How to Money

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Latest Episodes:

Friday Flight - Dumpster Diving, Insurance Dodging, & Pudgy Penguins #996 Jun 13, 2025

Show notes

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: matched 529 funds, luxury dumpster diving, the apps are spying on us, insurance dodging, wealthy home chefs, fresh Costco perks, God mode investing, leveraged fund retirement accounts, pudgy penguins, tighter used car market, Cybertruck losses, and Smartless cellular.

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.

The Power of Cash w/ Jay Zagorsky #995 Jun 11, 2025

Show notes

Will our guest today convince us to ditch digital payments?! Listen to find out!

Because here’s something that we hear all the time: “You can just Zelle me” or “Venmo me!”. It’s sort of like “I’ll just Uber to the airport” – once a company name has become a verb, is it possible to decouple it from culture? And of course the fact that they’re incredibly fast and easy makes the various payment options very attractive. They certainly make life easier when it comes to paying rent for our little office. It definitely takes the hassle out of receiving rent from tenants and I think they’d say the same thing. You don’t have to worry about lugging around your wallet and don’t get us started on credit card benefits! But you better believe that our guest today wholeheartedly disagrees! We’re joined by Professor Jay Zagorsky who is an economist at Boston University’s Questrom School of Business. And he's the author of a new book that was published a couple months ago: The Power of Cash: why using paper money is good for you and society. He makes arguments for why we’ll spend less, live healthier lives, and have a more resilient society when we treat actual, physical cash as king.

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 Sun Kissed by Edmund's Oast! 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 - Teenage Homebuyers, Best Type of Life Insurance, & Making Easy Money with Securities Lending #994 Jun 09, 2025

Show notes

Let’s kick off 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 - Should I participate in securities lending if that’s a service my brokerage is offering?

2 - Life insurance is on the horizon so should I get an indexed universal life plan like some friends of ours did?

3 - I’d like to purchase a home in the next few years… would it be beneficial to apply for a new Apple card?

4 - Does it make more sense to repair or replace an old Cadillac that’s due for some repairs?

5 - Should I keep the fancy portfolio that Bloom, now defunct, created for me or is there a better option?

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 Doom Volume by The Veil! 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 - Unemployment Uptick, Ridiculous Returns & The 4% Rule Debunked #993 Jun 06, 2025

Show notes

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: Southwest sale extension, unemployment uptick, you too U3?, 401k contribution cutbacks, 4% rule debunked, avoiding the annuities, high priced mocktails, Gen Z forgoing the bar tab, Kirkland Sig old fashioned, dressed by the internet, golden age of secondhand shopping, and ridiculous returns.

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.

Best friends out!

See omnystudio.com/listener for privacy information.

No New Things w/ Ashlee Piper #992 Jun 04, 2025

Show notes

I’m pretty sure everyone listening will want to either get out of debt, reduce the amount of clutter in their life, crush other financial goals, become healthier and happier… OR, why even choose? Why not select: d - all of the above?! That’s because that was the outcome of our guest today, Ashlee Piper, who documented her journey in her new book No New Things: A Radically Simple 30-Day Guide to Saving Money, the Planet, and Your Sanity. Ashlee is a political strategist turned sustainable living expert who has shared her message as a professor in Chicago, on Good Morning America, to her TED Talk, & everywhere between. We discuss the data and how much time we spend shopping or the time taking care of the items we’ve purchased, why she recommends making a “Love List” and how that curbs spending, the vital role our community plays in avoiding new things, utilitarian reasons vs emotional stimuli to purchase, and plenty more in this 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 Hanami by Japas Cervejaria! 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 - Early Retirement Target Date Funds, Frugal Personal Hygiene, & Coercive House Painting #991 Jun 02, 2025

Show notes

1 - What target date fund should I go with if I’d like to retire early?

2 - Frugal or cheap: pouncing on an incorrectly priced item at the store?

3 - Do I prioritize my HSA if I don’t receive a state tax deduction?

4 - My homeowners insurance says I need to cut back trees and paint the house… should I push back?!

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 Black Quad by Real Ale Brewing! 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 - TACO Trading, Pointless Points, & Millionaire Renters #990 May 30, 2025

Show notes

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: CPAP on the cheap, Southwest charging extra, TACO trading, tariffs getting blocked, investing via the Big Beautiful Bill, pointless points, Discover Capital One merger, getting priced out of the housing market, millionaire renters, and house swapping.

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.

Best friends out!

See omnystudio.com/listener for privacy information.

Pharmacist to Full Time Real Estate Investor w/ Ryan Chaw #989 May 28, 2025

Show notes

Newer listeners may not realize how OBSESSED with investing in real estate we were back in the day. In fact, when we were batting around ideas for a podcast, we initially thought it might be focused only on real estate... Luckily we zoomed out enough to cover personal finance more broadly. And it’s not that we’re not excited about rentals anymore, although the current state of the economy has changed our personal approach. But our guest today, Ryan Chaw, is most certainly all-in on real estate which is why we’re stoked to have him join us. Ryan grew his net worth to an astonishing $1.5 million at the age of 28, he completely replaced his pharmacist salary when he was 31, and is now helping others to do the same as a real estate investing coach. We discuss stepping away from a lucrative career, Ryan’s unique strategy of rentals in college towns, using his PRIME method for maximizing profit, high standards when it comes to due diligence, scaling his operations, and much more!

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 Hell or High Twilight by 21st Amendment! 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 - Buying a Used Mattress, Best Use of an Inheritance, & Disqualified from a Roth #988 May 26, 2025

Show notes

1 - Should I use an inheritance to pay off my house?

2 - Buying a used mattress- frugal or cheap?

3 - What should I do with Roth IRA contributions that I’ve already made, if I no longer qualify by the end of the year?

4 - Is it worth paying extra for an extended warranty on our new electric vehicle?

5 - How do I go about switching brokerages if I’m wanting investment options at a different company?

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 an Anatomical Transmutation by Burial! 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 Crunch, MAGA Money, & Gas Gouging #987 May 23, 2025

Show notes

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: flipping dishwashers, credit crunch, what a US downgrade means for us, $70k high school jobs, the Humble Dollar match, MAGA money, gas gouging, competition at the gas pump, rising home internet costs, newsletter overload, where gold and real estate stack up, & small businesses leading to stealthy wealthy.

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.

Best friends out!

See omnystudio.com/listener for privacy information.

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