How to Money

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Latest Episodes:

Friday Flight - Richer Refunds, Best Costco Buys, & $3 Dinners (don’t have to be this sad!) #1095 Jan 30, 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.

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.

Student Loan Chaos Explained w/ Stanley Tate #1094 Jan 28, 2026

Show notes

The whiplash student loan borrowers have experienced over the past few years has been staggering. Payments paused, forgiveness promised, forgiveness blocked, repayment systems rewritten, and now wage garnishment is back on the table for some folks. It’s no wonder navigating student loans has become a specialized skill. Few people know that landscape better than attorney Stanley Tate. He’s helped hundreds of borrowers get out of default, qualify for forgiveness programs, secure affordable payments, negotiate settlements, stop garnishments, and even discharge student loans in bankruptcy. Through his blog, newsletter, and videos, Tate has offered guidance to countless others. Some of the topics covered today:

How much time borrowers in default have had to address the elephant in the room
Why income-driven repayment plans are crucial for many borrowers
Why private student loans are expected to see a resurgence
Borrowers often misunderstand their repayment options and forgiveness paths
How emotional decisions often overshadow financial reasoning in education funding
The biggest student loan mistake that his clients make
Living life fully is essential, even amidst student loan burdens
And much more!

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

Stanley Tate: Newsletter, tools, and other resources up on his site and he’s got a great YouTube channel 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.

Ask HTM – Assets to Boost My Credit Score, Lifestyle Geographic Arbitrage, and Car Loans to get Wealthier #1093 Jan 26, 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 - Credit score: what assets should I focus on in order to boost my credit score?

2 - Geo arbitrage: how should I approach moving to Italy when all of my tax advantaged investing accounts will now be taxed?

3 - Down payment: should I invest my cash that I’d like to put down for my first house?

4 - Car loans: why do you guys recommend paying cash for a car when you can earn more by investing in the stock market?

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 NA Safe Sexride by Incendiary Brewing - a huge thanks to Brandon for donating this one to the show! 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 - Points for Paying your Mortgage, Credit Card Consultants, & AI UBI (to each according to his need!) #1092 Jan 23, 2026

Show notes

Dry January is still costing you
Background (credit) checks
Garnished student loan wages
Points for paying your mortgage
If the juice is still worth the squeeze
Credit card consultants
Smaller weddings saving money
Paying for guru chatbots (should we launch our own new AI or do traditional one-on-one coaching?)
Hey siri, reduce my medical bill by 80%
AI UBI
Tapping a 401k early
Greenland and the future of investing in US stocks

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.

The Art of Spending w/ Morgan Housel #1091 Jan 21, 2026

Show notes

Spending money is EASY… it’s the saving and investing that’s hard, right!? Not necessarily. Our guest today isn’t going to judge your spending habits, but he does want to help you learn what’s worth wanting. Morgan Housel wrote what many consider to be the most compelling money book in recent memory, The Psychology of Money. His new book is called The Art of Spending Money and a few of the ideas covered today:

Spending is the ultimate purpose of money
Independence is the most important thing money can buy
Understanding the difference between internal and external benchmarks is crucial
Identity should not be tied to financial metrics
How inconsistent spending habits can lead to happiness
Cultural shifts have changed how we view money and success
Finding purpose beyond money is essential for a fulfilling life
And plenty more!

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.

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 - Combatting Healthcare Premium Hikes, Purchasing Long Term Disability, and WTD with Nine-Figure Wealth #1090 Jan 19, 2026

Show notes

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?

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 Shift Experimental by Incendiary Brewing - a huge thanks to Brandon for donating this one to the show! 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 - Credit Card Caps, Free Rent, & Pokemon Investing #1089 Jan 16, 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.

Own Your Time: Build a Life You Control w/ Andy Hill #1088 Jan 14, 2026

Show notes

We all get the same 24 hours – but it sure doesn’t always feel that way, does it? Why is it that some people seem to have time for hobbies, meaningful conversations, even a slow cup of coffee, while others are just trying to survive the day on repeat? Today, we’re breaking down what it really takes to build a life that feels enjoyable, sustainable, and manageable… not rushed and reactive. And a crucial part of that equation are smart money decisions and intentional choices about how we spend our time. Our friend Andy Hill is here to share his wisdom. Andy runs Marriage, Kids & Money, and he’s the real deal – someone who has put in the work and built a life guided by values, freedom, and family. Everything he shares today comes from experience, not theory. Some of the topics we get to:

Best reason every for tracking and budgeting
Importance of effective communication with a partner
Cutting expenses shouldn't mean depriving yourself of joy
The debt hatred method focuses on paying off emotionally burdensome debts first
Transitioning to solopreneurship can provide more control over your time
Experimenting with work-life balance can lead to a more fulfilling life
What “FU” money affords you
Life is for living, not just saving for the future
And plenty more!

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

Andy: Own Your Time is the book, and Marriage, Kids, and Money is the podcast.
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.

Ask HTM - Gym Edition Frugal or Cheap, Blaming the Baby for Lifestyle Upgrades, and Dipping into Savings for a Camper #1087 Jan 12, 2026

Show notes

1 - Camper purchase: should I use my HELOC to replenish my emergency fund that we used to buy a used camper?

2 - Baby wealth: what accounts do I prioritize for my twins future and how should I be thinking about generational wealth?

3 - Expensive gyms: is it frugal or cheap to not tell my gym that I’m still paying the old rates?

4 - Apartment hunting: how should I approach the conversation with my landlord about breaking my lease due to our growing family?

5 - Crypto: is it a good idea to invest in individual stocks and crypto if they’re already represented in my portfolio via an index?

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 Dulce Muerte by Incendiary Brewing - a huge thanks to Brandon for donating this one to the show! 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 - Return Rabbits, Double Majoring, and Nihilistic Renters #1086 Jan 09, 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.

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