Top business sale tax planning financial advisors working with high-net-worth individuals in Chicago, IL
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.
Selling a business can trigger complex tax decisions that affect your net proceeds and future financial security. Without expert guidance, you might overlook strategies that reduce your tax burden or mismanage timing, costing you more than necessary.
- Capital gains insight. Confirm how the advisor plans to minimize taxes on your sale profits, not just overall income.
- Asset allocation post-sale. Ask how they adjust your investments after liquidity events to balance growth and risk.
- Estate and gift tax planning. Explore how they integrate your sale proceeds into your broader wealth transfer goals.
- High-net-worth experience. Ensure they understand the nuances of managing substantial assets and complex tax situations typical for affluent clients.
Here are top matches to get you started. Review each profile to compare experience, credentials, and approach.
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James P
Series 66
Chicago, IL
Greenstone Belt Wealth Advisors, LLC
James Petitpren II specializes in business sale tax planning for high-net-worth clients in Chicago, leveraging 19 years of experience and a Series 66 designation. His firm employs a tax-aware, diversified investment approach with negotiable flat fees, distinguishing him from others by focusing on tailored portfolios and fee minimization within a small, client-focused advisory setting.
Experience: 19 years
Avg account: $3,119,470
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Douglas O
CFP®, Series 66
Schaumburg, IL
Lifepoint Planning
Douglas Oosterhart specializes in business sale tax planning and equity compensation tax strategy, making him well-equipped to handle complex tax decisions for high-net-worth individuals in the Chicago area. His firm, LifePoint Planning, offers a blend of passive and active investment strategies with flat-fee and AUM-based pricing, serving both individuals and corporations, which provides a versatile approach compared to other advisors focused solely on individual wealth management.
Experience: 12 years
Avg account: $1,491,905
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Tyler M
Series 65
Riverside, IL
Forest Asset Management LLC
Tyler May specializes in business sale tax planning and has six years of experience advising high-net-worth clients, making him well-equipped to handle complex tax decisions related to selling a business. His firm, Forest Asset Management LLC, uses a long-term, asset-allocation driven investment approach with passive and evidence-based funds, and offers flexible fee structures including flat fees for accounts over $7 million, distinguishing him from other advisors in the Chicago area.
Experience: 6 years
Avg account: $2,072,836
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Andrew B
CFP®, Series 63, Series 66
Oak Park, IL
Two Trails Financial Planning
Andrew Baxley specializes in business sale tax planning and serves high-net-worth clients near Chicago, offering expertise in managing tax implications and post-sale asset allocation. His independent firm uses proprietary asset-allocation models and provides flexible flat-fee pricing, distinguishing him from others who may rely on percentage-based fees or larger team structures.
Experience: 10 years
Avg account: $1,459,494
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