Seasoned, 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 timing and strategy, you might miss opportunities to lower your taxes or accidentally trigger unwanted tax events. Seasoned advisors bring years of experience to navigate these complexities effectively.
- Loss identification timing. Ask how they spot and act on losses throughout the year, not just at tax time.
- Wash sale rules. Confirm they understand and avoid repurchasing the same security within 30 days, which can disallow your loss.
- Portfolio impact. Check how they balance harvesting losses with maintaining your investment goals and risk tolerance.
- State tax considerations. Since Illinois doesn’t tax retirement income, ask how they factor in local property taxes and other state-specific issues.
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. brings over 50 years of experience in tax-loss harvesting and wealth management, operating from Chicago with LPL Financial, a large firm known for its extensive research support. He offers flat-fee financial planning and consulting, catering to a diverse clientele including high-net-worth households and retirement plan sponsors, which may provide a broader perspective compared to advisors with narrower client focuses.
Experience: 51 years
Avg account: $399,489
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Angela I
Series 63, Series 66
Chicago, IL
Cetera
Angela Ip's 26 years of experience and expertise in tax-loss harvesting make her well-equipped to help clients in Chicago, IL, optimize their investment losses to reduce tax liabilities. Working with Cetera, a large firm offering diverse portfolio management and financial planning services, she provides flat-fee and hourly consulting options, catering to high earners and those approaching retirement, which distinguishes her from other advisors.
Experience: 26 years
Avg account: $306,089
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Joseph K
CFA®, Series 63, Series 65
Chicago, IL
Kruse Asset Management, LLC
Joseph Kruse offers seasoned expertise in tax-loss harvesting with 24 years of experience and CFA® credentials, making him well-equipped to manage complex tax strategies in Chicago. His firm employs Modern Portfolio Theory alongside proprietary quantitative equity models, serving a diverse client base including trusts and family offices, with a 1.75% annual fee on equity accounts, distinguishing him through a blend of advanced analytics and broad client services.
Experience: 25 years
Avg account: $765,775
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John F
CFA®, Series 63
Chicago, IL
FIFTH THIRD SECURITIES, Inc.
John Fisher brings 23 years of experience in tax-loss harvesting and passive investing, operating from Chicago with Fifth Third Securities, a large firm offering discretionary managed-account programs and tax-overlay services. His CFA® designation and Series 63 license complement his expertise, while his firm's direct indexing capabilities and municipal-advisor registration provide additional layers of service compared to other local advisors.
Experience: 23 years
Avg account: $230,450
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Loren P
Series 63, Series 65
Chicago, IL
Associated Investment Services, Inc.
Loren Piotrowski brings 26 years of experience in tax-loss harvesting and active portfolio management, making him well-equipped to navigate Chicago's tax nuances. As an independent advisor at Associated Investment Services, he serves a diverse client base including trusts and small corporations, with a fee structure ranging from 1.42% to 1.81% AUM, distinguishing him through a blend of seasoned expertise and broad service offerings.
Experience: 27 years
Avg account: $303,096
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