The change of fortune was especially clear over longer periods. In the first half of five-year periods, the median first-half winner beat the S&P 500 by an annualized 9.5% per year but underperformed by 0.9% in the second half. Looking at 10-year periods, the median first-half winner beat the S&P 500 by an annualized 6.7% but underperformed by 1.7% in the second 10 years.
Together, these findings define the single-stock challenge. Investors must first be fortunate enough to have a winner, own it at the right time and then reduce the concentrated risk before gravity takes over. For taxable investors, getting the timing wrong could be costly, and embedded capital gains can complicate plans to reduce the exposure.
Concentration Risk vs. Tax Impact: A Key Investor Trade-Off
That’s why the diversification decision shouldn’t be framed as a simple sell-or-hold choice. For investors with concentrated stock, the question is rarely “should I sell everything today?” More often, it’s “will my after-tax wealth be higher in five or 10 years if I pay taxes now to diversify?”
That decision involves three factors:
- Selling today pulls the tax bill forward, leaving less capital to reinvest and compound.
- Diversifying the portfolio may reduce the risk of pre-tax underperformance, especially if the concentrated stock isn’t among the relatively few standout winners.
- Paying some taxes now by trimming the position could make the eventual tax bill smaller later on.
Paying some taxes now can feel painful because the tax bill is immediate and visible. The cost of staying concentrated may seem less black and white, but diversifying today may narrow the range of after-tax wealth outcomes—most importantly by mitigating the downside risk if the concentrated stock falters.
Strategies such as staged selling, tax-loss harvesting, charitable gifting, donor-advised funds, exchange funds, Section 351 ETF exchanges or other customized approaches may reduce the tax drag of diversifying. They can also be combined through a multi-phase transition into a separately managed account. This approach enables investors to diversify gradually while also managing taxes and risk. The specific choice depends on individuals’ unique circumstances.
Lottery stocks that create strong gains exist, but they’re uncommon, hard to identify in advance and prone to losing momentum. Instead of ignoring taxes or trying to eliminate risk entirely, investors should balance the known cost of realizing capital gains against the less visible risk of not diversifying. In the end, the most valuable question may not be whether a stock can still win but whether a financial plan depends on it—and whether diversifying now could reduce the risk of falling short.