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Winning at Life Daily Wrap: 05.23.18

Do YOU know when you should turn on your Social Security retirement benefit? People over age 50 scored pretty badly on a Social Security survey, so don’t feel bad if you don’t know. Gregory explains some of the basics on figuring out when you should turn on Social Security. Now that the kids are out…

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Winning at Life Daily Wrap: 05.22.18

She was fed up with working, and asked Gregory help her retire at the end of the year. Gregory sets up a retirement income plan that’s over $50k a year, including Social Security, that will be virtually untaxed. The Guided Planning System shows where she will be financially throughout retirement. No matter what your age…

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Winning at Life Daily Wrap: 05.21.18

What happens if the rules on your employer’s retirement plan don’t match up with the rules of a regular 401k or IRA? Gregory explains how to tell which rule applies to your situation. The proportion of people over 65 still in the workforce is booming. Much of it is because we are healthier, maybe we…

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Winning at Life Weekly Wrap: 05.19.18

Gregory’s flight had an aborted landing at the New Orleans airport, and they had to go wait out the bad weather in Jackson. It’s a pretty harrowing experience, but the airline seemed to handle it OK. PT Barnum’s financial advice from the 1880s stands the test of time well. Gregory and James discuss some of…

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Winning at Life Daily Wrap: 05.16.18

How much does it REALLY cost to own a home in retirement? While it can be nice to have your home paid off in retirement, it may be better to have the cash on hand instead of plowing it into your house. An expert advisor on retirement planning admits to messing up her own distributions…

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Winning at Life Daily Wrap: 05.15.18

Is early retirement really worth financial hit? Gregory and James review a few scenarios that could help your money last if you decide to retire early. Cutting expenses and getting even a small income from a passion project can be the boost you need to stop working early. Gregory gives the real truth behind Peak…

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Winning at Life Daily Wrap: 05.14.18

The Supreme Court strikes down a ban on sports betting, making it legal in Mississippi! Before the decision to allow sports betting came down, MS had already passed the legislation necessary, and Gulf Coast casinos could be taking bets by football season. A Tesla car on autopilot smashes into a stopped fire truck at 60mph.…

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Winning at Life Daily Wrap: 05.12.18

What websites does Gregory prefer for financial resources and business news. Yahoo Finance was one of the best financial hubs for a long time until Google Finance showed up. However, Google Finance has been through some changes over the last year that hasn’t helped their standing. Ultimately, Gregory relies on market information most people don’t…

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