Top tax-loss harvesting financial advisors in Wisconsin
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, tax-loss harvesting can help reduce your tax bill by selling those losing assets strategically. The biggest mistake is treating it as a one-time event rather than an ongoing process that aligns with your overall tax situation.
- Timing matters. Ask how often they review your portfolio for harvesting opportunities, since market swings can create new chances to save.
- Wash sale rules. Confirm they understand the IRS rule that disallows a loss if you buy a substantially identical security within 30 days.
- Portfolio impact. Check how they balance tax benefits with maintaining your desired investment allocation and risk level.
- Coordination with other taxes. See if they consider how harvesting interacts with your income tax bracket and potential state taxes, especially in Wisconsin.
Here are top matches to get you started. Review each profile to compare experience, credentials, and approach.
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Kayla W
Series 63, Series 65
Madison, WI
Primerica Advisors
Kayla Wheeler specializes in tax-loss harvesting within a large firm setting in Madison, Wisconsin, offering expertise in ESG investing and income planning alongside her tax-focused services. Her firm, Primerica Advisors, provides discretionary asset management with model-delivery strategies and collaborates with BNY Mellon Advisors, which may appeal to clients seeking structured investment approaches and tiered wrap-fee arrangements.
Experience: 2 years
Avg account: $228,117
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Thomas P
Series 65
Brookfield, WI
Annex Wealth Management, LLC
Thomas Phillipsen specializes in tax-loss harvesting in Wisconsin, leveraging Annex Wealth Management's team-oriented investment process and core-and-tactical framework to balance tax benefits with portfolio goals. Unlike some advisors, he offers flat-fee consulting starting at $1,000 and serves high-net-worth clients, providing comprehensive wealth management and retirement consulting tailored to mid-career professionals and HENRY individuals.
Experience: 0 years
Avg account: $1,117,200
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Jonathan S
Series 65
Stevens Point, WI
Summit Financial, LLC
Jonathan Steffen specializes in tax-loss harvesting with a decade of experience and a Series 65 designation, making him well-equipped to manage ongoing tax-saving strategies in Wisconsin. His firm, Summit Financial, LLC, serves a diverse clientele including individuals and corporations, offers both discretionary and non-discretionary management, and charges flat fees, distinguishing him from advisors with different fee structures or narrower client focuses.
Experience: 11 years
Avg account: $1,318,898
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Steven K
Series 63, Series 65
Waukesha, WI
Robert Baird & Co.
Steven Kellogg specializes in tax-loss harvesting within Wisconsin, leveraging 30 years of experience and his role at Robert W. Baird & Co., a large firm known for comprehensive wealth management. He offers flexible fee structures including flat fees and hourly consulting, and serves a diverse client base through The DDK Group, balancing tax strategies with tailored portfolio management to align with client goals and risk tolerance.
Experience: 31 years
Avg account: $713,008
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Jacob U
Series 66
Onalaska, WI
Commonwealth Financial Network
Jacob Udermann specializes in tax-loss harvesting and offers both passive and active portfolio management, which can help optimize tax benefits while maintaining investment goals. Operating from Onalaska, WI, he provides flat-fee consulting options through Commonwealth Financial Network, a large firm supporting nearly 3,000 advisors with discretionary portfolio construction and proprietary models, distinguishing him from others with his access to extensive firm resources and flexible fee structures.
Experience: 1 year
Avg account: $568,323
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