Episodes

  • The Four Fundamental Rules of Investing
    Mar 13 2026

    On today's episode of Great Points, Matt talks about the four fundamental rules of investing and how to invest effectively over the long-term. With the vast amount of news and financial media inundating us daily, it's easy to get lost in the noise. Whether you are a new investor, have relatives who are just getting started, or just need a quick refresher, this episode is a great baseline to build on. The principles of investing are deceptively simple, but remembering these four rules will help you overcome common pitfalls that even professionals can succumb to in times of stress.

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    15 mins
  • How to use your 2025 tax return to plan for 2026
    Mar 11 2026

    There is very little you can do to at this point in March 2026 to manage your 2025 taxes. Pull all of your paperwork together, and file your return; it's all procedural and backward looking. However, there is a lot you can learn from your 2025 return.

    In today's episode, Matt talks about some of the key things to look at once you file your 2025 taxes, and some of the tools at your disposal to make tax season less painful in the future. From paycheck tax withholding, to estimated payments, to 401k contributions, and charitable gifts...there are a handful of different tools you can use to stay on top of your taxes in the coming year. With 15-20 minutes of planning, you can make a significant impact.

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    18 mins
  • The Patriots made the Super Bowl! Should I go?
    Jan 26 2026

    On today's special episode of Great Points, Matt reacts to the Patriots' big win yesterday. Now that the Pats are suddenly off to Santa Clara, CA for the Super Bowl...many New Englanders will make the snap decision to make the trip to watch live. Should you be one of them?

    Going to the Super Bowl is a once in a lifetime event for many, but is it worth the trade-offs? As with many things, there isn't one right answer, but there might be for you.

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    8 mins
  • Setting Financial Goals that Stick
    Jan 20 2026

    On today's episode of Great Points, Matt talks about setting financial goals and how you can make those goals a reality. There is value in big ambitious long-term goals, but how you handle medium and even short-term goals ultimately plays a significant role in attaining the big ones. Whether financial goals or otherwise, Matt offers some practical tips for turning "resolutions" into actions and ultimately results.

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    15 mins
  • I received a gift or inheritance, what should I do with it?
    Jan 7 2026

    On today's episode of Great Points, Matt runs through a scenario where a younger person receives a gift or an inheritance. As with any chunk of money, there are a variety of options what you might do with it. What would a $19k gift be worth in 40 years if I invest it? What if I pay off student loan or other debt? What if I spend it? There may not be one right answer, but thinking through the different scenarios can help you make the right choice for you.

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    15 mins
  • Financial Education Case Study with the O'Rourkes
    Nov 17 2025

    On today's episode of Great Points, Matt speaks with long-time friends Matthew and Natasha O'Rourke about their own financial journey and how they're teaching their kids about finances. From a start as self-proclaimed "F minus" financial students, Matthew and Natasha reflect on their rude awakening on entering adulthood, and how they are trying to teach their 16 and 13 year olds about money. As always, Matt Schroeder also has some great practical tips on how to introduce key money concepts. If you have dependent children, or if you are interested in financial education, this episode is a must listen.

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    46 mins
  • Medicare and Open Enrollment: Interview with Randall Gregory
    Oct 13 2025

    On today's episode of Great Points, Matt speaks with Randall Gregory, an independent benefits consultant at Core Benefits Group. As we enter into Open Enrollment season, they talk about the various terms related to Medicare enrollment and the different plans available before diving into what types of plans might be right for you. Confused by Part A, Medigap, Supplement, or Advantage plans? This episode is your one stop shop for deciding the right coverage for you.

    To learn more or consult with Randall, you can reach him at rgregory@mycoreinsurance.com

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    32 mins
  • What is the new "Trump account" and does it make sense for me?
    Sep 30 2025

    On today's episode, Matt explains the new "Trump Account" proposed as part of the One Big Beautiful Bill Act signed earlier this year. The new account type is set to be pre-filled with $1,000 for children born between 2025 and 2028. How much could that be worth in 65 years? What are the rules around the new account type and when might it make sense to add funds to the account as a parent? As always, the Personal Finance landscape is ever-changing. Listen in to learn more about what this change could mean for you.

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    18 mins