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Educational Videos

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Life Insurance, Muni Bonds, and Dividend Stocks in Retirement

Joe and Big Al discuss LIRPs, or life insurance retirement plans, they spitball whether to take full pension survivor benefits or buy a life insurance policy, and whether to sell losing stocks for even bigger losers to take advantage of the 0% capital gains tax bracket. Plus, zero coupon municipal bonds and the de minimis rule, and target date funds as part of Paul Merriman’s Two Funds for Life strategy. Finally, how do dividends figure into the 4% rule for retirement withdrawals, and should that 4% come from stocks or bonds?

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22
NOV
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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Working After Retirement and Wealth Gifting Strategies

When you retire and when you actually stop working may be two different things. How can you get a raise when you’re working for a startup in retirement? Should you do Roth conversions before or after you quit working? Plus, find out what Joe and Big Al think about a 529 and series I bond gifting strategy, and using whole life insurance to transfer wealth to the kids. 

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09
AUG
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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Free Financial Assessment

01
MAR
2022
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Spitballing the Sequence of Retirement Savings

In what order you should contribute into which accounts for retirement? Joe & Big Al explain the reasoning behind the sequence of retirement savings, and where a health savings account (HSA) fits in that sequence. Following some retirement plan spitball analyses and Roth conversion strategizing, the fellas explain whether capital gains are taxed progressively, how required minimum distributions are taxed, and they revisit indexed universal life insurance.

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02
NOV
2021
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HELOC, All-in-One Mortgages, and What to Do With Old Life Insurance Policies

Real estate and life insurance today on YMYW: what is a home equity line of credit? Is a HELOC better than a traditional mortgage? What are all-in-one mortgage loans? Does it make sense to ditch apartment living and buy a condo, or keep investing for retirement? Next up, Joe and Big Al spitball ideas on what to do with old whole life insurance policies. Plus, ABLE accounts for individuals with disabilities, and should you claim Social Security benefits before or after moving to a no income tax state?

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Free Financial Assessment

14
SEP
2021
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How to Spitball Your Most Tax-Efficient Retirement Withdrawal Strategy

Spitballing tax-efficient retirement withdrawals, savings, Social Security, and required minimum distributions (RMD). Plus, leveraging whole life insurance, and is investing 15% of an all-stock portfolio in preferred stocks too risky? But first, Joe and Big Al break down the mechanics and safety of doing a 401(k) to IRA rollover. 

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Free Financial Assessment

27
JUL
2021
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Should People in High Tax Brackets Save in Roth Retirement Accounts?

Questions answered about Roth 401(k) contributions and “Megatron” (that is, mega backdoor) Roth contributions for highly compensated employees, and the Roth conversion strategy of filling the tax bracket. Plus, moving a pension to an investment plan, owning real estate in a self-directed IRA, paying off the mortgage vs. refinancing, spousal vs. survivor Social Security benefits, rolling a whole life insurance policy to a variable annuity, and more.

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Free Financial Assessment

01
JUN
2021
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How to Get Tax-Free Growth on Investments for Life

Learn how to rack up tax-free Roth retirement income: Roth IRA vs. Roth 401(k), paying the tax on a Roth conversion, how to avoid violating the 60-day rollover rule on a mega backdoor Roth, and Roth IRA contributions when receiving restricted stock units (RSU) in retirement. Plus, moving money from solo 401(k) to IRA before age 59.5, suggestions for a CFP® to be, and matching your umbrella insurance policy to your net worth.

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Free Financial Assessment

18
MAY
2021
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Are These Three Investment Products Too Good To Be True?

Should you invest in a real estate investment trust (REIT)? What about a fixed indexed annuity or structured notes? What can be done about an indexed universal life insurance plan purchased by an employer to replace a defined benefit plan? Plus, understanding qualified small business stock gain exclusion. Joe and Big Al also discuss the […]

02
MAR
2021
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“Super Roth”: Should You Overfund Supplemental Executive Retirement Plan Insurance?

Whether you call it a SERP, an iSERP (individual supplemental executive retirement plan), a private pension, or the “Super Roth,” the strategy is overfunding life insurance, and the question is, is it a good idea for retirement planning? Also: a Social Security, pension, retirement withdrawal, and Roth conversion strategy, portfolio modeling scenarios, the earned income […]

09
FEB
2021
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What Is Your Retirement Number? YMYW Spitball Retirement Analysis

Joe and Big Al spitball considerations for a few listener retirement plans, including investing in brokerage and Roth instead of pre-tax, getting tax diversification, taking the pension lump sum or annuity, paying for college education, and calculating a “retirement number” to put your savings on autopilot. Plus, what life insurance “investment” has a purported “guaranteed” […]

28
JUL
2020
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Will These Three Things Affect Your Social Security?

What impact do ex-spouses, income, and early retirement have on collecting your Social Security benefits? Plus, indexed universal life insurance, estate planning with a step-up in basis on private placement real estate, and more on CRDs, RMDs, and stimulus checks. Joe and Big Al also submit their forecasts for whether Congress might tax Roth IRA […]

07
JUL
2020
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Tanja Hester on the Flexibility of Financial Independence

“The sooner we can understand the link between our money and how we spend our lives, the better.” Tanja Hester (called the Matriarch of the women’s FIRE movement by the New York Times) returns to YMYW to discuss the value of our time, how it’s connected to our finances, and the options financial independence provides […]

03
DEC
2019
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Why This Life Insurance Is for the Most Part a Scam

We tackle Indexed Universal Life Insurance one more time. And you may have heard that millionaires “buy term and invest the rest” to pay estate taxes, but is it a good idea? When you have appreciated company stock, how much should you NUA and when, and how do you deal with the taxes? Plus, can […]

05
NOV
2019
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