Flat-fee, tax-loss harvesting 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 have investments with losses that could offset gains, a tax-loss harvesting advisor can help you use those losses to reduce your tax bill. Without careful planning, you might miss opportunities to lower taxes or accidentally trigger unwanted tax events. Flat-fee advisors charge a set price, so you know your costs upfront without surprise fees.
- Loss identification process. Ask how they find and select investments to sell at a loss without harming your overall portfolio.
- Wash sale awareness. Confirm they understand rules preventing repurchasing the same security too soon, which can disallow the tax benefit.
- Portfolio impact. Discuss how they balance tax savings with maintaining your investment goals and risk tolerance.
- Coordination with tax preparer. Ensure they communicate with your tax professional to accurately report harvested losses on your return.
Here are top matches to get you started. Review each profile to compare experience, credentials, and approach.
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Michael O
Series 63
Chicago, IL
LPL Financial
Michael O'Malley Sr. specializes in tax-loss harvesting and offers flat-fee financial planning through LPL Financial in Chicago, making him well-suited for managing tax-efficient investment strategies. With over 50 years of experience and a Series 63 designation, he serves a diverse clientele including business owners and high-net-worth households, supported by a large firm's research resources and a flexible fee structure.
Experience: 51 years
Avg account: $399,489
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Angela I
Series 63, Series 66
Chicago, IL
Cetera
Angela Ip specializes in tax-loss harvesting and wealth management, making her well-suited for clients in Chicago seeking flat-fee financial advice to optimize tax strategies. With 26 years of experience at Cetera, a large firm serving diverse clients, she offers negotiated flat fees and manages tax compliance reporting, distinguishing her through extensive industry knowledge and a broad service approach.
Experience: 26 years
Avg account: $306,089
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Aristotle P
Series 65
Chicago, IL
North Star Investment Management Corporation
Aristotle Petruleas specializes in tax-loss harvesting and offers flat-fee financial planning services in Chicago, making him suitable for managing tax-efficient investment strategies. With four years of industry experience and a Series 65 designation, he works at North Star Investment Management Corporation, a firm managing $2.5 billion in assets and serving diverse clients including pension plans and trusts, which may provide broader portfolio management resources compared to other advisors.
Experience: 4 years
Avg account: $770,709
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Mario B
Series 63, Series 66
Chicago, IL
LPL Enterprise
Mario Bear specializes in tax-loss harvesting in Chicago, offering flat-fee financial planning through LPL Enterprise, a large firm serving diverse clients including retirement plans and charitable organizations. With 11 years of experience and Series 63 and 66 licenses, he combines expertise in general retirement planning and self-employed business owner needs, differentiating him with a broad service scope and a background in major financial institutions.
Experience: 11 years
Avg account: $239,757
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Nahal S
Series 66, Series 63
Chicago, IL
Apollon Wealth Management, LLC
Nahal Sabbagh Kermani specializes in tax-loss harvesting with a flat-fee structure, offering clear upfront costs starting at $5,000. Based in Chicago, she brings 10 years of experience and a background at Goldman Sachs and JPMorgan Chase, working through Apollon Wealth Management, which serves diverse clients with a blend of fundamental and tactical investment strategies and tax-aware tools.
Experience: 11 years
Avg account: $1,342,146
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