Top business sale tax planning financial advisors in Naperville, 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 often triggers complex tax decisions that can significantly impact your net proceeds. Without expert guidance, you might miss opportunities to reduce your tax bill or mismanage timing, leading to unnecessary costs.
- Tax timing strategies. Ask how they plan the sale timing to optimize tax outcomes, considering local and federal rules.
- Capital gains management. Confirm their approach to minimizing capital gains taxes specific to business sales.
- Post-sale planning. Inquire about strategies for handling proceeds to protect your wealth and plan for future taxes.
- Coordination with other advisors. Ensure they work closely with your CPA or attorney to align tax planning with your overall financial goals.
Here are top matches to get you started. Review each profile to compare experience, credentials, and approach.
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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 in the Naperville area. His firm, LifePoint Planning, serves high-net-worth clients with a flat-fee structure and employs a mix of passive and active investment strategies, offering a comprehensive approach compared to other advisors nearby.
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 offers expertise in retirement plans for business owners, making him well-suited for managing complex tax decisions in Naperville, IL. His firm uses a long-term, asset-allocation approach with passive investing, and he provides flat-fee options for high-net-worth clients with accounts over $7 million, distinguishing him from advisors with traditional AUM fees.
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 brings a decade of experience as a CFP®-certified advisor serving high-net-worth clients near Naperville, IL. His independent firm offers flat-fee financial planning with tailored asset-allocation models, differentiating him from others by providing flexible, project-based fees and a focus on comprehensive wealth management beyond just tax strategies.
Experience: 10 years
Avg account: $1,459,494
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Kristin S
Series 66
Burr Ridge, IL
Paradigm Money Management, LLC
Kristin Sweis specializes in business sale tax planning and retirement plans for business owners, bringing 17 years of experience and a Series 66 designation to clients near Naperville, IL. Operating independently with a flat-fee structure, she offers tiered financial planning services and coordinates with third-party managers, distinguishing her approach from advisors who may rely solely on asset-based fees or less collaborative strategies.
Experience: 17 years
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Luke S
PFS™
Arlington Heights, IL
Vidarrow Investment Advisors
Luke Sauter specializes in business sale tax planning and offers flat-fee, project-based financial planning, which can help manage complex tax decisions during a business sale. Based in Arlington Heights, IL, he brings a unique perspective from his prior corporate experience and works within an independent, fee-only firm that serves a diverse client base with both passive and active investment strategies.
Experience: 2 years
Avg account: $788,144
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