261. Save Money on Medical Bills and Navigate Health Insurance Like a Pro with Dan Weissmann

Financial Feminist

Her First $100K

Self-improvement, Education, How To, Business

4.7 • 6.2K Ratings

🗓️ 11 November 2025

⏱️ 72 minutes

🔗️ Recording | iTunes | RSS

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Summary

Healthcare in America shouldn’t feel like a rigged game––but too often it does. Leaving many people feeling swindled by confusing insurance plans, surprise medical bills, and endless fine print. To help navigate this complex system, I'm joined by Dan Weissmann, journalist and host of the NPR podcast An Arm and a Leg. Dan explains why U.S. healthcare feels broken––and how to get the most out of a flawed system. He'll share strategies to protect your finances and well-being, from selecting the right health insurance during open enrollment to identifying billing errors, challenging unfair charges, and saving hundreds on prescriptions. Dan’s links: Website: https://armandalegshow.com/ Visit ⁠https://herfirst100k.com/ffpod⁠ to stay up to date and find any resources mentioned on our show! 00:00 Intro 01:15 Why Healthcare Is So Expensive 03:00 The System Is Confusing by Design 06:00 Understanding What You Actually Owe 08:30 What To Do When You Get a Medical Bill 10:45 How To Talk to Your Insurance Company 13:00 The Hidden Traps in High-Deductible Plans 15:30 Should You Pay Your Bill Right Away? 18:00 How Medical Debt Affects Your Credit 20:15 How To Negotiate a Medical Bill 22:00 What To Do If You Can’t Afford Care 24:30 The Emotional Cost of Healthcare 27:00 Why Women Carry More Medical Debt 30:00 The Future of Healthcare Transparency 33:00 The Wildest Story From An Arm and a Leg 36:00 How To Be Your Own Healthcare Advocate 38:00 How To Find a Fair Price for Care 41:00 Quick Wins To Save on Medical Costs 43:00 What True Financial Wellness Means 44:00 Outro + Resources Special thanks to our sponsors: Squarespace Go to www.squarespace.com/FFPOD to save 10% off your first website or domain purchase. Learn more about your ad choices. Visit megaphone.fm/adchoices

Transcript

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0:00.0	Donald Trump wants to make your health care more expensive, and you need to know exactly how to navigate those changes.
0:05.6	Healthcare in the U.S. costs an arm and a leg, sometimes literally.
0:08.9	And my guest today would know because that's literally what he named this podcast.
0:12.6	Journalist and podcast host Dan Weissman joins us to unpack why our health care system feels like walking into a casino where the house always wins and what you can actually do about it.
0:21.7	We're not just playing against the house. We're kind of being ushered straight to the table where
0:26.3	the World Series of poker is being played. And around the table are people who belong at this
0:33.1	table, the health insurance companies and the pharmaceutical companies and the big hospital chains
0:38.1	and all the other people who really know how to make money on health care. We are playing against
0:43.2	them and they are basically all playing for our chips. We talk about everything from choosing
0:48.3	the right health insurance during open enrollment to what Medicare Advantage really means
0:52.7	to how to challenge unfair medical bills and save money on prescription.
0:56.5	Can you walk me through what people should look for when choosing a health insurance plan during open enrollment?
1:04.2	Yes. You're going to look at all the plans in front of you, and here's what you're not going to do.
1:08.5	If you've ever looked at a hospital bill and thought, this can't be right, this episode is your guide to fighting back and protecting your wallet and your health, especially amidst all of the crazy changes. Let's get into it. But first, a word from our sponsors. This newly independent podcast is brought to you by Squarespace. You know we love Squarespace. They're a reason they've
1:27.8	been one of our most trusted ad partners. And it's because I started our business on Squarespace.
1:33.3	Literally, the first investment we ever made was signing up for Squarespace website. They're super
1:37.5	easy to use. My favorite part is the drag and drop features. So you don't need to know how to code.
1:42.7	You just need to use their offerings to make your website look pretty. They also have SEO tools so you can get discovered fast so you don't have to be an SEO expert either. And you can not only start a Squarespace website from a design perspective, but also buy your domain on Squarespace, which is what I did with her first 100K. Head on over to Squarespace.com slash FFPod for a free trial.
2:02.8	And once you're ready to launch your brand new website, use offer code FFPod at checkout to save 10%
2:08.0	off your first purchase of a website or domain.
2:10.7	If you're struggling to figure out where to start with your financial journey, if you're so
2:13.5	overwhelmed and you're just like, I need the step-by-step plan and mentorship from you, Tori. Well, great. You can go to her first hundredk.com slash f-ffpod to take our free money personality quiz. We're going to ask you about six questions. We're going to see where you're at in your financial journey. This is not like a past fail-of-thing. I just want to know where you're at. Then we'll deliver resources cater to exactly where you are in your financial journey. The quiz takes less than two minutes and it's the perfect place to kickstart your financial
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