Educating the Rising Generation

NEWSLETTER

Family office insights this week:

• Educating and preparing the next generation

• Typical cost and size of family offices

• An uncomfortable truth for family office advisors

• Books: breaking the money silence

• When wealth, love & families collide—in an Oscar winning movie

Educating the Rising Generation

Preparing Heirs for the Great Wealth Transfer

With more than $100 trillion expected to change hands globally by 2048, the so-called Great Wealth Transfer is well underway. 

It brings with it new complications for both family members and family office teams working with them to manage their wealth.

An obvious but also commonly overlooked challenge is educating the next generation to become confident stewards of inherited wealth.

This week we spoke to Torri Hawley, Chief Learning Officer at Tamarind Learning, an interactive learning platform created specifically for this purpose.

She unpacks various intricacies on inheriting wealth, and notes how families should rethink how they prepare heirs to equip them with values, context and emotional readiness.

Vertical and Horizontal Transition

An overlooked element of inheritance that Hawley points out, is how it’s not just a vertical transition from one generation to the next. 

“Much of the wealth is going to pass horizontally first,” she explains. “Spouses—often women—will inherit before it flows down to Gen X or Millennials.” 

Hawley believes there is an education gap not because of any personal failing, but that it’s an industry blind spot built on precedent.

“Families assume heirs will figure it out when the time comes, but that time often arrives under pressure, after a triggering event. Proactive, structured education builds not only competence, but confidence—and helps create informed, collaborative participants in the long-term success of the family.”

From Technical to Transformational

Hawley notes how women and younger generations interact with wealth differently, and want more than financial knowledge. 

The old model of “next-gen education” focused heavily on this financial literacy: understanding compound interest, reading balance sheets, or interpreting a trust document. 

But for today’s inheritors—especially women, Millennials, and Gen Z—Hawley believes that is just the starting point.

“They want to understand the why behind the wealth. Where did it come from? What’s its purpose? What’s expected of me? You can’t just teach them about asset allocation—you have to tie that learning to meaning, legacy, and identity.”

This is especially important because most rising gens won’t directly control their wealth anytime soon. 

“They may be in trust structures or governed by family office policies for decades. That’s why we say: education isn’t a luxury. It’s essential.”

Annual Meetings Aren’t Enough

One of the most common missteps that Hawley sees families make is over-relying on the annual family meeting as their main education vehicle.

“You can’t expect someone to grasp complex trust structures from a one-hour presentation once a year. We forget most of what we learn in 24 hours if it’s not reinforced.”

What is her recommended solution? 

“Start with a solid, standardized foundation—clear vocabulary, shared learning goals, relevant content. Then customize where it matters. You don’t need to spend hundreds of thousands to make it effective.”

Embedding Education into Governance

Education is no longer a nice-to-have add-on. In the most forward-thinking families, it’s now part of the governance structure itself.

As an example, Hawley points out how Delaware recently updated its trust law to allow disclosure to beneficiaries only after they complete certain educational milestones. 

“That’s huge. It reflects what we’re seeing across the board: education isn’t the sidecar anymore—it’s part of the engine.”

It’s also finally nudging families to take action earlier on. 

“Families are starting years before transitions. They’re proactively seeking support on trust literacy, decision-making frameworks, and family office roles. It’s a major shift.”

If the Next-Gen Walks Away

Not every family member wants to play an active role in their family business or legacy, and Hawley cautions families on the danger of assumption.

“If someone opts out, and you’re shocked—it’s worth reflecting on the expectations and education that led there. There’s a difference between autonomy and being unprepared.”

She compares it to stories of lottery winners who regret the experience. 

“Wealth without understanding often leads to poor decisions, stress, even isolation. That’s why we believe in building emotional fluency, context, and self-awareness early on.”

More Transparency and Purpose

According to Hawley, the rising generation is pushing for more transparency and purpose around wealth.

It’s part of their awareness and avoidance of being labeled as entitled, and drives an interest in education.

“I’ve had learners ask not ‘what do I get?’ but ‘what does this mean, and how can I contribute?’ That’s powerful.”

They’ve also grown up in a world where information is readily available—even if their families remain silent. 

“Kids come home from sleepovers saying, ‘My friend looked up our house on Zillow.’ Silence doesn’t mean privacy anymore—it creates uncertainty. Transparency, on the other hand, builds trust.”

Learning on Their Terms

One of Tamarind’s core strategies is meeting learners where they are. 

“This generation grew up with YouTube, podcasts, and TikTok explainers. They don’t want hour-long lectures—they want flexible, mobile-first, self-directed learning they can engage with when it fits their life.”

Tamarind Learning’s platform includes short videos, curated readings, gamified exercises, and reflection tools. 

“If you’re going to teach budgeting, talk about the impact of trust distributions or annual gifts—not just spreadsheets. Connect technical learning to lived experience.”

When It All Clicks

The “lightbulb moments” are what keep Hawley and her team inspired. 

These turning points are often subtle, yet sometimes seismic: like when a next-gen family member moves from feeling like an outsider to stepping fully into their role.

She recalls how a woman in her 40s discovered she would inherit a significant trust, but felt hesitant and intimidated by the idea of legacy wealth.

But Hawley says with the right education came a shift from just understanding to realizing where she could add unique value.

“She didn’t just get more comfortable—she got confident. By the end of the program, she wasn’t just listening in on meetings; she was leading them.”

It’s this transformation that motivates Hawley, watching the next generation develop confidence, clarity and ownership.  

What Family Offices Should Do Now

Hawley says there is growing recognition that inheritance without education is a risk, not a reward. 

And it’s why she has a clear message for family office CEOs and advisors: don’t wait.

“Readiness isn’t a switch you flip. It’s something you build. Too many families wait until a triggering event—illness, death, a liquidity event—before they get serious about education. That’s when it’s already too late.”

This newsletter is supported by Clockwork.

Clockwork’s private investment management platform focuses on alternatives while covering all asset classes in one place. Its technology + team model integrates investment content, emails, documents, transaction data, and siloed private information, giving investors clarity and control over complex portfolios. As co-founder Cory Shea says, “While often a complex and opaque space, Clockwork helps investors navigate the chaos and make better investment decisions.” Today, Clockwork provides real-time, consolidated views of $6B+ in portfolio value across 10,000+ investments and 75,000+ transactions.

Find out more about Clockwork here.

𝕏 highlights

Back to basics: The typical size and cost of a family office

An uncomfortable truth for many family office advisors, a game-changing opportunity for others.

It’s a rollercoaster out there.. but always take the long-term view.

 💼 where to work

Three notable family office job opportunities this week…

Operations Manager - Trone Family Office (Bethesda, MD / SFO)

Family Office Client Service Associate - Private Family Office (New York / SFO)

Chief Operating Financial Officer - Private Family Office (San Francisco / SFO)

📚 what to read

A great recommendation from our guest Torri Hawley this week: Breaking Money Silence by Kathleen Kingsbur is a guide to overcoming the cultural taboo of talking about money. It encourages open, honest financial conversations within families, especially around wealth, inheritance, and values.

📻 what to listen to

​The Enterprising Families Podcast, hosted by family governance expert Tsitsi Mutendi, offers in-depth discussions on the challenges and dynamics affecting family businesses and enterprises. The podcast focuses on topics such as family governance, succession planning, and the complexities of multigenerational wealth transition.

📺 what to watch

Last month Anora swept the Oscars. It follows a Brooklyn stripper who impulsively marries a Russian oligarch's son in Las Vegas. What starts as a whirlwind romance spirals into chaos when the family gets involved.

Extreme wealth, messy families, sound familiar?

And finally…

Monday’s Buzz newsletter included a post about the Most Successful Family Businesses in History, why Europe's billionaires are struggling to find talent to manage their fortunes and how Mark Cuban hedged his non-liquid exit.

There’s a lot of noise in the market at the moment. But is that filtering though into family office hiring? Family offices, let me know your plans.

For now, I wish you a wonderful weekend. See you on 𝕏 or LinkedIn.

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