Episodes

  • 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
  • Swift, Kelce, and Financial Planning?
    Sep 15 2025

    On today's episode of Great Points, Matt reacts to recent news of Taylor Swift and Travis Kelce's engagement in the way he knows best: by relating it to financial planning. We're not talking about financial tactics of a celebrity wedding, but rather focusing on the things that can actually impact your life.

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    8 mins
  • Family and Divorce Law: Interview with Attorney Teresa La Vita
    Jun 25 2025

    On today's episode, Matt speaks with Family and Divorce Attorney, Teresa La Vita. Money is often a difficult topic, and even more so in family situations where many emotions are also at play. As a solo practitioner out of Danvers, MA, Teresa has seen all types of cases and offers valuable insight on a variety of issues related to family law. If you are getting married soon, should you consider a prenuptial agreement? What happens to a spouse's pension in a divorce? How are different cases settled and what options do you have? Teresa covers all of these topics and more in this blockbuster episode.

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    46 mins
  • Building Financial Foundations for Adulthood
    Jun 23 2025

    On today's episode of Great Points, Matt kicks off a series of conversations around building good financial foundations as an adult. He covers some basic definitions, and discusses the concepts that will be helpful for young adults to build good habits from the start. Financial wellness ultimately comes down to a combination of knowledge and good habits. This episode will help you or your adult child to establish both.

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    23 mins
  • Are you "tax scrambling" or tax planning?
    May 6 2025

    On today's episode of Great Points, Matt talks about doing your taxes. While the 2024 tax deadline was a few weeks ago, there are a handful of simple ways you can be better prepared for next year. Your tax preparer will thank you, but so will your future self for taking a few steps now to make tax season less stressful in the future. Furthermore, once you have your system down, there are numerous opportunities to engage in "tax planning" to minimize future taxes owed rather than just scrambling to get them done.

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    24 mins
  • Managing your emotions during Market Volatility
    Apr 28 2025

    On today's episode of Great Points, Matt talks through some key concepts and context that will help you manage negative emotions when there is market uncertainty. Taking inventory of your situation compared to many others can help you keep perspective. Furthermore, through Covid, recent world conflicts, and even in the more distant past, there are many examples of market resilience despite uncertainty.

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    20 mins
  • Using planning to reduce stress in periods of Market Volatility
    Apr 22 2025

    On today's episode, Matt offers some perspective during the current environment of high market volatility. While many investors look at their portfolio with fear when financial markets are highly variable, there are multiple things you can do to ease your stress. Having some cash for your near term expenses, diversifying your investments, and having a plan will help you weather times where there is market uncertainty.

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    12 mins