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How to Get Into the Stock Market: Dollar Cost Average or Go All In?

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).

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10
SEP
2024
LISTEN NOW
SEASON 9, EPISODE 7

Emotional Investing: You Are Your Own Worst Enemy

When you are investing, do you feel like you are on an emotional rollercoaster, careening from feelings of euphoria to depression? Most people admit they know they shouldn’t let their emotions drive their investment decisions, but when we see the highs and lows of the market, it can be difficult not to let our emotions […]

18
JUN
2023
WATCH NOW
SEASON 9, EPISODE 6

How to Build a Recession-Proof Portfolio

When you hear the word recession, what comes to mind: run for the hills, or golden opportunity? From bear markets to rising inflation, the conditions that create a recession can impact your investments and your ability to retire. If you make the wrong financial moves during a recession it can take decades for your portfolio […]

04
JUN
2023
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Should You Claim Social Security Early?

When deciding whether to claim Social Security early, how do taxes figure into the analysis? If Social Security creates too much provisional income so that you have to pay tax on your Social Security benefits, does it make sense to claim Social Security early? If you apply for Social Security at age 70 and learn you could’ve taken spousal benefits for four years, are you owed that money? Plus, a listener takes issue with YMYW’s dollar-cost averaging discussion. But first, how long did the recovery from the 1929 stock market crash really take, and do higher yield investments early in retirement offset sequence of returns risk?

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15
MAR
2022
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Dollar-Cost Averaging, Small Cap, and Stable Value Funds

What exactly are dollar-cost averaging and reverse dollar-cost averaging? Joe and Big Al explain as they answer questions about paying Medicare premiums with HSA funds, and ETFs vs mutual funds when dollar-cost averaging into small-cap value funds. Plus, why would you want to reduce the stock allocation in your emergency fund, and should a stable value fund be part of your portfolio? Is it possible to “re-identify” an inherited IRA as a spousal IRA to change the RMD calculation? Is the section 162 executive bonus plan just whole life insurance? And finally, Joe’s past comes back to haunt him with 9 cats, a neurotic beagle, and 200 IRAs.

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01
MAR
2022
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