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White Papers

Discover the positive impact a proper financial strategy can have on your life.

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$7M Tax-Free or $10M Retirement? Backdoor Roth or Lower Fees?

Should Carl Spackler stick with his backdoor Roth strategy, or go for lower fees? Should Kevin go all Roth, or stick with his current three tax-diversified buckets strategy? (That depends – would he rather have $7 million tax-free, or $10 million in tax-deferred retirement accounts?) Can Lily claim all the extra allowances she can, to jam as much money as possible into her Roth? Can Dave retire now and ride his motorcycle into the Bavarian Alpine sunset, and does Peggy Lee need to be feverish about the tax underpayment penalty with her Roth strategy?

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25
JUL
2023
LISTEN NOW

The Ultimate Guide to Roth IRAs

Updated for 2023: Interested in a retirement account that will expand your finances tax-free? Learn everything your need to know about Roth IRAs in this white paper. In this guide, you’ll learn… What a Roth IRA is and the benefits Differences between a Roth IRA and Traditional IRA Rules of Roth IRA contribution limits Roth […]

07
JUL
2023
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Survivor Social Security and Lowering Taxes in Retirement

Joe and Big Al explain when and how to claim Social Security survivor benefits, and how earning income impacts your benefit if you collect Social Security before full retirement age. Plus, how much should you withdraw in retirement from tax-free, taxable, and tax-deferred accounts? Also, RMDs, deciding whether to keep a life insurance policy, and of course, Roth conversion strategies – is the backdoor Roth better for long-term portfolio growth?

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11
OCT
2022
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Spitballing Retirement Planning in Your 40’s & 50’s

A compilation of some of Joe and Big Al’s retirement plan spitballing specifically for those in their 40s and 50s – a critical time on the path to retirement. Is your financial plan set up so you pay as little tax as possible? Does it take volatile markets and potential future tax increases into account? Have you got a strategy nailed down for Roth conversions, or backdoor Roth, or pension options? Maybe you’re making big decisions about what to do with your money between now and when you retire, like buying a house vs. saving for retirement? Are you comfortable with the retirement lifestyle you’re creating? Do you know what you’ll do with your time once you’re permanently off the clock? 

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27
SEP
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
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How to Deal With Taxes When Income Goes Through the Roof

If a fortunate equity event or liquidity event should cause your income to skyrocket, what will that do to your taxes? Joe and Big Al spitball tax strategies to help you manage this good problem to have. Plus, Backdoor Roth, contributions, conversions, and income limits explained, converting twelve and a half million bucks to Roth, and what happens to retirement accounts when you pass – will there be a tax bill due? Kicking it off with the 7-twelve portfolio – what is it?

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06
SEP
2022
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Is Now the Time for a Roth Conversion, or Wait Until Retirement?

Should you convert money from your pre-tax retirement accounts to Roth now, wait until retirement, or until required minimum distributions kick in? Should a mid-30s couple do Roth Conversions or a Backdoor Roth? Should a 93-year-old open his first ever Roth and start converting? What’s a good retirement savings mix between pre-tax and post-tax? And the fellas do a worst-case scenario retirement spitball analysis. 

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30
AUG
2022
LISTEN NOW
SEASON 8, EPISODE 11

Rock Your Retirement With Roth

One of the most powerful retirement tools that Congress has ever given taxpayers is the Roth, but not everyone is taking advantage of its big tax benefits. Many say they don’t even know investing in Roth is an option, much less how to maximize its advantages. Whether your workplace has the Roth option or not, […]

07
AUG
2022
WATCH NOW

Save for a Home or Save for Retirement?

Should you save for a house down payment or invest for retirement? How much long term capital gains tax do you pay on a rental property when you sell it after 20 years, and how does a 1031 exchange work? Also, opening a Roth IRA with the Backdoor Roth strategy, and the 5 year Roth withdrawal rules explained. Plus, a couple retirement spitball analyses: are you saving too aggressively for retirement? Can you avoid the Medicare IRMAA, or income related monthly adjustment amount, and high taxes from required minimum distributions?

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02
AUG
2022
LISTEN NOW

Pay Tax on This Move Now to Potentially Have More to Spend Later

The time may be right for a giant Roth IRA conversion, especially now while the market is down, to potentially give you more money to spend in retirement. How does that work with long-term capital gains and dividends, and how much should you convert to Roth, and when, and how? Plus, deciding how to invest 529 plan college savings, whether to save to pre-tax or post-tax retirement accounts, and the ever-popular Backdoor Roth strategy. 

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26
JUL
2022
LISTEN NOW

Roth Conversion Retirement Spitball Analysis

Does it make sense to do larger “Calvin Johnson” (Megatron, aka mega backdoor) Roth conversions when the financial markets are way down? Should you convert to Roth now, or in retirement? How do you spitball the right amount to have in 529 plans for education savings? And are the rules for doing a backdoor Roth the same if you’re married filing separately?

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Free Financial Assessment

26
APR
2022
LISTEN NOW

Why Is It So Difficult to Time the Market?

How statistically and practically difficult is market timing? What factors should you consider when choosing large-cap value funds? Should a $100,000 inheritance be invested in tax-deferred, taxable, or tax-free accounts? Plus, Backdoor Roth vs. Roth conversions; rules, limits, and strategies for 401(k) and IRA contributions; moving retirement money between custodians like Vanguard and Fidelity; and some negative but very entertaining listener comments.

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Free Financial Assessment

08
MAR
2022
LISTEN NOW

Roth Conversions vs. Roth Contributions

Should you use money intended for Roth contributions to pay the tax on Roth conversions instead? Does the IRS really penalize ineligible Roth contributions? How will a mega backdoor Roth contribution be taxed, and will the step transaction doctrine apply? Are family Social Security benefits affected if the spouse works? Plus, $1800 a month for life, or $2600 a month for 10 years? Joe and Big Al spitball retirement pension options and they take your comments.

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Free Financial Assessment

22
FEB
2022
LISTEN NOW

Early Retirement, Roth Conversion Tax: YMYW Best of 2021

Early retirement, backdoor and mega-backdoor Roth conversions, paying the tax on a Roth conversion, asset location, and more: it’s the most important topics from our most popular podcast episodes and YouTube videos of 2021. Plus, the most “impactful” listener comments of the year, and the funniest Derails of 2021 in real time! 

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Free Financial Assessment

25
JAN
2022
LISTEN NOW

Should You Invest in the Stock Market or Buy Real Estate?

You’ve saved money for a house downpayment. Should you invest it in the stock market until you’re ready to buy that property? Should a young saver take as much investing risk as possible, or buy a condo? Plus, the tax efficiency of robo-advisor brokerage account withdrawals, backdoor Roth conversions under the Build Back Better Act, using a charitable remainder trust to avoid inherited IRA tax under the SECURE Act, and listener comments on our pension and capital gains compilation episodes. 

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Free Financial Assessment

11
JAN
2022
LISTEN NOW
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