Flat-fee, business sale tax planning financial advisors in Chicago, 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 tax strategies that reduce your overall tax burden.
- Comprehensive tax mapping. Look for advisors who outline how different sale structures impact your immediate and long-term taxes.
- Integration with legal counsel. Confirm they coordinate closely with your attorneys to align tax planning with sale agreements.
- Post-sale cash flow planning. Ask how they help manage your income and investments after the sale to optimize tax outcomes.
- Flat-fee clarity. These advisors offer straightforward pricing, so you know costs upfront without surprises.
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 in Chicago, offering flat-fee financial planning with negotiable rates based on complexity. His firm emphasizes tax-aware investment strategies and serves high-net-worth clients, differentiating him through a focus on diversification and fee minimization alongside his 19 years of industry experience and Series 66 designation.
Experience: 19 years
Avg account: $3,119,470
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Tyler M
Series 65
Riverside, IL
Forest Asset Management LLC
Tyler May specializes in business sale tax planning and offers flat-fee arrangements that can be negotiated annually for accounts over $7 million, making him suitable for high-net-worth clients in the Chicago area. His firm employs a long-term, asset-allocation driven investment approach using passive and evidence-based funds, and he brings six years of experience along with expertise in retirement plans for business owners and tax-loss harvesting.
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 with a flat-fee structure ranging from $3,000 to $20,000, providing clear upfront costs for clients in the Chicago area. His independent firm serves high-net-worth individuals and employs proprietary asset-allocation models, distinguishing him with tailored investment strategies and a decade of industry experience.
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 with 17 years of experience and offers flat-fee financial planning services ranging from $750 to $6,000, making her well-suited for managing complex tax decisions in Chicago's business sales. Her firm, Paradigm Money Management, focuses on coordinated financial planning and retirement-plan advisory, emphasizing tiered planning engagements and independent recommendations, which may appeal to clients seeking comprehensive, fee-transparent guidance.
Experience: 17 years
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Luke S
PFS™
Arlington Heights, IL
Vidarrow Investment Advisors
Luke Sauter specializes in business sale tax planning with a flat-fee structure, offering project-based financial planning fees ranging from $2,000 to $50,000, which provides cost clarity for sellers in the Chicago area. His firm, Vidarrow Investment Advisors, combines independent, fee-only services with a mix of passive and active investment strategies, catering to both individual investors and organizational clients, which may offer broader financial planning support compared to other advisors.
Experience: 2 years
Avg account: $788,144
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