Top business sale tax planning financial advisors working with high-net-worth individuals in Des Plaines, 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 key deductions or timing strategies that reduce your tax burden.
- Capital gains insight. Confirm how the advisor approaches minimizing taxes on the sale's profit, including timing and allocation strategies.
- Estate and gift tax planning. Ask how they integrate business sale proceeds into your broader wealth transfer goals.
- Liquidity management. Understand their plan for managing cash flow and investments immediately after the sale to preserve wealth.
- High-net-worth experience. These advisors are familiar with the unique tax challenges faced by affluent clients in Des Plaines, IL, ensuring strategies fit your financial profile.
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 clients in the Des Plaines area. His firm employs a tax-aware, diversified investment approach with negotiable flat fees, and his 19 years of experience include serving executives and business owners, distinguishing him from advisors with less tailored fee structures or narrower client focuses.
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, supported by his ownership of an estate planning law firm. His firm manages $470 million using a tax-oriented investment approach and charges a 1.65% AUM fee, distinguishing him through integrated legal and financial strategies near Des Plaines, IL.
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 equity compensation tax strategy, making him well-suited for high-net-worth clients in Des Plaines, IL facing complex tax decisions. His 12 years of experience, CFP® certification, and flat-fee structure distinguish him, while his firm employs both passive and active investment strategies and serves a diverse client base including executives and business owners.
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 serving high-net-worth clients, making him well-equipped to handle complex tax strategies in Des Plaines, IL. His firm, Forest Asset Management LLC, uses a long-term, asset-allocation approach with passive investing and offers flexible fee structures including flat fees for large accounts, distinguishing him from advisors with more traditional fee models.
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 complex tax issues in Des Plaines, IL. As an independent CFP®-certified advisor with 10 years of experience, he offers flat-fee and hourly pricing through Two Trails Financial Planning, which uses proprietary asset-allocation models tailored to client goals, distinguishing him from advisors with percentage-based fees.
Experience: 10 years
Avg account: $1,459,494
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