Winning at Life with Gregory Ricks: The Weekly Wrap

On this week's episode of Winning at Life, Gregory Ricks and Dwayne Stein cover rising mortgage rates, real estate pitfalls, and how global tensions may influence markets. Hear Gregory’s personal scam story, tips to protect seniors from fraud, and more about Roth IRAs, annuities, and investment strategies.

 
For LIVE financial news talk radio, tune into "Winning at Life with Gregory Ricks" LIVE on Saturday Mornings o...

In this special 15th anniversary episode of Winning at Life with Gregory Ricks, Gregory reflects on the journey of building a financial radio show and firm over the past 15 years. Packed with heartfelt stories, guest appearances from team members and advisors, and meaningful listener calls, the show celebrates the lives impacted through thoughtful financial advice and a commitment to service. Topics include the evolution o...

 In this week’s episode, Gregory Ricks dives into the unexpected risks of not having your estate planning in place—with expert insight from estate planning attorney Wes Blanchard. From last-minute will changes to health scares that can derail your financial future, they cover the must-do documents and how to handle things a la carte if life catches you off guard. Then, CPA Jude Heath joins the show to break down real-world...

In this week's episode of Winning at Life, Gregory Ricks is joined by CPA Jude Heath for a deep dive into smart tax planning strategies for 2025 and beyond. From surviving correction notice season to maximizing Roth conversions, Jude brings insider insights fresh off the heels of a hectic tax season. Plus, they unpack the latest on proposed “MAGA” savings accounts for kids, creative legacy planning ideas, and the surprisin...

Winning at Life with Gregory Ricks | The Weekly Wrap 05.10.25
 
He’s back! Gregory Ricks has returned to Winning at Life after a brief break—refreshed and ready to help you take control of your financial future. 

This week, Gregory sat down with wealth advisor Brandon Blanchard for a powerful conversation on planning strategies and how to make your money work harder—especially when it comes to giving and long-...

In this comprehensive episode of "Winning at Life® with Gregory Ricks," host Gregory Ricks tackles a wide range of critical financial topics, from the latest developments in government legislation and economic trends to the importance of having open conversations with family members about their financial well-being.

Gregory is joined by Dwayne Stein, a contributor to the show, as they discuss the impact of the real ...

In this episode, Gregory covers Investment strategies and diversification, Medicare, Tax implications of Social Security benefits, and Strategies for managing healthcare costs and choosing the right plan.

Joined by Brandon Blanchard Wealth Advisor at Gregory Ricks & Associates. Brandon works alongside Gregory Ricks and specializes in helping clients navigate Medicare decisions, offering personalized guidance on heal...

In this episode of Winning at Life® with Gregory Ricks, Gregory discusses government spending, concerns about national debt, the need to reduce deficit spending, and the importance of balancing the budgets. 

Gregory shares insights on market volatility and recent market downturn. 

This episode is a must-listen for anyone concerned about maximizing their retirement income and protecting their nest egg.

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In this episode of Winning at Life® with Gregory Ricks, Gregory is joined by Jude Heath, CPA, and Janae Bridges, Wealth Advisor at Gregory Ricks & Associates. They discuss smart money moves for using your tax refund, including saving for emergencies, paying off debt, and investing in yourself.
 
The conversation also covers important updates on the Social Security Fairness Act, which aims to increase benefits for...

In this episode of Winning at Life®, host Gregory Ricks dives into the latest updates on the Social Security Fairness Act and how it will impact retirees. He's joined by Wealth Advisor Brandon Blanchard to discuss the challenges the Social Security Administration is facing in implementing the new law, and the importance of having a diversified retirement portfolio to weather market volatility. Mortgage professional Dwayne ...

Tax Season Strategies, Social Security Changes, and Retirement Planning Insights!
In this jam-packed episode, host Gregory Ricks welcomes Jude Heath, a CPA from J. Heath & Company, to dive deep into the world of taxes, financial planning, and preparing for the future.
First, Jude shares critical deadlines and tips to get your tax documents in order before the April 15th filing deadline. From the importance of h...

In this comprehensive episode of "Winning at Life® with Gregory Ricks," host Gregory Ricks tackles a wide range of critical financial topics, from the latest developments in government legislation and economic trends to the importance of having open conversations with family members about their financial well-being.

Gregory is joined by Dwayne Stein, a contributor to the show, as they discuss the impact of declining...

Gregory Ricks and Jude Heath discussed financial planning and tax preparation strategies. They emphasized the importance of proactive tax planning, especially with the recent stay on the beneficial ownership reporting requirement. Jude highlighted the need to update digital currency transactions and the potential impact of upcoming tax law changes. They advised listeners to maximize retirement contributions, including Roth...

Gregory Ricks and Wes Blanchard discusses the importance of estate planning, emphasizing the need for wills and powers of attorney. They highlight the risks of holographic wills, which can often be challenged in court. Wes shared insights from a seminar at Loyola Law School, noting that most estate litigation cases involve handwritten wills. They stressed the benefits of having a professional handle estate planning to avoi...

Gregory Ricks and Dwayne Stein discussed the importance of home ownership and financial planning. They highlighted the recent rate cut's minimal impact on mortgage rates and emphasized the long-term benefits of home ownership, including building equity. Dwayne noted that 40% of U.S. households are free and clear of mortgage debt, underscoring the stability of the housing market. They also stressed the importance of budgeti...

Gregory Ricks and Jude Heath discussed the future of taxes, focusing on the potential impact of the new administration. They highlighted the importance of tax efficiency and the benefits of no tax on overtime and tips. They also addressed the need for Social Security tax reform, suggesting inflation-adjusted brackets. Additionally, they covered the FinCEN and IRS requirements for entity notifications, emphasizing the Decem...

On this week's episode of Winning at Life with Gregory Ricks, Gregory discusses the upcoming time change, emphasizing the importance of being proactive with health and finances. He highlighted the benefits of reading articles and staying informed through his news blog. Gregory shared his health journey, including weight loss and visceral fat reduction, and stressed the importance of early detection and prevention. He advis...

Gregory Ricks and Dwayne Stein discuss the current state of the mortgage market, emphasizing the importance of understanding the difference between federal funds rates and mortgage rates. They note that despite the Fed's recent 50 basis point rate cut, mortgage rates have risen, with 30-year conventional rates now at 6.9%. They highlight the challenges of inventory shortages and the impact of interest rates on homeownershi...