Top tax-loss harvesting financial advisors working with high-net-worth individuals 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 a sizable investment portfolio with unrealized losses, tax-loss harvesting can help reduce your tax bill by selling those investments to offset gains. Without careful timing and understanding of wash sale rules—which prevent repurchasing the same security within 30 days—you might miss out on potential tax benefits or trigger unintended tax consequences.
- Wash sale rule expertise. Confirm how the advisor navigates repurchase restrictions to maintain your portfolio's strategy while capturing losses.
- Portfolio turnover management. Ask how they balance harvesting losses without excessive trading that could increase costs or disrupt your investment plan.
- Integration with tax planning. Effective tax-loss harvesting should align with your broader tax situation; check how they coordinate with your tax advisor or consider your income changes.
- High-net-worth focus. These advisors understand complexities like alternative minimum tax and state-specific rules that can impact harvesting strategies for wealthy clients.
Here are top matches to get you started. Review each profile to compare experience, credentials, and approach.
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Thomas P
Series 65
Brookfield, WI
Annex Wealth Management, LLC
Thomas Phillipsen specializes in tax-loss harvesting for high-net-worth clients in Wisconsin, leveraging his Series 65 license and expertise in options and derivatives strategies to optimize tax outcomes. Operating through Annex Wealth Management, which manages over $8 billion with a team-based core-and-tactical investment approach, he offers flat-fee consulting starting at $1,000, providing a flexible alternative to traditional AUM fees and serving a diverse client base including pension plans and charitable organizations.
Experience: 0 years
Avg account: $1,117,200
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Nicholas P
Series 63, Series 66
Madison, WI
Creative Planning
Nicholas Parker specializes in tax-loss harvesting for high-net-worth clients in Wisconsin, leveraging 17 years of experience and expertise in private and alternative investments. Operating within Creative Planning, a large firm managing $217 billion in assets, he employs a financial planning–led approach emphasizing low-cost indexing and buy-and-hold strategies, offering flat-fee and negotiable hourly fee structures that may suit clients seeking comprehensive, cost-conscious portfolio management.
Experience: 18 years
Avg account: $2,113,277
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Peter S
Series 63, Series 65
Milwaukee, WI
Oarsman Capital, Inc
Peter Schumacher specializes in tax-loss harvesting for high-net-worth clients in Wisconsin, leveraging 34 years of experience and a focus on active portfolio management and income planning. Based in Milwaukee at Oarsman Capital, he offers a 1.0% annual AUM fee and emphasizes tax-aware management combined with long-term equity investing, distinguishing him through a blend of fundamental analysis and independent research.
Experience: 35 years
Avg account: $1,732,454
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Dave I
Series 63, Series 65
Menomonee Falls, WI
Morgan Dempsey Capital Management LLC
Dave Isaacson specializes in tax-loss harvesting for high-net-worth clients in Wisconsin, leveraging his expertise in active portfolio management and options strategies to optimize tax outcomes. His role at Morgan Dempsey Capital Management, which uses a value-driven, bottom-up research approach and serves qualified purchasers with equity-focused strategies, distinguishes him by combining tailored portfolio management with a negotiable 0.50% annual fee for large cap value accounts.
Experience: 9 years
Avg account: $470,745
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Roger R
CFA®, Series 63
Milwaukee, WI
Silvercrest Asset Management Group LLC
Roger Rama specializes in tax-loss harvesting for high-net-worth clients in Wisconsin, leveraging his CFA® designation and expertise in active portfolio and concentrated stock management. Based in Milwaukee, he works with Silvercrest Asset Management Group LLC, which offers tailored investment and family-office services with proprietary strategies and quantitative risk analytics, charging a 1.00% AUM fee, distinguishing him through a comprehensive, data-driven approach.
Experience: 1 year
Avg account: $17,515,235
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