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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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Spitballing Diversified Portfolios for Retirement

How should young savers invest pensions and estimate their retirement income needs? Is going into your employee stock purchase plan a good portfolio diversification strategy? What do Joe and Big Al think of multi-year guaranteed annuities (MYGA), and dividend-paying stocks vs. ETFs? Plus, a $10.6M retirement spitball analysis, making extra mortgage payments vs. saving to a brokerage account, and contributing to Roth 401(k) vs. traditional 401(k). Also, will a 403(b) held by an insurance company be subject to separation costs or surrender fees when rolled to an IRA? And the specifics on when to file tax form 5500. 

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24
JAN
2023
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SECURE Act 2.0 & Retirement Rich, Cash Poor

Joe and Big Al are back with a SECURE Act 2.0 recap and a proposed backdoor 529 plan strategy from the new law. Plus, is there a scenario where it makes sense to not max retirement accounts, to avoid being retirement rich and cash poor? Also, the fellas’ thoughts on a break-even point for Social Security, required minimum distributions (RMD) from inherited IRAs, and of course, Roth IRA strategies: as in, the 5-year rules for Roth withdrawals, preserving Roth money and avoiding early withdrawal penalties, and Roth conversions to offset brokerage account losses. 

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17
JAN
2023
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Bear Market Survival & the 5W1H of Roth Conversions: YMYW Best of 2022

Down market retirement withdrawal strategies, the 5W1H (that is, the who, what, when, where, why, and how) of Roth conversions, the retirement spitball analysis, and the funniest Derails of 2022 on this, YMYW podcast’s Best of 2022.

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10
JAN
2023
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Retirement Planning, Investing, and Tax Reduction Made Fun: YMYW Trailer

Your Money, Your Wealth is retirement planning, investing, and tax reduction made fun! Listen to the podcast trailer and follow on your favorite podcast app.

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03
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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Where to Save for Early Retirement?

Asset location strategies, liquidity, and building up tax-free Roth IRA money when retiring early, how growth is taxed in taxable accounts, the pros and cons of rolling an employer retirement plan into a traditional IRA, how stock futures are determined and why stock price matters, and buying 8-week treasuries. And, if you’re planning to make a killing on eBay or at your next garage sale, the fellas get into the weeds on how to maximize your tax savings.

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13
DEC
2022
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Fixed Indexed Annuities, RMDs, and Early Social Security

We’re hearing more about fixed indexed annuities with these volatile financial markets. Is it time to reconsider? Plus, clarification on required minimum distributions being waived for non-spouse IRA beneficiaries in 2021 and 2022, taxation on trusts, and suggestions for a 40-year-old considering an early mini-retirement. Also, can a 62-year-old immediately withdraw Roth conversion money? Finally, a strategy to claim Social Security early while working and invest the difference in a Roth, and Joe and Big Al attempt to explain family Social Security benefits without phoning it in.

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06
DEC
2022
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How to Forecast Your Expenses in Retirement

What will you actually need to spend in retirement? Joe and Big Al explain how to really think about and calculate your retirement expenses. Plus, if you want to reduce your tax-deferred account balances, does it make more sense to do Roth conversions or reinvest? What about doing Roth conversions to a higher tax bracket than the one you’ll be in during retirement? Also, the fellas explain the alternative minimum tax, how Social Security spousal benefits work, and when in the year you turn 72 you must take required minimum distributions from your retirement accounts. And finally, what should someone with no credit history, who hasn’t paid taxes, do with a sudden $100,000 windfall?

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29
NOV
2022
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Roth IRA 5-Year Rules: How to Withdraw Money With No Taxes or Penalties

Joe and Big Al clarify once and for all those 5-year clocks for withdrawing money from your Roth accounts. How do the 5-year Roth IRA rules impact the taxation of dividend income? Do the 5-year rules impact thrift savings plan (TSP) to Roth conversions as well? Plus, why contribute to a Roth in the first place and lose today’s tax savings? Joe and Big Al rise to that challenge and they discuss Roth conversions and required minimum distributions from an inherited IRA. 

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15
NOV
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
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Will Your Retirement Savings Last Until You’re 90 Years Old?

Are you behind on your retirement savings? What do you need to do to catch up? If you retire in just a few years, will your money last until age 90? Based on the 5-year Roth withdrawal rules, do you need to open a new Roth IRA for each Roth conversion? Plus, Joe and Big Al spitball a health insurance, capital gains, and real estate strategy to save more money and have more wealth in retirement. Finally, they revisit the SECURE Act rules for withdrawing money from an inherited IRA, and Social Security income limits. 

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01
NOV
2022
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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
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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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How to Manage Financial Market Stress? With the Help of a Caddie

As the financial markets fall and then surge, Joe and Big Al talk about market timing, reallocating retirement contributions, and portfolio rebalancing. Plus, your questions answered on estimated taxes, Roth conversions, and the logistics of inheriting IRAs and passing assets on. Finally, how is a financial advisor like a golf caddie when markets get volatile? Joe and his Pebble Beach golf caddie buddy, Big G from the Real Life Caddie Podcast, discuss how their professional knowledge and experience can help the rest of us avoid big mistakes.

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04
OCT
2022
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