Top business sale tax planning financial advisors 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.
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.
- State-specific knowledge. Illinois has no tax on retirement income but high property taxes; ensure they factor this into your post-sale planning.
- Integration with advisors. Check how they coordinate with your CPA and legal team to align tax and legal strategies effectively.
Here are top matches to get you started. Review each profile to compare experience, credentials, and approach.
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Colin B
CFP®, Series 66
Chicago, IL
Ameriprise
Colin Bonnett specializes in business sale tax planning and retirement income strategy, making him well-equipped to handle complex tax decisions related to selling a business in the Skokie area. As a CFP®-certified advisor at a large firm with six years of experience and a 0.15% AUM fee, he offers wealth management services that integrate executive compensation and legacy planning, distinguishing him from others by combining tax planning with comprehensive retirement and estate strategies.
Experience: 7 years
Avg account: $471,167
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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®-certified advisor serving high-net-worth clients near Skokie, IL. His independent firm offers flat-fee pricing and uses proprietary asset-allocation models, distinguishing him from others by combining tailored investment strategies with flexible, transparent fees.
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 offers expertise in business sale tax planning with 12 years of experience and a Series 66 designation, serving clients from Wheeling, IL near Skokie. His firm uses a passive investment approach with index funds and ETFs, providing flat-fee financial planning ranging from $3,500 to $15,000, which may appeal to those seeking transparent, independent advice alongside comprehensive portfolio oversight.
Experience: 13 years
Avg account: $264,346
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James R
Series 66
Northbrook, IL
Merrill
James Ruddy specializes in business sale tax planning and wealth management, offering expertise in tax-loss harvesting and retirement income strategies, which are crucial for optimizing tax outcomes during a business sale in the Skokie area. Affiliated with Merrill, a large firm, he brings four years of industry experience and a 1.10% AUM fee structure, focusing on mid-career professionals and high earners, distinguishing him with a balanced approach to risk, taxes, and fees.
Experience: 4 years
Avg account: $860,085
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Collin W
Series 65
Chicago, IL
Greenstone Belt Wealth Advisors, LLC
Collin Woulfe specializes in business sale tax planning and retirement income strategy, making him well-equipped to handle complex tax decisions in Skokie, IL. His firm, Greenstone Belt Wealth Advisors, serves high-net-worth clients with flat-fee and hourly options, applying modern portfolio theory for diversified, tax-efficient investment management, which distinguishes him from other advisors in the area.
Experience: 0 years
Avg account: $3,119,470
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