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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
LISTEN NOW

How to Choose, Buy and Sell Rental Property: Real Estate Investing for Retirement Income Explained

Boost your monthly income in retirement by investing in residential real estate? Learn the pros, cons, and mistakes to avoid, things to consider before buying investment properties, rental real estate finances, and how to minimize taxes through real estate investments.   Transcript: Andi: Hello and welcome and thank you all for joining us for this […]

12
JUL
2023
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Bonus Depreciation, Retirement Income, and Portfolio Diversification with Real Estate

How does bonus accelerated depreciation work when it comes to commercial real estate? Is real estate a good source of retirement income, and can it take the place of safe assets like bonds in your investment portfolio? 

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13
JUN
2023
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Spitballing Retirement Real Estate and Tax Strategies

Gidget wants to find her very own Moon Doggie so she can get married and reap that sweet, sweet capital gain exclusion when she sells her house. What do Joe and Big Al think, and can they help her find a man? Plus, is real estate a good investment for retirement income? Is taking out a TSP (thrift savings plan) loan to pay off your mortgage a good idea? Also, the fellas spitball a tax and ACA (Affordable Care Act) strategy, a FIRE strategy – well, financial independence, but not necessarily retire early – and they discuss capital gains taxes on RSUs (restricted stock units.)

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25
APR
2023
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Estate Planning Checklist | Financial Tip

Deciding who will inherit your estate is a big decision and an important part of life planning. Smart estate planning helps protect families with young children as well as helping your heirs from overpaying on taxes. Pure’s Financial Planner, Dean Heimbach, CFP®, AIF®, covers four key steps to get you started on your estate plan: […]

03
APR
2023
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Set-and-Forget Investing, Real Estate vs. Bonds, Pension, Social Security & Medicare

Joe and Big Al spitball on set-and-forget brokerage investments for 30-something investors, real estate as a substitute for bonds in a diversified portfolio, and options for taking a state pension with or without sick time pay. The fellas also discuss how to bridge the gap until collecting Social Security, strategies for claiming spousal Social Security benefits, and whether you need to sign up for Medicare if you’d rather keep the healthcare you already have. 

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14
FEB
2023
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Medicare IRMAA, Roth Pro-Rata, & Real Estate Strategies

Joe and Big Al attempt to clearly and succinctly explain modified adjusted income for Medicare and IRMAA, and the pro-rata and aggregation rules for Roth conversions. Will a combat zone TSP transfer be subject to those rules? Plus, joint tenants with rights of survivorship vs. transfer on death for a brokerage account, reducing taxes on the sale of a timeshare, how much to spend on home improvements, and using a reverse mortgage instead of long-term care insurance. And wait ’til you hear the fellas’ thoughts on the best way to pay the least amount of tax when you cash out your retirement savings to buy gold and silver.

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31
JAN
2023
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SEASON 8, EPISODE 21

Rate Your Retirement Plan: Pass or Fail?

Would you go to a restaurant that has a C rating or even a B rating? How about your retirement plan? Do you know how your financial plan rates, or are just satisfied that you have one? Having a plan is a big step in the right direction, but is it actually going to meet […]

22
JAN
2023
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Who to Trust? Second Opinion Retirement Spitball

Can you trust the opinion of just one advisor when planning for your entire financial future? Joe and Big Al spitball their second opinions for some retirement plan and Roth conversion strategies, they illustrate one way some financial advisors may be acting in their own best interests, and they explain how to determine if you’re on track for a successful retirement. Plus, can you take penalty-free withdrawals from a Roth TSP to Roth IRA rollover in order to bridge the gap until age 59 and a half? Will paying for a home remodel with Roth conversion funds avoid tax? And, should you use Roth conversion money for these purposes?

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20
DEC
2022
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Inflation Investing, Asset Location, and Real Estate Retirement Spitball

Following the Fed’s fourth consecutive interest rate hike last week, should you be changing your investing strategy to time this inflationary market, moving from bonds to 3-year annuity CDs? Plus, Joe and Big Al spitball on asset location and Roth Conversions for the in-laws and a net unrealized appreciation (NUA) strategy for company stock in a 401(k). They also discuss whether extra home mortgage payments are part of an investment portfolio, and what real estate expenses are tax deductible. 

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08
NOV
2022
LISTEN NOW

Anything Stupid or Overlooked in Your Retirement Plan Spitball?

Are there any holes in a 5 year plan to retire from the Air Force, buy a house and a plane, and become a commercial pilot? Can you claim an unpaid loan to a start-up as a tax loss, do a Roth conversion, and pay no tax? Are Roth Conversions a good idea in a low-earnings year? Does it matter if you convert to Roth before or after changing custodians? What retirement savings options do independent contractors have besides the Solo 401(k)? Does it make sense to cash out a 529 college savings plan that’s losing money? Plus, Joe and Big Al spitball a real estate strategy, and they discuss a state retirement account held at an insurance company. 

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18
OCT
2022
LISTEN NOW

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

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
LISTEN 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

A Model Retirement Plan Spitball Analysis

Learn how to craft a retirement plan email question that’ll get you a model retirement spitball analysis. Plus, when should you contribute to Roth IRA, and when and how much of a Roth Conversion should you do? Is it hypocritical to prioritize investment returns over your conscience and values? Joe and Big Al talk ESG, or environmental, social, and governance investing, and they evaluate a strategy to keep taxes low while helping your kids buy a house. Finally, your comments about YMYW.

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19
JUL
2022
LISTEN NOW
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