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Year-end tax planning for wealthy families
Tax savings to consider heading into this holiday season As we approach the end of another year, it’s important to take stock not only of our blessings heading into the holiday season, but also of our taxes. Below are five tax-related items every wealthy family should review before December 31st: Update your tax estimates Gift highly appreciated stock to charity Harvest losses (or gains) across your portfolio Reviewing gifting of assets to your children Maximize retirement pl
Nov 20, 20254 min read


Navigating the Risks of a 351 Exchange
We wrote earlier this year about strategies to diversify out of highly appreciated stock , including a solution called Section 351 exchange. While a 351 exchange allows you to defer (not eliminate) taxes by exchanging a “diversified” portfolio of appreciated stocks for a diversified ETF, there are risks to be mindful of. The takeaway is to engage in this type of transaction only with experienced ETF sponsors who also can reliably grow their fund after launch. In this post, we
Nov 7, 20254 min read


What is a 351 exchange and how can it help you?
If you hold an outsized and highly appreciated position that you would like to diversify out of, then this post is for you. Many people find themselves in this situation, whether you acquired it by working at a successful company for many years, buying early, or receiving the holding as a gift. In this post, we assess several options available, with a focus on the 351 exchange as a tax-efficient and low-cost way to diversify. Tools for diversification Some solutions are simpl
Aug 22, 20253 min read


Long/short tax loss harvesting: pros and cons
Tax-aware hedge fund strategies promise outperformance and tax efficiency but are their claims overstated? We just released a white paper titled "Tax-Aware Hedge Fund Strategies: Separating Hype from Substance" which analyzes these claims. Tax deferral is valuable, as delaying taxes allows for greater investment growth. This value increases with longer deferral periods and higher returns. All tax-efficient investing offers this benefit, including buying and holding individual
May 8, 20252 min read
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