Baby Boomer advisors focused on tax strategies for small businesses in the US

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 and want to keep more of your earnings, you need an advisor who understands tax strategies tailored to your unique business structure and goals. Without this focus, you might miss deductions or credits that could save you money.

  • Business-specific tax knowledge. Confirm they understand the tax rules that apply to your type of business, whether it's a sole proprietorship, partnership, or corporation.
  • Cash flow impact. Ask how their tax strategies affect your business’s cash flow throughout the year, not just at tax time.
  • Retirement plan integration. See if they coordinate tax planning with retirement options that benefit both you and your employees.
  • Succession and exit planning. Discuss how they help plan for selling or passing on your business with tax efficiency in mind.

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

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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
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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)
View complete list of Baby Boomer advisors specializing in tax strategies for small businesses
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