Roy Williams' (Unintentional) Investment Wisdom

Ol’ Roy, a frickin North Carolina icon.  Former players rave about their playing experience, and his success on the court speaks for itself. For the basketball community and especially UNC fans, Roy’s abrupt exit from coaching was seismic.  Despite exiting the spotlight, he continues to be visible around the basketball program, the university, and college athletics.

Over his 18 seasons at UNC, he was a gold mine of content for journalists. His press conferences were wide-ranging and always entertaining: Dean Smith stories, third-person self-references, and a fair share of “daggums” — all fond memories now left behind. One quote Roy frequently repeated after wins, sticks with me: “Everything is better when the ball goes in the basket”.  

Pretty simple, right? After all, the object of the game is putting the ball in the basket.  Allow me to draw some parallels between Ol’ Roy’s message in basketball terms and the investing world.  

Everyone is Happier When You’re Making Shots the Market is Going Up 

•  It’s no secret. As a player, making shots gives you confidence that can translate to other parts of your game. And when the whole team is making shots, that’s great for morale.

•  Watching your portfolio rise is both rewarding and encouraging. It’s a well-earned reflection of your participation and discipline — and it’s perfectly natural to take pleasure in this success!
   

A "Hot Hand" Can Lead to Overconfidence

• There are two sides to every coin. While some players use a good shooting performance to elevate their game, others let it go to their head or become complacent. “Heat checks” – when a shooter is on a hot streak and starts taking harder shots, can derail a team’s hard work.   

• A string of strong investment returns can create overconfidence. The assumption that current market conditions will continue in perpetuity can lead to riskier behavior — chasing performance, abandoning diversification, or ignoring long-term goals. A strong market is a gift, but it’s not a reason to lose investment discipline.

Coaches & Advisors Guard Against Complacency 

• Winning cures a lot. Coaches will frequently use a win as a good time to dissect the smaller imperfections of their team, knowing they are riding a wave of momentum. Addressing those weaknesses tend to prove valuable in future games. 

• Advisors have a responsibility to guide clients’ expectations – especially in surging markets. It’s easy to get swept up in the excitement of a boom, which makes it all the more important to discuss the reality of future downturns. Every rational investor understands it’s not a matter of if, but when the next decline will come—and they need to be prepared.

Don't Confuse Luck with Skill

• In basketball, not every made shot is a good one. Limit the bad shots in favor of the good ones.

• The same applies to investing. A risky investment might pay off, but that doesn’t mean it was the right play. Long-term success comes from repeatable, disciplined decisions.  

“Everything is better when the ball goes in the basket” — sure, but the best teams know why it’s going in. Momentum feels great, but smart decisions and strong habits are what sustain it. That’s true whether you’re on the court or managing your financial future.