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Best friends Joel and Matt are the co-hosts of How to Money which is all about providing the knowledge & tools that normal folks need to thrive in areas like debt payoff, DIY investing, and crucial money tricks that will provide continuous help along your journey. We believe that access to unbiased and jargon-free personal finance guidance is more necessary than ever before. When you handle your money in a purposeful, thoughtful way that works for your lifestyle, you can really start living a rich life.

How to Money

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.

Can Millennials Count on Social Security? w/ Mike Piper #1127

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 credit card?
 
3 - Rising Insurance Premiums: What’s the deal with opting for higher deductibles for lower premiums?
 
4 - Social (in)Security: Why don’t lawmakers raise the income cap in order to help keep the trust fund solvent?
 
5 - PTO Cash-Out: Should I cash-out my paid time off to pay off our house sooner, or actually kick back a little more?
 
 
 
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 Soft Static by Inner Voice! 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.

Ask HTM - Free Fidelity Funds, Credit Card Maxxing, & Debating a PTO Cash-Out #1126

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 have the cash on hand to build an Accessory Dwelling Unit (ADU), but should I use a construction loan instead?
 
4 - Should I stick $6,500 into a Roth IRA, a Health Savings Account, or a 457b?
 
5 - Listener win: reaching out directly to a company resulted in cash in my mailbox!
 
 
 
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.

Ask HTM - Inflating the 25x Rule, Online Car Refinancing, & Affordable ADUs (Bestie Ep) #1125

“The Budgetnista” needs no introduction, but here’s a quick one anyways: Tiffany Aliche has helped millions of people change the trajectory of their finances through her books, courses, and podcasts. What I especially love about Tiffany is that she’s a teacher at heart which is something shaped by a decade in the classroom and a master’s degree in education. Her passion for helping people truly thrive with money is contagious. It’s been 7 years since we’ve had Tiffany on the podcast so listen as we discuss a range of topics from practical approaches to budgeting, to dealing with financial shame and anxiety.
 
 • Creative, age appropriate ways to teach young kids about money
 • Financial choices have consequences, good or bad
 • Shame shields solutions
 • Your money will never do more than what your mindset will allow
 • Budgets exist to say “Yes…”
 • Knowing your noodle budget
 • Financial wholeness
 • Real luxury is living without financial worry
 • Money anxiety when you have enough
 • … and additional topics!
 
Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
 
 The Budgetnista: • Head to 
GetGoodWithMoney.com • to check out Tiffany’s book!
 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.

The Blueprint to Financial Wholeness w/ Tiffany Aliche #1124

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 FIRE: How are we doing based on how much we’ve got in our state retirement accounts?
 
2 - Savings Bonds: What do I do with these 30 year old savings bonds that I was gifted back in the 90s!?
 
3 - Frugal or Cheap: Is it worth spending 4 hours disputing a $3.60 incorrect charge on a medical bill?
 
4 - S&P 500: After recently wising up and switching to fully invest in the S&P, how do I eventually rebalance before retirement?
 
5 - Appliance Land: Refrigerator died so what should we keep in mind as we buy our new one?
 
 
 
Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
 
 Coast FI: • 
Not FIRE, But Not Retirement. Something in Between. 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 Blonde Fat Ale (CORRECTION: Fatale… I’m guessing bc of the ABV? But it really looks like Fat Ale on the can) by Backpocket Brewing – thanks Clint for sending this one along to us! 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.

Ask HTM - 4 Hours to Dispute $3.16, All-In on the S&P 500, and Hitting Coast FIRE #1123

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:
 
 Best affordable eyeglasses Stellar staycations Avoiding travel fuel surcharges Recession reminder Dr. Doom sounds reasonable! Pay cut gut punch Where you work matters Nursing your way to middle class (Don’t) Stop contributing to your 401k Sam’s • , 
Netflix • , and the 
postal service getting pricey Devilish destination fees EV & hybrid searches spike 
 
 
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.

Friday Flight - Stellar Staycations, Devilish Destination Fees, & Pay Cut Gut Punch #1122

You might expect someone who experienced homelessness as a kid to grow up angry at the financial system. Instead, John Hope Bryant set out to understand it and help more people succeed within it. Our guest today believes financial literacy isn’t just helpful but foundational to economic opportunity and even human dignity. John is the founder, chairman, and CEO of Operation HOPE, one of the nation’s leading organizations focused on financial literacy, credit access, and economic empowerment. Today, we’re talking about his personal story, economic mobility, entrepreneurship, and what it really takes to build a financial system that works for everyone. We cover:
 
 • The ‘third reconstruction’
 • Doing well and doing good
 • Improving over burning our current system
 • How our economy is driven by consumer spending
 • AI upskilling and its impact on jobs
 • Capitalism isn’t a blue vs red political choice
 • Ladders of economic mobility
 • Incentivizing corporations to help those in need
 • The ‘American bet’ and what he thinks will give you a good shot at success
 • And plenty more!
 
Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
 
 John Hope Bryant: • Check out 
Operation Hope • , John’s non-profit that works to expand economic opportunity via free enterprise, as well as his latest book, 
Capitalism For All: Inclusive Economics and the Future-Proofing of America • .
 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.

Capitalism for ALL: Making the System Work for Everyone w/ John Hope Bryant #1121

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 - Marriage goals: Now that we have more cash coming in, should we invest more or have a wedding?
 
2 - Skipping life insurance: Why shouldn’t I just forego term life if I can claim social security survivor benefits?
 
3 - DCFSA: Is it legal for my partner to claim our new daughter in order to contribute more to a dependent care flexible spending account?
 
4 - New cars: First-time mama asking what the best rides are with a baby in tow?
 
5 - $100,000: What should we do with an inheritance if we have a serious medical condition but also have investing goals?
 
 
 
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 Wonder Struck by Singlespeed Brewing – thanks Clint for sending this one along to us! 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.

Ask HTM - Marriage Goals Over Investing, SS Survivor Benefits at Age 30, & Best Cars for New Mamas #1120

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:
 
 Tooth fairy inflation WTD with Long Airport Lines • (
Qsensor • )
 Rent now pay later Accidental landlords I regret buying a house Treasury taking over student loans Personal loans are popping Blundering credit bureaus Bad credit = expensive home owners policy Plasma paydays • (
Plasma Pay Calculator • )
 Burden of healthcare 
 
 
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.

Friday Flight - Long Airport Lines, Rent In Installments, & Plasma Payday! #1119

This show exists to help you make smart decisions with your money. But if we’re being honest, How To Money might not be as necessary if the financial system weren’t so confusing in the first place. For a lot of people, navigating modern money realities feels like swimming in shark-infested waters with high stakes, unclear rules, and the potential for costly mistakes at every turn. Our guest today is Professor John Campbell, author of the book Fixed: Why Personal Finance is Broken and How to Make It Work for Everyone. John is an economics professor at Harvard, who believes the financial system has a responsibility to serve ordinary people with products they can understand, afford, and safely use. Today, we’re talking about what’s broken in personal finance and what real solutions could look like. We specifically discuss:
 
 • Disparities in financial products
 • Complexity in personal finance
 • Problematic financial products
 • Human behavior when it comes to money decisions
 • Dangers of loyalty
 • Limitations of individual responsibility
 • What a rebuilt financial system could look like
 • Balancing protection and freedom
 • … and additional topics!
 
Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
 
 John Campbell: • Be sure and check out 
John’s new book, Fixed • .
 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.

Why Money Decisions Feel Rigged w/ John Campbell #1118

Today’s interview completely revolves around technology and we’re excited to have Kevin Roose joining us today. Kevin is an award-winning tech columnist for the New York Times, and a Times bestselling author of three books: Futureproof, Young Money, and The Unlikely Disciple. He is the host of the “Rabbit Hole” podcast, and writes and speaks regularly on all topics related to our modern age including automation and AI, social media, cybersecurity, and digital wellness. But today, we are narrowing his focus to discussing some of the different ways that we can ensure your career can continue to grow as AI is taking over many different areas of our lives. Plus we’re going to do a deep dive into crypto and how you should be thinking about it today.
 
 
 
During this episode we enjoyed an Analog Life by Good Word 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.

Futureproofing Your Career & Crypto Advice for Noobs with Kevin Roose #529

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