How Tax-Aware Long-Short Can Make a Big IPO Payday Even Bigger

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All investing involves risk, including the potential loss of principal, and there is no guarantee that any investment plan or strategy will be successful.

Advisory services are provided by Hendershott Wealth Management, LLC (“HWM”), an investment advisor registered with the U.S. Securities and Exchange Commission. Registration does not imply a certain level of skill or training.

Content discussed is for information purposes only and does not constitute an offer, or solicitation of an offer, or any advice, or recommendation to purchase any securities or other financial instruments–and may not be construed as such.

All information or ideas provided should be discussed in detail with an advisor, accountant, or legal counsel prior to implementation–and all examples are hypothetical, not reflective of actual executed transactions or client experiences.

The realized tax benefits associated with tax-aware strategies may be less than expected or may not materialize due to the economic performance of the strategy, an investor’s particular circumstances, prospective or retroactive change in applicable tax law, and/or a successful challenge by the IRS. In the case of an IRS challenge, penalties may apply. The discussed tax-aware strategies have additional costs that will increase investors’ expenses and as a result will reduce returns.

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All content originates with the Hendershott Wealth Management team. AI software was used to support clarity and tone during editing. Final content was written and reviewed by the Hendershott Wealth Management team for accuracy.



Timestamps
00:06 – How tax-aware long-short reduces your lifetime tax bill.
00:23 – $9M IPO case study and Jennifer’s concentrated stock position.
00:55 – The IPO tax problem that shrinks $9M to $6M.
01:33 – Simple math showing her $6M portfolio lasts only 26 years.
01:57 – Why she’s financially stuck without a tax-efficient strategy.
02:35 – How UTEWM® helps diversify without triggering capital gains.
02:44 – Avoiding the immediate $3M tax bill through long-short investing.
03:03 – Portfolio projection showing growth to over $20M.
03:43 – Schedule a conversation with our advisory team.