Top advisors focused on self-employed 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 your own business or freelance, you face unique challenges like managing irregular income and planning for taxes without a traditional employer withholding. The biggest mistake is treating your finances like a regular paycheck scenario, which can lead to cash flow problems or missed tax deadlines. Advisors here often work on a flat-fee basis, so you know what you’ll pay upfront without surprises.

  • Cash flow planning. Look for advisors who help you build a budget that accounts for income ups and downs, not just average earnings.
  • Tax strategy. Confirm they understand self-employment tax rules and can guide you on quarterly estimated payments.
  • Retirement options. Ask how they recommend retirement plans suited for self-employed individuals, like SEP IRAs or solo 401(k)s.
  • Business and personal finance. Check if they help separate your business expenses from personal spending to keep your finances clear and organized.

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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Kristin M

Series 66

Mt Pleasant, SC

Primerica Advisors

Kristin Manna is a financial advisor with Primerica Advisors and holds a Series 66 designation. She has one year of industry experience, including roles at Park Avenue Securities, Guardian Life Insurance Company, and Consolidated Planning Holdings, Inc. Prior to entering the financial industry, she worked in education for eight years. Outside of advising, Kristin is an author and publisher of a basketball coaching notebook and works as a math tutor for high school students. Park Avenue Securities serves a broad retail client base with a range of brokerage and advisory services, utilizing proprietary and third-party investment strategies across various account types and investment vehicles.

Business exit / sale strategy Tax-loss harvesting Self-Employed Founder/Business Owner
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Geoffrey T

Series 66

Chicago, IL

Sanctuary Advisors, LLC

Geoffrey Tomes is a financial advisor at Sanctuary Advisors, LLC with 26 years of industry experience. He holds a Series 66 designation and has worked at Noyes Advisors LLC and David A Noyes & Company since 2000. His other business activities include involvement with fixed life and health insurance and fixed annuities. Sanctuary Advisors provides investment advisory and financial planning services to a diverse client base, including individuals, corporations, charitable organizations, and retirement plans. The firm offers customized investment programs through a network of independent advisors and affiliated broker-dealer services, utilizing various account structures and third-party model platforms.

Retirement income strategy Business exit / sale strategy Active portfolio management Private / alternative investments Founder/Business Owner Self-Employed Retired
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Ryan V

CFP®, Series 63, Series 66

Richfield, OH

Schwab Wealth Advisory

Ryan Vollweiler is a CFP® professional with 21 years of industry experience, currently serving as a financial advisor at Schwab Wealth Advisory. His prior roles include positions at Charles Schwab and Schwab Retirement Plan Services, as well as a brief tenure at Voya Financial Advisor. Schwab Wealth Advisory provides non-discretionary investment advice and wealth-management services to Schwab brokerage clients who meet eligibility requirements, utilizing Schwab’s asset-allocation models and proprietary research tools. The firm is part of The Charles Schwab Corporation’s integrated product and service ecosystem.

Wealth management Passive / index investing Active portfolio management Tax-loss harvesting Retired Founder/Business Owner Executive Self-Employed
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Jonathan L

Series 66

Roseville, CA

LPL Enterprise

Jonathan Levatino is a financial advisor with LPL Enterprise, holding a Series 66 designation and three years of industry experience. His prior work includes roles at The Prudential Insurance Company of America, Pruco Securities LLC, and Apple Inc. Outside of his advisory work, he is also employed as a driver for rideshare and delivery services including Uber, Lyft, and DoorDash. LPL Enterprise provides advisory services through a large network of investment adviser representatives to individuals, retirement plans, charitable organizations, and corporate clients. The firm offers financial planning, access to model wealth portfolios, and third-party asset management programs, combining advisory and brokerage capabilities.

General retirement planning Tax-loss harvesting Self-Employed Founder/Business Owner
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Rachel G

Series 63, Series 65

Ronkonkoma, NY

Verity Asset Management

Rachel Gentz is a financial advisor at Verity Asset Management with six years of industry experience. She holds Series 63 and Series 65 designations and has worked at firms including Menna Wealth Planning Group and The Leaders Group DBA Simplicity Investments. In addition to her advisory roles, she is president and owner of Rachel A Menna Advisors Inc. Verity Asset Management is an SEC-registered investment adviser that provides discretionary portfolio management, retirement-plan advisory, and financial planning to individual, corporate, institutional clients, and other advisers. The firm uses a model-driven investment process emphasizing tactical asset allocation across diverse asset classes and offers both internally managed and third-party models under fiduciary standards.

Concentrated stock management Active portfolio management Tax-loss harvesting ESG / Sustainable investing Private / alternative investments Self-Employed Executive
View complete list of advisors specializing in self-employed in District of Columbia
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