HeyJaredFriends Talk Money
Whatever life after 50 looks like to you, thinking about money in retirement shouldn't keep you up at night.
- Indexed episodes, last 90 days
- 5
- Latest publication
- Sep 28, 2026
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- Earliest in this view
- Jul 10, 2026
Latest episodes
Medicare Open Enrollment 2027: A Free, No-Sales-Call Way to Compare Every Plan (Part 3 of 3) (opens the original)
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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 t
Medicare Open Enrollment 2027: Advantage Plan Traps & the Real Cost of Part D (Part 2 of 3) (opens the original)
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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 Ad
Medicare Open Enrollment 2027: Premiums, Part D & the Advantage Plan Crisis (Part 1 of 3) (opens the original)
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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
The 10 Fears Killing Your Retirement (opens the original)
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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,
Social Security Insolvency: What It Really Means for Your Retirement (opens the original)
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Social Security is back in the headlines, with warnings that the trust fund could become insolvent as early as 2032. Does that mean your benefits are at risk? Should you claim early? Economist Larry Kotlikoff joins us to separate fact from fear. We explain what "insolvency" really means, why the long-term funding gap may be much larger than most people realize, what Congress could do to fix it, and—most importantly—what today's headlines should (and shouldn't) mean for your own retirement decisi
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