Top 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 miss opportunities to reduce your tax bill or mismanage timing, leading to unexpected costs.
- Capital gains insight. Confirm how the advisor approaches minimizing taxes on the sale's profit, including strategies tailored to your business type.
- Timing strategies. Ask how they recommend scheduling the sale and related transactions to optimize tax outcomes.
- State tax considerations. Even though retirement income isn't taxed here, property taxes can be high; see how they factor this into your overall plan.
- Post-sale planning. Understand how they help integrate sale proceeds into your broader financial goals, including investment and estate planning.
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 ownership of an estate planning law firm, equip him to navigate 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, offering both discretionary and non-discretionary portfolio management with a 1.65% AUM fee.
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 brings 12 years of experience, including expertise in retirement income strategy and equity compensation tax strategy, which can help optimize tax outcomes for business sales. Operating from Schaumburg, IL, he offers flat-fee and asset-based pricing, serves high-net-worth clients, and employs a mix of passive and active investment strategies, distinguishing him from other advisors in the area.
Experience: 12 years
Avg account: $1,491,905
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Ivan H
Series 66
Wheeling, IL
Outside The Box Financial Planning, LLC
Ivan Havrylyan specializes in business sale tax planning with 12 years of experience, offering strategies that consider capital gains, timing, and state tax implications to optimize your sale proceeds. His firm uses a passive investment approach with index funds and ETFs, serving both individuals and business entities, and offers flat-fee financial planning ranging from $3,500 to $15,000, distinguishing him from advisors with different fee structures or investment styles.
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 retirement income strategy, offering tailored advice from his role at Vidarrow Investment Advisors in Arlington Heights, IL. His firm’s independent, fee-only approach includes flat fees and a mix of passive and active investment strategies, distinguishing him with a comprehensive planning perspective despite his relatively recent entry into the industry.
Experience: 2 years
Avg account: $788,144
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James R
Series 66
Northbrook, IL
Merrill
James Ruddy specializes in business sale tax planning and wealth management, offering strategies that address tax-loss harvesting and retirement income for executives and business owners. Operating within Merrill, a large firm, he combines a focus on risk management and tax minimization with a 1.10% AUM fee, making him a practical choice for mid-career professionals and high earners seeking comprehensive post-sale financial guidance.
Experience: 4 years
Avg account: $860,085
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