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 - Home sale: should I sell my house to an iBuyer?

2 - Life insurance: is my work provided life insurance enough or should I go ahead and get an affordable policy while I’m young?

3 - Retirement: my 401k has a ‘true-up’ feature but does investing just once, at the end of the year, stymie compounding returns?

4 - Investment property: does it make sense to build a brand new house and then rent it out as an investment property?

5 - Pod talk: how can I grow my podcast- how did y’all grow your podcast audience?!

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.
• 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.

During this episode we enjoyed a Chubby Unicorn by Common Space! 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.

A big thanks to our friend Joe Saul-Sehy for inviting us to join an episode of Stacking Benjamins – we had a blast, and we think you'll enjoy this convo as well!

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It's the most wonderful time of the year in the basement, and we're kicking off the holiday season with our biggest, most packed episode yet.

Joe Saul-Sehy, OG, and Neighbor Doug welcome Joel Larsgaard and Matt Altmix from the How to Money podcast for a year-end celebration of everything that mattered in money during 2025. Think of this as the holiday parade of personal finance episodes. There's a lot happening, it's all connected, and you'll want to stick around for the whole thing.

First up, Joel and Matt join the crew for their Top 5 Lessons from the Events of 2025. From AI's real impact on everyday work to market surprises nobody saw coming, this segment unpacks the money moments that actually changed how we think about our finances. These aren't just headlines rehashed. They're the insights that'll help you make smarter moves in 2026.

Then the show shifts to a fascinating trend everyone's noticing but nobody's quite figured out yet. Why is everyone suddenly betting on everything? Prediction markets are exploding, retail investors are taking bigger risks, and the line between investing and gambling feels blurrier than ever. Joe, OG, Joel, and Matt dig into what's driving this shift, whether it's brilliant or reckless, and how to think about risk when it seems like the whole world just discovered the casino.

But wait, there's more. Nick from Alaska calls in with a real-world budgeting challenge that proves even the most prepared Stackers face seasonal money surprises. His situation sparks the kind of practical, helpful conversation this show does best.

And because this is a holiday kickoff episode, we're wrapping with big news about the Stacking Benjamins Vault, the new tool designed to help you organize and protect your most important financial documents without the headache.

–

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.
• 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.

Sherlock Holmes is a literary character we’re all familiar with who has the uncanny ability to solve any mystery he comes across. And one of the things that sets the British detective apart from others is his use of inductive reasoning to solve his cases. He begins with observations which then propel him in his search for the truth. Deductive reasoning, on the other hand, begins with a hypothesis and then uses the facts in order to confirm a theory. And so as we’re trying to figure out how wealthy we need to be, we think that taking the Holmsian approach is most helpful. Rather than picking a nice round number out of thin air like $1 million, we’re doing some observing and we’re asking some questions! Because regardless of how much money you already have set aside for retirement, you could be missing the mark if you’re only reading the headline numbers reported by the ‘experts’. Today’s episode should help you to realize you probably don’t need as much money as you think, you’ll gain a healthier view of work vs retirement, and we’ll go over some practical calculations to help you decide how much money you’ll *literally* need.

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.
• 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.

During this episode we enjoyed a Double Clutch Nitro Oatmeal Stout by Gruner Brothers- thanks for donating this one to the show Katie! 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.

Traveling for free sounds like a lofty goal for most folks. Sure if you’re single or if you’re a DINK couple- but there’s no way you can pull that off with an entire family in tow! Well, it’s actually easier than you think and our guest, Lyn Mettler, is here to explain how. Lyn is a long-time travel journalist who has been featured on the Today Show and US News & World Report. And she practices what she preaches as she and her family travel and fly, for free, about six times every single year! We cover her simple approach, what three credit cards to focus on in order to give you the most bang for your buck, a smart approach to the Southwest Companion Pass, getting into Disney on the cheap, how to use points to erase travel expenses, and plenty more travel tips on today’s episode.

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

• Lyn: You can learn every detail there is to know about scoring free airfare over at Lyn's site Families Fly Free. And check out her podcast while you're at it!
• 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.

During this episode we enjoyed a Che Si Dice by Halfway Crooks! 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.

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 - Caring for parents: how do I financially prepare to take care of my parents as they enter their later years?

2 - Partial retirement: would contributing to a Roth or traditional IRA allow me to pay less taxes and retire earlier?

3 - Charitable giving: can I use a donor advised fund to strategically give to my local church, even if they don’t accept electronic payments?

4 - Extra mortgage payments: should I stop making extra payments on our house and instead invest those dollars?

5 - Old 401k: what should I do with my old 401k after accepting a new job?

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

• Credit card perks: one of our favorite credit cards currently has a $300 bonus when you spend $500 in the first 3 months!
• 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!

During this episode we enjoyed a Polotmavý by von Trapp 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.

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:

• Deceptive dollar stores
• When it pays to go cheap
• Warrior dividends
• Less great target date funds
• Moderate millionaires
• The wealth effect
• Underperforming financial advisors
• Time to update those beneficiaries
• Wanna be real estate moguls
• Frustrated flippers
• Don’t gamble
• Robinhood pushing prop bets
• Betting your credit card balance
• Debit card cashback

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.
• 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.

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!

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

• 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.

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.

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:

• Fancy, frugal, or cheap advent calendars
• Political money planning
• Wild “FI Number” Guesses
• Free electricity
• AI replacing jobs
• And the jobs it CAN’T replace
• Cash is cringe
• Time for the kids to pay rent
• Owning nothing and renting it all
• Instacart iniquity- how much more convenience is costing you

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!

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.

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.

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.