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

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.

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.   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

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)   

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

Nearly 1 in 4 Americans over 50 are planning a job change this year, according to a new AARP survey—but here's the surprising part: 65% haven't taken any steps to prepare.In this episode of Friends Talk Money, hosts Terry, Richard, and Pam dig into what's really driving career changes for people over 50, 55, and 60—and what older job seekers need to know to stay competitive in today's market. We cover: Why boomers and Gen Xers are rethinking retirement and launching second-act careers How to avoid the black hole of job applications and get results through networking and research Smart strategies for updating your resume and LinkedIn profile after decades in the workforce Using AI tools like ChatGPT (carefully) to improve your job search How to prepare for Zoom interviews and make a strong impression The realities of ageism in hiring—and how to position your experience as a strength Negotiating job offers: when to push, when to say yes, and how to show employers you solve their problems Whether you're worried about layoffs, craving more flexibility, or simply ready for a new challenge, this episode is packed with practical job search tips for older workers who want to thrive in today's shifting economy. Links: Certified Age Friendly Employer Program (Age-Friendly Institute) Employer Pledge Program (AARP) Retirementjobs.com Layoffs This Year Reach Highest Levels Since Pandemic, According to One Measure (Yahoo Finance) Survey Shows a Sharp Increase in the Number of Older Americans Seeking a Job Change (AARP) Best Ways to Prepare for a Job Search After 50 (Next Avenue)

Generation X is often called the "forgotten middle child" between Boomers and Millennials, but with 65 million Gen Xers moving into their 50s and early 60s, they're facing a massive financial challenge: skyrocketing healthcare costs. In this episode of Friends Talk Money, Pam Krueger, Terry Savage, and Richard Eisenberg unpack why healthcare, not retirement savings, is now the #1 financial concern for Gen X. From high insurance premiums and long-term care to hidden out-of-pocket costs, we break down: Why Gen X is more worried about healthcare than retirement savings How rising costs are squeezing families still raising kids & saving for retirement What Medicare will and won't cover Smart planning tools: HSAs, catch-up contributions & employer health benefits Why fee-only fiduciary advisors can help Gen Xers plan ahead and avoid surprises If you're Gen X (or love someone who is), this is a must-listen to help prepare for a healthier, more financially secure retirement.  Links: This is Generation X's biggest retirement worry — and it's not money (MarketWatch) Gen X Is Headed for Retirement Crisis: 5 Ways To Avoid Being Part of the Trend (GoBankingRates) Three Things You Should Do – And Not Do – To Prepare For Your Retirement (Wealthramp) Health Savings Account (Terry Savage) Want to Retire at 67? See if You Can Answer These Five Questions (Kiplinger)

More Americans in their 50s, 60s, and beyond are starting businesses than ever before—but they're also facing new, mounting challenges. In this episode of Friends Talk Money, we unpack what's fueling this surge in encore entrepreneurship and how recent policy shifts—especially cuts to the Small Business Administration (SBA) and new trade barriers—are making it harder for older founders to succeed. Special guest Hedy Ratner, co-founder of the Women's Business Development Center, joins us to discuss how older entrepreneurs, particularly women and minorities, are being affected. We cover: Why older Americans are launching businesses in record numbers How Trump-era policy changes are shrinking access to critical SBA support Why tariffs and trade policy shifts are squeezing small business margins What this means for women-, minority-, and veteran-owned businesses What encore entrepreneurs need to do now to protect and grow their ventures If you're starting or running a small business later in life, you'll want to hear what's changing—and what resources are still out there to help you thrive.   Links: Women's Business Development Center (WBDC) SCORE Small Business Administration (SBA) Most boomers and Gen X-ers are terrified about running out of money in retirement — even if they're already retired (Marketwatch)  

The 2025 Budget Bill — aka the "One Big Beautiful Bill" — is now law. But behind the headlines and hype, how does it impact your taxes, Social Security, Medicare, estate plan, and healthcare costs? In this episode of Friends Talk Money, Pam Krueger, Terry Savage, and Richard Eisenberg break down what really matters — no politics, no spin, just the facts that can help (or hurt) your financial future. What you'll learn: What the $6,000 senior tax deduction really does — and who qualifies Whether your Social Security will still be taxed Big changes to the SALT deduction and why it matters in high-tax states Updates to Medicare, Medicaid, and long-term care planning New tax breaks on car loans, overtime, and tips (but only for some!) How the $15M estate tax exemption could affect your legacy A powerful HSA change most people haven't noticed Bottom line: If you're retired or planning for retirement, this bill changes the game. Talk to your CPA, estate attorney, or fiduciary financial advisor now.

Artificial intelligence is quietly reshaping the way we plan—and pay—for long-term care. In this new episode of Friends Talk Money, Richard, Pam, and Terry sit down with Lily Vittayarukskul, Co-Founder and CEO of Waterlily, for a candid conversation about what most people get wrong about long-term care and how AI is changing the game. In this episode, you'll learn: Why most Americans underestimate the true cost and likelihood of needing long-term care How Waterlily uses AI and over 500 million data points to predict your personal care needs The real numbers behind self-funding vs. insurance for long-term care How to make smarter, unbiased decisions for your future, your family, and your finances What's ahead for AI in financial planning and eldercare Lily also shares her inspiring journey from NASA intern to health tech entrepreneur, and how her family's experience sparked a mission to help others plan ahead with confidence. If long-term care planning has been on your mind—or should be—this is a conversation worth hearing.  

Special Guest: Lisa Gomez Big changes are coming to your 401(k) and workplace retirement plans in 2025 — are you ready for them? In this new episode, the Friends Talk Money team sits down with retirement policy expert Lisa Gomez (former Assistant Secretary of Labor for Employee Benefits Security) to unpack what's changing and how it could affect your money. We're covering: How catch-up contributions are getting a big boost for people aged 60-63 Why Roth 401(k)s are becoming a bigger deal — especially for higher earners The growing trend of adding private market and crypto investments inside retirement plans (should you be excited or concerned?) New guaranteed lifetime income options and what they mean for your future paychecks in retirement Lisa Gomez, who oversaw over 800,000 workplace retirement plans as head of the Employee Benefits Security Administration, shares expert insights on how these changes impact your retirement readiness, the pros and cons of more investment choices, and the crucial role of professional advice.If you're saving for retirement, planning your exit, or already retired, this conversation is for you. Listen now to learn: How to make the most of new catch-up contribution rules What "Rothification" means for your taxes and withdrawals The pros and cons of adding alternative investments to your 401(k) Smart questions to ask your employer or financial advisor