How to Money

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.

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.

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:

• Rivian repair
• Robinhood Platinum
• AI in our mortgage underwriting and our taxes
• Side hustle salad days
• 56% of Zoomers hustling
• Sullen savers
• More actively managed assets (is what we don’t need)
• Same with new venture funds
• Real estate headwinds for investors
• Tariff refunds on the way
• Ticking tax bomb on forgiven student loans

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.

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.

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!

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.

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 - 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.

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:

• Jump at the pump
• We have ‘oil insurance’
• Most fuel efficient cars
• Cheapest new cars
• Fewer work from home roles
• Lack of job-hopping leverage
• We’re all time poor
• 401k raiders
• HELOC pillagers
• Small biz 401k plans on the rise
• Joel hates cashmere
• Printer companies have us over a barrel
• Affordable Apples

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.

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.

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!

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.

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 - 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.

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:

• Tariff turmoil
• New retirement plan on the horizon, with a match
• Housing maintenance costs
• Gen Z content to rent
• Frozen home sales in January
• Lowest mortgage rates since 2022
• Trolling from beyond the grave
• Prenups in vogue again
• Got insurance, but still not immune to bankruptcy
• Border hopping for bargains
• Always check the pantry
• Passing on the steak

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.

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.

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!

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.