Ben Carlson of Ritholtz Wealth Management has flagged what he calls “one of the biggest trends that I’ve seen in the wealth management space in the last 5 years”: clients walking in the door already asking for tax-aware diversification, rather than advisors having to sell it to them. The two archetypes he cited on The Long View podcast will sound familiar to a lot of 24/7 Wall St. readers.
The first: “I have stock options in Google because I work there. It’s 90% of my net worth. I know I need to diversify, but I also don’t want to just rip the Band-Aid off and sell.” The second: “I put money in NVIDIA 7 years ago and it’s worth way more than it was, but help me diversify so I don’t lose it all, but also make the tax bill easier to withstand.”
Why the Problem Is Bigger Than Ever
NVIDIA (NASDAQ:NVDA | NVDA Price Prediction) closed at $225.32 on May 15, 2026, after touching an all-time high of $236.54 the day before. A holder who bought seven years ago is sitting on a position with a trailing P/E of 46 and a beta of 2.24. The stock fell from $110.15 on April 1, 2025 to an intraday low of $86.62 on April 7, 2025, a reminder that concentrated winners can give back more than 20% in a week.
The Google example is just as live. Alphabet (NASDAQ:GOOGL) is up 137.35% over the last year and 25.43% year-to-date, with Q1 2026 revenue growth of 21.8%. A long-tenured Googler with vested RSUs is staring at embedded gains taxed at federal long-term rates up to 20%, plus state, plus the 3.8% net investment income surtax.
The Toolkit (and the Kitces Caveat)
Carlson credits lower fees and the rise of direct and custom indexing for making tax-loss harvesting accessible to regular investors. A custom-indexed S&P 500 sleeve can harvest losses on individual constituents while the holder gradually unwinds the concentrated stake, often paired with exchange funds, charitable remainder trusts, or 10b5-1 plans for employees.
Christine Benz pushed back, citing a prior conversation with Michael Kitces who “felt that they were being kind of grossly oversold in terms of the dollar benefit or the percentage benefit to a portfolio.” Translation: the marketed alpha from tax-loss harvesting is often smaller than the brochures suggest, particularly in trending markets where losses are scarce.
Where the Money Tends to Land
Microsoft (NASDAQ:MSFT) is a common landing spot for diversifiers. Its beta of 1.09, -11.26% year-to-date performance, and recently raised $0.91 quarterly dividend illustrate the trade-off: lower torque, steadier cash flow. Carlson’s framing on The Long View is the right starting point. The right answer is rarely all at once.
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