The Scorecard

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In 2016, after 5 years of investing solely in passive index funds, I began allocating a moderate amount of my funds to active equity investments. I started out with approximately 20% of net worth and planned to slowly increase the allocation as my investment skills grew, provided early results were promising. The tricky thing about judging investment performance is that over short to medium timeframes it's impossible to know whether to attribute results to skill vs. luck (or the lack of it). But we're approaching the 10-year mark of my active investment journey and I think it's time to do an honest accounting of the results thus far, while acknowledging that even 10 years is an inadequate timeframe to declare anything conclusively.

The benchmark for this comparison will be the S&P 500 index fund, a formidable competitor and a realistic representation of my opportunity cost as it is where all of my passive funds are invested. The assumption will be that any time I made an active investment I instead would have invested those funds in Vanguard's traditional S&P 500 index fund (VFIAX), with all dividends reinvested, and that any time I sold an active investment I would have sold a proportionate amount of these theoretical S&P 500 holdings.

Here are the results for my active investments thus far:

• Holding Period: April 2016 - August 2024
• Return: +817%
• S&P 500 Return: +189%

• Holding Period: March 2020 - Present
• Return: +185%
• S&P 500 Return: +211%

• Holding Period: April 2021 - July 2024
• Return: -8%
• S&P 500 Return: +54%

• Holding Period: May 2024 - June 2025
• Return: +3%
• S&P 500 Return: +14%

• Holding Period: September 2024 - Present 
• Return: +17%
• S&P 500 Return: +16%

So how have I faired overall? The good news is that I've outperformed the S&P 500 by a meaningful, though far from astronomical amount. For every dollar I would have made invested in the S&P 500 my active portfolio has earned $1.31. The bad news is that this outperformance is due almost entirely to a single investment in Apple. I do not think this disqualifies the result, as it's the nature of investing that a few big winners tend to make up a disproportionate amount of the returns—even Warren Buffett has stated that Berkshire's success can be attributed to just 12 truly good decisions in 60 years—but I admittedly would feel more confident if two of the five investments had significantly outperformed rather than just one.

It's worth noting that the overall outperformance is weighed down by the fact that although Apple was my largest investment in terms of percentage of net worth at purchase, it was actually my smallest investment in dollar terms as it was my first active investment, with my net worth growing significantly from earned income and investment returns over this 10-year period. If an equal dollar amount had been contributed to each investment the outperformance would have been 109% rather than 31%. I don't think this is the correct way to judge the performance, but it is an interesting demonstration of how a single superior investment result can carry a portfolio.

In any case, the results are good. The S&P 500 has been on an absolute tear these past 10 years and shows some signs of being overvalued, so it will be interesting to see how things go from here [1].

January 9, 2026