
Navigating the Insane Insurance System w/ Consumer Reports' Lisa Gill #950
02/26/25 • 52 min
The price of gas, the price of eggs and milk- these are the kinds of expenses that we’re very sensitive to as consumers because of how frequently we make these purchases. And don’t forget visibility of course with the price per gallon essentially plastered on electronic billboards we consistently drive past! But the cost of insurance feels like the exact opposite. We rarely shop for coverage, it’s not often discussed, and automatic payments insulate us from rising premiums. In the case of homeowners insurance there’s an additional layer of insensitivity in the form of escrow. But insurance is becoming more of a burden and here to tackle this problem is Lisa Gill from Consumer Reports. Lisa is an investigative journalist and we’re going to discuss everything from wildfires to prescription drugs, what to do if you receive an insurance cancellation notice, the steps to take when you receive a medical bill that’s way too high, and much more during our episode!
Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
- Knowing your ‘money gear’ is a crucial part of your personal finance journey. Start here.
- Sign up for the weekly HTM newsletter. It’s fun, free, & practical.
- Join a thriving community of fellow money in the HTM Facebook group.
- Find the best credit card for you with our new credit card tool!
- Massively reduce your cell phone bill each month by switching to a discount provider like Mint Mobile.
During this episode we enjoyed a Primordia by Freak Folk Bier! And please help us to spread the word by letting friends and family know about How to Money! Hit the share button, subscribe if you’re not already a regular listener, and give us a quick review in Apple Podcasts or wherever you get your podcasts. Help us to change the conversation around personal finance and get more people doing smart things with their money!
Best friends out!
See omnystudio.com/listener for privacy information.
The price of gas, the price of eggs and milk- these are the kinds of expenses that we’re very sensitive to as consumers because of how frequently we make these purchases. And don’t forget visibility of course with the price per gallon essentially plastered on electronic billboards we consistently drive past! But the cost of insurance feels like the exact opposite. We rarely shop for coverage, it’s not often discussed, and automatic payments insulate us from rising premiums. In the case of homeowners insurance there’s an additional layer of insensitivity in the form of escrow. But insurance is becoming more of a burden and here to tackle this problem is Lisa Gill from Consumer Reports. Lisa is an investigative journalist and we’re going to discuss everything from wildfires to prescription drugs, what to do if you receive an insurance cancellation notice, the steps to take when you receive a medical bill that’s way too high, and much more during our episode!
Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
- Knowing your ‘money gear’ is a crucial part of your personal finance journey. Start here.
- Sign up for the weekly HTM newsletter. It’s fun, free, & practical.
- Join a thriving community of fellow money in the HTM Facebook group.
- Find the best credit card for you with our new credit card tool!
- Massively reduce your cell phone bill each month by switching to a discount provider like Mint Mobile.
During this episode we enjoyed a Primordia by Freak Folk Bier! And please help us to spread the word by letting friends and family know about How to Money! Hit the share button, subscribe if you’re not already a regular listener, and give us a quick review in Apple Podcasts or wherever you get your podcasts. Help us to change the conversation around personal finance and get more people doing smart things with their money!
Best friends out!
See omnystudio.com/listener for privacy information.
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Ask HTM - Is Direct Indexing Worth It, Sticky Cosigning Situations, & Kiddos With Credit Or Debit #949
Let’s dive into the week with some fresh listener questions we have lined up for you! And don't just stand on the sidelines- if you have a question you’d like us to answer, toss your voice memo our way. It only takes about 90 seconds to record and you can find a step by step guide over at HowToMoney.com/ask . Regardless of how random or bizarre you might think it is, we want to hear it!
1 - What do I do about money being taken out of my savings because of a student loan I co-signed?
2 - Should I invest in a 401k with unfavorable terms or my brokerage account instead?
3 - Is it worth paying extra for direct indexing, given the additional benefits like tax loss harvesting?
4 - Do I link a credit card or a savings with a debit card, to my 11 year old’s Apple Watch?
5 - If I had to choose one: IRA or HSA?
Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
- Knowing your ‘money gear’ is a crucial part of your personal finance journey. Start here.
- Sign up for the weekly HTM newsletter. It’s fun, free, & practical.
- Join a thriving community of fellow money in the HTM Facebook group.
- Find the best credit card for you with our new credit card tool!
- Massively reduce your cell phone bill each month by switching to a discount provider like Mint Mobile.
During this episode we enjoyed a Tiny Esses by Prairie Artisan Ales! And please help us to spread the word by letting friends and family know about How to Money! Hit the share button, subscribe if you’re not already a regular listener, and give us a quick review in Apple Podcasts or wherever you get your podcasts. Help us to change the conversation around personal finance and get more people doing smart things with their money!
Best friends out!
See omnystudio.com/listener for privacy information.
Next Episode

Friday Flight - Brainless Borrowing, DOGE Dividends, & Abroad on a Budget #951
Time for a Friday Flight- our little sampling of the week’s financial news and what it means for your personal finances. There are a lot of headlines out there, but we boil them down to specific takeaways that will allow you to kick off the weekend informed and help you to get ahead with your money. In this episode we explain some relevant and helpful stories like: renting the fancy clothes, lowest cost airports, the frequent flier switch, going abroad on a budget, secondary credit card benefits, referral bonus taxation, (not so) unlimited PTO, saving the most with health sharing, ghost tax preparers, DIY vs tax pros, brainless borrowing, updated Money Gear #1, and DOGE dividends.
Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
- Knowing your ‘money gear’ is a crucial part of your personal finance journey. Start here.
- Sign up for the weekly HTM newsletter. It’s fun, free, & practical.
- Join a thriving community of fellow money in the HTM Facebook group.
- Find the best credit card for you with our new credit card tool!
- Massively reduce your cell phone bill each month by switching to a discount provider like Mint Mobile.
And please help us to spread the word by letting friends and family know about How to Money! Hit the share button, subscribe if you’re not already a regular listener, and give us a quick review in Apple Podcasts or wherever you get your podcasts. Help us to change the conversation around personal finance and get more people doing smart things with their money. Have an awesome weekend!
Best friends out!
See omnystudio.com/listener for privacy information.
How to Money - Navigating the Insane Insurance System w/ Consumer Reports' Lisa Gill #950
Transcript
Welcome to Had of Money. I'm Joel, I'm Matt.
Speaker 2Today we're talking about navigating the insane insurance system with Consumer Reports Lisa Gill.
Speaker 1Yeah, so our conversation today is going to be all about reducing some major expenses in our lives. Insurance, the premiums that we pay. They've skyrocketed over the past several years for many reaso
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