Ask HTM - Combatting Healthcare Premium Hikes, Purchasing Long Term Disability, and WTD with Nine-Figure Wealth #1090
How to Money
iHeartPodcasts
4.6 • 3.2K Ratings
🗓️ 19 January 2026
⏱️ 54 minutes
🧾️ Download transcript
Summary
We’re kicking off the week by answering your listener questions! And if you have a question that you’d like for us to answer on the show, we’d love for you to submit your own via HowToMoney.com/ask , send us your voice memo. Regardless of how random or bizarre you might think it is, we want to hear it!
1 - Nine-figure wealth: what do we do after our company sells for $300 million?!
2 - Healthcare subsidies: are health sharing plans my only other option to keep my healthcare costs down?
3 - Landlord liability: should I really go with the formality of holding each of my properties in it’s own LLC to safeguard my personal assets?
4 - 401k snatch: does it make sense to continue contributing to my 401k after my employer has lowered the match?
5 - Long term disability: when does it make sense and do I need to get a policy in place?
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Best friends out!
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Transcript
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| 0:00.0 | This is an I-Heart podcast. |
| 0:02.6 | Guaranteed Human. |
| 0:04.0 | Welcome to How to Money. |
| 0:05.7 | I'm Joel. |
| 0:06.3 | And I am Matt. |
| 0:07.6 | Today, we're answering your listener questions. That's right, everyone. |
| 0:29.4 | Listener questions on the way. |
| 0:30.9 | We hope everyone had a fantastic weekend and that you are ready to buckle in with us here at the beginning of this week |
| 0:38.0 | with listener questions. |
| 0:38.8 | If you're not more than 48 inches tall, you will not be allowed to ride. You cannot ride the How to Money train. You see the disappointment on my kids' face when they face that. I think they're all basically, well, I don't know, the six-year-old maybe not quite tall enough to ride some of them. the last time you went to six flags or something. |
| 0:53.9 | It's been a while. |
| 0:54.5 | Did you go recent? |
| 0:55.4 | No, it's been a while. |
| 0:56.2 | I just remember the little of their faces when they're like wait i can't write that after waiting in line for the scorcher yeah or something like that and you're like oh it's actually too short well and well then sometimes they're like actually that's good i was a little scared so they're thankful they couldn't ride what you don't want is for there to be some teenager who's just like, ah, it doesn't matter. They can ride. And then you're like, actually? You sure about that? Okay, I am changing my mind now, and we are no longer going to visit this establishment. Because I value our safety when it comes to these carnival rides on steroids. But Joel, we're going to hear from the richest |
| 1:29.4 | how to money podcast listener, I think, of all time. I'm actually really excited. Did Warren finally |
| 1:34.6 | reached us? Not Warren, but someone else. Another listener is wanting to know what he should do with |
| 1:39.1 | higher health care premiums. And someone else, he's considering long-term disability, whether or not he's a good candidate for that. |
| 1:46.7 | Plus, other questions during our episode today, buddy. |
| 1:49.4 | All right. |
| 1:49.8 | Looking forward to it. |
| 1:50.9 | I came across this article about economists saying, hey, you know what, for kids who are dropping out in certain school districts, |
| 1:59.0 | maybe the best way to get them to finish their degree, their high school degree in particular, is to pay them to stay in school. |
... |
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