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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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First Quarter Investment Report – 2026

First Quarter Investment Report – 2026

April 14, 2026

Executive Summary The first quarter of 2026 was defined by a sharp shift in narrative. What began the ...

From Final Decree to Financial Freedom

From Final Decree to Financial Freedom

April 6, 2026

A step-by-step guide to the first 100 days after divorce by Lindsay Taylor, J.D., CFP® After months of...

Monthly Recap – March 2026

Monthly Recap – March 2026

April 2, 2026

March Observations Geopolitics Trigger Sharp Global Selloff Global markets declined significantly in M...

Independence Without Compromise

Independence Without Compromise

March 18, 2026

By Eric Kittner  Independence Has a Definition Problem, Especially at Scale  I don...

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