How to Money

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Latest Episodes:

Ask HTM – HYSA Handicaps, Donor Advised FUN, & 401k Rollover Tax Triggers #1216 Nov 09, 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! But first we discuss Matt’s Fidelity fiasco,, but then we get into:

1 - Startup stability: when do you know it’s time to part ways or stick with a startup that has good potential?

2 - Donor advised FUN: can I use my DAF to fund my charity goal for a race I’m signed up for?

3 - 401k rollover: I really wants my funds in a Roth IRA so how should I go about it?

4 - Kid insurance: why are my friends getting life insurance policies for their kids?

5 - HYSA trade-offs: should I consider moving our savings over to CIT or Betterment?

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!
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 - Post-Election Prognosis, Turnkey Turkey, & Paying for Pals #1215 Nov 06, 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:

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

The New Rules of Christmas Shopping w/ SlickDeals' Vitaly Pecharsky #1214 Nov 04, 2026

Show notes

Remember those old Christmas movies where somebody would pop into a store at the last minute, grab a gift for a loved one, and everything worked out perfectly? Sure, it’s adorable and a big dose of nostalgia, but in real life, waiting until the last minute is a terrible strategy! You’d have no time to wrap anything, you’d overpay, and all the while you’re super stressed out. But there’s another way Christmas shopping has changed that I think is even more interesting: it’s gone from being a concentrated, predictable expense to something that’s increasingly omnipresent, frictionless, and (worst of all) easy to finance. Too many people aren’t just paying for Christmas late in December, they’re still cleaning up their financial mess well into the next year. We’re joined by Vitaly Pecharsky from Slickdeals to talk about how holiday shopping has changed, what it’s doing to our budgets, and how we can avoid turning Christmas gifts into next year’s financial problem. We specifically discuss:

Inflation’s impact on holiday budgets
Strategies to win during Black Friday
Good vs great deals
Price matching and refund policies
Gaming consoles and TV shopping
Dynamic pricing in retail
The role of urgency and scarcity in retail marketing
Treat yo self?
Gift cards
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!
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 - Side Hustles for Your Stocks, Capital Gains Harvesting, & Maxxing HSA Benefits #1213 Nov 02, 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! But first we debate if Joel is frugal or cheap for sending in his Darn Tough socks, but then we get into:

1 - Fully Paid Lending: Vanguard is offering it so should I opt in to make extra on my portfolio?

2 - Capital gains harvesting: my CPA says I can take $40,000 in capital gains and pay no tax… legit?

3 - HSA benefits: I want to make the most of my wife’s health savings account, but is it worth dropping my state provided health coverage?

4 - Debt payoff: what app or formula is best for me to eliminate my debts the most effectively?

5 - Catch-up: should my catch-up contributions be made as pre-tax or post-tax dollars?

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 - Pruning Property Taxes, Midterm Madness, & Passive Income Poppycock #1212 Oct 30, 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!
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.

Why Smart Investors Make Crazy Decisions w/ Alex Edmans #1211 Oct 28, 2026

Show notes

We investors like to think we’re rational. We carefully weigh the facts, analyze the fundamentals, and make smart decisions with our money. Except… we’re human. And when it comes to investing, humans can behave a lot more like a herd of wildebeest than a lion stalking its prey. We chase what’s hot, panic when things fall, and routinely get swept up in the mood of the market. Our guest today argues that markets can look like they’re being driven by cold, hard economic fundamentals, when underneath it all, investor sentiment can be pulling the strings. In his new book, The Madness of Markets, Alex Edmans discusses that AND what individual investors can do about it. Alex is a writer, speaker, and professor of finance at London Business School. We discuss:

How sports outcomes can impact market sentiment and stock prices
Investing should be based on personal circumstances and risk tolerance
Corporate culture can be a predictor of company performance
Speculation can be a part of investing, but should be limited
Playing it too safe can lead to significant financial losses
International diversification can protect against domestic downturns
Understanding your own investment psychology is key to success
Investing in the stock market generally yields good returns
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 - Job Offer Conundrum, $55,000 Landing in Checking Account, & Teen Trading Tightrope #1210 Oct 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! But first we debate if Joel is frugal or cheap for sending in his Darn Tough socks, but then we get into:

1 - Job offer: is it smart to take a job that has lower base pay if the upside potential is better?

2 - Disability insurance: should we consider long-term disability with my wife’s mobility waning?

3 - Child support: how should I allocate a lump-sum child support payment of $55,000?

4 - Pre or post tax: now that I have a Roth 401k available, should I go all-in with pre-tax investments?

5 - Teen trading: how can I teach my teenager about investing and should he use a platform like Bloom?

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 – Souring Sentiment, Time Famines, & Rich Ol' Renters #1209 Oct 23, 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.

Owning Unsexy Businesses to Build Wealth w/ Alex Smereczniak #1208 Oct 21, 2026

Show notes

America has a long history of entrepreneurship. Some of the biggest, most recognizable companies in the world started with one person taking a risk and building something from scratch. And for good reason: owning a business can be an incredibly powerful path to building wealth. But there’s a problem. A lot of people want to be their own boss… they dream about leaving the 9-to-5, having more control over their time, and building something they actually own. But when it comes time to take the leap, the fear of the unknown can be pretty powerful. Here’s the good news: you don’t necessarily have to invent the next great thing in your garage at 2 a.m. There’s another path to business ownership that’s been around for decades: buying a franchise. Alex Smereczniak is an entrepreneur who started Franzy, a platform that connects aspiring business owners with franchise opportunities. Today we discuss the realities of owning a small business, who should consider it, how to evaluate an opportunity, whether buying a franchise is actually a good way to build wealth, and much more including:

His lessons learned from early business ventures
Navigating partnerships and relationships
The role of passion in business
Buying vs starting a business
Understanding franchising and SBA loans
Current marketplace opportunities
Balancing lifestyle and business ownership
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 - Selling an EV to Get Ahead, Juicing Your Down Payment Returns, and Hacking an HSA to the Max #1207 Oct 19, 2026

Show notes

1 - Home reno: but should I goose my savings with special bank offers in the meantime?

2 - HSA overload: what are the tax DISadvantages if I set aside too much in my Health Savings Account?

3 - Baby car: does it make sense for me to sell the Tesla now that we’re expecting our second kid?

4 - Life insurance: what do I do about a previous benign cancer diagnosis now that I need life insurance?

5 - Avoiding medical debt: check out the AI clone advocating for you at the MarshallAllenProject.org!

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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