Baby Boomer advisors 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.

You might be planning for retirement income, managing healthcare costs, or considering estate plans tailored to your stage in life. Without an advisor who understands the unique financial challenges Baby Boomers face, you risk missing opportunities to optimize your savings and protect your legacy.

  • Retirement income sequencing. Confirm how they plan withdrawals to balance taxes, Social Security, and investment growth.
  • Healthcare cost planning. Ask how they incorporate Medicare, long-term care, and unexpected medical expenses into your financial roadmap.
  • Estate and legacy considerations. Look for advisors who discuss trusts, beneficiary designations, and tax implications relevant to your goals.
  • Experience with Baby Boomer issues. Ensure they recognize the timing and impact of life transitions common to your generation.

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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Willie M

Series 63, Series 66

Cary, NC

Equitable Advisors

Willie Myles is a financial advisor at Equitable Advisors with 16 years of industry experience. He holds Series 63 and Series 66 credentials and has worked at Equitable Advisors since 2016, previously affiliated with Axa Advisors. Outside of his advisory role, he serves as co-chairman of a fundraising campaign for Alpha Light Fund Inc., a nonprofit organization. Equitable Advisors serves individual investors, retirement plan sponsors, corporations, and charitable organizations by providing financial planning, retirement-plan support, and access to asset management through various third-party programs. The firm operates a hybrid referral and implementation model, offering both advisory and brokerage channels to implement client recommendations.

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

Series 65

Knoxville, TN

Rather & Kittrell, Inc.

Chase Burton is a financial advisor at Rather & Kittrell, Inc. with two years of industry experience. He holds a Series 65 designation and has worked in various roles including at the University of Tennessee and Northwestern Mutual. Outside of finance, he owns a sole proprietorship focused on pressure washing services. Rather & Kittrell, Inc. provides wealth management, financial planning, and retirement plan advisory services to individuals, high-net-worth clients, and institutional investors. The firm uses globally diversified, multi-asset class model portfolios based on Modern Portfolio Theory and manages approximately $1.855 billion in assets.

Wealth management Retired Founder/Business Owner Baby Boomers (Born 1946-1964) Mid-Career Professionals
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Ryan P

CFP®, Series 66

Winter Garden, FL

wealth Enhancement Advisory Services, LLC

Ryan Paul is a CFP® with 13 years of industry experience, currently affiliated with Wealth Enhancement Advisory Services, LLC since 2016. His prior experience includes roles at Morgan Stanley from 2014 to 2016. Outside of his advisory work, he is involved in tax preparation and accounting activities. Wealth Enhancement Advisory Services, LLC is an SEC-registered enterprise advisory firm serving a diverse client base, including individuals, trusts, charitable organizations, corporations, and retirement plans. The firm offers financial planning, asset management, and specialized consulting, employing a strategic investment process that combines passive and active management guided by an internal Investment Committee.

Active portfolio management Factor investing / smart beta Retirement plans for business owners (SEP, solo 401k) Business exit / sale strategy Executive Founder/Business Owner Retired HENRY (High Earners, Not Rich Yet) Mid-Career Professionals Approaching retirement Baby Boomers (Born 1946-1964)

Stephen B

CFP®

Charlotte, NC

Flat Fee Financial LLC

As a comprehensive financial planning firm we can assist you with your investment management, social security, debt management, budgeting, net-worth tracking, overall organization, tax planning, charitable planning, insurance review, and much more. As a flat fee firm we know the stock market isn't the only solution for your investment problems and love to brainstorm real estate, small business, private credit, and other alternative investment options that lead to the main goal. To improve your financial life and increase your net-worth. If you want a second set of eyes on your investments or financial decisions then feel free to give us a call and we'll talk through if we are a good fit for you. If not, then we will point you in the right direction.

Inherited wealth Student loan debt Dentist Baby Boomers (Born 1946-1964)
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John D

CFP®, Series 66

Potomac, MD

Pathstone

John Decker is a CFP® and Series 66-registered financial advisor with 21 years of industry experience. He has been with Pathstone since 2016 and previously worked at Convergent Wealth Advisors, LLC for nine years. Pathstone primarily serves ultra-high-net-worth families, single-family offices, institutional investors, and other pooled investment vehicles. The firm employs a multi-asset, manager-centric investment approach and offers a combination of investment advisory and family-office services, including in-house accounting and affiliated fiduciary companies.

Tax-loss harvesting ESG / Sustainable investing Private / alternative investments Wealth management Business exit / sale strategy Founder/Business Owner Executive Baby Boomers (Born 1946-1964)
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