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: Rivian repair Robinhood Platinum AI in our mortgage underwriting and our taxes Side hustle salad days 56% of Zoomers hustling S...
Mar 13, 2026•42 min•Ep. 1113
Joel married into a family of teachers. His father-in-law has spent nearly 40 years in the classroom, his mother-in-law has taught for 30, and his brother-in-law is an outstanding Spanish teacher. While it’s clear that every one of them truly loves their work, we also know that passion alone doesn’t pay the bills. Teaching requires some real sacrifice, especially in today’s economy. And while no one enters the profession expecting to get rich, we believe that shouldn't mean teachers are destined...
Mar 11, 2026•57 min•Ep. 1112
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 - Raise vs lifestyle: Should I take a 50% pay increase or maintain the flexibility of working from home? 2 - Nvidia: How do I go about rebalancing my portfolio when I have $800,000 of Nvidia in ...
Mar 09, 2026•58 min•Ep. 1111
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: Jump at the pump We have ‘oil insurance’ Most fuel efficient cars Cheapest new cars Fewer work from home roles Lack of job-hopp...
Mar 06, 2026•41 min•Ep. 1110
Joel met Phil halfway through a marathon a few months ago – literally in the middle of the race. It’s funny how life works and after running side by side and chatting for half an hour it was clear he’d only scratched the surface of his story. Phil Sanders is a serial entrepreneur and like most entrepreneurs, not every venture has been a home run. He’s experienced the highs, the lows of bankruptcy, and everything in between when it comes to building businesses. Today, Phil runs a company called M...
Mar 04, 2026•56 min•Ep. 1109
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 - Housing costs: What’s a good rule of thumb to stick with to help me keep my mortgage payment in check? 2 - 401k rollover: Can you share the penalties and benefits of a retirement account rollo...
Mar 02, 2026•56 min•Ep. 1108
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: Tariff turmoil New retirement plan on the horizon, with a match Housing maintenance costs Gen Z content to rent Frozen home sal...
Feb 27, 2026•41 min•Ep. 1107
Most money advice is a broken record: save more, invest early, and wait for freedom. But what if the real risk isn't running out of money but instead is running out of time? In this episode, we’re challenging the "accumulation at all costs" mindset with Bill Perkins, author of the cult classic Die With Zero . It turns out that a healthy money relationship isn’t just about building wealth but it’s also about intentional spending . Bill argues that time is the most precious asset we have, and that...
Feb 25, 2026•49 min•Ep. 1106
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 - Student loans: what can I do to avoid being in student loans for the rest of my life?! 2 - Lower income, higher net worth: should I be nervous that our monthly spending is more than what we’re...
Feb 23, 2026•58 min•Ep. 1105
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: 401k mullets and quarter-zips Don’t sleep on the solo 401k Crappy coffee Surveillance pricing 1.3 trillion in credit card debt ...
Feb 20, 2026•42 min•Ep. 1104
How often do you stop to consider that your hormones might be the ones clicking "Add to Cart"? We like to pretend money is just logic and spreadsheets, but let’s be real: it’s emotional, it’s messy, and it’s never just about the numbers. If you’re tired of carrying the weight of old financial mistakes or wondering why you’re stuck in the same self-sabotaging loops, this episode is your manual for a reset. Today, we’re joined by Shannah Game, a CFP and Money Therapist who bridges the gap between ...
Feb 18, 2026•55 min•Ep. 1103
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 - Collections: Is waiting for my unexpected medical bill to head to collections a good or great strategy? 2 - Student loans: What should I do while my student loans are in administrative forbear...
Feb 16, 2026•53 min•Ep. 1102
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: Hidden skimp-flation Plunging prices Full coverage premiums on the decline Costco bests Aldi DoorDash dependency Headhunters tu...
Feb 13, 2026•42 min•Ep. 1101
Money fights are one of the most common, and most damaging, sources of tension in a relationship. Whether it’s spending, debt, or mismatched financial goals, those arguments can quietly erode trust and connection over time. But here’s the good news: money doesn’t have to be the thing that drives couples apart . When partners develop healthy financial habits and learn how to communicate about money, it can actually strengthen their relationship. Which is why we’re excited to welcome Dr. Sonya Lut...
Feb 11, 2026•54 min•Ep. 1100
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 - iBonds: What is the actual rate that I’m earning and should I dump them to fund an ADU (Accessory Dwelling Unit)? 2 - Trusts: Should I implement a trust in order to protect my sizeable investm...
Feb 09, 2026•52 min•Ep. 1099
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: Mr. Beast meme coin The Lipstick Effect Non-negotiable travel Travel as a work perk Stretching your dollar with Goodwill Vangua...
Feb 06, 2026•42 min•Ep. 1098
Jumbo shrimp. Open secret. Bittersweet. We call these oxymorons - ideas that shouldn't work together, yet somehow do. Most people put 'frugality' and 'hedonism' in that same category, assuming you can't have a blast while saving a buck. But our guest today, Annie Raser-Rowland, is here to shatter that myth. An Australian horticulturalist and author, Annie argues that true pleasure isn't bought, instead it’s found in the more sensual and free moments we overlook when we're too busy working to pay...
Feb 04, 2026•1 hr•Ep. 1097
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 - Money Gears: I’m confused… why do you recommend getting a 401k match before paying off high interest credit card debt? 2 - Cash windfall: What should I do with the rest of my inheritance? 3 - ...
Feb 02, 2026•52 min•Ep. 1096
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: $119 for an entire year of cell service NYC tipping company Don’t panic tip Richer refunds Tax refund advance loans Save by sho...
Jan 30, 2026•43 min•Ep. 1095
The whiplash student loan borrowers have experienced over the past few years has been staggering. Payments paused, forgiveness promised, forgiveness blocked, repayment systems rewritten, and now wage garnishment is back on the table for some folks. It’s no wonder navigating student loans has become a specialized skill. Few people know that landscape better than attorney Stanley Tate. He’s helped hundreds of borrowers get out of default, qualify for forgiveness programs, secure affordable payment...
Jan 28, 2026•43 min•Ep. 1094
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 - Credit score: what assets should I focus on in order to boost my credit score? 2 - Geo arbitrage: how should I approach moving to Italy when all of my tax advantaged investing accounts will no...
Jan 26, 2026•55 min•Ep. 1093
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: Dry January is still costing you Background (credit) checks Garnished student loan wages Points for paying your mortgage If the...
Jan 23, 2026•41 min•Ep. 1092
Spending money is EASY… it’s the saving and investing that’s hard, right!? Not necessarily. Our guest today isn’t going to judge your spending habits, but he does want to help you learn what’s worth wanting. Morgan Housel wrote what many consider to be the most compelling money book in recent memory, The Psychology of Money . His new book is called The Art of Spending Money and a few of the ideas covered today: Spending is the ultimate purpose of money Independence is the most important thing mo...
Jan 21, 2026•48 min•Ep. 1091
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 - Nine-figure wealth: what do we do after our company sells for $300 million?! 2 - Healthcare subsidies: are health sharing plans my only other option to keep my healthcare costs down? 3 - Landl...
Jan 19, 2026•53 min•Ep. 1090
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: Longevity calculators ( Matt’s preference ) Credit card caps The youths ditching credit cards Free rent Gambling on housing Pri...
Jan 16, 2026•40 min•Ep. 1089
We all get the same 24 hours – but it sure doesn’t always feel that way, does it? Why is it that some people seem to have time for hobbies, meaningful conversations, even a slow cup of coffee, while others are just trying to survive the day on repeat? Today, we’re breaking down what it really takes to build a life that feels enjoyable, sustainable, and manageable… not rushed and reactive. And a crucial part of that equation are smart money decisions and intentional choices about how we spend our...
Jan 14, 2026•52 min•Ep. 1088
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 - Camper purchase: should I use my HELOC to replenish my emergency fund that we used to buy a used camper? 2 - Baby wealth: what accounts do I prioritize for my twins future and how should I be ...
Jan 12, 2026•55 min•Ep. 1087
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: World Cup ticket prices Retailers charging for returns Return rabbits Garnished wages on the way Education Department loan simu...
Jan 09, 2026•40 min•Ep. 1086
“The quality of your life pretty much exists outside of the realm of money.” That’s a quote from today’s guest and we’re going to spend a good amount of time talking about everything BUT money! Personal finance and handling your money effectively is important of course, but don’t confuse the means to the end, with the end itself. Money is simply a tool, and like the adage about dying with ‘the most toys,’ it’s easy to see how taking the approach of maximizing your wealth accumulation would leave...
Jan 07, 2026•59 min•Ep. 1085
New year, new outlook, and a fresh strategy for your wallet. Welcome to 2026! In this episode, we’re setting the table for the year ahead. After the unique challenges and "did that really just happen?" moments of 2025, it’s time to stop reacting and start orchestrating your own financial future. We’re stripping away the jargon to talk about what actually matters: building wealth slowly, steadily, and with a craft-beer-level appreciation for the process. To give you a taste of what we’re diving i...
Jan 05, 2026•57 min•Ep. 1084
