Independent, business sale tax planning financial advisors 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 triggers complex tax decisions that can affect your net proceeds and future financial plans. Without expert guidance, you might overlook key deductions or timing strategies that reduce your tax burden.
- Tax timing strategies. Ask how they plan the sale date and payment structure to optimize your tax outcomes.
- Capital gains insight. Confirm they understand how to manage your gains to minimize taxes, including potential installment sales.
- Independent advice. Since these advisors operate independently, check how they tailor recommendations without firm product pressures.
- Post-sale planning. Inquire about their approach to reinvesting proceeds and managing tax implications after the sale.
Here are top matches to get you started. Review each profile to compare experience, credentials, and approach.
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Dean H
Series 63, Series 65
Lincolnshire, IL
Hedeker Wealth LLC
Dean Hedeker's 35 years of experience and expertise in business sale tax planning, combined with his independent status, make him well-equipped to handle complex tax decisions for business sales near Des Plaines, IL. His firm manages $470 million with a tax-oriented investment approach and serves high-net-worth clients, differentiating him through a blend of legal and financial planning expertise and a 1.65% AUM fee structure.
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-equipped to handle complex tax decisions during a business sale. Based in Schaumburg, IL, he offers independent, flat-fee services tailored to high-net-worth clients, combining 12 years of experience with a CFP® certification and a firm approach that blends passive and active investment strategies.
Experience: 12 years
Avg account: $1,491,905
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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 brings a decade of experience as a CFP® and founder of Two Trails Financial Planning, an independent firm near Des Plaines, IL. His firm serves high-net-worth clients with flat-fee structures ranging from $3,000 to $20,000 and employs proprietary asset-allocation models, distinguishing him from advisors who may use percentage-based fees or less tailored investment approaches.
Experience: 10 years
Avg account: $1,459,494
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Ivan H
Series 66
Wheeling, IL
Outside The Box Financial Planning, LLC
Ivan Havrylyan specializes in business sale tax planning and operates independently, offering flat-fee financial planning that ranges from $3,500 to $15,000. Based in Wheeling, IL, he brings 12 years of experience and focuses on passive investment strategies using index funds and ETFs, serving both individuals and business entities with comprehensive financial planning and portfolio management.
Experience: 13 years
Avg account: $264,346
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Luke S
PFS™
Arlington Heights, IL
Vidarrow Investment Advisors
Luke Sauter specializes in business sale tax planning and offers independent, flat-fee financial advice from Arlington Heights, IL, near Des Plaines. With a Personal Financial Specialist designation and experience at a fee-only firm serving diverse clients, he combines passive and active investment strategies, making him a distinct choice for tailored tax timing and post-sale planning compared to other advisors.
Experience: 2 years
Avg account: $788,144
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