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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

Some families have lived on the same plot of land for generations… what’s more Americana than passing down the family farm to the next generation?! But the US also has a history of moving towards opportunity – the settling of the west and the gold rush in California, returning veterans moved at higher rates in the aftermath of WW2, and then more recently the pandemic led to an uptick in people reconsidering their living situation. BUT, what if the next great place to move to is an island in the Caribbean Sea? Not just because it’s beautiful, but because it offers certain tax perks that are unavailable anywhere else. Rachel Farris, CPA and tax strategist, joins the show to share the unique tax benefits of moving to Puerto Rico, particularly under Act 60, which offers significant savings for individuals and businesses. We discuss the implications of relocating including cultural adjustments of expat life, cost of living, the eligibility requirements for tax benefits, the appeal for W2 workers and entrepreneurs alike, the community of expats on the island, and much more!
 
 
 
Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
 
 • To learn more about the Act 60 Tax Strategy, head to 
MaximizeWealth.com • and to reach out to Rachel directly, head to 
RachelFarrisCPA.com • Knowing your ‘money gear’ is a crucial part of your personal finance journey. 
Start here. • 
 • Sign up for the weekly 
HTM newsletter • . It’s fun, free, & practical.
 • Find a thriving community of fellow money nerds by joining the 
HTM Facebook group! • Massively reduce your 
cell phone bill • each month by switching to a discount provider like Mint Mobile.
 
 
 
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.

Move to Puerto Rico to Axe Taxes w/ Rachel Farris #1028

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 pay for Acorns to help me invest and what about real estate investing?
 
2 - How can I plan for the Social Security Trust Fund running out earlier than expected?
 
3 - Does it make sense to go with the financial advisor that my sister has recently hired?
 
4 - How long does a cash gift need to season in order for it to boost my credit score?
 
5 - FHA loan with a mortgage insurance premium vs waiting and saving up more?
 
 
 
Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
 
 • Knowing your ‘money gear’ is a crucial part of your personal finance journey. 
Start here. • 
 • Sign up for the weekly 
HTM newsletter • . It’s fun, free, & practical.
 • Join a thriving community of fellow money in the 
HTM Facebook group. • Massively reduce your 
cell phone bill • each month by switching to a discount provider like Mint Mobile.
 
 
 
During this episode we enjoyed a Dawn Patroller by Hana Koi 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.

Ask HTM - Acorns to Jumpstart Investing, Seasoning a Cash Gift, & Social Security Running Out #1027

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: autopay fees, school supplies and sloppy joes, Aldi item of the week, a recipe for mediocrity, digital nomad fatigue, treat culture, crowdfunded real estate investing flop, adjustable rates mortgage applications on the rise, retired renters, and lease purchase agreement attraction.
 
 
 
Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
 
 • Knowing your ‘money gear’ is a crucial part of your personal finance journey. 
Start here. • 
 • Sign up for the weekly 
HTM newsletter • . It’s fun, free, & practical.
 • Join a thriving community of fellow money in the 
HTM Facebook group. • Massively reduce your 
cell phone bill • each month by switching to a discount provider like Mint Mobile.
 
 
 
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. Have an awesome weekend!
 
 
 
Best friends out!

See omnystudio.com/listener for privacy information.

Friday Flight - Digital Nomad Fatigue, Treat Culture, & Retired Renters #1026

The pace at which technology advances is straight up disorienting in our current age. So much so, that it’s likely digital natives and even our kids who can figure out new tech gadgets faster than we can! For those of you who are using apps and AI regularly but not feeling like a pro – you’re worried about your privacy, passwords, & data as you navigate the online world – this episode is for you. Nathan Bartram founded TheNewOil.org in 2018 to equip everyday folks with the resources, websites, and alternatives they need to navigate the online world with confidence. We discuss why to even be concerned about privacy at all, favorite password managers, why Nathan detests Amazon, basic steps that everyone should take, and plenty more!
 
 
 
Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
 
 • Knowing your ‘money gear’ is a crucial part of your personal finance journey. 
Start here. • 
 • Sign up for the weekly 
HTM newsletter • . It’s fun, free, & practical.
 • Find a thriving community of fellow money nerds by joining the 
HTM Facebook group! • Massively reduce your 
cell phone bill • each month by switching to a discount provider like Mint Mobile.
 
 
 
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.

Defend Your Digital Life w/ Nathan Bartram #1025

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 hard should I push to be a landlord if I’m able to buy our next house without selling the current house?
 
2 - Should I dial back my investing for the kids’ college given the recent market volatility?
 
3 - What should I do with a recent inheritance of six figures?
 
4 - My daughter is going to Europe for a high school trip- what’s the best way for her to spend while abroad?
 
5 - What’s the most affordable way for my 11 year old to text and call, without internet or social media access?
 
 
 
Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
 
 • Knowing your ‘money gear’ is a crucial part of your personal finance journey. 
Start here. • 
 • Sign up for the weekly 
HTM newsletter • . It’s fun, free, & practical.
 • Join a thriving community of fellow money in the 
HTM Facebook group. • Massively reduce your 
cell phone bill • each month by switching to a discount provider like Mint Mobile.
 
 
 
During this episode we enjoyed a Cordial Saison by Burial! 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 - Spending Cash Windfalls, Retirement Investing vs College Savings, & So You Think You Can Landlord?! #1024

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: ridic Peloton fee, housing boom bust, where home prices go from here, realtors slowly fading away, medical debt to be aware of, contagious financial habits, crypto and private equity in the 401k, crypto mortgage applications, AI-induced outrage, employer perceptions and success, hybrid workdays are out, & infinite workdays are in.
 
 
 
Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
 
 • Knowing your ‘money gear’ is a crucial part of your personal finance journey. 
Start here. • 
 • Sign up for the weekly 
HTM newsletter • . It’s fun, free, & practical.
 • Join a thriving community of fellow money in the 
HTM Facebook group. • Massively reduce your 
cell phone bill • each month by switching to a discount provider like Mint Mobile.
 
 
 
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. Have an awesome weekend!
 
 
 
Best friends out!

See omnystudio.com/listener for privacy information.

Friday Flight - Housing Boom Busts, AI-Induced Outrage, & Infinite Workdays #1023

We’re glad to have friend of the show and newly married, Nick Maggiulli back on the podcast! He’s been given the nickname Nicky Numbers because he has a special gift for conveying wonky money information in a straightforward and digestible way. We’ve been fans of his blog, Of Dollars & Data, for years now. This episode is for everyone out there who wants to grow their net worth while finding more spending freedom which is our focus today. We discuss plenty of great issues like investing as a couple, prenups, what level of net worth means Nick considers to be middle class, how a Jay-Z lyric provides spending freedom, Nick’s favorite flavor of FIRE, biggest reasons individuals fall down the wealth ladder, what skills it takes to get you to the different levels of the wealth ladder, and much more!
 
 
 
Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
 
 • Knowing your ‘money gear’ is a crucial part of your personal finance journey. 
Start here. • 
 • Sign up for the weekly 
HTM newsletter • . It’s fun, free, & practical.
 • Find a thriving community of fellow money nerds by joining the 
HTM Facebook group! • Massively reduce your 
cell phone bill • each month by switching to a discount provider like Mint Mobile.
 • Don’t be cheap and forego getting a life insurance policy. 
Compare rates with Policygenius. 
 
 
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.

Moving Up The Wealth Ladder w/ Nick Maggiulli #1022

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 do I calculate whether it’s worth it to jump back into the work force?
 
2 - Should I take out a HELOC on my home in order to pay off other debts?
 
3 - Doesn’t it make sense to take Social Security early, even if the payout is smaller?
 
4 - Is the free life insurance offered to me through my local credit union legit?
 
5 - Can I utilize a “goodwill letter” in order to ask my student loan service to remove a late payment?
 
 
 
Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
 
 • Knowing your ‘money gear’ is a crucial part of your personal finance journey. 
Start here. • 
 • Sign up for the weekly 
HTM newsletter • . It’s fun, free, & practical.
 • Join a thriving community of fellow money in the 
HTM Facebook group. • Massively reduce your 
cell phone bill • each month by switching to a discount provider like Mint Mobile.
 
 
 
During this episode we enjoyed a Summer Lihing Mango by Lanikai 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.

Ask HTM - Jumping Back Into the Workforce, HELOC Cash Grab, and Free Life Insurance Gotchas #1021

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: a 100 year old’s purchasing power, passage of the One Big Beautiful Bill Act, boosting SALT deductions, waning EV tax credits, bad RAPs, student loan advice on TikTok, $80 popcorn buckets, Target price match murder, rising Amazon prices, premium points credit cards, and what to do instead!
 
 
 
Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
 
 • Knowing your ‘money gear’ is a crucial part of your personal finance journey. 
Start here. • 
 • Sign up for the weekly 
HTM newsletter • . It’s fun, free, & practical.
 • Join a thriving community of fellow money in the 
HTM Facebook group. • Massively reduce your 
cell phone bill • each month by switching to a discount provider like Mint Mobile.
 
 
 
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. Have an awesome weekend!
 
 
 
Best friends out!

See omnystudio.com/listener for privacy information.

Friday Flight - Bad RAPs, Price Match Murder, & Premium Points Credit Cards #1020

Finally… a freshie! We’re done with bestie episodes for the summer and are excited to sit down and fill everyone in on what we’ve been up to for the past six weeks. We recount how lucky and blessed we are to be able to take a break from our 9-5, share some of our favorite ways we saved money while traveling (somehow in our first episode back we managed to discuss Aldi and Costco for those playing HTM bingo at home), and we only begin to touch on some of the lessons and takeaways from our time off. Active volcanoes, beef tongue, regenerative braking, EVs, lunchables, and padcrashing all make an appearance!
 
 
 
Thank you for hanging in there and we are excited to get back to our regularly programmed money earning-saving-spending-investing content. Y’all are the best listeners!
 
 
 
Want more How To Money in your life? Here are some additional ways to get ahead with your personal finances:
 
 • Knowing your ‘money gear’ is a crucial part of your personal finance journey. 
Start here. • 
 • Sign up for the weekly 
HTM newsletter • . It’s fun, free, & practical.
 • Find a thriving community of fellow money nerds by joining the 
HTM Facebook group! • Massively reduce your 
cell phone bill • each month by switching to a discount provider like Mint Mobile.
 • Don’t be cheap and forego getting a life insurance policy. 
Compare rates with Policygenius. 
 
 
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.

WE BACK - Frugal Fun, Travel Tips, & Sabbatical Takeaways #1019

Health Savings Accounts aren’t just for paying your medical bills- when used properly, they are pure retirement gold! If you have a qualifying healthcare plan and aren’t taking advantage of an HSA, you’re missing out on massive amounts of money that you could be socking away. This is because an HSA is the most tax advantaged retirement account that exists, maybe even dethroning the Roth IRA as our favorite retirement account! Have a listen as to why we think you should seriously consider opening a Health Savings Account.

If you want to learn more, head over to Lively as they have lots of helpful information and answers to your eligibility questions. It's completely free for individuals and families and they make it easy to open your HSA to start investing today.

During this episode we enjoyed a Mirror Universe by Fair State Brewing Cooperative- another big thanks to Riley in Minnesota for donating this beer to the show! And if you enjoyed this episode, be sure to subscribe and give us a quick review in Apple Podcasts or wherever you get your podcasts- we’d love to hear from you.

Best friends out!

 
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See omnystudio.com/listener for privacy information.

Are HSAs the Best Retirement Account? #105

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