Episódios

  • Move to Puerto Rico to Axe Taxes w/ Rachel Farris #1028
    Aug 27 2025

    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.

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    52 minutos
  • Ask HTM - Acorns to Jumpstart Investing, Seasoning a Cash Gift, & Social Security Running Out #1027
    Aug 25 2025

    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.

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    53 minutos
  • Friday Flight - Digital Nomad Fatigue, Treat Culture, & Retired Renters #1026
    Aug 22 2025

    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.

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    38 minutos
  • Defend Your Digital Life w/ Nathan Bartram #1025
    Aug 20 2025

    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.

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    57 minutos
  • Ask HTM - Spending Cash Windfalls, Retirement Investing vs College Savings, & So You Think You Can Landlord?! #1024
    Aug 18 2025

    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.

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    58 minutos
  • Friday Flight - Housing Boom Busts, AI-Induced Outrage, & Infinite Workdays #1023
    Aug 15 2025

    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.

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    37 minutos
  • Moving Up The Wealth Ladder w/ Nick Maggiulli #1022
    Aug 13 2025

    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.

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    50 minutos
  • Ask HTM - Jumping Back Into the Workforce, HELOC Cash Grab, and Free Life Insurance Gotchas #1021
    Aug 11 2025

    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.

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    51 minutos