Tax
Sep. 30, 2026
The real value of tax-aware long/short investing
Tax-aware long/short investing seeks to generate capital losses that can offset taxable gains while maintaining market exposure; in the first of a two-part series, the strategy's mechanics and potential economic value are examined.
Mohan Ananda
Mohan Ananda is a California attorney, entrepreneur, author and family-office executive. He practiced corporate and intellectual-property law for approximately four decades and has founded and advised public and private companies. His writings address entrepreneurship, technology, wealth stewardship and multigenerational legacy planning.
For investors with substantial taxable portfolios, the return shown on a brokerage statement does not tell the entire story. What ultimately matters is how much wealth remains after federal and state taxes, investment expenses and transaction costs.
This distinction is particularly important for entrepreneurs, executives and families who periodically realize significant capital gains from concentrated sto...
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