View in portrait for best experience

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®

A WEALTH OF INFORMATION

Dive into the latest insights from our expert team with our personal touch.

Monthly Recap – December 2025

Monthly Recap – December 2025

January 8, 2026

December Observations Subdued Month Brings the End to a Solid Year U.S. equity markets closed a robust...

The Derivative Income Dilemma: Balancing Yield, Complexity, and Risk

The Derivative Income Dilemma: Balancing Yield, Complexity, and Risk

January 6, 2026

by John Costello, Investment Risk Analyst *Readers unfamiliar with options terminology may wish to con...

Is your business worth what you think it is? Understanding business value drivers

Is your business worth what you think it is? Understanding business value drivers

January 5, 2026

By Michael Torney, J.D., CFP®, LL.M., CEPA Business value drivers are the underlying factors that infl...

Moneta Tops Financial Planning’s Ranking of 2025 RIA Leaders 

Moneta Tops Financial Planning’s Ranking of 2025 RIA Leaders 

December 8, 2025

We’re proud to share that Financial Planning ranked Moneta No. 1 in its 2025 ...

VIEW ALL ARTICLES

Let’s make every moment count together…