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Best friends Joel and Matt are the co-hosts of How to Money which is all about providing the knowledge & tools that normal folks need to thrive in areas like debt payoff, DIY investing, and crucial money tricks that will provide continuous help along your journey. We believe that access to unbiased and jargon-free personal finance guidance is more necessary than ever before. When you handle your money in a purposeful, thoughtful way that works for your lifestyle, you can really start living a rich life.

How to Money

Let’s talk about money and “the youths” today! While a lot of personal finance advice is evergreen and helpful to folks of all ages, it’s also important to reach people where they are and in the way they like to consume information. As middle-aged dads, we hope to stay relevant, but we don’t have the same street cred as our guest today. We’re joined by Lillian Zhang who, as a first generation born American, carved her own path by figuring out the job search, learning how money works, and building wealth from scratch. She earned a degree from the Haas School of Business at UC Berkeley and now works in Silicon Valley by day while writing and publishing her book: The New Money Rules. Today we discuss:
 
 • Gen Z feeling pressure to catch up with peers financially
 • Social media influencing Gen Z's perception of wealth
 • Riskier investments are appealing to younger generations
 • Traditional 'get rich slowly' strategies are less popular among Gen Z
 • Financial literacy is crucial for informed investing
 • Having money, practicing personal finance early on to cement concepts like tradeoffs
 • … and much more!
 
 
 
Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
 
 • Lillian’s new book: 
The New Money Rules • , but you can also keep up with her on 
Insta • , 
TikTok • , 
LinkedIn • , and 
YouTube • .
 • 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.
 • Find a thriving community of fellow money nerds by joining the 
HTM Facebook group! • 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!
 
 
 
Best friends out!

See omnystudio.com/listener for privacy information.

Gen Z vs. The Old Money Rules w/ Lillian Zhang #1070

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 - Accelerated Mortgage Payoff - is velocity banking a smart way to quickly pay off my mortgage?
 
2 - Donor Advised Funds - do I get to deduct more from my taxes if my donor advised contribution grows after investing?
 
3 - Retirement Investing - am I better off contributing to my Roth IRA or my employee sponsored 457b?
 
4 - Medical Bills - should I take an offer for a medical bill discount by paying before the end of the year, or is there a better option?
 
5 - Life Insurance - I already have rental properties and a 401k that my baby could inherit so do I also need life insurance?
 
 
 
Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
 
 • We talked about 
Donor Advised Funds • in depth with Adam Nash.
 • If you’re looking for the best place to open a donor advised fund then look no further than 
Joel’s review of Daffy. • A great physical fitness newsletter by friend of the pod, Drew: 
Move To Improve • 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. • Massively reduce your 
cell phone bill • each month by switching to a discount provider like Mint Mobile.
 
 
 
During this episode we enjoyed an Automatic IPA by Creature Comforts! 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 – Mortgage Payoff Loophole, DAFs to Maximize Tax Deductions, and Legally Evading a Medical Bill #1069

We’re taking a moment to slow down and reflect on what HTM listeners are truly grateful for during this busy holiday season. And yes… doing this on Black Friday is intentional. Instead of swapping stories about the hottest deals, we’re choosing to hit pause on consumption and appreciate what we already have.
 
 
 
We also want to connect the dots between the financial sacrifices and smart money moves you’ve made and the deeper parts of life they impact, like family, time, peace, and purpose. Money matters, but what matters more is what it makes possible. So ask yourself:
 
 • What does life feel like now that you’re not buried in credit card debt?
 • Has building an emergency fund reduced your stress in a meaningful way?
 • Does having a retirement investing plan give you more freedom to be present with your kids?
 • Does saying “no” to a high-pressure promotion feel right now that you’re within reach of coast FIRE?
 
 
 
These are the reflections we hope you’ll sit with today!
 
 
 
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. • 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.

Friday Flight: Leftover Turkey Edition! #1068

Though it seems like the world is in shambles, humanity has progressed quite impressively when you look at virtually any length of history. Our modern society has produced a slew of nice things that would have been hard to fathom 50 years ago, much less 250 years ago- smartphones, duct tape, GPS. They’ve all, to greater or lesser degrees, made our lives better and that’s simply looking at consumer goods. Think of other clear markers like infant mortality, literacy rates, longer lifespans and how they all point to incredible progress. But how did those innovations and that abundance come about? Why does 2025 look so radically different in the developed world than 1825? Marian Tupy’s book Superabundance explains it all and demonstrates how far we’ve come in easy-to-understand language. Marian Tupy is a senior fellow at the Cato Institute. He’s also the founder and editor of HumanProgress.org, a site that seeks to evidence these dramatic improvements. Listen as we cover how:
 
 • Progress is not guaranteed and can regress under certain conditions
 • Life expectancy has dramatically increased over the last 200 years
 • Economic freedom and openness to trade drive prosperity
 • Nostalgia often overlooks the harsh realities of the past
 • Environmental concerns can be addressed through innovation and technology
 • Time prices illustrate the abundance of resources available today
 • Gratitude for our current circumstances can lead to greater happiness
 • And plenty more!
 
 
 
Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
 
 Superabundance: The Story of Population Growth, Innovation, and Human Flourishing on an Infinitely Bountiful Planet • is the book and 
HumanProgress.org • is the site!
 • 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.
 • Find a thriving community of fellow money nerds by joining the 
HTM Facebook group! • 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!
 
 
 
Best friends out!

See omnystudio.com/listener for privacy information.

The World Is Getting Better w/ Marian Tupy #1067

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 - Home repair: should I get a new roof based on a roof inspector who says my insurance will cover it for free?
 
2 - Roth conversion: as an average wage earner who is maxing out my Roth IRA, should I convert my 401k as well?
 
3 - Tech heavy portfolio: should I rebalance my retirement portfolio away from AI if I think it’s a bubble?
 
4 - Savings rates: should I ditch Ally for another bank that’s paying a higher rate on their savings account?
 
5 - Open enrollment: I’ve always gone with my employer provided Health Reimbursement Arrangement, but is the HSA better?
 
 
 
Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
 
 • We referenced a bunch of previous episodes:
 • Finding 
financial freedom making less than $40,000 • a year with Hope Ware.
 Timing a Roth conversion • with CFP Cody Garrett.
 AI and your investments with Vanguard’s Joe Davis • .
 • I’m not sure who needs to hear this but 
Health Savings Accounts, or HSAs, are the ultimate retirement accounts. • 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. • Massively reduce your 
cell phone bill • each month by switching to a discount provider like Mint Mobile.
 
 
 
During this episode we enjoyed a Kirkland Signature Vintage Ale 2025 by Deschutes! 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 - Filing a Claim for a New Roof, Rebalancing Away from Tech/AI, & Taking Advantage of a Health Reimbursement Arrangement #1066

We’re sharing another podcast we think you’ll enjoy, The Big Short Companion from Against the Rules, hosted by bestselling author Michael Lewis. The Big Short is now 15 years old and to mark the occasion, Lewis narrated a new audiobook version of The Big Short and is looking back on how the 2008 financial crisis still affects the world today. To make sense of Wall Street’s hangover from the crash described in The Big Short, Lewis calls up Matt Levine, author of the Money Stuff newsletter for Bloomberg Opinion. He’s also a former investment banker who was working at Goldman Sachs during the market crisis of 2008. He and Lewis talk about Bitcoin, bank regulation, and new forms of risk-taking—all ways Wall Street has changed since the crisis. Find The Big Short Companion from Against the Rules wherever you get podcasts and The Big Short audiobook wherever you get audiobooks.

See omnystudio.com/listener for privacy information.

Introducing: The Big Short Companion from Against the Rules: How the Financial Crisis Broke Wall Street

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:
 
 • Help us dominate the 
Daffy Voices for Good Campaign • !
 Burdensome credit card benefits Frankenstein BNPL cards Robinhood Gold 3% cashback credit card Cash delivered to your doorstep Soft switching Tariff turnaround Eat more chicken Delayed flight compensation iPhone pocket sock $300 water bottle Discounted drugs GLP-1 in the C-suite End of electric (cars) Credit history vs car insurers Car-play diem 
 
 
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. • 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.

Friday Flight - Soft Switching, Tariff Turnaround, & Ozempic Face #1065

“Taxes for creatives” could have also been the title of this episode, giving the more entrepreneurially minded the boost they need to officially launch a little business they’ve been considering. But for most folks the topic of taxes isn’t comforting, it’s straight up terrifying… even though it shouldn’t be. Today’s guest, Hannah Cole, is on a mission to create fearless folks who launch into the world of deductions, bookkeeping, tracking, tax filing, and all the other terms that strike a little fear in your heart, with full confidence. Her new book, Taxes For Humans, acts as a field manual for self-employed folks to simplify their taxes and take the bull by the horns. Topics covered today:
 
 • Taxes can be intimidating, but understanding them is empowering
 • Creatives often struggle with the business side of their work, including taxes
 • The IRS is more forgiving than many people think
 • Receipts, tax forms, and bookkeeping are the key three systems
 • Deductions are available for ordinary and necessary business expenses
 • When and how much in quarterly estimates, in order to avoid penalties
 • A visual guide to tax deductions
 • And much more!
 
 
 
Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
 
 • Be sure and check out Hannah’s new book, 
Taxes For Humans • , or just get it 
on Amazon • . And her 
visual guide to tax deductions • is especially cool for folks looking to organize their business expenses, who also hate IRS forms ;)
 • 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.
 • Find a thriving community of fellow money nerds by joining the 
HTM Facebook group! • 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!
 
 
 
Best friends out!

See omnystudio.com/listener for privacy information.

Don’t Let Taxes Terrify You w/ Hannah Cole #1064

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 - Home renovation: what factors did Matt consider when deciding to add on to his existing house?
 
2 - Credit cards: I want to cancel my oldest credit card, but how concerned should I be about dinging my credit score?
 
3 - Student loans: should I pay off my student loans or wait for forgiveness if I have the cash on hand to eliminate them?
 
4 - Medical expenses: could I fully subsidize my healthcare costs were I to aggressively invest my HSA dollars?
 
 
 
Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
 
 • Converting your primary into an investment property is one of the easiest ways to create some 
semi-passive income • . 
 • I’m not sure who needs to hear this but 
Health Savings Accounts, or HSAs, are the ultimate retirement accounts. • 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. • Massively reduce your 
cell phone bill • each month by switching to a discount provider like Mint Mobile.
 
 
 
During this episode we enjoyed a Jeremy’s Changed by Fonta Flora! 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 - Vital Home Reno or Moving Factors, Dropping Credit Without Dinging Your Score, & Student Loan Forgiveness or Payoff #1063

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:
 
 • Help us dominate the 
Daffy Voices for Good Campaign • !
 50 year mortgages Robinhood getting into the mortgage game Cash for Christmas FindHelp.org • is a great resource for those in need of food, shelter, transportation and more
 Flights not quite as delayed Expense ratio transparency Investment nudges by Vanguard $2,000 tariff rebate checks Fancy credit cards potentially no longer accepted RIP Direct File Avoiding all the scams Voice authentication via code words 
 
 
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. • 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.

Friday Flight - Forever Mortgages, Ruining Reward Cards & Free Tax Filing Fail #1062

Whether you’re planning to score a deal on Amazon Prime day or not, chances are you do a good bit of purchasing online. Obviously we love getting a great deal and the convenience of online shopping is unmatched, but what other considerations should be taken into account? Just because we’re getting a deal now, does that mean we’re spending less money in the long run? During this episode we cover when shopping at a local brick and mortar is better, some serious downsides of shopping online, and then we wrap things up by covering our favorite ways to get deals buying online using deal sites, techniques, and our favorite Chrome extension.

During this episode we enjoyed a Fort by Dogfish Head- another big thanks to our friend Tyler here in Atlanta for donating this rare (to us!) beer to the show! And if you enjoyed this episode, be sure to subscribe and give us a quick review in Apple Podcasts, Castbox, or wherever you get your podcasts- we’d love to hear from you.

Best friends out!

 
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See omnystudio.com/listener for privacy information.

Before You Click 'Buy' On Your Next Online Purchase #103

Lyssna när som helst, var som helst

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