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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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How to Spitball Retirement Taxes and the 4% Rule

How do you determine how much you need in retirement when you factor in taxes, and how does the 4% rule apply? Has one YMYW listener spitballed retirement well enough to convince his wife that they can afford a new luxury truck? Can another YMYW listener take advantage of what seems to be a big opportunity to sell company stock, pay no capital gains tax, and do Roth conversions? Can Big Al’s high school friend do a 1031 exchange to buy a rental property, make it his primary residence in 5 or 10 years, and pay no tax when selling? Is earned income from stock trading still taxable for Social Security if your LLC is in a trust? Finally, a compliment comes in, and Joe and Big Al assume it’s for them. 

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23
AUG
2022
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Roth Conversions, the Rule of 55, and Retirement Withdrawal Regrets

Joe and Big Al spitball, what else, Roth conversions: a conversion and pension lump sum strategy, converting vs. harvesting 0% long-term capital gains, and how to avoid double-taxation on a Roth conversion. Plus, how to allocate assets when preparing to use the Rule of 55? Do retirees regret not spending more in retirement? Will paying a thrift savings plan loan with real estate income avoid income tax? And will assets be better protected against litigation when transferred from a 401(k) to a TSP or an IRA?

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28
DEC
2021
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Which States Are the Most Tax-Friendly in Retirement?

Which states are best for retirement taxes? When moving to a state with a lower cost of living, is it wise to take on mortgage debt to invest in the market? Does it make a difference if you do a Roth conversion before or after moving to another state? Plus, is it better to do Roth conversions with ETFs or mutual funds? Is zero percent long-term capital gains “a hoax”? Also, ABLE accounts for those with disabilities, and healthcare costs vs. taxes as they relate to medical debt, health savings accounts (HSA), and high deductible health plans (HDHP).

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20
JUL
2021
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New Retirement Legislation: Death to the Stretch IRA?

Professor Jamie Hopkins (Carson Wealth & Heider School of Business/Creighton University) talks about impacts the SECURE Act could have on retirement planning – particularly the end of the stretch IRA provision, which allows inherited individual retirement accounts to remain tax-deferred. Plus, how to reduce taxes when you have significant capital gains, when you can take […]

04
JUN
2019
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This Myth is the #1 Barrier to Financial Freedom

Grant Sabatier (author, Financial Freedom) share some of the steps that led him from $2.26 in the bank to over a million bucks in just 5 years, and the myth that he believes is the #1 barrier keeping the rest of us from achieving the same thing. Plus, a conversation about Senator Elizabeth Warren’s wealth […]

05
FEB
2019
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How to Avoid the Five Horsemen of the Retirement Apocalypse

Larry Swedroe from Buckingham Strategic Wealth talks about his 16th book, Your Complete Guide to a Successful and Secure Retirement. Larry discusses the two biggest retirement mistakes, and what he calls the five horsemen of the retirement apocalypse. Plus, is there a way to consolidate your investment portfolio before you retire and avoid paying capital […]

29
JAN
2019
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How to Pay a 0% Capital Gain Tax Rate

Income taxes are never simple and the capital gain taxes are no different. Learn how to understand the new capital gain tax rates. Transcription Did you know that there is a zero percent capital gains rate? Well, I’m going to tell you how to pay zero taxes on your capital gains. But first, what is a […]

20
OCT
2017
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