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Oliver Cragan

Advisor

CFP®

Oliver has been with The Berry Group since 2013, serving clients in a variety of capacities while bringing strong initiative and commitment to his role as an Advisor. He provides financial advice and investment management to clients, in addition to assisting with daily operational tasks. Oliver became a CERTIFIED FINANCIAL PLANNER® professional in October of 2020. He enjoys challenging himself daily to learn more about the ever-changing world of financial planning.

After graduating from The College of the Holy Cross in 2012, Oliver held a variety of jobs around the country, including serving as a ranch foreman in Wyoming, repairing churches as a steeplejack throughout New England, and exploring the worlds of advertising and software sales in Greater Boston.

Oliver resides in Princeton, MA with his wife and two children. They travel as far and often as possible, but frequent the Adirondack Mountains where they enjoy fishing and hiking.

  • CERTIFIED FINANCIAL PLANNER®

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Monthly Recap – July 2026

Monthly Recap – July 2026

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July Observations Markets Catch a Summer Downdraft Markets faced pressure in July after a recent run o...

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Why Most UHNW Families Have the Right Trusts and the Wrong Mix

Why Most UHNW Families Have the Right Trusts and the Wrong Mix

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By Benjamin Trujillo and Elizabeth Sheehan  For most ultra-high net worth (UHNW) families, the questio...

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Creating a Purposeful and Purpose-filled Philanthropy Practice | Part 2 of 3 As you consider the ways ...

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