Sterling Oak Advisors
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About
Sterling Oak provides discretionary investment management, financial planning, and retirement plan advisory services to high‑net‑worth individuals and retirement plans. The firm acts as a fiduciary for retirement accounts and frames engagements around ongoing personal contact with clients.
Portfolios are built primarily from dividend‑paying and dividend‑growing blue‑chip stocks and low‑cost ETFs, with a long‑term orientation while allowing shorter‑term trades for rebalancing, tax harvesting, or changing client needs. Sterling Oak employs macroeconomic, fundamental, technical and trend analysis, conducts ongoing monitoring with formal reviews at least annually, and may retain legacy holdings for tax or portfolio‑fit reasons.
The brochure highlights two features that distinguish Sterling Oak from many peers: it offers performance‑based fee arrangements to “Qualified Clients” subject to high‑water mark calculations, and the firm’s principal is a licensed insurance professional who may receive commission‑based compensation for insurance sales. The firm discloses that insurance activities are separate from advisory services and notes the potential conflict of interest this creates.
Client services
Expertise
Fee options
Up to 2.00% annually, negotiable based on complexity, asset level, and overall relationship
Insurance commissions earned by Mr. O’Connor as a licensed insurance professional, separate and in addition to advisory fees
Financial planning services at $400/hour, negotiable
Performance-based fees up to 20% of gains for Qualified Clients (minimum $1,000,000 under management or $2,100,000 net worth), subject to high-water mark calculation
Account minimum: $500,000 (can be waived at sole discretion of Advisor) Fee-only: Investment management fees up to 2.00% annually, financial planning hourly fee of $400, retirement plan advisory fees up to 2.00% annually
Main office
77 Exeter Street, Suite 1603
Boston MA 02116
Advisors at this office
2
Most active in
Massachusetts
Also doing business as
O'connor, Brian Thomas · Sterling Oak Advisors · Sterling Oak Asset Management, LLC
Disclosures
Exclamation point means they have disclosures of this type. Check mark means no disclosures of this type were found.
Business activities & affiliations
Is active or affiliated with:
Insurance agent
They sell insurance products and may earn commissions on those sales.
Is not active or affiliated with:
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Broker-dealer / trader
They provide brokerage services and may earn transaction-based compensation in addition to advisory fees.
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Bank
They're affiliated with a bank that may offer its own financial products and services.
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Trust company
They provide trust and estate administration services, typically for separate fees.
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Fund sponsor
They manage or sponsor investment funds and may earn management or performance-based fees if clients invest in them.
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Accountant / CPA / tax prep
They offer tax and accounting services, typically for separate fees.
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Lawyer
They provide legal services, typically billed separately.
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Real estate agent
They facilitate real estate transactions and may earn commissions.
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Other specialized services
They may provide services such as pension consulting or municipal advisory work, typically for separate fees.
Forms ADV
Quick links
Advisors at this firm
Ryan O
Series 65
Boston, MA
Sterling Oak Advisors
Ryan O'Connor is a financial advisor at Sterling Oak Advisors in Boston, MA, holding a Series 65 designation with five years of industry experience. He has worked at Sterling Oak Wealth Advisors since 2020 and previously held roles at Eli's on Whitney, Quinnipiac University, and The Cottage Wellesley. Sterling Oak Advisors provides discretionary investment management, financial planning, and retirement plan advisory services primarily to high-net-worth individuals and retirement plans. The firm employs a long-term investment approach focused on dividend-paying blue-chip stocks and low-cost ETFs, combined with various analytical methods and ongoing client engagement.
Brian O
Series 63, Series 66
Boston, MA
Sterling Oak Advisors
Brian O'Connor is a financial advisor at Sterling Oak Advisors in Boston, MA, with 17 years of industry experience. He holds Series 63 and Series 66 licenses and has been with Sterling Oak Advisors since 2009. O'Connor is also a partner and equity analyst at Sterling Oak Asset Management, a small investment management company specializing in equity portfolio management. Sterling Oak Advisors serves primarily high-net-worth individuals and retirement plans, offering discretionary portfolio management, financial planning, and retirement-plan advisory services. The firm focuses on concentrated portfolios of dividend-paying and dividend-growing blue-chip equities and low-cost ETFs, using a long-term investment approach informed by various analytical methods.
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