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Herbert Elwin Montgomery III

Advisor at The Montgomery Financial Group, Inc. — Orleans, MA

Updated today

Credentials

CFP®, Series 63

Experience

20 years

Location

Orleans, MA 02653-3240

The Montgomery Financial Group, Inc. logo

The Montgomery Financial Group, Inc.

Supported

Total advisors

2

Clients per advisor

124 Very High

Avg AUM per client

$195,502 Very Low

HNW client ratio

3% Very Low

About

Herbert Montgomery is a CFP® with 19 years of industry experience and has been with The Montgomery Financial Group, Inc. since 2006. He holds a Series 63 license and is a 50% owner of Fitz-Mont Environmental Solutions, Inc., a company that provides environmentally sound electricity, water, waste, and lighting solutions. The Montgomery Financial Group serves individual and high-net-worth clients as well as small business owners, offering discretionary investment management, financial planning, and a range of non-investment advisory services such as tax preparation and bookkeeping. The firm employs a Modern Portfolio Theory framework focusing on cost-efficient index funds and ETFs, with a significant portion of its efforts dedicated to non-investment services for individuals and small businesses.

Client services

Based on The Montgomery Financial Group, Inc.

Financial planning Portfolio management Hourly investment consultations

Expertise

Based on The Montgomery Financial Group, Inc.

General retirement planning Social Security optimization General tax planning Retirement plans for business owners (SEP, solo 401k)

Occupation focus

Based on The Montgomery Financial Group, Inc.

Self-Employed Founder/Business Owner

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Fee options

Percentage

0.55% annually, assessed monthly in arrears

Project-based

Typically $200 per hour, billed in 15-minute increments for financial planning and investment consultation services

Other

Fee-only: Financial planning and investment consultation services at $200 per hour, billed in 15-minute increments; written financial plans estimated between $650 and $2,500

Location

Orleans, MA

195 Route 6 A, Suite 8

Orleans MA 02653-3240

Advisors at this office

2

Most active in

Massachusetts

Work history

20 years of industry experience

The Montgomery Financial Group, Inc.

2006 - Present • 20 years

Orleans, MA

Disclosures

Exclamation point means they have disclosures of this type. Check mark means no disclosures of this type were found.

Business activities & affiliations

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Carey R

Series 63, Series 66

Brewster, MA

Carey S. Roebuck Financial Services, LLC

Carey Roebuck is the sole advisor at Carey S. Roebuck Financial Services, LLC, an independent firm based in Brewster, MA. He holds Series 63 and Series 66 licenses and has 18 years of industry experience. Roebuck has operated his own advisory firm since 2015. The firm provides portfolio management and investment advice to individuals, corporations, businesses, and high-net-worth clients, managing approximately $5.54 million in assets across 36 discretionary accounts. Its investment approach combines charting, fundamental, technical, and cyclical analysis, utilizing strategies such as long- and short-term purchases, active trading, option writing, and investments in ETFs and ETNs.

Active portfolio management Options & derivatives strategies
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Jeremy B

Series 63, Series 65

Yarmouth Port, MA

Bogle Wealth Management, LLC

Jeremy Bogle is the principal of Bogle Wealth Management, LLC, an independent firm based in Yarmouth Port, MA. He holds Series 63 and Series 65 licenses and has 12 years of industry experience, operating his own advisory practice since 2010. Bogle Wealth Management provides investment management and advisory services primarily to high-net-worth individuals, families, trusts, and estates, focusing on customized portfolios using ETFs, individual stocks, and bonds. The firm manages approximately $20.5 million on a non-discretionary, fee-only basis and integrates tax and accounting services through an affiliated Enrolled Agent.

Passive / index investing Tax-loss harvesting
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Luke K

Series 65

Chatham, MA

Kearing Capital LLC

Luke Kearing is the sole advisor at Kearing Capital LLC, holding a Series 65 credential with one year of industry experience. Prior to founding the firm, he worked for five years at Chatham Bars Inn and has a Harvard degree earned in 2026. Kearing Capital provides discretionary separately managed account services focused on a specialized equity index options strategy. The firm serves a range of clients including individuals, trusts, corporations, and family offices, using quantitative and options-pricing analysis to manage risk and implement strategies primarily on broad equity indices.

Options & derivatives strategies Factor investing / smart beta Young Professionals

Vincent R

CFP®

South Dennis, MA

Pier 42 Advisors

At Pier 42 Advisors, we understand that successful wealth planning is about more than just plugging numbers into a formula and generating a generic plan. Instead, it’s about taking the time to understand your specific needs and the “why” behind your motivations. Our goal is to serve as your trusted partner by working alongside you to incorporate your values, emotions, concerns and motivations into a tailored financial plan to guide your actions. By focusing primarily on building relationships, trust and understanding, we are better able to help you achieve your version of financial success, whatever that may be.

General retirement planning Retirement income strategy Wealth management Founder/Business Owner Baby Boomers (Born 1946-1964)
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Joseph W

CFA®

East Dennis, MA

J. Williams Wealth Management, LLC

Joseph Williams is a CFA® charterholder with 21 years of industry experience. He is the sole advisor at J. Williams Wealth Management, LLC, an independent firm based in East Dennis, MA. In addition to his advisory work, he is a partner in a home-based bed and breakfast business, Mermaid Cottage, where he participates in hosting and managing the business. J. Williams Wealth Management provides portfolio management and investment advice to individual clients, employing a tactical asset-allocation strategy that adjusts equity and bond allocations based on market cycles. The firm consolidates clients’ accounts into a single portfolio and uses a scoring system to evaluate investments, offering both discretionary and non-discretionary services with a focus on a small client base.

Active portfolio management
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Harry B

CFA®, Series 63, Series 65

Dennis, MA

Harry S. Bower, LLC

Harry Bower is the sole advisor at Harry S. Bower, LLC, an independent firm based in Dennis, MA. He holds the CFA® designation along with Series 63 and Series 65 licenses and has 17 years of industry experience. He has led his firm since 2006. Harry S. Bower, LLC provides non-discretionary investment consulting to individuals, trusts, estates, and charitable organizations, focusing on portfolio construction, equity market conditions, and asset allocation. The firm emphasizes large-cap domestic and international equities and investment-grade fixed income, and advises on complex strategies such as options and derivatives without discretionary trading authority.

Active portfolio management Options & derivatives strategies
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