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 - Debt-fueled lifestyle inflation: Should I sell a rental property to pay off my 401k loan used to install a pool?

2 - Car financing: Does it make more sense to pay for a new/used car in cash or make payments and invest the difference?

3 - Military service/VA loans: What are the pros and cons of going with a VA loan for a new home we’d like to purchase?

4 - 403b: Leave it, transfer it, roll it, or convert it? (or maybe even BOP it?!... Capitalize could be a part of the solution)

5 - 529 plans: How should I sort through all the options available?! (Virginia's direct-sold site is Invest529.com)

 

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 DDH Cosmik Debris by Creature Comforts… thanks for donating this one to the pod Nick! 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:

• 3-year bachelor’s degrees and degree hacking
• Private student loans around 3%
• Insurance premium factors
• Predictive credit scores
• APR reduction scams
• Phishing for zoomers
• Work perk pruning
• Swapping iPhones for icedreams
• Combatting food waste
• Pre-gaming to avoid high priced booze
• $50 movie tix
• Booking on a Tuesday!

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.

Most of our best memories (and stories) come from trips we’ve taken. Some were incredible international adventures while others were ridiculously cheap road trips across different parts of the U.S. It’s been said that travel is the only thing you buy that makes you richer, and we’re inclined to agree. Our guest today does too. Kyle Potter is the Executive Editor at Thrifty Traveler, a site dedicated to helping people travel more for less. He’s been to more than 30 countries, and his passion is helping people navigate the confusing world of airlines, travel points, and miles. We don’t even want to know how many miles Kyle’s got sitting around, but we do know he’s willing to spend a few of them on a nice bottle of champagne from time to time. Today we discuss:

• How fuel prices, supply & demand, and competition impact ticket prices
• Saving the most by being flexible and following the deals
• Why you should plan to splurge
• Booking a more expensive ticket allows you to save
• Researching fares after booking
• Packing smarter and traveling lighter to save
• How Kyle saves when renting cars
• Roundtrip tickets to Dublin for $134
• 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.

 

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.

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 - Torn: We’re behind when it comes to investing but it seems silly when we don’t have enough liquid savings… what do we do?!

2 - Pension: How aggressively should I invest my Roth IRA dollars when I have a safe pension to fall back on?

3 - Mortgage recast: What’s a good rule of thumb when I’m considering recasting my mortgage to shrink my monthly payment?

4 - Social Security: Why do y’all always say to delay and wait to draw on Social Security?

5 - Work-provided insurance: Should I pay extra for accidental death and dismemberment insurance or stick with the free option?

 

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 Comeback Sauce by Creature Comforts and Edmund’s Oast… thanks for donating this one to the pod Nick! 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:

• $23 apples
• Allbirds AI audacity
• Returns that are too good to be true
• One more year syndrome
• ALTs in 401ks
• Boycotting college savings
• 529 flexibility
• Horrible HELOCs
• Preparing for property taxes increases (check out our review of Ownwell to automatically save)
• Gen Z meets credit cards
• WSJ finally understanding the ‘craft beer equivalent’
• BNPL at Coachella
• The annoyance economy

 

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

The housing market is currently at a massive crossroads, and frankly, the old rules don't seem to apply anymore. We’re seeing a landscape of shifting interest rates, a potential reset in supply, and a level of volatility we haven't seen in decades. That’s exactly why we're going to hear from Dave Meyer - the Chief Investment Officer at BiggerPockets and a grounding voice in real estate data. We’re going to dig into the forces shaping the market right now in 2026, and then zoom out to look at the bigger trends that could influence how we buy homes in the years ahead... both as individuals and as investors. Today we discuss:

• Defining “The Great Stall”
• More analysis needed before purchasing a home
• Factors leading to reduced housing demand
• The impact of interest rates
• Adjustable rate mortgages gaining in popularity
• How investors should approach real estate today
• Strategies for getting a 10% discount
• Recency bias on homeowners and investors
• Rising vacancy
• House hacking
• And much more!

 

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

• Dave: More housing talk on The Real Estate Podcast and On the Market and Dave’s over on Insta too.
• 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.

 

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.

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 - Financial advisors: What’s a good price for a financial advisor and is it worth the cost?

2 - Paying for a minivan: Should I pay cash or take the 1.9% loan they’re offering?

3 - Set for life: Why aren’t y’all talking about the Trump accounts to supercharge your kids retirement accounts?

4 - eSIM: Is this the best option for travel abroad and where should I get one?

 

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 Satisfied by Piedmont 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:

• Stocks at all-time highs
• Bag fees and fuel surcharges
• Surging HOA fees
• This old house
• Spending those tax refunds
• You’re owed some money (Unclaimed.org & MissingMoney.com)
• Don’t be a victim
• Degree doubts
• Free degrees
• Upper-middle class ascendency
• Tough times for rideshare
• Life insurance in the back of a Lyft (better -> Life Insurance: A Step By Step Guide)

 

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.

Let's talk about Social Security. More than music, clothing, or even political views, Social Security might be the single biggest generational fault line in America right now. Boomers are thrilled to finally be collecting on a promise decades in the making while Millennials and Gen Z are quietly wondering if there'll be anything left by the time we get there. And honestly? That concern isn't crazy! Social Security almost certainly isn't going away entirely, but it's probably not going to look exactly the same as it does today either. Mike Piper, CPA and Social Security expert, joins the show today to explore the future of Social Security, optimal claiming strategies, and how to plan for retirement amid uncertain benefits. Specifically covered: 

• What happens when the trust fund is gone?!
• Downsides of overly conservative financial plans 
• Claiming strategies when we’re living longer
• Adjusting plans after a health diagnosis
• The Open Social Security strategy calculator
• Taking opportunity cost into account
• Early retirement considerations
• Common mistakes with DIY investors
• … and plenty more!

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

• Mike Piper: Head over to Mike’s site, Oblivious Investor for his latest writings and Open Social Security for his free open-source strategy calculator.
• 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.