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Is It Crazy to Be Happy Paying Tax on Massive Stock Market Gains?

Is it better to pay tax on $5 million than on $1 million, or is that crazy talk? Also, an asset location strategy to lower RMDs and taxes but still maintain portfolio growth, and an argument against Roth IRAs. Is it a valid one? Plus, what counts as contributions if you withdraw from your Roth IRA after 5 years? Why not pay the tax on a Roth conversion out of your IRA? Roth conversions vs. the medical insurance ACA subsidy, and what? Joe, arrogant?!

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03
AUG
2021
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How to Protect Investments Against a Stock Market Crash?

Joe & Big Al discuss various strategies to protect your portfolio from a stock market crash: stop losses, put options, collars, non-correlated alternative investments, and tax-managed buy-and-hold. Also: how should you 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 our first “Dear Joe” question, in the Derails: how do you get your mother-in-law to stop smoking in your car without starting a fight? 

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08
JUN
2021
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Retirement Portfolio Strategies and Making Sense of Fees

Does it matter if you put retirement savings in the older spouse’s accounts first? Does Marion have a good VTSAX to VTWAX tax-loss harvesting and portfolio rebalancing strategy? Plus, Joe and Big Al help you make sense of fees – both from your financial advisor and on exchange-traded funds, or ETFs. Big Al will provide […]

03
NOV
2020
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Ask The Experts: Take the Sting Out of Taxes For High Income Earners

Tired of writing a big check to Uncle Sam? You can help take the sting out of your tax bill by using financial planning tools and strategies. Financial professionals Joe Anderson and Alan Clopine discuss how tax-loss harvesting can help create tax savings. They caution against counting on antiques or rare coins to fund your […]

26
DEC
2019
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Money Saving Year-End Tax Strategies: Tax Loss Harvesting

Looking for ways to save money on your taxes? While losing money on an investment may not seem like the ideal plan for your retirement savings, the loss may be used in a strategy to maximize your bottom line. Financial professionals Joe Anderson and Alan Clopine walk you through the concept of tax loss harvesting […]

06
SEP
2019
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Take the Sting Out of Taxes For High Income Earners: Tax Loss Harvesting

Want to learn how to earn tax-free income in retirement? Taking the sting out of your tax bill can be as easy as using a simple strategy called tax loss harvesting. Financial professionals Joe Anderson and Alan Clopine explain how creating a tax loss can actually increase your bottom line. Click here to watch the […]

10
JUL
2019
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