Trisha Yearwood Talks Money, Family, and Holiday Magic

Can you really retire on investment income alone? This episode of The Retirement Roundtable with John Scallan breaks down real-life strategies for building sustainable income, managing risk, and making smart decisions as you approach retirement. Hear how personalized planning beats cookie-cutter ru…

From Stage Lights to Christmas Nights with Trisha Yearwood (Bonus Episode)

Step inside Trisha Yearwood’s world as she opens up about music, family, and the stories behind her new Christmas album Christmastime. In this intimate conversation with Cypress Financial's John Scallan, Trisha reflects on her journey from shy performer to beloved entertainer, the business lessons …

What If Your Social Security Check Shrinks Overnight?

Imagine waking up on your 67th birthday only to find your Social Security check suddenly slashed. In this episode, John Scallan breaks down why relying on a single income source can put retirees at risk and explains how strategic planning, diversification, and smart rebalancing help protect your fu…

Replaced Overnight: The True Cost of Waiting to Retire

What happens when a lifetime of hard work is replaced in a single day? This episode with John Scallan reveals the real cost of delaying retirement, the importance of planning for both legacy and life, and how small business owners can protect their teams and themselves. Discover why time—not money—…

DIY Retirement: Are You Missing Hidden Risks?

Is DIY retirement planning putting your future at risk? This episode explores the pitfalls of going it alone, the realities of annuities and CDs, and why liquidity matters for financial security. Host John Scallan breaks down how market changes, surrender charges, and tax strategies can impact your…

Spendophobia: Why Retirees Fear Their Own Money

Are you afraid to spend your own retirement savings? Nearly half of American retirees suffer from “spendophobia”—the fear of using the money they worked so hard to save. This episode with John Scallan explores why making the leap from saving to spending is so difficult, how simple mistakes can leav…

RMDs, Roths, and Resilience: Navigating Sudden Change

What happens when your retirement timeline is suddenly rewritten by a layoff? This episode with John Scallan tackles the emotional and financial impact of unexpected job loss near retirement, offering practical strategies for bridging income gaps, managing healthcare costs, and making smart moves w…

Are You Winging Your Retirement—or Planning for It?

This episode with John Scallan explores the realities of required minimum distributions (RMDs), the pros and cons of lump sum versus monthly withdrawals, and why annuities are making a comeback as a source of guaranteed income. Discover how staying engaged with your finances and building a plan for…

Diversified or Duped? The Overlap Trap in Your 401(k)

Are hidden “termites” quietly eating away at your retirement savings? This episode of the Retirement Roundtable exposes the fees you don’t see, the dangers of overlapping investments, and why a second opinion could be your best financial move. John Scallan explains how debt, diversification, and ad…

Trick or Treat: The Surprises Lurking in Your Retirement Plan

What do Halloween and retirement have in common? More than you think. This episode uses spooky season as a lens to explore the biggest fears in retirement—running out of money, declining health, and boredom—and how preparation, adaptability, and honest conversations can help you face them head-on. …