How to Money

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Latest Episodes:

Friday Flight - Faltering Friendships, Super Intelligence for Savers, & Birthdayzillas #1203 Oct 09, 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:

Joel evades a parking ticket?
Faltering friendships
Super intelligence for savers (it’s already here)
60 million enrolled in Trump Accounts
Most think the stock market is unsustainable
Over-optimistic Coast FIRE adherents
New Robinhood features
Birthdayzillas (vs celebrating like a normie)
Debt payoff determination
The new debt-free scream?
Check cash advance apps

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

YouTube: You thought you’d never see it… the How To Money channel over on YouTube - LIKE and SUBSCRIBE!
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.

Scoring the Most Financial Aid for College w/ Phillip Levine #1202 Oct 07, 2026

Show notes

The economics of higher education are pretty messed up and colleges know it. Sure, we're sometimes our own worst enemies when it comes to spending. But the pricing system itself seems almost designed to confuse: opaque, inconsistent, and nearly impossible to decode from the outside. Which means there's real money on the table for families who take the time to learn how admissions and financial aid actually work… and which hoops are worth jumping through and which aren't. Get fluent in this system, and you could save yourself tens of thousands of dollars. Stay in the dark, and you're leaving that money on the table. We're joined by Phillip Levine, an economist and professor who's spent his career studying education finance and his new book, Hidden Tuition, pulls back the curtain on how the system really works, and what families can do to navigate it on their own terms. Today we discuss:

Differences between sticker price and actual cost
Enrollment trends and their impact on college prices
Understanding the FAFSA and need-based aid
Merit aid and how colleges use discounts
Negotiating financial aid offers
Tools and resources for estimating college costs
The role of 529 plans and early savings
Manipulating finances to maximize aid
And much more!

Can’t get enough How To Money? Here are some additional ways to get ahead with your personal finances:

YouTube: You thought you’d never see it… the How To Money channel over on YouTube - LIKE and SUBSCRIBE!
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 - Getting Political, Paying for Hot Stock Tips, & Fixing an Old Toyota #1201 Oct 05, 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 - Stock tips: why do so many people pay for stock tip subscriptions?!

2 - Toyota time: is it worth dropping a lot of money on our old Corolla?

3 - Income bump: how can I offset my taxes while still achieving some financial goals?

4 - Political: does iHeart prevent you guys from talking politics on the podcast more often?

5 - Medical debt: what’s the site that helps you to get out of medical debt?

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

YouTube: You thought you’d never see it… the How To Money channel over on YouTube - LIKE and SUBSCRIBE!
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.

Friday Flight - Muse is Meh, Homebuying with Homies, & Commuting Costs Climb #1200 Oct 02, 2026

Show notes

Happy Birthday Pete!
Will Joel regret his Midea purchase?
Whether iced coffee is off-limits in an interview
Love/Hate relationship with self-employment
Saying no to commuting
The best year to be alive
Homebuying with homies
Softening housing market
Muse is meh
AI getting financial answer wrong
Wacky ETFs
Social Security age could be lowered

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

YouTube: You thought you’d never see it… the How To Money channel over on YouTube - LIKE and SUBSCRIBE!
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.

You Saved It. Now Give Yourself Permission to Spend It w/ Jean Chatzky #1199 Sep 30, 2026

Show notes

61% of Americans say they’re more afraid of running out of money than they are of dying… the idea of spending our later years stressed about money is so terrifying that some people would rather face the great unknown than deal with their own financial plan. And yet, far too many people are taking the “I’ll figure it out someday” approach when it comes to retirement. They’re hoping things work out instead of building a plan that gives them confidence and freedom. Our guest today believes retirement doesn’t have to be defined by fear and uncertainty. With the right decisions, we can worry less about money and spend more time enjoying the life we’ve worked so hard to build. Jean Chatzky has spent decades helping people make smarter decisions with their money through her work on the Today show, her AARP columns, her books (the latest of which is titled The Forever Paycheck), and her podcast. Today we discuss what retirement looks like in this modern era, how we can prepare for it without letting fear take over, and we dig into topics like:

The retirement crisis and how to address it
A 'forever paycheck' and how to create one
Role of annuities and other income products in retirement planning
Shifting from accumulation to decumulation and behavioral challenges
The impact of longevity and market risks on retirement strategies
How to balance risk and guarantees in retirement income
Psychological aspects of spending and saving in retirement
And much more!

Can’t get enough How To Money? Here are some additional ways to get ahead with your personal finances:

YouTube: You thought you’d never see it… the How To Money channel over on YouTube - LIKE and SUBSCRIBE!
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 - Early Retirement with a 457b, Surrendering Life Insurance, & Moving to a Bigger House #1198 Sep 28, 2026

Show notes

1 - Cash surrender: or keep a life insurance policy around and how will it impact my student loan payment?!

2 - Early retirement: should I prioritize my 457 if I’m interested in retiring as a firefighter at age 53?

3 - Best yield: where should we keep the downpayment for a new home purchase?

4 - Buy my car: wise advice if you want to sell your car for the most money.

5 - 1% AUM: how do I keep my parents from getting ripped off?

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

Referenced: Breaking up with your financial advisor.
YouTube: You thought you’d never see it… the How To Money channel over on YouTube - LIKE and SUBSCRIBE!
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.

Friday Flight - Illiterate Americans, Shrinking Shoulder Season, & Rate Hike Reactions #1197 Sep 25, 2026

Show notes

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

YouTube: You thought you’d never see it… the How To Money channel over on YouTube - LIKE and SUBSCRIBE!
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.

Fighting Back Against a Broken Healthcare System w/ Dr. Jordan Grumet Sep 23, 2026

Show notes

Does anyone look at the U.S. healthcare system and think, "Yep, everything's working great"? Probably not. It's not because we don't have talented doctors or dedicated healthcare workers. It's because a growing web of corporate interests, distorted incentives, and financial middlemen has turned healthcare into one of the most expensive and frustrating systems in the developed world. In his new book, The Healthcare Heist, Dr. Jordan Grumet – who is also a personal finance podcaster, writer, & speaker – exposes how that happened. Medical bills remain a major source of debt and bankruptcy for American families, but Jordan argues that none of this is inevitable. More importantly, he lays out practical solutions to help individuals. Today we discuss:

The corporate influence on healthcare
Healthcare insurance complexity
Intimacy gap in doctor-patient relationship
Innovation in the US
The role of pharmaceutical companies
Medical tourism
Alternatives like health sharing
Learning from global healthcare models
Emotional side of money management
And much more!

Can’t get enough How To Money? Here are some additional ways to get ahead with your personal finances:

Cashback credit cards: 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 - New(ish) Phones, New(ish) Cars, and New Big Financial Goals! #1195 Sep 21, 2026

Show notes

1 - Big goals: what should I focus on next after I’ve paid off my house?!

2 - Parent help: should I get a power of attorney or keep it simple with a joint account to help my aging parents?

3 - Mach E: am I the only one using an electric vehicle as a way to save a ton?

4 - Newish iPhones: where’s the best place to look if I don’t want to buy brand new?

5 - Venmo vs Zelle: which are the best P2P payment apps for my daughter to use?

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

YouTube: You thought you’d never see it… the How To Money channel over on YouTube - LIKE and SUBSCRIBE!
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.

Friday Flight - Guilt-Ridden Spending, Sneaking Socialism & Home Buying Help #1194 Sep 18, 2026

Show notes

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

YouTube: You thought you’d never see it… the How To Money channel over on YouTube - LIKE and SUBSCRIBE!
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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