• Episode 1371: Planning for Social Security | S1E20 Winning at Life
    Sep 21 2026

    In this episode, Gregory Ricks presents an overview of Social Security planning, emphasizing that claiming age and strategy can materially affect lifetime retirement income.

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    28 mins
  • Episode 1370: Does Your Spouse Know What To Do When You Pass? | S1E19 Winning at Life
    Sep 21 2026

    In this episode, Gregory discusses how surviving spouses can manage finances and estate matters after a partner's death. Gregory emphasized that both spouses should participate in financial-planning meetings, understand the plan, and know whom to contact.

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    24 mins
  • Episode 1369: Common Misconceptions About Annuities | S1E18 Winning at Life
    Sep 8 2026

    In this episode, Gregory Ricks talks about how retirement planning should blend market investments with fixed annuities rather than relying on anti-annuity assumptions.

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    28 mins
  • Episode 1368: The Mid Year Financial Checklist | S1E17 Winning at Life
    Sep 8 2026

    Gregory Ricks provides a mid-year financial checklist to help individuals and business owners assess their goals, savings, and preparedness. He outlines several key areas for individual financial checkups and identifies several frequent errors that can hinder long-term wealth.

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    24 mins
  • Episode 1367: Blending Investments and Annuities | S1E16 Winning at Life
    Sep 8 2026

    Gregory Ricks discusses a new Investopedia study regarding the benefits of blending market investments with annuities to mitigate retirement risks. Gregory highlights the dangers of volatility and "sequence of return risk," which occurs when poor market returns during the early years of retirement permanently drain savings. This risk is exacerbated when retirees are forced to sell assets at a loss to cover living expenses, leaving fewer assets to participate in future market growth. The discussion emphasizes that the first five to ten years of retirement are particularly critical for protecting account balances.

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    28 mins
  • Episode 1366: A Deeper Dive Into Trump Accounts Pt. 2 | S1E15 Winning at Life
    Sep 8 2026

    Are Trump accounts the right move for your child’s future or your family’s financial goals? In this episode, Gregory Ricks takes a deeper dive into Trump accounts—how they work, who can contribute, how taxes apply, and how they compare to popular savings options like 529 plans, UTMA, and UGMA accounts.

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    24 mins
  • Episode 1365: The Business of Land Acquisition | S1E14 Winning at Life
    Sep 8 2026

    Gregory Ricks hosts the Winning at Life podcast, featuring Pat Huber from First South Farm Credit. They discuss the benefits of buying land, including recreational and investment purposes. First South Farm Credit, a cooperative established in 1916, finances rural America and returns profits to borrowers. They offer flexible loan terms from one day to 30 years, tailored to borrowers' income cycles. Pat shares examples of loans for land acquisition, including buying out family members and financing timber sales. Gregory emphasizes the importance of financial planning and resources available through his firm, Gregory Ricks Total Wealth.

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    28 mins
  • Episode 1364: A Deep Dive into Trump Accounts | S1E13 Winning at Life
    Aug 3 2026

    Gregory Ricks discusses the complexities of Trump accounts, a new tax-deferred savings vehicle for children. Contributions include a one-time $1,000 seed from the federal government for children born between 2025 and 2028, individual contributions up to $5,000 annually (indexed for inflation), employer contributions up to $2,500 per year, and contributions from tax-exempt organizations without a limit.

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    28 mins