Manage Your Investments Like Your Fantasy Football Team

Manage Your Investments Like Your Fantasy Football Team

September 18, 2026

Fantasy football notes illustrating investment strategy and portfolio management

Manage Your Investments Like Your Fantasy Football Team

September 18, 2026

By Justin May, Portfolio Manager

This weekend marks week 2 of the NFL season. For me, it’s week 2 of the fantasy football season. I haven’t watched a football game since high school, but I’m an avid fantasy football player. So avid, in fact, that I fly across the country every year for my league’s draft weekend. Many of the principles behind good fantasy football management also apply to investing. Here are some:

  1. Past performance does not guarantee future success. In 2025, I used my first-round pick to draft the previous year’s top running back, Saquon Barkley. The year prior, he scored over 22 points per game, an incredible number. How did he do on my team? 14 points per game, a huge disappointment. Last year’s top players, and investments, have a high chance of underperformance in the next year.
  2. Diversify. Every single year, one of my players gets injured for the remainder of the season. If that player is my main source of points, my season is basically over. So, I try to keep my stars’ backups on hand, and where possible I might prefer two good players over one great one. Every year, the loser of my league must complete a punishment. This year, the loser must eat 66 hotdogs consecutively before eating any other food. In real life, the punishment is more severe. If you’re too exposed to one investment, or the market generally, you may lose what you can’t afford to.
  3. Don’t swing for the fences. I play in a PPR (points per reception) league. That means that my player scores a fantasy point every time they catch the ball. I love to take advantage of this rule and load up on players who don’t usually make flashy big-yard plays, or score touchdowns, but who simply catch the ball a lot and build up fantasy points steadily. The same goes for investments – don’t swing for the fences, especially if you are withdrawing from your portfolio. Create a portfolio that will perform consistently in a variety of possible market outcomes, because nobody knows what tomorrow will bring.
  4. Buy low, sell high. I drafted Derrick Henry this year. Derrick Henry is a human bowling ball and an incredible running back. But at 32 years old and after 10 seasons in the NFL, people expect him to slow down. I got him for a great deal much later in the draft than expected. I’m a value investor in both fantasy football and in my profession. This past Sunday, Derrick Henry scored more fantasy points than any other running back in the NFL. His value immediately shot up. I just traded him away, and received players who didn’t do so well. Why? Because, like investing, trimming your recent winners to buy things that are out of favor through regular rebalancing is a winning strategy.

These are the rules that have served me well managing both fantasy football teams and investment portfolios for years. They don't guarantee a win in either arena, but they keep me from making the mistakes that cost the most. We'll see what this season brings.

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This article is not intended to provide tax, legal, accounting, financial, or professional advice. Readers should seek advice from qualified professionals who can review their specific circumstances. Old Peak Finance endeavors to provide information that is accurate and current. However, we cannot guarantee that this information has not been outdated or otherwise rendered incorrect by new research, legislation, or other changes. Old Peak Finance has no liability or responsibility to any individual or entity with respect to losses or damages caused or alleged to be caused, directly or indirectly, by the information contained on this website.

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