEP
2022
LISTEN NOW
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