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Participant: Richard Eisenberg

Season 10
The Money Conversation Every Couple Needs to Have But Never Does

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Nearly 3 in 4 couples say money is a source of tension in their relationship. But most never figure out why, or what to do about it.

In this episode of Friends Talk Money, Richard, Pam, and Terry talk with Heather and Doug Bonaparte, a married couple and co-authors of the book Money Together. Heather is a business and legal affairs attorney. Doug is a certified financial planner and founder of Bona Fide Wealth. And together, they have had every hard money conversation you have been putting off.

If you are married, partnered, or thinking about combining finances with someone, this conversation will change the way you think about money together.

They cover:

  • Why debt and shame are silently running your relationship
  • How financial power really works between partners
  • Joint accounts vs. separate accounts, what actually works
  • Navigating money in second marriages
  • What to do when you and your spouse have different risk tolerances

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Season 10
New Deductions Could Get You More Money Back

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Tax season just got a major overhaul. The One Big Beautiful Bill changed more tax rules than anything since 2017, and if you're over 65, retired, or earning tip or overtime income, you could be leaving serious money on the table.

In this episode of Friends Talk Money, we sit down with Lisa Green-Lewis, TurboTax spokesperson and trusted tax expert, to break down every major change you need to know before you file.

  • The NEW $6,000 deduction for seniors and who qualifies
  • Tips & overtime income deductions - brand new for 2025
  • Auto loan interest deduction - what cars qualify
  • Social Security & taxes - the surprise that shocks retirees
  • RMDs, Roth conversions & how to avoid a massive tax bill
  • IRS audits - should you be worried? Free filing options and how to get help
Whether you use TurboTax, work with an accountant, or file on your own - this episode could save you thousands. Don't miss it.

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Season 10
Financial Caregiving for Aging Parents: What You Must Do Now

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Becoming a financial caregiver for an aging parent can happen overnight. And even financially savvy families can find themselves unprepared.

In this episode of Friends Talk Money, we talk with Beth Pinsker, author of My Mother's Money and personal finance writer at MarketWatch.

Beth shares what she learned while managing her mother’s finances during a long medical crisis, including:

• Why a durable power of attorney is critical• The mistakes people make with Medicare• How long-term care insurance really works• IRS issues after a parent dies• Estate planning gaps that cause family conflict• What every adult child should do now

This is a practical and emotional conversation about money, aging, and protecting the people you love.

If you have aging parents or want to make things easier for your own children one day, this episode is essential.

Links:

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Season 10
Is a Market Crash Coming? AI Bubbles, Bear Markets & Retirement Risk With Special Guest Jim Stack

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The Dow is hovering near 50,000. AI stocks are dominating the market. And investors are feeling both confident and anxious at the same time.

It's the first Friends Talk Money episode of 2026, and we’re joined by expert market strategist Jim Stack, founder of InvestTech Research, to unpack what’s really happening beneath the surface of today’s stock market and what it means for investors nearing or in retirement.

Jim explains why extreme market valuations don’t cause bear markets, but dramatically increase the risk. He also breaks down why indexing may no longer feel as diversified as investors think, how the “K-shaped economy” is being driven by paper wealth, and why capital preservation matters more than chasing upside late in a bull market.

In this episode, we cover:

  • Why today’s market feels eerily similar to past bubbles
  • The real danger of AI stock mania (and what history tells us)
  • How a 50% loss can delay retirement by years
  • Jim Stack’s “Ulcer Index” and the true cost of bear markets
  • Why Warren Buffett is sitting on hundreds of billions in cash
  • Defensive portfolio strategies for investors 50+
  • Index fund concentration risk most investors overlook
  • Housing, interest rates, and what retirees should consider next

Jim has successfully helped investors navigate market downturns for over 40 years, including the 1987 crash, the dot-com bust, and the 2008 financial crisis. His message is clear: this isn’t about market timing, it’s about risk management.

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Is ChatGPT Smart Enough to Retire You?

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AI is now answering millions of financial questions every day, but how much of it can you actually trust? In this episode of Friends Talk Money, Pam Krueger, Terry Savage, and Richard Eisenberg dive deep into the surge of AI-generated financial advice and unpack the risks, myths, and surprising mistakes that tools like ChatGPT, Claude, Gemini, and DeepSeek are making. A major study shows AI gives incorrect financial answers up to 35% of the time, and the consequences can be huge when it comes to Social Security, Medicare, retirement timelines, investing, or even basic budgeting. To separate hype from reality, we’re joined by special guest Jason Lilly, a highly respected Wealthramp-network fee-only advisor, CFA, CFP®, and founder of Tenere Wealth Advisors. Jason shares exactly how he integrates AI responsibly in his practice: what it’s great for, where it falls apart, and why human judgment still matters more than ever.

You’ll learn:
  • Why AI sounds confident even when it’s wrong
  • What AI can actually do well in financial planning (and what it can’t)
  • Why budgeting, Medicare decisions, and Social Security claiming can be dangerous when left to AI
  • Hidden errors of omission most chatbots make
  • How advisors like Jason use AI to communicate better, analyze data faster, and stay human-centered
  • Why AI will never replace real fiduciary advisors (and how to spot one who’s overly reliant on it)
Whether you’re already using AI for your finances or just curious, this episode will change how you think about these tools.

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