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 - Should I participate in securities lending if that’s a service my brokerage is offering? 2 - Life insurance...
Jun 09, 2025•52 min•Ep. 994
Time for a Friday Flight- our little sampling of the week’s 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: Southwest sale extension, unemployment uptick, you too U3?, 401k contribution cutbacks, 4% rule debunked, avoiding the annuities, hi...
Jun 06, 2025•38 min•Ep. 993
I’m pretty sure everyone listening will want to either get out of debt, reduce the amount of clutter in their life, crush other financial goals, become healthier and happier… OR, why even choose? Why not select: d - all of the above?! That’s because that was the outcome of our guest today, Ashlee Piper, who documented her journey in her new book No New Things: A Radically Simple 30-Day Guide to Saving Money, the Planet, and Your Sanity. Ashlee is a political strategist turned sustainable living ...
Jun 04, 2025•56 min•Ep. 992
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 - What target date fund should I go with if I’d like to retire early? 2 - Frugal or cheap: pouncing on an inc...
Jun 02, 2025•51 min•Ep. 991
Time for a Friday Flight- our little sampling of the week’s 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: CPAP on the cheap, Southwest charging extra, TACO trading, tariffs getting blocked, investing via the Big Beautiful Bill, pointless ...
May 30, 2025•34 min•Ep. 990
Newer listeners may not realize how OBSESSED with investing in real estate we were back in the day. In fact, when we were batting around ideas for a podcast, we initially thought it might be focused only on real estate... Luckily we zoomed out enough to cover personal finance more broadly. And it’s not that we’re not excited about rentals anymore, although the current state of the economy has changed our personal approach. But our guest today, Ryan Chaw, is most certainly all-in on real estate w...
May 28, 2025•56 min•Ep. 989
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 - Should I use an inheritance to pay off my house? 2 - Buying a used mattress- frugal or cheap? 3 - What shou...
May 26, 2025•51 min•Ep. 988
Time for a Friday Flight- our little sampling of the week’s 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: flipping dishwashers, credit crunch, what a US downgrade means for us, $70k high school jobs, the Humble Dollar match, MAGA money, g...
May 23, 2025•36 min•Ep. 987
We’re trying something completely new for our episode today: we’re hearing from a listener. Not in the form of a question submitted via voice memo, but we’re actually sitting down and having a ‘real money’ conversation, with Nick Gangwer. We met Nick at a listener hang about a year ago and his personal story and the proactive steps that he had taken to completely change his trajectory in life was incredibly inspirational to us as personal finance creators. And then more recently we realized that...
May 21, 2025•53 min•Ep. 986
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 - Where should I open a Roth IRA for my kiddo now that she’s earning some money? 2 - What is it about reverse...
May 19, 2025•51 min•Ep. 985
Time for a Friday Flight- our little sampling of the week’s 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: home warranties, bringing down renovations costs, streaming sports, AMC Stubs, set-jetting to luxury resorts, Carvana making it too ...
May 16, 2025•37 min•Ep. 984
What it means to have a practical and beautiful portfolio. How recent policy decisions have roiled the stock market. Right-sizing your risk tolerance… These are just a few of the topics we discuss with our guest Callie Cox who is a part of the Ritholtz Wealth Management team. She is also the author of OptimistiCallie, her newsletter where she seeks to deliver sane and rational advice to everyday investors, just like us (don’t think we’re completely immune to these turbulent times)! Callie works ...
May 14, 2025•57 min•Ep. 983
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 - How necessary is a credit card to get by in life? 2 - What are some creative ways to pay for graduate schoo...
May 12, 2025•53 min•Ep. 982
Time for a Friday Flight- our little sampling of the week’s 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: Best Buy and Walmart policy updates, homes are getting smaller, paper wealth effect, target date trends, gold beating out VOO, bye b...
May 09, 2025•36 min•Ep. 981
Gone are the days of constantly job hopping in order to rapidly boost your salary! Remember when perusing new job listings during your lunch break while WFH led to a 10-30% pay bump?! Now, with the uncertainty we’re experiencing in the overall market, it’s not just the new hires who are a bit nervous about hanging onto their jobs. Even government workers who thought they had fairly secure positions might be on the chopping block. Long-time employees are experiencing job insecurity! Which is why ...
May 07, 2025•55 min•Ep. 980
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 - How can I find a financial coach to help me to quit living paycheck to paycheck? 2 - Should I put my saving...
May 05, 2025•46 min•Ep. 979
Time for a Friday Flight- our little sampling of the week’s 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: secondhand gifts, the #1 thing for financial well-being, how much you actually need in an emergency fund, thrifty trucks, the most a...
May 02, 2025•35 min•Ep. 978
The Feds are cracking down on defaulted student loans! According to the new US Education Secretary, it’s time for student borrowers with federal loans to begin making payments. The clock is ticking and May 5th is the date that nearly 2 million borrowers are going to be moved into repayment plans and collections will begin for loans that are in default with over 5 million borrowers at risk of garnished wages. This is a massive shakeup from what borrowers have experienced over the past 5 years, an...
Apr 30, 2025•1 hr•Ep. 977
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 - How should I strike the balance between paying off my student loans versus investing? 2 - Since I loan mone...
Apr 28, 2025•48 min•Ep. 976
Time for a Friday Flight- our little sampling of the week’s 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: student loan repayments resume, debt defaults, the rise of 84 month car notes, VIP investments, tapping money in a turbulent market,...
Apr 25, 2025•37 min•Ep. 975
Who doesn’t wish that they were currently listening to this episode while lounging at the beach, on a European adventure, or even completely off the grid hiking somewhere amazing?! Of course we all want to do that but c’mon, it’s too expensive! That is the unfortunate excuse that we give ourselves for why we don’t travel as much as we’d like, but our guest is here to set the record straight. Scott Keyes is the founder of Going, the travel platform that was formerly known as Scott’s Cheap Flights...
Apr 23, 2025•54 min•Ep. 974
Let’s dive into the week with some fresh listener questions we have lined up for you on this Special Tariffs Edition of Ask HTM (more on that further down). But 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! But as the title states, we’re going to...
Apr 21, 2025•58 min•Ep. 973
Time for a Friday Flight- our little sampling of the week’s 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: Elon stickers, panic pre-purchasing, used car prices ticking up, tariff surcharges, make used great again, untrustworthy TikTok tren...
Apr 18, 2025•34 min•Ep. 972
We’re joined by the Chief Economist at Redfin, Daryl Fairweather, so you know we’re talking about the current state of the real estate market today. But before she was knee-deep in housing data Daryl was the senior economist at Amazon, and before that she was a researcher at the Federal Reserve Bank of Boston which is when she was working with Freakonomics author Steven Levitt. Now, she has a new book that just came out last week, Hate The Game: Economic Cheat Codes for Life, Love, and Work. The...
Apr 16, 2025•50 min•Ep. 971
Let’s dive into 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 - Should I follow the investment portfolio modeled by Yale’s endowment fund? 2 - Are there DIY ways to scrub...
Apr 14, 2025•46 min•Ep. 970
Flexibility is a characteristic that will serve you well! This reminded Joel of his summer beach trip with his family to Tybee Island. Shortly after they left, there was a massive swarm of jellyfish that meant beachgoers couldn’t even get in the water. Lifeguards treated around 300 visitors for jellyfish stings in a single weekend. And while that would’ve been a bummer if you were wanting to spend some time in the ocean, it didn’t mean that you couldn’t have any fun in the sun. It just would’ve ...
Apr 11, 2025•48 min•Ep. 969
Whether it’s too late to get in on BTC, hackers targeting crypto, what a Federal Bitcoin Reserve means for the price of BTC… these are just a few of the topics we get into today with our guest, Natalie Brunell. When we occasionally talk about Bitcoin, it’s typically within the context of investing, and even then our approach is for it to be a relatively small portion of our overall portfolio. Could most folks do without it? Totally. Don't overly focus on what we see as a more alternative investm...
Apr 09, 2025•52 min•Ep. 968
Let’s dive into 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 - As newlyweds, how do we decide how much money we each get to spend as fun money? 2 - Should I further inve...
Apr 07, 2025•50 min•Ep. 967
Time for a Friday Flight- our little sampling of the week’s 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: thrift stores and radon tests, last minute tax tips, Liberation Day and tariffs, wage deflation, secondhand phones, dumb beautiful e...
Apr 04, 2025•35 min•Ep. 966
Imagine a scenario where you purchase pretty much whatever you want at the grocery store, you frequently go out to eat, and on top of that you always buy drinks for friends- no questions asked. That’s about what it would take to get food spending up to around 15% of average household income… but that sounds a bit insane! Most folks shop for sales, attempt to eat their leftovers, and on special occasions cover the check. But that spendthrift approach is exactly how a lot of Americans pay their ta...
Apr 02, 2025•50 min•Ep. 965
