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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

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

In the world of wealth management, conventional wisdom often focuses solely on financial accumulation. However, a recent book...

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

This is our mid-year update on the long-term expected returns of various asset classes, a calculation we perform twice annually. After April lows for stock prices, the rebound in stock prices has been rapid. High returns for stocks today often mean lower returns in the future. This update aims to quantify for you just how much of future returns have been pulled forward. Our estimates are grounded in first principles: the fundamental driver of value is future cash flows. For b

Much has already been written about the updates in the new tax bill that was just passed. Most changes for individual tax payers are...

Every time the stock market falls, media headlines suggest reasons to wait before buying (i.e. trying to time markets). In early 2025, the S&P 500’s price-to-earnings (P/E) ratio was 27, which was the highest it had been in 25 years, excluding a short period during the 2021 COVID lockdowns.  While this implied that US stocks were expensive and future returns would be low, bank research departments held a bullish outlook on future returns. During the “tariff tantrum” in April,

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

There's a lot of buzz around Roth IRA conversions, and for good reason. Converting your traditional IRA can be a powerful financial move,...