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Tax-Savvy In-Plan Roth Conversions and Inherited IRA Withdrawals

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? 

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01
OCT
2024
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3 Strategies to Pay Roth Conversion Taxes

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). 

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17
SEP
2024
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Alternative Investments, Annuities, and Real Estate Syndications

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?

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20
AUG
2024
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Can You Retire? Here’s How to Calculate How Much You Need

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?

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13
AUG
2024
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Are Roth Conversions Really as Good as They Sound?

Christine isn’t sure that Roth conversions are all they’re cracked up to be. Erick needs a retirement spitball analysis for his Roth conversions, annuities, and the real estate in his self-directed IRA, Billy the disgruntled attorney wants to know if he can retire now, and Zach wonders just how bad is it to rely on the lottery for retirement? But first, Joe and Big Al spitball retirement strategies for three members of the US military.

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01
AUG
2023
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How to Reduce Taxes and Get Better Investing Returns? Asset Location

Generating “tax alpha” to get better returns on your investments: which investments should go in your traditional IRA vs your Roth IRA, and does that asset location depend on your age? Plus, Joe and Big Al spitball whether to roll a TIAA 403(b) to an IRA or take the annuity, and they spitball retirement, Roth conversion, and Roth contribution strategies for an overseas officer with a military pension, and for Americans working abroad who qualify for the foreign earned income exclusion.

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28
MAR
2023
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Fixed Indexed Annuities, RMDs, and Early Social Security

We’re hearing more about fixed indexed annuities with these volatile financial markets. Is it time to reconsider? Plus, clarification on required minimum distributions being waived for non-spouse IRA beneficiaries in 2021 and 2022, taxation on trusts, and suggestions for a 40-year-old considering an early mini-retirement. Also, can a 62-year-old immediately withdraw Roth conversion money? Finally, a strategy to claim Social Security early while working and invest the difference in a Roth, and Joe and Big Al attempt to explain family Social Security benefits without phoning it in.

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06
DEC
2022
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Annuities, Social Security, and Real Estate Taxes

When is it appropriate to buy an annuity? Joe and Big Al run a retirement annuity spitball analysis. Plus, 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?

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Free Financial Assessment

19
APR
2022
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Spitballing Retirement and the Build Back Better Tax Proposal

Should those in the 35% tax bracket contribute to traditional 401(k) or Roth 401(k)? Should a self-employed cryptocurrency investor do Roth conversions or tax gain harvesting? Also, a retirement spitball for a couple, age 35, wanting to retire with $5M at age 60. Plus, do the SECURE Act rules for required minimum distributions (RMDs) apply when inheriting an inherited IRA? Finally, comments on some of the proposals in the latest version of the Build Back Better Act, which is currently being considered by the Senate.

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Free Financial Assessment

14
DEC
2021
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Which Asset Classes Are Good Investments to Hedge Against Inflation?

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-qualified annuity?

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Free Financial Assessment

04
MAY
2021
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Roth Conversions, Annuities and Inherited IRAs

Answering questions across the financial and retirement spectrum, with topics like when your traditional IRA is growing faster than you can convert to Roth, consolidating retirement savings, annuities, the SECURE Act and inherited IRAs, undoing SEP-IRA contributions, Roth conversions after age 72, offsetting conversion gains against tax-harvested losses, tax diversification beyond conversions, and what to […]

15
SEP
2020
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Roth Conversion Tax Planning Strategies and Annuities

Tax planning for Roth conversions with itemized deductions, dividends, and long term capital gains, the difference between a Roth conversion and investing a 401(k) distribution in your Roth, separating pre-tax and post-tax money for a rollover – and gong baths. Plus, is a 3 year fixed annuity a safe place to earn more than 20 […]

18
AUG
2020
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Real Estate, Roth Conversions and Annuities

A mixed bag of questions on everything from spousal solo 401(k) contributions and renaming inherited IRAs to real estate buying strategies (should you cash out the 401(k) to buy a house?) and a perennial fan-favorite, ripping on annuities. Plus a healthy dose of Roth conversion planning thrown in the middle. Subscribe to the YMYW podcast […]

12
MAY
2020
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In Market Volatility, Beware of Annuity Pitches

In these volatile markets, pitches for fixed indexed annuities will be on the upswing. Here’s how to analyze them for yourself. Plus, CARES Act stimulus payments for kids, retirement account distributions, and rethinking your retirement savings strategy. Also, SECURE Act stretch IRA rules, evaluating long term care insurance options, and why thrift savings plan (TSP) […]

21
APR
2020
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Appreciate How Good the Economy is Now

According to Dr. Chris Thornberg of Beacon Economics, the US economy and real estate market are currently extremely healthy, so we should appreciate it and focus now on fixing the retirement crisis we’re facing in 10-15 years. Plus, Joe and Big Al answer your money questions: Why is owning a home considered “profitable”? Is it […]

23
JUL
2019
LISTEN NOW
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