Top tax strategies for small businesses financial advisors in Worcester, MA

The right financial advisor for you depends on how you weigh location, expertise, experience, the clients they typically serve, and how they work with you.

If you run a small business, managing your taxes efficiently can free up cash flow and reduce stress during tax season. Without a focused approach, you might miss deductions or credits that could lower your tax bill.

  • Surtax awareness. Ask how they navigate Massachusetts' 'Millionaire's tax' that adds extra surtax on high incomes.
  • Entity structure impact. Confirm how they evaluate your business type to optimize tax benefits and liabilities.
  • Expense categorization. Look for advisors who help you track and classify expenses correctly to maximize deductions.
  • Tax timing strategies. Inquire about their approach to timing income and expenses to smooth tax obligations across years.

Here are top matches to get you started. Review each profile to compare experience, credentials, and approach.

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Michael H

ChFC®, Series 63, Series 65

Worcester, MA

Cutler Capital Management

Michael Hogan is a ChFC® credentialed financial advisor with 38 years of industry experience. He has worked at Cutler Capital Management since 2019 and previously held roles at Wellesley Investment Advisors, Foreside Fund Services, and had a brief period of unemployment. Outside of his advisory work, he serves as secretary on the board of Fashion for Friends, a nonprofit focused on mental health awareness and suicide prevention supporting women with breast cancer. Cutler Capital Management is a SEC-registered investment adviser serving individuals, trusts, retirement plans, and pooled private investment funds. The firm specializes in convertible securities, financial-sector equities, and publicly traded REITs, employing both fundamental and technical analysis and using various hedging and leverage techniques tailored to client objectives and risk tolerance.

Concentrated stock management Real estate investing Active portfolio management Options & derivatives strategies Private / alternative investments
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Robert O

Series 63, Series 65

Worcester, MA

Capitol Securities Management, Inc.

Robert Oftring is a financial advisor with Capitol Securities Management, Inc. in Worcester, MA, holding Series 63 and Series 65 credentials and 44 years of industry experience. He has been with Capitol Securities since 2009. Outside of his advisory role, he is a partner in a real estate development business involving the purchase, development, and management of two buildings. Capitol Securities Management serves individual investors, high-net-worth clients, institutions, retirement plans, trusts, and small businesses, offering portfolio management, financial planning, and consulting through a combination of broker-dealer and registered investment adviser services. The firm delivers investment advice via IAR-managed programs, separately managed accounts, model portfolios, and third-party money managers.

Founder/Business Owner Retired Executive
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Brett K

Series 66

Worcester, MA

Capital Analysts

Brett Kubiak is a financial advisor at Capital Analysts with four years of industry experience and a Series 66 designation. Prior to joining Capital Analysts and Lincoln Investment in 2023, he worked at Cambridge Investment Research and Cetera Advisor Networks. In addition to his advisory role, Kubiak has served with the Worcester Police Department since 2016. Capital Analysts serves a diverse client base including individual and high-net-worth investors, trusts, foundations, businesses, and charitable organizations. The firm offers portfolio management, custom and model portfolios, third-party manager access, and retirement-plan advice through a network of independent advisors and its in-house investment management team.

Tax-loss harvesting ESG / Sustainable investing Passive / index investing Active portfolio management
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Kerri M

Series 66

Worcester, MA

Mass Mutual Investors Services

Kerri Melley is a financial advisor at Mass Mutual Investors Services with 21 years of industry experience. She holds a Series 66 designation and has worked at Mass Mutual Investors Services and Mass Mutual Life Insurance Company since 2015. In addition to her advising role, she is an insurance broker specializing in individual and group life and health insurance. Mass Mutual Investors Services is a broker-dealer and SEC-registered investment adviser serving individuals, business owners, trusts, estates, charitable organizations, and employers. The firm offers financial planning, asset management, and educational programs, with financial planning structured as annual collaborative engagements using firm-approved analytical tools.

Divorce financial planning General estate planning guidance Multi-generational wealth transfer Cash flow / budgeting Founder/Business Owner Attorney Executive Married/Couples/Partners Divorced
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Justin G

Series 65

Worcester, MA

New Harbor Financial Group, LLC

Justin Griffin is a financial advisor with New Harbor Financial Group, LLC in Worcester, MA. He holds a Series 65 designation and has 14 years of industry experience, with over a decade at New Harbor Financial Group. Outside of his advisory role, he serves as a trustee for the Princeton Land Trust, where he attends board meetings and conducts site visits to oversee land use and compliance. New Harbor Financial Group is a team-based registered investment adviser that provides investment management, wealth management, and financial planning to individuals, trusts, estates, charities, and business entities. The firm uses a blend of fundamental, technical, and cyclical analysis in managing client portfolios across a range of investment vehicles and offers both discretionary and non-discretionary services.

Options & derivatives strategies Wealth management Tax-loss harvesting
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Kenneth B

Series 63, Series 65

Portland, ME

Headinvest

Kenneth Blaschke is a financial advisor at HeadInvest in Portland, ME, holding Series 63 and Series 65 licenses with 16 years of industry experience. He has been with HeadInvest since 2009. HeadInvest serves a diverse range of clients, including individuals, trusts, endowments, and government entities, providing discretionary portfolio management and financial planning. The firm employs a holistic, asset-allocation driven approach, combining fixed-income selection with low-cost ETFs and emphasizing tax efficiency.

Wealth management General retirement planning Tax strategies for small businesses Founder/Business Owner Retired
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Jeffrey M

CFP®, ChFC®, Series 66

Greenville, DE

Investment Management & Planning LLC

Jeffrey Macdonald is a CFP® and ChFC® with 18 years of industry experience. He has worked at Investment Management & Planning LLC and LPL Financial since 2010, following two years at Wells Fargo Clearing. Investment Management & Planning LLC provides investment advisory and financial planning services primarily to individual and high-net-worth clients. The firm constructs tailored portfolios using mutual funds, ETFs, equities, and fixed-income securities, employing fundamental analysis and continuous supervision, and operates as both a wrap program sponsor and affiliated registered representatives of LPL Financial.

General retirement planning Business succession planning Tax strategies for small businesses Retirement plans for business owners (SEP, solo 401k) Founder/Business Owner Executive Mid-Career Professionals Approaching retirement
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Matthew S

Series 66

Austin, TX

49 Financial

Matthew Sims is a financial advisor at 49 Financial with the Series 66 designation and 21 years of industry experience. His prior work includes roles at Oakwood Capital Securities, Purshe Kaplan Sterling Investments, Thrivent Advisor Network, and Axa Advisors. Outside of his advisory work, he also provides nonprofit consulting through 25 Giving, assisting organizations in developing charitable plans. 49 Financial serves a diverse client base, including individuals, trusts, corporations, and retirement plans, offering comprehensive financial planning and investment management with an emphasis on diversified, long-term asset allocation. The firm provides tiered fractional family office services and employs a strategy that integrates fundamental, cyclical, technical, and behavioral analysis.

Charitable giving & philanthropy Retirement plans for business owners (SEP, solo 401k) Executive Founder/Business Owner Established Professionals Values-based investing

Drew F

CFP®

Avon, IN

Migration Wealth Management, LLC

Drew Feutz, CFP®, is a CERTIFIED FINANCIAL PLANNER™ professional and Founder of Migration Wealth Management, LLC, a fee-only wealth management firm that specializes in providing financial planning and investment management to people in their 30s and 40s. Drew got his start in financial planning as an Intern in May 2014, began working part-time as a Financial Planning & Investment Analyst during his final semester of college, and started working as a Financial Planner full-time upon graduation. Drew graduated Summa Cum Laude from Indiana State University where he earned a Bachelor of Science with a double major in Financial Planning and Investments. During his time at ISU, Drew was a Scholar in the Networks Professional Development Program, a Service-Learning Scholar partnered with Junior Achievement of the Wabash Valley, President of the ISU Financial Planning Association Student Chapter, member of the Investment Club, and a University Honors Program student. He spent his summers during college studying abroad at the Athens Centre in Athens, Greece, interning at First Direct Logistics in Dublin, Ireland, and interning at a fee-only wealth management firm in Indianapolis. He is a Board Member for the Hendricks County Community Foundation as well as Susie's Place Child Advocacy Centers and previously served as Chair of the NAPFA Genesis Committee, Treasurer of Young Professionals of Central Indiana, and as a board member of the Indiana State University Financial Planning Advisory Board. Additionally, Drew co-founded and co-hosts the Circle City Success Podcast. Drew is also a former Fellow in Class V of the Mitch Daniels Leadership Foundation Fellowship and Member of Leadership Hendricks County Class of 2023. Read Drew's blog here: https://migrationwealthmanagement.com/blog/

Business ownership considerations Tax strategies for small businesses Founder/Business Owner Dual Income Family HENRY (High Earners, Not Rich Yet) Gen Y/Millennials (Born 1980-1995)
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Shawn J

Series 63, Series 66

Nashville, TN

Kingsview Wealth Management, LLC

Shawn Johnson is a financial advisor with Kingsview Wealth Management, LLC in Nashville, TN, holding Series 63 and Series 66 licenses and bringing 28 years of industry experience. He previously worked at Edward D. Jones & Co., L.P. for 29 years. Outside of his advisory role, he officiates college football and track and field events. Kingsview Wealth Management is a multi-advisor firm serving a diverse client base including individuals, retirement plans, endowments, and municipal clients. The firm offers comprehensive financial planning and wealth management services, utilizing both in-house strategies and third-party managers across various investment products.

Options & derivatives strategies Tax-loss harvesting Concentrated stock management Real estate investing Retirement plans for business owners (SEP, solo 401k) Founder/Business Owner Executive Retired
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