Friends Talk Money

In the final part of this Medicare Open Enrollment series, Terry, Pam, and Richard sit down with Michael Boshardy — a licensed Medicare attorney and co-founder of MedicarePocketProtector.com — to answer the question Parts 1 and 2 left hanging: once you know you need to shop, where do you actually go.

Michael explains how MedicarePocketProtector.com compares every available plan in a user's zip code (not just the ones that pay commissions), how it's funded entirely by carrier commissions rather than consumer fees, and why that model still leaves room for unbiased recommendations — including plans that pay the company nothing.

A key ingredient is the promise that they will never call you or send you a sales pitch! The comparison tools are free to use – even if you don't purchase a plan. Whether you're deciding between traditional Medicare with a supplement or Advantage, the website walks you through the decision. If you decide on Advantage, you can enter your doctors, hospital and drugs before starting the search, so the plan can personalize your recommendation. On every page there is a "Talk to Someone" button, so you can get help at any time.

The conversation covers the free deadline and "should-I-enroll" tools for people still on employer coverage, how the built-in IRMAA calculator and appeal-letter drafting works, and the free app that reviews medical bills, drafts drug-formulary exceptions, and monitors your doctors' network status all year, not just during enrollment.

Michael also gives a clear rule of thumb: if you can afford it, a Medicare Supplement Plan G is usually the strongest option — and explains why the cheapest Medigap plan often isn't the smartest one.

Links:

• The Medicare Pocket Protector
• State Health Insurance Assistance Program
• Find the plan that works for you (Medicare.gov)

Medicare expert Diane Omdahl of 65 Incorporated — author of Medicare for You: A Smart Person's Guide — joins Terry, Richard, and Pam for Part 2 of this Medicare Open Enrollment series, and the message gets more specific: your Annual Notice of Change won't tell you everything.

Diane explains why you have to dig into your plan's provider directory yourself (Medicare's official tool has real accuracy problems), what's really happening to dental, vision, and "extra benefit" allowances in Medicare Advantage plans, and why PPOs offering out-of-network flexibility often aren't the safety net people think they are. She also breaks down a guaranteed-issue loophole most people don't know about — if your Advantage plan disappears entirely with no replacement offered, you get a short window to buy a Medigap policy with no health underwriting.

The back half digs into standalone Part D drug plans: disappearing $0-premium options, coinsurance creeping into cheaper drug tiers, the end of the federal premium cap, and why the cheapest monthly premium is often the most expensive plan overall. Diane also shares how her tool, HeyMOE (heymoe.com), compares far more drug plans and pharmacies than Medicare.gov's Plan Finder.

Coming up next: trusted, no-sales-pitch resources to help you make these decisions with real, personalized help.

Links:

● Sixty-Five Incorporated

● Find the plan that works for you (Medicare.gov)

● Medicare For You: A Smart Person's Guide (Amazon)

● 34 health systems dropping Medicare Advantage plans | 2026 (Beckers Hospital Review)

● Humana exit notices loom for 600,000 Medicare Advantage members (Healthcare Finance)

● HeyMOE – Medicare Part D Comparison Tool (HeyMOE.com)

Medicare's Open Enrollment window (Oct 15–Dec 7) is quickly approaching, and Terry, Richard, and Pam kick off a three-part series with a simple but urgent message: even if you're happy with your coverage, you can't skip your review this year.

In this episode, they break down what's changing for 2027 — rising Part B premiums, IRMAA surcharges, Medigap and Part D premium hikes, the new Part D out-of-pocket cap, and a mounting crisis in Medicare Advantage as insurers like Humana pull back hundreds of thousands of plans nationwide. They explain why reading your Annual Notice of Change (ANOC) letter matters more than ever, and why switching from Medicare Advantage back to Original Medicare might not be so easy.

Coming up next: Part 2 brings in Medicare expert Diane Omdahl of 65 Incorporated to unpack Advantage and drug plan strategy, and Part 3 reveals trusted, no-sales-pitch resources for personalized help.

Links:

● A Medicare Question (Terry Savage)

● What to know for Medicare open enrollment (Terry Savage)

● IRMAA Help (Terry Savage)

● These are the 10 biggest retirement fears - and what you can do about them (Richard Eisenberg - MarketWatch)

● Get started with Medicare (Medicare.gov)

● Find the plan that works for you (Medicare.gov)

● Medicare Advantage in 2026: Enrollment Update and Key Trends (KFF)

● Health insurers are dumping Medicare Advantage plans. Here's how many seniors could be affected (Morningstar)

Retirement fears are rising. But what are people really afraid of? Former Fidelity wealth management executive turned retirement coach David Conti joins us to break down his new Retirement Fear Index, ranking the top 10 things Americans fear most as they approach and live through retirement. At the top: healthcare and long-term care costs, running out of money, the future of Social Security, and inflation. We dig into what's driving those fears and which ones deserve the most attention. Richard, Terry, and Pam push back on whether fear is even the right lens and dig into what's actually actionable (32%), what takes behavior change (38%), and what you just have to sit with. Plus: how the Fear Index compares to the VIX and the Crypto Fear & Greed Index, why "confidence" isn't the same as "fear," and the real difference between a financial advisor, a retirement coach, and a financial therapist.

Links: RetireMentors.net and RetirementFearIndex.com (David Conti's websites) I'm turning 70. Here's how I'm making this decade the richest of my retirement. (Marketwatch) Dealing with fear in retirement (Yahoo Finance) 2026 Retirement Confidence Survey (EBRI) Boston College Center for Retirement Research The 2025 OASDI Trustees Report University of Michigan Consumer Sentiment Survey

• MaximizeMySocialSecurity.com
• Maxifi.com
• Economics Matters by Laurence Kotlikoff (Substack)
• Get What's Yours: The Secrets to Maxing Out Your Social Security (Larry Kotlikoff)
• Social Security Horror Stories: Protect Yourself from the System — and Avoid Clawbacks (Larry Kotlikoff and Terry Savage)
• Social Security Insolvency (Terry Savage)
• How to work in retirement without seeing your Social Security checks slashed (Richard Eisenberg)
• Social Security: Make smarter decisions to maximize your lifetime benefits (Wealthramp)
• A Summary of the 2026 Annual Reports

Retirement confidence has hit its lowest point since post-COVID — and for good reason. From skyrocketing Medicare premiums to housing costs, Social Security uncertainty, growing debt, and the crushing weight of caregiving, retirees are facing a financial storm no one fully planned for.

In this episode, Terry, Richard, and Pam break down the top 5 worries from the brand-new 2026 Retirement Confidence Survey (Employee Benefit Research Institute) and, more importantly, what you can actually do about them.

• Why 40% of retirees say expenses are higher than expected
• The shocking truth about Medicare costs in 2026 (Plan G premiums up 40%!)
• How housing — even if you downsize — can blow up your retirement budget
• Social Security: what the 2033 trust fund depletion really means for YOU
• The debt crisis is quietly growing among retirees (39% are affected)
• Why 74% of workers plan to work in retirement — but only 31% actually do
• Caregiving: the retirement wildcard nobody budgets for

Links:

• EBRI 2026 Retirement Confidence Survey
• These are the top 5 things retirees are worried about right now (Richard Eisenberg)
• IRMAA Increases Medicare Premiums (Terry Savage)
• Inflation Isn't the Real Problem: Having No Plan to Account for It Is (Pam Krueger)
• National Foundation for Credit Counseling

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 Bonafide 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
• Why every couple needs a "Sorry I'm Dead" letter

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

• TurboTax Free Filing: https://www.turbotax.com
• AARP Free Tax Help: https://www.aarpfoundation.org/taxhelp

Description: 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)

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.