I recently had the chance to meet Howie Roseman, GM of the Philadelphia Eagles, at an event hosted by Causeway Capital. I’ve followed his career a bit, not because of the two Super Bowl wins, but because we have a bunch in common.

He grew up rooting for the Jets. He tried endlessly to get a job with the team only to be rejected every time. I unfortunately still root for the Jets and while I never applied for a job with the team, I certainly feel his pain!

I went to sleepaway camp with a kid named Jedd Fisch. Howie shared a college apartment with Jedd Fisch.

Jedd Fisch coached at the University of Arizona. Nick Foles, Super Bowl LII MVP, played quarterback at the University of Arizona. I am a proud alum of the University of Arizona, GO CATS!

It’s clear to me that in another dimension, Howie and I are best friends who talk about football and personal finance all day, but I digress….

What really stuck with me about his talk was his mindset.

Howie talked about his journey from being rejected by nearly every NFL franchise to running one of the most successful organizations in sports. He started as a teen writing letters to teams literally begging for a shot. When those teams said no, he didn’t take no for an answer he kept writing back. Eventually he had a dialogue going with several teams even though they thought he was crazy (his words, not mine) and would give him advice hoping he’d go away. That feedback led him to law school, where he learned how to structure contracts around the salary cap system. This was his “in” and the rest is (recent) history.

His story was a reminder that success isn’t linear. It’s built on persistence, humility, and self-awareness. As strange as it sounds, the lessons of building a football roster aren’t that different from building a great advisory team or a great portfolio.

1. Know Your Team—and Your Gaps

Howie said his most important job is knowing his team better than anyone else: who they are, where they shine, and where the holes are. That struck me.

In wealth management, the same principle applies. As advisors, we’re not just managing portfolios, we’re managing people, relationships, and skill sets. The best leaders know the strengths on their roster and where they need support. Whether that’s pairing a great client with a detail-oriented planner or recognizing when to bring in a tax or estate specialist, the idea is the same: you can’t win if you don’t know your people.

It’s the same for investors. Knowing your “team” means understanding what’s in your portfolio and how each piece fits. It’s easy to focus on top performers, but ignoring weak spots like concentrated risk, overexposure to one sector, or an outdated strategy can undo years of progress. Like a good GM, part of our job is identifying those blind spots early and adjusting before they cost us the game.

2. Fit Matters More Than Flash

Roseman spoke about team chemistry, how culture and fit often matter more than pure talent. Super Bowl teams aren’t just built on stars; they’re built on alignment. Players buy into the system, understand their role, and trust the people around them.

That lesson hits home for business leaders and investors alike.
In corporate America, we often hire for resumes and credentials. In investing, we chase shiny new ideas like hot funds, trendy asset classes, or the latest “can’t-miss” opportunity. But as Howie said, talent without chemistry rarely works.

When building a firm, I’ve learned that the best hires aren’t always the flashiest. They’re the ones who make the team better. When building portfolios, the best investments aren’t always the ones with the biggest returns, they’re the ones that fit your goals, risk tolerance, and time horizon.

Winning, in football or finance, comes from cohesion. It’s the compounding effect of many right fits, not one lucky pick.

3. Embrace Failure as Part of Growth

What impressed me most about Howie was how openly he talked about failure. He didn’t sugarcoat it, he’s made big mistakes, both in personnel and leadership. Instead of hiding from them, he studied them, learned from them, and came back stronger.

In our world, the same mindset separates good advisors from great ones. Markets humble everyone. Strategies don’t always work. Clients’ lives evolve in unpredictable ways. How we respond, whether we retreat or refine, determines our long-term success.

In portfolio management, this means reviewing what didn’t work, not just what did. In business, it means being honest about what needs to change even when it’s uncomfortable. Growth starts where ego ends.

4. Shared Goals Create Alignment

Another takeaway: Howie emphasized that great teams share common goals and challenge each other to be better every day. Compromise, he said, is a sign of indecision and leads to suboptimal results.

That’s true in wealth management, too. Everyone on a team should be aligned around the same mission: delivering clarity and confidence for clients.

When we work with clients, that same alignment matters. The best outcomes come when spouses, children, and advisors are all on the same page. Financial goals are shared, not siloed. Just like a locker room, unity drives execution.

5. The Game Plan: Preparation Meets Passion

What made Howie’s story resonate most was his drive. He didn’t wait for opportunity; he prepared relentlessly for it. He studied, he networked, he adapted. That combination of passion and preparation is the same energy I see in the best clients, the ones who stay engaged, ask questions, and play the long game.

Financial success, like football success, isn’t about guessing the next play. It’s about having a system, surrounding yourself with the right people, and sticking to your plan when others panic. It’s about building chemistry—within teams, families, and portfolios—that endures through every market cycle.

Final Thoughts

Walking away from that evening, I couldn’t help but think: leadership, whether on the field or in finance, is about knowing your people, owning your mistakes, and staying relentlessly curious.

That’s how great teams are built and how lasting wealth is, too.

Every great team starts with the right strategy. Let’s talk about yours.

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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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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. 

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