Is a Roth Conversion Right for You? Guest Larry Kotlikoff Helps You Decide
Release Date: 01/31/2025
Is a Market Crash Coming? AI Bubbles, Bear Markets & Retirement Risk With Special Guest Jim Stack
Friends Talk Money Podcast
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 , 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...
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Is ChatGPT Smart Enough to Retire You?
Friends Talk Money Podcast
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...
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Gen X Retirement Wake-Up Call: Debt, Kids, Aging Parents & The Future of Social Security
Friends Talk Money Podcast
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 . 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...
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The High Cost of Doing Nothing: Medicare Open Enrollment Mistakes to Avoid for 2026
Friends Talk Money Podcast
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...
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Job Search After 50: Career Change, Ageism & AI Tips
Friends Talk Money Podcast
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...
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Gen X’s Retirement Shock: The Truth About Healthcare Costs
Friends Talk Money Podcast
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...
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Older Americans Are Starting Businesses—and Why It’s Getting Harder
Friends Talk Money Podcast
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 , joins us to discuss how older entrepreneurs, particularly women and minorities, are being affected. We cover: Why older Americans are...
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The ‘One Big Beautiful Bill’: What It Really Means for Your Taxes, Medicare & Retirement
Friends Talk Money Podcast
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...
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How AI Is Revolutionizing Long-Term Care Planning
Friends Talk Money Podcast
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....
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4 Big 401(k) Changes in 2025: What You Need to Know
Friends Talk Money Podcast
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...
info_outlineThinking about a Roth conversion but not sure if it's the right move? The Friends Talk Money team breaks down six key things you need to know before making a decision! From tax implications to future benefits, we've got you covered. Curious about how a Roth conversion could impact your financial future?