Tax Alpha Insider

Tax Alpha Insider

With stocks at all-time highs, reasons to diversify are apparently at all-time lows

A certain slice of humanity loves concentrated risk

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Brent Sullivan
Jan 20, 2026
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Welcome back to work after a long, hopefully relaxing weekend.

Friends in the industry are collectively wondering when their friends, family, and clients will take a few (highly concentrated) chips off the table.

Although continuing to hold a concentrated stock might seem like a status-quo stance, it is, in fact, one of the most risky investment strategies an investor could pursue, and it is especially problematic for those wealth creators who seek to become guardians of wealth for themselves and their families… Bessembinder (2018) shows that, during the 1926–2016 period, for all the 25,967 common stocks in the Center for Research in Securities Prices (CRSP) database, by far the most frequent one-decade buy-and-hold return is -100%.

Nathan Sosner (2022) “When Fortune Doesn’t Favor the Bold: Perils of Volatility for Wealth Growth and Preservation” The Journal of Wealth Management

But, of course, a certain slice of humanity loves concentrated risk, and there’s a huge counternarrative…

This post is confusing. Choosing friendship over a trillion dollars, or something? Or maybe that diversification is bad, or something? Or that choosing a friend who recommends diversification is bad financially, but ultimately worth it… in hindsight… or something? This is the modern internet, where pictures of billionaires with gibberish prose get clicks, hence why I included it in this blog post.

For the third post in a row, I will copy/paste Morgan Stanley’s “eyeroll” table of reasons people continue holding concentrated positions. We should, apparently, include “Hindsight” as another reason.

Relatedly, Meg makes an interesting point by arguing that holding “the one” stock is kind of a male thing.

Latest Tax Alpha Trends

With markets near all-time highs, concentrated position management is the top line of the latest issue of Tax Alpha Trends (below).

Tax Alpha Trends is a one-pager about hot topics in taxable wealth for HNW/UHNW advisers. It is the radar that I frequently have in front of me when folks ask, “What’s on your radar?”

You can see every issue of Tax Alpha Trends going back to 2023 here…

Tax Alpha Trends

Tax Alpha Trends

Brent Sullivan
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February 1, 2025
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