Independent, 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.
If you recently sold a business, you need an advisor who understands the tax implications specific to that event, including timing and structuring to minimize your tax burden. Without this expertise, you might miss opportunities to reduce taxes or trigger unexpected liabilities. Independent advisors here operate without firm constraints, which can mean more flexible approaches tailored to your unique sale.
- Sale timing strategies. Ask how they evaluate the best timing for your sale to optimize tax outcomes.
- Tax deferral options. Confirm if they discuss ways to defer taxes legally after your business sale.
- State tax considerations. Since Illinois has no tax on retirement income but high property taxes, check how they factor this into your post-sale planning.
- Coordination with other professionals. Ensure they work closely with your CPA or tax attorney to align strategies effectively.
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, leveraging 19 years of experience and a Series 66 designation to address tax implications and timing strategies for high-net-worth clients. His firm, Greenstone Belt Wealth Advisors, LLC, employs a tax-aware, diversified investment approach with negotiable flat fees ranging from $500 to $25,000, offering personalized service in a small firm setting compared to larger alternatives.
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 serves high-net-worth clients, making him well-suited for managing tax implications after a business sale in the Chicago area. His firm employs a long-term, asset-allocation approach using passive and evidence-based funds, and offers flexible flat-fee arrangements for accounts over $7 million, distinguishing him from advisors with standard AUM fees or less tailored fee structures.
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 serves high-net-worth clients, making him well-equipped to address the tax implications of selling a business near Chicago. As an independent CFP®-certified advisor with 10 years of experience, he offers flat-fee and hourly pricing through his firm, Two Trails Financial Planning, which uses proprietary asset-allocation models tailored to client goals.
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 offers expertise in business sale tax planning and retirement plans for business owners, supported by 17 years of experience and a Series 66 designation. Operating independently with a flat-fee structure, she provides tiered financial planning services from Paradigm Money Management in Burr Ridge, IL, emphasizing coordination with third-party managers to align with client goals.
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 retirement income strategy, making him well-suited for managing tax implications after a business sale in the Chicago area. His firm, Vidarrow Investment Advisors, is an independent, fee-only firm offering both flat-fee and asset-based pricing, with a focus on combining passive and active investment strategies, which may appeal to clients seeking a tailored approach beyond standard advisory services.
Experience: 2 years
Avg account: $788,144
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