Here We Go Again: How to Leave Money to Your Kids Without Fumbling the Handoff
Written during football season while Tyler's mom tries to master the concession stand nacho cheese dispenser…
Here we are again, deep into another football season. As I've been spending countless hours working the concession stand (and learning that managing portfolios is easier than operating a hot dog warmer), I've been thinking about patterns that repeat themselves.
Let me be honest - I really dislike using sports analogies. As a former cheerleader, not a player, they often feel forced and inauthentic. But fall is the one time of year I break this rule, because football season makes certain truths about preparation, teamwork, and protection impossible to ignore.
Just like Tyler's team runs the same proven plays week after week, families have been dealing with the same wealth transfer challenges for generations. And just like I keep making the same mistakes with that nacho cheese dispenser, families keep repeating the same mistakes when preparing the next generation for financial responsibility.
The Pattern That Won't Break
There's a sobering statistic that keeps repeating: 70% of family wealth transfers fail. It's been happening for centuries across every culture. Italians call it "from the stalls to the stars to the stalls again.” In China, it's "teacup to teacup.” Americans say "shirtsleeves to shirtsleeves in three generations.”
Different languages, same pattern.
The Football Analogy That Changed Everything
Roy Williams, founder of the Williams Group and former NFL player, uses this analogy: How can you surround your heirs with professionals you trust (like an offensive line) so that when it's their time to catch the ball, they are ready?
This became deeply personal this season. Tyler plays right guard on his team's offensive line. Every Friday night, I watch him and his teammates create a protective pocket around their quarterback, giving him time and space to make good decisions under pressure.
Yet when it comes to wealth transfer, parents often expect their kids to catch a financial "pass" worth millions without the same preparation and protection.
The opposing team? Bernie Madoffs, friends with hidden agendas, and well-meaning people with bad advice. One heir lost two-thirds of his wealth within six years because a friend suggested he try "social impact investing" through the friend's brother.
From Cheerleader to Coach
When it comes to family wealth, parents often stay stuck in the cheerleader role when they need to become coaches. Cheerleaders support from the sidelines (which is important!). But coaches prepare players for the game, teach strategy, and help them handle pressure.
When it comes to your family's financial future, your kids need you to coach them, not just cheer for them.
The Real Issues Behind the 70% Failure Rate
After studying over 2,500 wealthy families for 20 years, the Williams Group identified the top three reasons wealth transfers fail. None of them are about investment strategies or tax planning.
Issue #1: Trust and Communication (60% of failures)
Parents don't want to tell kids about wealth because they fear it will kill motivation. Kids don't trust parents to handle the transfer well. Siblings don't trust each other.
The financial services industry doesn't help. We're great at discussing what happens after you die, but terrible at addressing emotions around family money while you're still alive.
Issue #2: Heir Preparedness (25% of failures)
Most families focus on financial literacy - how to read account statements, understand stocks and bonds. That's like teaching football rules without teaching how to handle Friday night pressure.
The real education needs to be about the social dynamics of wealth. How do you handle friends with "investment opportunities"? How do you maintain values when you have more money than peers?
Issue #3: Values and Mission (10% of failures)
When wealth transfers, you're transferring communication practices, values, and family mission. If those aren't clearly defined and consistently modeled, wealth becomes a burden rather than a blessing.
The Concession Stand Wisdom
Working the concession stand taught me this about wealth transfer: The behind-the-scenes preparation is just as important as the Friday night game.
Nobody sees me burning hot dogs or wrestling with the hot dog warmer, but if I don't do that work, players and fans don't get fed. Similarly, the conversations and values work you do with your kids while you're alive - that nobody else sees - determine whether your wealth transfer succeeds or becomes another statistic.
Breaking the Pattern: Questions to Start With
Instead of jumping into estate planning documents, start with the Williams Group's powerful question for every family member:
"What do you care about and why?"
Then ask yourself:
Are we building the right "offensive line" of trusted professionals around our heirs?
Are we preparing our kids for the pressures that come with wealth?
Are we clearly communicating our values through our actions?
Here We Go Again... But This Time Different
Tyler's football team runs the same plays because they work. But they spend countless hours practicing, adjusting, and preparing for different scenarios.
Your family's wealth transfer doesn't have to follow the same failed pattern. You can be the generation that breaks the cycle - but only if you're willing to do the hard work of preparation, communication, and values alignment.
The game is won or lost in practice, not just on game day.
And if you'll excuse me, I need to watch some YouTube videos about nacho cheese dispensers. Some patterns are worth breaking.
Let's create a game plan that prepares your family for generational wealth transfer.
This article is for informational purposes only and is not a replacement for real-life advice, so make sure to consult your tax, legal, and accounting professionals before modifying your investment strategy for tax considerations. The content is developed from sources believed to be providing accurate information. The information in this material is not intended as tax or legal advice. It may not be used for the purpose of avoiding any federal tax penalties. Please consult legal or tax professionals for specific information regarding your individual situation. This material was developed and produced by FMG Suite to provide information on a topic that may be of interest. FMG, LLC, is not affiliated with the named broker-dealer, state- or SEC-registered investment advisory firm. The opinions expressed and material provided are for general information, and should not be considered a solicitation for the purchase or sale of any security. Copyright FMG Suite.
