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:

• My Mother's Money By Beth Pinsker (Amazon)
• Terry Savage Personal Financial Organizer (Terry Savage)
• Estate Planning Search (Search Attorneys)

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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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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.

• 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)

Links:

• 'Well-Recognized Issues': ChatGPT Gave Wrong or Misleading Answers to 35% of Financial Questions Asked in a New Test (MSN)
• Should you trust AI for Medicare, Social Security for long-term-care advice? (MarketWatch)
• How AI Is Revolutionizing Long-Term Care Planning (Friends Talk Money)
• What will happen to Social Security once AI kicks in? (Terry Savage)
• Tenere Wealth Advisors

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Gen X is officially in the retirement danger zone — and many are worried about outliving their savings. In this episode of Friends Talk Money, Richard Eisenberg, Terry Savage, and I sit down with author and workplace/retirement expert Kerry Hannon to dig into the findings from her new book, Retirement Bites: A Gen X Guide to Securing Your Financial Future.

We explore:

• Why more than half of Gen X fears they won’t be financially ready
• How DIY retirement planning, disappearing pensions & late savings habits created a perfect storm
• The crushing impact of student loans, credit card debt & supporting both kids and aging parents
• Why so few Gen Xers work with a financial advisor — and how to find the right kind of help
• The truth about Social Security’s future for Gen X
• Health costs, layoffs, age discrimination — and how to stay employable into your 50s and 60s
• The new definition of “retirement” and why working longer can be a superpower
•  Plus: What Gen Xers can control right now to course-correct

Kerry also breaks down the huge differences between older Gen Xers nearing 60 and younger Gen Xers in their late 40s, including who may benefit from the next major wealth transfer. Whether you're a lifelong DIY investor or navigating retirement planning for the first time, this episode is a must-listen for the most overlooked generation in personal finance.

Links:

• Retirement Bites: A Gen X Guide to Securing Your Financial Future (Amazon)
• Reality Bites: Gen X is Nearing Retirement and More than Half Don't Believe They'll be Financially Ready When the Time Comes (Northwestern Mutual)
• Portfolio Perspectives: Gen X Isn’t Ready for Retirement – How Financial Advisors Can Help and Harness SECURE 2.0 (Dynamic Advisor Solutions)
• Gen X Nearing Retirement With Worries About Limited Savings, Allianz Life Study Finds (Allianz)
• Gen X’s Retirement Shock: The Truth About Healthcare Costs (Friends Talk Money) 
• Why Retirement Doesn't Need to Bite for Gen X (Next Avenue)

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Three-quarters of Medicare beneficiaries say choosing a Medicare plan is confusing, and nearly 7 in 10 (69%) Medicare beneficiaries have not compared their own source of Medicare coverage with other Medicare options offered in their area during past open enrollment periods, according to surveys. These actions can cost you money and limit your medication coverage and pharmacy access.

In this episode of Friends Talk Money, we unpack what you need to know about Open Enrollment and your plan options, diving into the pros and cons of Original Medicare plus a supplement and Part D plan versus Medicare Advantage. We explain what’s different this year, including the inconsistency around premiums and the discontinuation of Anthem standalone Part D plans.

Our special guest is Diane Omdahl, a nationally recognized expert in Medicare. She’s the creator of 65incorporated.com, which guides seniors in their Medicare choices, and author of the bestselling book, Medicare For You. She joins us to explain what steps you can take now to ensure your coverage is fully meeting your medical needs and isn’t costing you more than you need to spend in 2026.

• Medicare Beware! A Special Report (Terry Savage)
• Survey: 75% of Medicare Beneficiaries Say Selecting a Plan Is Confusing
• Nearly 7 in 10 Medicare Beneficiaries Did Not Compare Plans During Medicare’s Open Enrollment Period

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