How to Money

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:

Try to explain consciousness. Go ahead… we’ll wait. It’s almost impossible, but that doesn’t make it any less real! Same with gravity. You can’t see it, but it shapes every movement you make, and it did long before anyone could fully explain it, even after Isaac Newton put words and math to it. Economic forces work similarly to gravity. You don’t always see them, you might not fully grasp them, but they quietly influence every financial decision you make, from the biggest to the smallest. That’s what today’s show is all about. Alex Mayyasi is...

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 - JL Collins: Do you guys agree with the same investing principles in The Simple Path to Wealth?

2 - Mortgage ripoff: Even though I have a 4% mortgage, why am I paying closer...

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:

In Rockin' the Suburbs, Ben Folds pokes fun at the “struggles” of middle-class life… it’s angsty, a little whiny, but also tongue-in-cheek. It’s killer piano rock that makes you laugh because deep down, it’s a little too relatable. And that tension is still alive today. A lot of Americans, and plenty of HTM listeners, feel like they’re doing all the right things: saving diligently and investing wisely but at the cost of flexibility, and maybe even some joy right now. So how do you balance building wealth for the future without squeezing the life out of the present...

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 - Retirement rollover: Should I pay the fee with Capitalize to expedite my 403b rollover, just wait, or are there other options?

2 - Too liquid: How do I know if I have to...

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:

Optimization is everywhere in the personal finance world. If we just invest perfectly, we’ll get where we want to go, faster… What's not to love?! Well, retirement planning might be a lot more like horseshoes and hand grenades, where getting close enough is actually good enough. And chasing perfection? That can come with some real downsides. Our guest today is a dear friend who brings clarity to the world of personal finance. Jesse Cramer began his career as a mechanical and aerospace engineer designing telescopes, and now brings that same precision (plus a genuine desire to help people) into...

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 - Pet insurance: As I’m expecting some big vet expenses, should I continue to pay for insurance for my dog?

2 - Roth vs 529: Should we save for our son’s college in...

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:

Most of us think of college as an investment… one that hopefully pays off over decades. And for a lot of people, it does. But with costs skyrocketing, it’s not quite the slam dunk it used to be. So what if you could flip that equation? What if instead of paying for college, college paid you? Our guest today did exactly that. Nia Baiyeroju earned over a million dollars in scholarships and now she’s helping others do the same. She’s here to break down how it works and how you can take advantage of the estimated $100 billion...

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 - Kid IRAs: How do I go about setting up a Roth IRA for a minor?

2 - Advisor fees: By my math, most folks are paying closer to 20-25% for financial advice...

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:

The vast majority of HTM listeners are Gen Z and Millennials - people who are starting early and taking the bull by the horns. But that’s not true for everyone in our audience, and it’s certainly not true for the average American. Our guest today didn’t even start thinking about financial independence until age 50. But he made up for lost time in a big way and now he’s helping thousands of other late starters do the same. Bill Yount is an emergency room physician on a mission to help people escape the rat race, live more bal...

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 - Coast FI: How intentionally should I shift my retirement portfolio to bonds if I’m nearing financial independence?

2 - Credit card bonuses: Does it make much sense for me to budget an...

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:

Shark attacks, plane crashes, and lightning strikes… these are the dramatic and headline-grabbing events that are terrifying but incredibly rare. The odds you’ll ever experience those unfortunate events are tiny, so is it technically risky? Meanwhile, something as ordinary as driving to work should be considered more often since in the US, there are 6 million car accidents a year! When you start looking closely, risk and reward show up everywhere in our lives. And for investors especially, understanding the REAL risks we face, not the ones that dominate headlines, is essential to building a strategy that truly works. Our...

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 n...

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:

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 mile...

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 R...

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:

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...

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 o...

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:

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...

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 - Free Fidelity Funds: Are they the “cheap” option or a great way to get wealthy?!

2 - 3% Cashback: Will paying for a Robinhood Gold membership allow me to get my hands on the Gold...

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 should I account for inflation when using the 25x rule to forecast my retirement?

2 - Are sites like RateGenius and Autopay legit places to refinance my car?

3 - I hav...