Top business sale tax planning financial advisors working with high-net-worth individuals in Skokie, 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.
If you recently sold a business or are preparing to, you need an advisor who understands the tax implications specific to business sales. A common mistake is overlooking how timing and structure of the sale affect your overall tax bill, which can lead to unexpected liabilities.
- Sale timing insight. Ask how they evaluate the best time to sell to minimize taxes and maximize after-tax proceeds.
- Tax strategy integration. Confirm they consider how the sale fits into your broader financial and estate plans.
- High-net-worth focus. These advisors understand complexities that come with significant assets, including strategies to protect and grow your wealth post-sale.
- Local tax knowledge. Property taxes in Illinois can be high; check how they factor this into your ongoing tax planning.
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 and wealth management, making him well-suited for high-net-worth individuals in the Skokie area navigating complex tax implications of selling a business. His firm emphasizes tax-aware investment strategies and fee minimization, offering flat-fee financial planning with negotiable rates, which may appeal to clients seeking transparent and tailored portfolio management near Chicago.
Experience: 19 years
Avg account: $3,119,470
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Dean H
Series 63, Series 65
Lincolnshire, IL
Hedeker Wealth LLC
Dean Hedeker offers expertise in business sale tax planning with 35 years of experience and a focus on high-net-worth clients, making him well-suited for managing complex tax implications of business sales. Based in nearby Lincolnshire, IL, he leads Hedeker Wealth LLC, which manages $470 million using a tax-oriented investment approach and charges a 1.65% AUM fee, differentiating him through integrated estate planning and alternative investments.
Experience: 36 years
Avg account: $2,909,161
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Douglas O
CFP®, Series 66
Schaumburg, IL
Lifepoint Planning
Douglas Oosterhart specializes in business sale tax planning and serves high-net-worth clients, making him well-suited for managing complex tax implications of business sales in the Skokie area. His firm, LifePoint Planning, offers a blend of passive and active investment strategies with flat-fee and AUM-based pricing, providing flexible options compared to other advisors who may have different fee structures or investment approaches.
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 serves high-net-worth clients, making him well-suited for managing the tax complexities of selling a business. Based in Riverside, IL, he offers a flat-fee structure for large accounts and employs a long-term, asset-allocation investment approach using passive funds, differentiating him from advisors with different fee models or investment styles.
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, making him well-equipped to address the tax complexities of selling a business in the Skokie area. His independent firm offers flat-fee and hourly pricing, uses proprietary asset-allocation models, and he brings a decade of experience including roles at major financial institutions, distinguishing him from advisors with less flexible fee structures or narrower service scopes.
Experience: 10 years
Avg account: $1,459,494
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