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Can You Shorten Your Working Years?

Can Sven and Olga in Minnesota shorten their working years? Should PJ in Michigan take his pension lump sum or the annuity payments, and should he maintain an aggressive asset allocation in retirement? Plus, the fellas spitball early retirement strategies for Joe in Massachusetts and Nick in California, and they discuss how to tell the difference between post-tax contributions and pre-tax funds converted to Roth at tax time for Victor.

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19
SEP
2023
LISTEN NOW

DIY Early Retirement Planning

Should Jackson and Elsa from Wyoming fire their financial advisors and shop for lower fees, or switch to do-it-yourself financial planning? Can 34-year-old Bob in Texas retire early at 50, and what’s the best way for him to put an extra $30K to work? How much should 35-year-old Matthew in the middle of nowhere Wisconsin be saving for retirement in pre-tax accounts vs. post-tax accounts? And finally, should Michelle in Minnesota leave excess education savings in a 529 plan or move it to a Roth IRA?

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12
SEP
2023
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Spitballing Retirement and Social Security for Worst Case Scenarios

Harsh realities of life can very quickly change your retirement plans and your entire financial future. In this episode, spitball on dealing with these realities. What financial strategies can they suggest for William and his 33-year-old wife, who has metastatic breast cancer? Debbie and Emily each experienced the unexpected sudden passing of their partners. Is it possible to minimize the capital gains tax on Debbie’s son’s inheritance, and can Emily retire in a year? Josie has lousy longevity in her family and wants to plan for the worst-case scenario of dying before her husband. Alfred is 81 and concerned that he’s going to run out of money before he runs out of time, and Richard has a sobering story that changed his thoughts about when to collect Social Security. Finally, Irene is subject to the Government Pension Offset (GPO) – can she withdraw the money she paid into Social Security?

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22
AUG
2023
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RSU, Mutual Funds, Bonds, and Annuities

What’s the best strategy for E-Dog’s restricted stock units with his employer, how are RSUs taxed, and how do Roth conversions fit into the mix? Should Jay in Raleigh liquidate his annuities or follow “Stan the Annuity Man’s” advice and take the annual payments? Elisa wants to know how a mutual fund portfolio would work in retirement, and what’s a good way for listener Joe to invest in bonds in a taxable account to bring his portfolio back into proper balance? Finally, the fellas spitball on Medicare savings vs. Roth conversions for David, and an unrealized gain strategy on an UTMA education savings account for Jay in California.

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15
AUG
2023
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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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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
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$7M Tax-Free or $10M Retirement? Backdoor Roth or Lower Fees?

Should Carl Spackler stick with his backdoor Roth strategy, or go for lower fees? Should Kevin go all Roth, or stick with his current three tax-diversified buckets strategy? (That depends – would he rather have $7 million tax-free, or $10 million in tax-deferred retirement accounts?) Can Lily claim all the extra allowances she can, to jam as much money as possible into her Roth? Can Dave retire now and ride his motorcycle into the Bavarian Alpine sunset, and does Peggy Lee need to be feverish about the tax underpayment penalty with her Roth strategy?

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25
JUL
2023
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When Will You Be Able to Retire?

Steven has got “one more year” syndrome. Can he retire at age 65? Joe and Big Al spitball retirement for him, and for MB – can she and her husband live comfortably if she retires at age 59½? And for Johnny – does he have enough to fill the gap until retirement, and should his dad do Roth conversions before Johnny inherits his wealth? Plus, is Austin maximizing his future gains by saving to his 401(k) at age 29, rather than his Roth IRA? How can Mike and his wife leave their kids a lower tax bill when they pass?

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18
JUL
2023
LISTEN NOW

Invest or Pay Off the Mortgage?

It’s a common question: should you pay off your mortgage when you have extra cash, or invest for retirement? Joe and Big Al spitball on how Ms. Moneybags and her wife-to-be should use their upcoming windfall. Plus, what should Bob’s asset allocation be as he nears retirement? Should Harley and Harlene do Roth conversions after tax rates increase, and should they take advantage of net unrealized appreciation (NUA) on Harlene’s company stock? Pete needs a 13-year retirement plan sanity check, Lauren wants to know if she can retire early or at least go part-time, and Michael and Carol want the fellas to spitball whether they’re on track for retirement.

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04
JUL
2023
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Ready to Retire? 5 Retirement Spitball Analyses

Joe and Big Al spitball five different retirement plans: Is Jaybird on track to retire with a decent nest egg? Should Ted and his wife use the retirement smile spending pattern and spend more early in retirement? Is it safe for Aaron to retire at age 59 and a half? How much can Karla convert to Roth for the most tax-efficient retirement withdrawal plan? LEO Jay has Roth TSP retirement strategy questions, and Lynn suggests a super-easy Roth conversion calculator – but Big Al’s got an even easier idea. 

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20
JUN
2023
LISTEN NOW

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
LISTEN NOW

Tax “Jailbreak” Early Retirement Strategy: Sense or Nonsense?

Can you retire before age 55 simply by contributing to your 401(k) only up to the company match and then saving to a brokerage account? Joe and Big Al spitball on using this so-called tax “jailbreak” strategy to retire early. Plus, is Christine on track to have $150,000 present value to live on in retirement? Is John stuck just watching his money grow and turn into big required minimum distributions? Can Jackie contribute to a SEP IRA and convert it all to Roth? And what do the fellas think of Lee’s I-Bond emergency fund? 

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06
JUN
2023
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How to Calculate Your Retirement Needs in Future Dollars

How much will money will you need in retirement, adjusted for inflation? Joe and Big Al spitball on your future dollars, how to calculate the tax on Roth conversions, and the benefits of converting to Roth when financial markets are down. Plus, should retirement savings contributions be half pre-tax and half post-tax? And finally, saving to a 529 plan for your kids, or sending them to Hollywood stunt training camp – which would you do!? 

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30
MAY
2023
LISTEN NOW

How to Consider Your Pension Options for Retirement

When should you take your pension, what types of things should you think about when it comes to deciding between a lump sum or a monthly annuity payment – risk protection, for example – and how do you work your pension into your overall retirement plan? Spitballing on retirement pension options, and saving to a taxable account when you’re concerned about required minimum distributions or RMDs, on today’s YMYW.

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23
MAY
2023
LISTEN NOW

What to Do With Inheritance Money?

So you’re about to receive a large inheritance – what should you do with it? Joe and Big Al spitball on suddenly becoming $85 million dollars richer. Plus, is it nuts to semi-retire early? Should retirement contributions be split between Roth and traditional accounts? Can you do conversions to your kids’ custodial Roth accounts? The fellas also spitball tax bracket-based Roth conversion strategies to help you pay the least amount of tax possible, long term, and they discuss RMDs on inherited assets and whether to pay off a 401(k) loan if it’s “paying” you 8% per year.

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09
MAY
2023
LISTEN NOW
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