How to Money

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Latest Episodes:

Becoming a Rational Investor w/ Ben Felix #1076 Dec 17, 2025

Show notes

Tall fellas UNITE! Joel has to contend with talking with someone who is taller than him for a change, but that’s mostly besides the point (unless tall guys actually invest differently than the rest of the population!?). We’re joined by Ben Felix – one of the clearest voices in finance and investing who is co-host of the Rational Reminder podcast and also runs a killer YouTube channel full of thoughtful, evidence-based investing advice. Ben is a CFA, CFP, the Chief Investment Officer at PWL Capital and more importantly, he helps regular folks understand the why behind their investing decisions. We discuss topics like:

The biggest reason to invest rather than save
Savings rates based on individual circumstances
How more financial advisors are shifting to behavioral coaching
The only free lunch in invested
Why target date funds aren’t optimal
What DIY investors need to look out for
And plenty of other topics!

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Check out Ben’s podcast over on Youtube along with his helpful channel where he posts on investing, financial decision-making, and living a good life.
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.

Ask HTM – Double Dipping Expense Ratios, Wealth Building with High Deductibles, and when 50 Year Mortgages Make Sense #1075 Dec 15, 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 - Target date fund: is my brokerage double dipping expense ratios if my target date fund has other funds as well?

2 - High deductible healthcare plan: help me to determine whether or not my HDHP makes sense!

3 - Promissory note: did I make a massive mistake in selling my house with a promissory note?

4 - Pro bono: what certifications should I get if I’d like to help others with their finances for free?

5 - 50 year mortgage: “change my mind” that a 50 year mortgage isn’t a great option for folks to build wealth with homeownership!

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.

During this episode we enjoyed a Contrast, which is a collaboration between Burial and Allagash! 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 - Political $ Planning, Free Electricity, & Cash is Cringe (plus Instacart Iniquity, Advent Calendars, more...) #1074 Dec 12, 2025

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.
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.

Jade Warshaw on Escaping the Debt Trap and Rewriting Your Story #1073 Dec 10, 2025

Show notes

In Greek mythology, Atlas holds the heavens on his shoulders as a punishment from Zeus. And every time you see an image of Atlas, remember the hundreds of millions of Americans who are perpetually burdened by debt. To many of those consumers, the weight of credit cards, personal loans, and car loans feels like an eternal struggle… the new normal with no end in sight. But like our guest today, you can reject that fate and rewrite your story. Jade Warshaw paid off almost half a million dollars in consumer debt over the better half of a decade. Now she uses her hard-earned knowledge to teach others how to do the same. She’s a Ramsey personality and is the author of the new book ‘What No One Tells You About Money’ which explores the emotional side of personal finances. We dive into that and also cover:

Facing deep emotional struggles when dealing with debt
Financial discussions should include emotional health
Debt can strain personal relationships significantly
Understanding money involves more than just numbers
Feeling isolated in financial struggles
Role of debt in growing a family
Good debt vs bad debt
Jade’s final piece of advice
And much more!

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

Jade’s new book, out January 6th: What No One Tells You About Money

Instagram, TikTok, Facebook, and X.

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.

Best friends out!

See omnystudio.com/listener for privacy information.

Ask HTM – Newlywed Downpayment Debate, Good Car Loans, and Failing to Max Retirement Account #1072 Dec 08, 2025

Show notes

1 - Downpayment debate: should we put down more than 20% if we have extra money in our investment accounts?

2 - Car loan: is it worth signing up for a car loan with the dealership if it means I snag a four-figure discount?

3 - Special needs: how do I support my son with Down Syndrome while also preparing for retirement some day?

4 - Annuities: are annuities the ticket as a safe alternative investment?

5 - Maxing accounts: how discouraged should I be that I’m no longer able to max my HSA and Roth IRA?

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

Our episode with the Shefska’s on how to pay as little as possible for your new car!
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 Measured Procession of Veracity 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 - AI Toys, Homeowners Held Hostage, & Impoverished Americans Dec 05, 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:

BTW, here is that site that allows you to donate gift cards for good.

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.

Best friends out!

See omnystudio.com/listener for privacy information.

Gen Z vs. The Old Money Rules w/ Lillian Zhang #1070 Dec 03, 2025

Show notes

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.

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 Dec 01, 2025

Show notes

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.

Friday Flight: Leftover Turkey Edition! #1068 Nov 28, 2025

Show notes

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.

Best friends out!

See omnystudio.com/listener for privacy information.

The World Is Getting Better w/ Marian Tupy #1067 Nov 26, 2025

Show notes

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.

Best friends out!

See omnystudio.com/listener for privacy information.

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