How to Money

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:

Spain. Vietnam. Tanzania. Georgia… the one in Europe of course. Ever catch yourself daydreaming about building a life somewhere far beyond the borders of the US? There’s a lot to love about living here. But for many, the pull to see more of the world never really goes away. What’s fascinating is that moving abroad isn’t just a lifestyle decision, it can be a financial one too. Different countries come with different costs, and entirely different ways of thinking about work, money, community, and quality of life. Our guest today is Richelle, founder of Move Abroad Coach. S...

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 - Other people's money: Is financing more of our new home the best way to get the lowest rate?

2 - $300,000 windfall: Help me to efficiently drain an inherited 401k and invest for the...

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:

Anyone else a little tired of hearing about ‘retirement?’ It can feel like this vague, far-off finish line that we're told to obsess over for decades. But here's the thing: when you look at the research, a surprising number of people who are retired—or about to retire—are anxious. They've got regrets. Some of those regrets are financial. But many have nothing to do with money at all. So if we're going to spend years working toward retirement, we should probably make sure we're aiming for one we'll actually enjoy. Joel has known Wes Moss for a long time. Th...

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 - Extra cash: Should we use our savings to pay down a mortgage that’s at 2.8% for 30 years?

2 - Brokerage taxes: How do I prepare for paying taxes on dividends and could you...

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:

“There’s nothing new under the sun.” That comes from Ecclesiastes. But it’s a piece of wisdom we tend to neglect. It's often said that those who forget history are doomed to repeat it. But what if a poor understanding of history does something else too: leaving us less grounded and giving us unrealistic expectations about how life used to be? It’s time for a history lesson today, but not just for the sake of memorizing names, dates, and events. Drawing on countless examples from history, national bestseller Joseph Moore argues that while we're constantly looking back with nosta...

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 - HSA: I don’t see how investing money in a Health Savings Account is going to move the needle for me?

2 - Dividend stocks: I keep buying individual stocks, but maybe it’...

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:

What’s harder: parenting… or the cost of it? We’re huge fans of having kids. They teach you so much, force you to become less self-absorbed, and – let's be real – it’s incredible to watch little mini versions of yourself running around bringing so much joy, purpose, and chaos to your daily life. But financially? Raising a family can feel more daunting than ever. Between housing, childcare, activities, and expenses that seem to multiply overnight, many parents are left asking: How do we make this work? That’s why we’re joined today by Kristy and Bryce of Millennial Revolut...

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 - House poor: What to do when all your money goes towards your mortgage?

2 - Aldi: Is it true that the best budget grocery store isn’t taking the AMEX Blue Cash Pref...

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:

Frugality is a cornerstone of personal finance advice: cut back, spend less, reduce waste. And for the average American drowning in debt, that’s often solid advice. But money isn’t meant to just sit there untouched—it’s also meant to be spent, experienced, and enjoyed. In fact, even the money you save is really just deferred spending. And let’s face it: money isn’t easy to come by. We work hard for every dollar we earn. So maybe the answer isn’t simply spending less. Maybe it’s spending with more intention. Our guest today wants you to worry les...

Big money mistakes usually come from doing the “smart” thing too soon. We break down listener decisions that look simple on the surface, but could cost you thousands if you get the timing wrong… from where to park a home-sale windfall, to whether a refi is actually worth it, to why stock-picking advice from family can be a trap, and more! 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...

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:

There’s a lot packed into your 20s. You’re getting an education — formal or otherwise. You’re figuring out what you believe about work, money, relationships, success, and who you want to become. Sure, that process doesn’t stop at 30, but your 20s are especially formative. And there’s no shortage of advice aimed at young adults. Commencement speeches. Career gurus. Personal finance influencers. But a lot of it misses the deeper question of what actually matters. And in a world full of noise, it’s getting harder to separate wisdom from status signaling. Today we’re joined by Jack Raines...

Join our first ever video podcast as we explore the latest in personal finance, technology, and lifestyle, sharing insights and practical tips to improve your financial well-being and enjoy life to the max! Today we get into:

Searing your steak as a way to ‘lock in the juices’ is something we’ve heard folks recommend for years! Get that grill hot as blazes, toss on your steak, and reap the juicy medium-rare rewards. But even though there might be a kernel of truth here, culinary scientists tell us that it’s not actually the best method. It turns out that the reverse sear is the better way to do it! Similarly, there are phrases and ideas in the personal finance space that get preached as though they’re the gospel truth. And there are a number of reasons...

Dying without the proper documents in place can cost your loved ones a ton of money! The latest research shows that probate can easily take a 3% to 7% bite out of your estate. And this is a topic that’s been on our minds for months since episode 704, when we had our wives on the podcast. We realized that the ladies might have a general idea of what to do if one of us died, but for the most part they would be rudderless since both of us handle the bulk of our finances in both of our families. That’s wh...

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 - How do I go about creating a budget with a highly variable income?

2 - As new parents we want to start saving money into a 529 plan but how much should we aim...

Check out our first ever AMA: an ‘ask me anything’ where we focused on personal questions as opposed to personal finance related content! Typically we’re either interviewing someone in the personal finance space, answering listeners’ money questions, doing a deep dive on a particular topic, or covering the latest personal finance news- but we thought it’d be fun for y’all to get to know us more on a personal level. These are the kinds of topics you might hear us talking about if we were grabbing a bear at a local brewery! So have a listen as we answer...

The fundamentals of personal finance aren’t all that complicated- there’s a reason why we came up with the Money Gears: 7 straight forward steps to take with your money. We could probably boil it down even more: spend less than you make, and invest the rest! So while the core principles of growing wealth are fairly simple, then why aren’t more Americans handling their money better? One reason is because we, as individuals, are incredibly complex! And that complexity can lead to a disconnect between what we know we should be doing with our money, and what we act...

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 - What are the tax consequences of selling a single stock within my Roth IRA?

2 - How do I shift my mindset from saver to spender as I enter my retirement years?<...

We love nerdy board games! And one of the things that makes them fun, besides getting to play them with friends and family, is the competition for scarce resources. For instance with the Settlers of Catan, it takes a few rounds of play to get the resources you need to build the settlements, cities, and development cards that help you rack up victory points in Catan. It’s a classic that still holds up, and like most games it's all about tradeoffs. Should you focus on building a road or upgrading to a city? You can’t do it all...

Sure you could simply invest in a target date fund, or even take the more aggressive path by going all-in on equities and investing solely in the S&P 500. But what if that means you’re potentially leaving millions on the table by the time you reach retirement? That’s the question at the center of our conversation today with our guest Paul Merriman. He is the author of eight books, has a regular column at MarketWatch, is a legend in the DIY investing arena, and is an advocate of the Two Funds for Life investing strategy. That strategy outp...

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 - I have a recurring transfer to my Roth IRA but is that money actually invested?

2 - How do I keep a bill in collections from hitting my credit report?

3 - S...

Who is the greatest actor of all time? You might have an opinion- maybe it’s Meryl Streep or Daniel Day-Lewis, but this would likely lead to a pretty fierce debate. And the same could be said about athletes- who is the greatest? Is it Michael Jordan or Michael Phelps? Well it depends on who you’re asking because it’s in the eye of the beholder to a certain extent. We all want to know what sets the  greatest in their given field apart from the ones who were just really good. Luckily the greatest investor conversation isn’t nearly...

There’s a massive difference between how something feels versus the actual reality. We’re talking about vibes as opposed to empirical evidence. And that’s why we’re happy to talk with Dr. Jean Twenge who is a professor of psychology over at San Diego State University. She has researched the personal finances of the different aged cohorts and few experts have addressed the topic of generational change as well as she has. Dr. Twenge has written multiple books on the defining characteristics of specific generations- she did that in her book iGen where she focused on Gen Z, and h...

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 - Should I exit a managed retirement account even though I have seven figures in there?

2 - Is there any benefit to paying off a mortgage earlier in the life of the loa...

Is homeschooling the best move for your family? Maybe!? That depends on so many factors like your family values, the goals for your career, what resources are available to you, and even what school your kids are currently attending. We’re both products of basic public schooling, but it’s a topical question as the percentage of children who are homeschooled has basically doubled in the past few years- but, homeschooling isn’t a slam dunk decision. And the same is true on the real estate investing front. We love that path for some people and it’s a strategy...

Only 9% of young Americans have shown an interest in serving in the military according to the latest figures- we’ve seen a precipitous drop which means that our nation’s security could be at risk in the future. And not only that but when you look at it through a simple economic lens, the lower the supply (in this case of individuals willing to serve), the higher the benefits those individuals will receive. So not only are new enlistees fulfilling a patriotic duty, but they also have the opportunity to reap some serious financial rewards as well. That’s why we...

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 - Inheritance windfall: Should I keep an inheritance with financial advisors or is it time to trust myself?

2 - ESPP: What’s the best way of taking advantage of my Employee Stock Pur...

Clark Kent has a nerdy newspaper job, he’s got thick glasses- he’s definitely not cool in the city of Metropolis. But when he pulls back the white button up, he’s a beast and becomes Superman! He has superhuman strength, heat vision, freeze breath, and all sorts of special powers that allow him to kick butt and save the world. But Clark Kent doesn’t need everyone to know what he’s capable of- his power is understated and somewhat disconnected from his everyday life. And when it comes to our finances, there’s massive power that we hold as i...

Student loan balances are climbing, credit card debt is hitting new highs year after year, new forms of borrowing like buy now pay later seem to appear out of thin air (which is a testament to just how creative the financial lending industry can be)! We’re a nation steeped in debt and it’s become so normal that we barely question it anymore. But once you realize the emotional toll it’s taking, digging your way out of a debt hole is a lot harder than it sounds. In fact, studies show the biggest barriers to getting help aren’t...

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 - Gift house: My future in-laws might gift us a home… that we’ll eventually own… good idea?

2 - Prepaid Visa: Is it frugal or cheap to leave an entire prepaid Visa during a...

Getting your driver’s license was a liberating milestone worth celebrating because it meant you no longer needed your parents to drop you off at work, or it meant that your friends didn’t need to pick you up to hang out- you had some freedom to do what you wanted! It was a period of life that was likely accompanied by significant change that we can only truly appreciate in hindsight. And as fun as it was to drive on your own for the first time, graduating high school or college is an even more momentous occasion that come...

Some of the best things in life are free, but many of the most meaningful goals demand serious time, effort, and sacrifice. The problem is, we rarely get a clear look at what it actually takes to reach those heights. Instead, we see the highlight reel, not the hard parts, which can leave us with a warped sense of the work required to achieve our own ambitions. Our guest today is here to set the record straight. She believes you can earn your freedom but only if you’re willing to put in the work. Bola Sokunbi is a fi...

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 - Jumbo downpayment: What’s the downside of putting down more on a house in order to reduce my monthly payment?

2 - Saving rate stress: Should I worry about contributing to my Roth i...

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: