Top advisors focused on tax strategies for small businesses in District of Columbia

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, you need tax strategies that fit your unique cash flow and growth plans. Without a specialist, you might miss deductions or tax credits that could save you money or cause costly errors in your filings.

  • Business structure insight. Ask how they tailor tax plans based on whether you’re a sole proprietor, LLC, or corporation.
  • Expense categorization. Confirm they help identify deductible expenses specific to small businesses, not just general personal deductions.
  • Quarterly tax planning. Check if they assist with estimated tax payments to avoid surprises or penalties.
  • Growth and hiring impact. See how they adjust strategies when you add employees or expand operations, as these changes affect your tax obligations.

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

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Dexter W

Series 63, Series 66

Washington, DC

Morgan Stanley

Dexter Walker is a financial advisor at Morgan Stanley with 28 years of industry experience. He holds Series 63 and Series 66 licenses and has worked at Morgan Stanley Private Bank, N.A. since 2015 and MORGAN STANLEY SMITH BARNEY llc since 2009. Outside of his advisory role, he is a 40% owner of Washington DC Inferno, LLC, a professional women's squash franchise. Morgan Stanley Wealth Management serves individual and institutional clients with a wide range of advisory programs and tailored financial planning, managing approximately $2.74 trillion in client assets. The firm’s planning process includes structured discovery and firm-approved tools but does not provide individual security recommendations as part of standalone planning.

General estate planning guidance
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David C

Series 63, Series 65

Annapolis, MD

Westbourne Investment Advisors Inc.

David Cunningham is a financial advisor with Westbourne Investment Advisors Inc. in Annapolis, MD, holding Series 63 and Series 65 licenses and having 27 years of industry experience. He has worked at Westbourne Investment Advisors since 2007 and has been with Cunningham Capital Management, LLC since 2012. Westbourne Investment Advisors provides discretionary portfolio management to individuals, trusts, pension plans, and non-profit organizations. The firm employs an equity-oriented, buy-and-hold investment strategy supported by fundamental analysis and technical review, managing approximately $359 million across about 420 accounts.

Active portfolio management Options & derivatives strategies Concentrated stock management
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Stephen D

Series 66

Atlanta, GA

Equitable Advisors

Stephen Dunbar III is a financial advisor with Equitable Advisors in Atlanta, GA, holding a Series 66 designation and 19 years of industry experience. He has been with Equitable Advisors since 2010, previously associated with AXA Advisors, LLC during the same period. Outside of advising, he writes a monthly financial column for Kiplinger and is involved as an owner and investor in a family-run baking business. Equitable Advisors serves individual investors, retirement plan sponsors, corporations, and charitable organizations, providing financial planning, retirement-plan support, and access to asset management through LPL programs and third-party asset managers. The firm operates a hybrid referral and implementation model that combines advisory and brokerage services tailored to clients’ goals, risk tolerance, and time horizons.

Retirement income strategy Social Security optimization Founder/Business Owner Retired Executive Approaching retirement Baby Boomers (Born 1946-1964)
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Anne W

Series 63, Series 66

Chicago, IL

Thrivent Investment Management

Anne Whiting is a financial advisor with Thrivent Investment Management in Chicago, IL, holding Series 63 and Series 66 licenses and possessing 14 years of industry experience. Her prior work includes roles at O Long Law, LLC, Churchill Capital USA, Inc., and Rodan + Fields. Thrivent Investment Management provides Dedicated Planning Services to individuals, families, businesses, and nonprofit clients, focusing on holistic, goal-based financial planning rather than portfolio management. The firm offers these planning services either on a one-time or ongoing basis and allows clients to integrate planning with managed accounts through a consolidated billing option called “WealthPlan.”

Business ownership considerations
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Heather R

Series 63, Series 65

Laurel, MD

Transamerica Financial Advisors

Heather Ramlal is a financial advisor with Transamerica Financial Advisors, holding Series 63 and Series 65 licenses and nine years of industry experience. She has held roles at HLR Financial Solutions Inc and Amplify, an education company, alongside her ongoing work with Transamerica Financial Advisors since 2016. Ramlal is also president of HLR Financial Solutions Inc, an S corporation established for expense documentation purposes. Transamerica Financial Advisors provides investment advisory, brokerage, and retirement-plan services to a diverse client base, including individual investors, employer-sponsored plans, trusts, and charitable organizations. The firm utilizes a model portfolio approach implemented through third-party managers and proprietary platforms such as Transamerica ONE and TFA365.

ESG / Sustainable investing Concentrated stock management Wealth management Founder/Business Owner
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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 17 years of industry experience. He has been with Investment Management & Planning LLC since 2010 and is also affiliated with LPL Financial LLC. Investment Management & Planning LLC provides fee-based investment advisory and comprehensive financial planning primarily for individual and high-net-worth clients, offering portfolio management on both discretionary and non-discretionary bases. The firm emphasizes ongoing account supervision and individualized asset allocation, often utilizing LPL-sponsored platforms and model portfolios.

General retirement planning Business succession planning Tax strategies for small businesses Wealth management Founder/Business Owner Retired Mid-Career Professionals Established Professionals
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Matthew S

Series 66

Austin, TX

49 Financial

Matthew Sims is a financial advisor with 21 years of industry experience, currently practicing at 49 Financial in Austin, TX. He holds the Series 66 designation and has held prior roles at Oakwood Capital Securities, Thrivent Advisor Network, Purshe Kaplan Sterling Investments, and Axa Advisors. Outside of his advisory work, he contributes as a contractor to 25 Giving, a nonprofit consulting organization that helps develop charitable plans for donors of nonprofits. 49 Financial provides advisory services to a diverse clientele, including individuals, trusts, estates, corporations, and retirement plans. The firm employs a diversified asset allocation strategy based on Modern Portfolio Theory, utilizing proprietary model portfolios and third-party managers, with oversight from an internal Investment Committee.

Wealth management Tax strategies for small businesses Real estate investing Founder/Business Owner Executive

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 Edward Jones in Nashville, TN, holding Series 63 and Series 66 designations and 28 years of industry experience. He has been with Edward Jones since 1997. Outside of his advisory role, he officiates college football and track and field events at various levels. Edward Jones is a full-service wealth management firm serving individual and institutional clients with a range of advisory programs, including managed solutions and separately managed accounts. The firm manages over $1 trillion in assets and is distinguished by its extensive network of advisors and branches, as well as affiliated mutual funds and trust services.

College savings (529s, UTMA, etc.) Tax strategies for small businesses Options & derivatives strategies Founder/Business Owner Retired
View complete list of advisors specializing in tax strategies for small businesses in District of Columbia
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