How to Money

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Latest Episodes:

Knowing Your Rights & Crushing Medical Bills w/ Jared Walker #1115 Mar 18, 2026

Show notes

Every year, patients are billed and stuck with $14 billion in medical debt that should be wiped out under existing hospital financial assistance rules. This debt isn’t inevitable, it’s unnecessary! Given the fact that medical debt is the number one cause of bankruptcy and a huge source of stress for families, is it a step too far to say that there is a medical debt crisis in America? We don’t think so and our guest today is doing something about it. Jared Walker is the founder of DollarFor, an organization helping people crush hospital bills they don’t legally owe. Since 2012, DollarFor has helped eliminate more than $125 million in medical debt nationwide. Some of the topics covered today:

The unnecessary strain of medical bills that many are not obligated to pay
Simply letting others know about “charity care” could drastically help their situation
Taking your time to negotiate bc medical bills don’t impact your credit score for a year
Hospitals often do not inform patients about available financial assistance programs
Medical debt impacting personal possibilities and economic progress
Avoiding products like Care Credit which sound nice but are just credit cards in disguise
And much more!

Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:

Dollar For: You must check out the resources and tools at DollarFor.org if you are staring down a medical bill because there’s a good chance you can get it waived! Health Care Bluebook was also mentioned but be sure and look into Jared’s organization.
Credit card perks: Check out our favorite credit cards that we use to maximize rewards and optimize our spending.
Money Gears: knowing what to do with your money is crucial to your personal finance journey.
Newsletter: Sign up for the weekly HTM newsletter. It’s fun, free, & practical.
Other money nerds: Find a thriving community of fellow money nerds by joining the HTM Facebook group!

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.

Ask HTM – Deploying Cash to Recast or Invest, Free $ in Trump Accounts, & David Ramsey Falling Short #1114 Mar 16, 2026

Show notes

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 - Mortgage recast: Should we take a windfall and recast our mortgage or use the lump sum to invest?

2 - Trump accounts: Where should 530a accounts land among the Money Gears… high or low priority?

3 - Thin credit: What should I do since I was denied a credit card due to a thin file?

4 - Used cars: Is buying a car from a private seller the best option and where’s the best place to look?

5 - Debt relief: So it turns out the company I signed up with for debt relief might be a scam, what should I do?!

Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:

Credit card perks: Check out our favorite credit cards that we use to maximize rewards and optimize our spending.
Other money nerds: Find a thriving community of fellow money nerds by joining the HTM Facebook group!
Newsletter: Sign up for the weekly HTM newsletter. It’s fun, free, & practical.
Money Gears: knowing what to do with your money is crucial to your personal finance journey.
MG7: and maybe you’re well on your way to financial independence but you’re looking for some financial reassurance, that’s when heading over to HowToMoney.com/Advisor and getting matched with a highly vetted financial advisor makes sense.

During this episode we enjoyed a Wavelength by Equilibrium Brewery! 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.

Friday Flight - AI Money Impacts, Side Hustle Salad Days, & Sullen Savers #1113 Mar 13, 2026

Show notes

Time for a Friday Flight- our little sampling of the week’s best 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:

Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:

Credit card perks: Check out our favorite credit cards that we use to maximize rewards and optimize our spending.
Other money nerds: Find a thriving community of fellow money nerds by joining the HTM Facebook group!
Newsletter: Sign up for the weekly HTM newsletter. It’s fun, free, & practical.
Money Gears: knowing what to do with your money is crucial to your personal finance journey.
MG7: and maybe you’re well on your way to financial independence but you’re looking for some financial reassurance, that’s when heading over to HowToMoney.com/Advisor and getting matched with a highly vetted financial advisor makes sense.

Best friends out!

See omnystudio.com/listener for privacy information.

Are Teachers Doomed to a Broke Retirement? w/ Shaun Morgan #1112 Mar 11, 2026

Show notes

Joel married into a family of teachers. His father-in-law has spent nearly 40 years in the classroom, his mother-in-law has taught for 30, and his brother-in-law is an outstanding Spanish teacher. While it’s clear that every one of them truly loves their work, we also know that passion alone doesn’t pay the bills. Teaching requires some real sacrifice, especially in today’s economy. And while no one enters the profession expecting to get rich, we believe that shouldn't mean teachers are destined for a life of financial stress or a mediocre retirement. In fact, our guest today argues that those assumptions are flat-out wrong. While educators face unique financial hurdles, they also have powerful, underused advantages. When those tools are understood, retiring comfortably isn't just a dream - it’s a reality. Shaun Morgan is a full-time teacher who is just as passionate about teaching personal finance to his fellow educators as he is about his work in the classroom. Some of the topics covered in this episode:

How teachers can achieve financial independence with the right strategies
Public service loan forgiveness is a significant advantage for teachers
Overcoming the “teacher vow of poverty”
Budgeting on teacher pay cycles
Stop spending on classroom supplies
Pensions vs defined contributions plans
Understanding 403b and 457b plans
The role of side hustles
And plenty more!

Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:

Teacher Money Show: If you’re an educator, look for the Teacher Money Show wherever you listen to podcasts.
Credit card perks: Check out our favorite credit cards that we use to maximize rewards and optimize our spending.
Money Gears: knowing what to do with your money is crucial to your personal finance journey.
Newsletter: Sign up for the weekly HTM newsletter. It’s fun, free, & practical.
Other money nerds: Find a thriving community of fellow money nerds by joining the HTM Facebook group!

Best friends out!

See omnystudio.com/listener for privacy information.

Ask HTM - Debating a Raise vs WFH Flexibility, Investing in Nvidia, & Digital Hygiene Frugal or Cheap #1111 Mar 09, 2026

Show notes

1 - Raise vs lifestyle: Should I take a 50% pay increase or maintain the flexibility of working from home?

2 - Nvidia: How do I go about rebalancing my portfolio when I have $800,000 of Nvidia in my brokerage account?

3 - Feedback: Maybe Joel is being cheap not frugal and should you really let a medical bill go to collections?

4 - Insurance: What’s the best way to get an agent to shop multiple different providers to get me the best deal?

5 - Books: My son is 25 years old - what book should I get him to help kick off his personal finance journey?

Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:

Credit card perks: Check out our favorite credit cards that we use to maximize rewards and optimize our spending.
Other money nerds: Find a thriving community of fellow money nerds by joining the HTM Facebook group!
Newsletter: Sign up for the weekly HTM newsletter. It’s fun, free, & practical.
Money Gears: knowing what to do with your money is crucial to your personal finance journey.
MG7: and maybe you’re well on your way to financial independence but you’re looking for some financial reassurance, that’s when heading over to HowToMoney.com/Advisor and getting matched with a highly vetted financial advisor makes sense.

During this episode we enjoyed a Delirium Tremens by Huyghe Brewery! 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.

Friday Flight - Jump at the Pump, Lessening Leverage, & Tapping Too Soon #1110 Mar 06, 2026

Show notes

Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:

Credit card perks: Check out our favorite credit cards that we use to maximize rewards and optimize our spending.
Other money nerds: Find a thriving community of fellow money nerds by joining the HTM Facebook group!
Newsletter: Sign up for the weekly HTM newsletter. It’s fun, free, & practical.
Money Gears: knowing what to do with your money is crucial to your personal finance journey.
MG7: and maybe you’re well on your way to financial independence but you’re looking for some financial reassurance, that’s when heading over to HowToMoney.com/Advisor and getting matched with a highly vetted financial advisor makes sense.

Best friends out!

See omnystudio.com/listener for privacy information.

Bouncing Back from Bankruptcy & Business Failure w/ Phil Sanders #1109 Mar 04, 2026

Show notes

Joel met Phil halfway through a marathon a few months ago – literally in the middle of the race. It’s funny how life works and after running side by side and chatting for half an hour it was clear he’d only scratched the surface of his story. Phil Sanders is a serial entrepreneur and like most entrepreneurs, not every venture has been a home run. He’s experienced the highs, the lows of bankruptcy, and everything in between when it comes to building businesses. Today, Phil runs a company called Multiply, where he helps business owners sharpen their strategy, build more successful companies, and he’s here today to share some of his hard-earned wisdom. We discuss:

How Phil is balancing current enjoyment with future savings
Profitability should be a primary focus from day one
Overcoming ego and temptation to find identity in work and business
Identifying what you want out of your business
How bankruptcy can lead to personal growth and new opportunities
Vulnerability and overcoming fear to building strength and resilience
Embracing change for professional and personal growth
And much more!

Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:

Phil: his financial services and strategy business is Multiply, and you can keep up with him on LinkedIn and Instagram
Credit card perks: Check out our favorite credit cards that we use to maximize rewards and optimize our spending.
Money Gears: knowing what to do with your money is crucial to your personal finance journey.
Newsletter: Sign up for the weekly HTM newsletter. It’s fun, free, & practical.
Other money nerds: Find a thriving community of fellow money nerds by joining the HTM Facebook group!

Best friends out!

See omnystudio.com/listener for privacy information.

Ask HTM - Housing Rule of Thumb, Axing a Boat Payments, & Making Bank on the World Cup #1108 Mar 02, 2026

Show notes

1 - Housing costs: What’s a good rule of thumb to stick with to help me keep my mortgage payment in check?

2 - 401k rollover: Can you share the penalties and benefits of a retirement account rollover?

3 - Boat payment: How much should I pull out of my savings to finally get rid of my boat loan?

4 - World Cup: How do I ensure that I make the most money and avoid any pitfalls when renting my place for the World Cup this summer?

5 - Down payment: My down payment is in stocks but I might be buying a house next month… what do I do?!

Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:

401k rollovers: Capitalize is the site we discussed where you can easily roll over an old 401k for free- don’t let your retirement dollars languish with an inferior provider!
Credit card perks: Check out our favorite credit cards that we use to maximize rewards and optimize our spending.
Other money nerds: Find a thriving community of fellow money nerds by joining the HTM Facebook group!
Newsletter: Sign up for the weekly HTM newsletter. It’s fun, free, & practical.
Money Gears: knowing what to do with your money is crucial to your personal finance journey.
MG7: and maybe you’re well on your way to financial independence but you’re looking for some financial reassurance, that’s when heading over to HowToMoney.com/Advisor and getting matched with a highly vetted financial advisor makes sense.

During this episode we enjoyed a Harpeth by Living Waters! 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.

Friday Flight - Tariff Turmoil, Winning So Much, & Border-Hopping for Bargains #1107 Feb 27, 2026

Show notes

Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:

Prenups… are for lovers according to Aaron Thomas!
Credit card perks: Check out our favorite credit cards that we use to maximize rewards and optimize our spending.
Other money nerds: Find a thriving community of fellow money nerds by joining the HTM Facebook group!
Newsletter: Sign up for the weekly HTM newsletter. It’s fun, free, & practical.
Money Gears: knowing what to do with your money is crucial to your personal finance journey.
MG7: and maybe you’re well on your way to financial independence but you’re looking for some financial reassurance, that’s when heading over to HowToMoney.com/Advisor and getting matched with a highly vetted financial advisor makes sense.

Best friends out!

See omnystudio.com/listener for privacy information.

Die with Zero w/ Bill Perkins #1106 Feb 25, 2026

Show notes

Most money advice is a broken record: save more, invest early, and wait for freedom. But what if the real risk isn't running out of money but instead is running out of time? In this episode, we’re challenging the "accumulation at all costs" mindset with Bill Perkins, author of the cult classic Die With Zero. It turns out that a healthy money relationship isn’t just about building wealth but it’s also about intentional spending. Bill argues that time is the most precious asset we have, and that waiting too long to enjoy it can be a costly mistake because we don’t want to reach the finish line with a full bank account and a lifetime of missed opportunities! We discuss how:

Time is the most precious asset we have
Travel makes you a richer person
Your health impacts your wealth
Timing your life experiences
Memory dividends are inflation protected fulfillment
Delayed gratification as a form of prison
His concept of time buckets
Life is full of risk and we have to decide what's worth it
And much more!

Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:

Bill Perkins: Check out the book yourself: Die With Zero, be sure to not follow (Bill’s own recommendation) on Insta or X, and more resources can be found at the site for the book as well.
Credit card perks: Check out our favorite credit cards that we use to maximize rewards and optimize our spending.
Money Gears: knowing what to do with your money is crucial to your personal finance journey.
Newsletter: Sign up for the weekly HTM newsletter. It’s fun, free, & practical.
Other money nerds: Find a thriving community of fellow money nerds by joining the HTM Facebook group!

Best friends out!

See omnystudio.com/listener for privacy information.

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