From Fantasy Football to Financial Strategy: Lessons From Draft Season

Summer is winding down. Kids and grandkids are back in school, trips to the shore are giving way to cooler evenings, and my favorite season is finally here—football. More specifically, fantasy football.

I’ve been playing fantasy sports since before it was “cool.” Back then, there was no ESPN app or live scoring. We’d get reports via fax (yes, fax), and if you wanted to know how your players did, you had to check the box scores in the next morning’s newspaper. Today, I’ve got four drafts on four straight nights. My sons are more involved each year, and I love watching them get into it—studying projections, debating draft picks, and (sometimes) reminding me not to let my Jets fandom cloud my judgment. (Being a Jets fan builds character. We’re used to heartbreak by Week 4, so at least fantasy football gives me a shot at a winning season.)

Draft Day and the RITE Framework

In fantasy football, success isn’t just about nabbing the best player. It’s about balancing a roster that can withstand injuries, bye weeks, and the unpredictability of a long season. That’s not so different from managing wealth through our RITE framework—Risk, Investments, Tax, and Estate.

Risk: You wouldn’t draft only running backs, no matter how good they are. Diversification matters. In financial planning, that means balancing asset classes, managing liquidity, and preparing for the unexpected.

Investments: A strong draft requires discipline—knowing when to grab value and when to pass. Investing works the same way. Chasing headlines or hot tips rarely wins championships. Thoughtful allocation does.

Tax: Fantasy players know the scoring rules inside and out. In wealth management, the “rules of the game” are the tax code. Whether it’s Roth conversions, harvesting losses, or taking advantage of deductions, strategy here often determines the real outcome.

Estate: In fantasy, you think beyond Week 1—you’re planning for the playoffs. Estate planning works the same way. It’s not just about today’s balance sheet; it’s about positioning assets to carry forward, with clarity for the next phase.

Teaching the Next Generation

What I love most about fantasy football is sharing it with my kids. They’re learning strategy, math, probability, and maybe a little humility when a sleeper pick doesn’t pan out. More importantly, they’re learning that success comes from preparation, adaptability, and long-term thinking. Those are lessons that extend well beyond football.

In our house, the conversation shifts easily from draft rankings to investment ideas. The parallels are clear: pick with intention, know your downside, and always keep an eye on the future.

Why This Matters

Fall is a season of new beginnings. Just as football teams reset and students head back to class, families have a chance to revisit their financial playbooks. Maybe that means rebalancing investments after a volatile summer, updating estate documents, or revisiting your tax strategy before year-end. Whatever it is, the goal is the same: create a lineup that works not just for today, but for every stage ahead.

At Members’ Wealth, we use the RITE framework to help families do just that. Because while a fantasy football trophy is fun (and bragging rights at home are priceless), the real win is building a financial strategy that supports your life in every next phase.

The information provided is for educational and informational purposes only and does not constitute investment advice and it should not be relied on as such. It should not be considered a solicitation to buy or an offer to sell a security. It does not take into account any investor's particular investment objectives, strategies, tax status or investment horizon.

These examples are for illustrative purposes only and do not represent actual client experiences. Individual results will vary based on personal financial circumstances and tax laws.

About the Author – Stu Caplan, CFP®

Stu Caplan is Senior Wealth Strategist at Members’ Wealth, a boutique wealth management firm that offers a comprehensive approach to serving individuals, families, business owners, and institutions.

The firm’s goal is to preserve and grow its clients’ wealth to endure over time, while thoughtfully evolving its strategy to suit an ever-changing world. With over 20 years of industry experience, Stu and the Members' Wealth team thrive on bringing clarity and confidence to clients' unique situations.

Stu received his MBA from The Robert H. Smith School of Business at the University of Maryland and his bachelor’s degree from the Eller College of Management at the University of Arizona. Stu resides in Bucks County, PA with his wife and two sons. He’s an avid golfer and is thrilled that his boys have embraced the game. He also volunteers his time as a board member of the PKD Foundation and Abrams Hebrew Academy.

To get in touch with the Members’ Wealth team today, I invite you to email info@memberswealthllc.com or call (267) 367-5453. 

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Investment strategies, including rebalancing, do not guarantee improved performance and involve risk, including potential loss of principal. Past performance does not guarantee future results.

The information provided is for educational and informational purposes only and does not constitute investment advice and it should not be relied on as such. It should not be considered a solicitation to buy or an offer to sell a security. It does not take into account any investor's particular investment objectives, strategies, tax status or investment horizon. 

All information has been obtained from sources believed to be reliable, but its accuracy is not guaranteed. There is no representation or warranty as to the current accuracy, reliability or completeness of, nor liability for, decisions based on such information and it should not be relied on as such.

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