Our Team

Our Company Values

For those who are looking for financial advice, we realize the available options are many and deciding who to work with is a challenging problem. Listed below are our Company Values which we hope will give you a better understanding of how we operate.

  1. People – We believe that each person is innately valuable and worthy of respect and honor. We believe that relationships matter and that business is relational, top to bottom. People First, Money Second is a priority statement that places people and relationships ahead of financial matters.
  2. Integrity– We believe that integrity and truth matter. We believe we need to conduct our business in such a way that we are above reproach. We believe suitability and ethical practices come from placing a high value on other people and their needs before our own.
  3. Communication– We believe that communication with our client partners builds and maintains the trust that is necessary for business relationships to reach their full potential. We believe that our client partners deserve the type of communication that is frequent, timely, truthful, & relevant.
  4. Service– We believe that good service is practical and that great service is necessary for the pursuit of business excellence. We will pursue perfection and in so doing “catch a little excellence along the way.” (Vince Lombardi)

Brian O’Connor

Managing Partner

Brian O’Connor is the President and Chief Investment Officer of Sterling Oak Advisors. He has held this role since the successful launch of Sterling Oak Asset Management, Sterling Oak Partners and Sterling Oak Advisors in 2007.

Brian graduated from Northeastern University in 1986 with a Bachelor of Science in Economics and Finance.

Brian began his career in 1986 as an Investment Advisor for the Investment Banking firm Lehman Brothers in Boston.  In 1987 was named the youngest Vice President of in the firm’s 150 year history. After nine successful years at Lehman Brothers, Brian moved his practice to Oppenheimer & Company in 1993 and was named a Senior Vice President.

Subsequent to CIBC’s acquisition of Oppenheimer, Brian joined Morgan Stanley in 1998 as a Senior Vice President and advised on matters including Portfolio Management, Restricted Stock Risk Management and Monetization Strategies, as well as Retirement Income Planning. In 2000, Brian was recognized as Morgan Stanley’s top revenue producer in New England and a member of the firm’s Chairman’s Council.

In 2001 Brian was asked to open an office for Raymond James Financial Services in Boston advising Retail and Institutional Investors and as a Principal of the firm.  In 2007, with over 20 years of successful investment management experience, Brian launched Sterling Oak Partners, a Long/Short Equity Markets Limited Partnership.  This fund was named the Top Performing Fund in all categories by Barron’s Financial for February 2009 and the #1 performing Long/Short Equity Fund by Barclay Hedge for June 2009.

Brian has been featured in Forbes Magazine for his compelling individual equity market strategies and thematic approach to stock selection. Following the Great Recession, the magazine solicited Brian for three unique ideas, which were highlighted for their significant appreciation: Louisiana Pacific (up 100% between August 2009 and April 2010), Orient Express Hotels (up 88% between August 2009 and April 2010), and Allot Communications (up 250% between August 2009 and February 2011).

Ryan O’Connor


Ryan O’Connor is a Registered Investment Advisor who graduated from Quinnipiac University in 2020 with a bachelor’s degree in finance and a minor in accounting. He excels in analyzing financial data and making informed investment decisions. With a strong academic background and practical experience, Ryan brings a detail-oriented approach to his work. He possesses excellent analytical skills, allowing him to identify market trends and provide valuable insights to clients. Ryan’s dedication and expertise make him a reliable and driven professional in the finance industry.

Plan For Your Future

There is no one “best place” to put your retirement money because each individual and couple has unique requirements, different tolerances for risk, and need their money at different times. Likewise, there is no one place to keep your money that fits everyone for exactly the same reasons. Your unique circumstances must be taken into consideration if you seek to find the “most favorable place” for your retirement money. This is where we can be of service.

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