Considering The Effect of Taxes Considering The Effect of Taxes

Considering the
Effect of Taxes

Robert H. Wyche, Partner and Managing Director, relates the story of a coordinated carryforward strategy.


“Just because something is in the federal tax code, there’s no guarantee every state follows suit in a similar way. We had a client who’d been living in Georgia and wanted to move back home to Pennsylvania. That year, he had a highly appreciated security with a low cost basis. He also had a $5 million capital loss carryforward from his prior advisor. The client was already on a glide path to reduce his exposure in his highly appreciated, concentrated stock, but the new problem was that the state of Pennsylvania does not recognize the federal capital loss carryforward the way Georgia does. Could moving when he wanted to really cost him an additional $150,000 in state taxes? We found a solution.”

Our Advice

Waldron recommended the client reset his tax basis by recognizing the capital gain of his stock and immediately buying it back. He did just that, stepping up his cost basis from $10,000 to $5 million prior to establishing residency in Pennsylvania. Since the stock sale was at a gain, and not a loss, it was deemed to not fall under the IRS ‘wash sale rule’, which prohibits the sale and re-purchase of identical or similar stocks within 30 days in an effort to avoid taxes. Once the client was back in the state of Pennsylvania, he continued his long-term plan to reduce his overall exposure to the single stock, but did so in a way that was exempt from Pennsylvania state tax.

Interested in learning more about the effect of taxes on business owners? View our additional resources and get a free copy of John Waldron’s “The Entrepreneurial Journey” below.


Team Members Who Can Help

Benjamin Greenfeld
Chris J. Roe
Michael Krol

Income Tax Planning


Income Tax Review Summary
Income Tax Mitigation Analysis and Strategies
Change in residency (Domestic or International)
Intra-family Loan Structuring and Tracking

Captive Insurance Company Analysis, Implementation and Management
Legal Planning
Coordination of Investment Portfolio with Entity Ownership

Expertise for Every Scenario

Business Sale
John Waldron

John J. Waldron, CEO and Founder, highlights pre- and post-sale approaches to maximizing the sale of a business.

Preparing Your Kids
for Wealth
Matthew Helfrich,

Matthew Helfrich, Partner and President, relates how Waldron helps heirs grow into responsible stewards of their family’s wealth and legacy.


Robert H. Wyche, Partner and Managing Director, shows how we help highly compensated corporate executives and other professionals to make the most of their compensation packages.

Supporting Your
Family Office

Michael Krol, CFP®, CPA, Partner and Head of Wealth Advisory, explains how Waldron efficiently helps family offices provide expanded services for their clients.

Considering the
Effect of Taxes

Robert H. Wyche, Partner and Managing Director, relates the story of a coordinated carryforward strategy.


Benjamin Greenfeld, CFP®, Partner and Chief Investment Officer, illustrates the wisdom of an investment model based on needs and objectives.

Complete Financial

Kevin Searfoss, CFP®, CDFA™, Senior Wealth Advisor, puts all the pieces together to show the strength of integrated services.


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