Transforming Family Values into Lasting Impact with Robyn Schein and 21/64

Robyn Schein, Senior Consultant, 21/64

If you’ve ever watched a family try to talk about money, legacy, and “where the giving should go,” you know it can get complicated fast. That’s why I wanted to sit down with Robyn Schein, Senior Consultant, at 21/64—a firm that specializes in multigenerational and next-gen philanthropy. Robyn’s superpower is turning big, sensitive conversations into clear, values-aligned action.

Below is Robyn’s story and the 21/64 approach—told through the lens of what I see working with donors, boards, and nonprofit leaders every day.

How she got here (and why it matters)

Robyn has spent her entire career in the nonprofit world—consulting in NYC and DC, then 12 years at The Minneapolis Foundation, where she built Fourth Generation, a program that helps emerging donors learn by doing. That experience shaped her core belief: philanthropy is a practice you grow into, together. The work is about more than cutting checks. It’s learning about your identity, values, and family dynamics in real time.

At 21/64, she brings that same clarity to families and the advisors who serve them—guiding conversations that many people avoid because they feel too personal or fraught. Robyn calls the work “sacred,” and it shows in how she listens, frames choices, and helps groups move forward.

Lessons from engaging the next generation

At Minneapolis, Fourth Generation taught Robyn two truths that still guide her work:

1. Learning changes behavior. When rising donors pool funds, do site visits, and make grants together, they build muscles they’ll use for decades.

   
   

2. Impact ≠ organizational loyalty. Next-gen donors often ask, “What issue are we moving? What’s the outcome?” They look at portfolios of action—grants, investments, networks, and voice—rather than single institutions.

   
   

That shift matters for nonprofits: the annual report alone won’t sustain relationships. Engagement, transparency, and two-way learning will.

When families sit down to talk about giving

The most common snag Robyn sees: families start with “Here’s where we give.” That’s a list, not a strategy. The 21/64 move is simple and powerful, ask why. What values are underneath those choices? Once the “why” is named, common ground appears, even if the “how” looks different across generations.

Two 21/64 tools Robyn reaches for again and again:

• Motivational Values Cards. A structured way to identify and rank values. One couple realized their “responsive” giving to friends was actually a direct expression of their top values—family, friendship, and relationships. Clarity replaced guilt, and their giving got more intentional.

  
  

• Picture Your Legacy. Image-based prompts that unlock language around legacy. Robyn described an 80-something donor who, through imagery, moved beyond “I was a homemaker” to a richer vision—lifelong learner, traveler, curios—and that translated into guidance her kids could act on.

  
  

These are conversation catalysts, not gimmicks. They turn a tense debate into a shared vocabulary. If you want to learn more about their tools, click here.

What sets 21/64 apart

The field used to treat legacy like a baton pass: assets move after someone dies and the next generation “figures it out.” Robyn sees a different model taking hold: shared experience while everyone is at the table.

That’s where 21/64 lives, equipping families (and community foundations, federations, and large nonprofits that serve them) with processes and tools to work together across generations.

A few pillars of the approach:

• Multi-gen by design. Five adult generations are often in the room. 21/64 builds frameworks that honor different worldviews and decision styles.

  
  

• Values first, tactics second. Start with identity and purpose; then align grants, investments, time, relationships, and advocacy. (Think time, talent, treasure, ties, and testimony.)

  
  

• Practice for practitioners. They don’t just advise families.  21/64 trains the people who advise families (philanthropic advisors, gift officers, and planned giving teams) so the ecosystem can meet donors where they are.

  
  

The future of giving

Robyn is bullish on the next generation. They’re giving earlier, asking smart questions, and viewing impact beyond grants. A few questions Robyn has heard from younger philanthropists:

1.       Are our investments aligned with our values?

2.       How do we use our networks?

3.       What’s our voice? 

Established families can take a page from that playbook, invite younger voices in sooner and broaden the definition of “how we give.”

If you’re working with rising donors (or are one), keep an eye on Grand Street, 21/64’s long-running learning community for next-gen Jewish philanthropists. A new alumni study captures what worked and why—and a fresh cohort launches in January. Here’s a link to the report: https://2164.net/grand-street-2026/

Board lens

Robyn doesn’t just teach this stuff, she lives it. She’s served since 2015 on the Smith Jewish Academy board and on national committees with National Center on Family Philanthropy and the Council on Foundations.

Boardroom seats keep her grounded in governance realities like role clarity, decision rights, and the hard work of aligning values with budgets and calendars. It also gives her credibility in family rooms. Robyn balances passion with process and knows how to move from “we care” to “we decided.”

A quick toolkit you can use

If you’re facilitating a family conversation (or prepping your development team):

• Start with values. Ask each participant to choose their top 5 values and explain why. Create the overlaps and honor the differences.

  
  

• Name the portfolio. Don’t stop at grants. Map time, talent, treasure, ties, testimony across the causes you care about.

  
  

• Decide small, then scale. Make one 90-day commitment together (e.g., a learning visit + a pilot grant + a volunteer day). Debrief and iterate.

  
  

It’s not magic—just structure and intention. But as Robyn proves, that’s often what unlocks momentum.

Why this resonates

I coach organizations and boards every week. The theme I see, without structure and accountability, even generous and smart people stall.

Robyn and 21/64 give families a way to move, grounded in values, respectful of differences, and focused on outcomes. That’s good for donors, and it’s a gift to the nonprofits counting on them.

If you’re curious about 21/64’s tools, the Grand Street findings, or how to host a multi-gen values session for your donor community, contact 21/64: https://2164.net/contact/

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I help nonprofits raise more money through education, coaching, and strategic planning. If your organization is ready to strengthen its fundraising strategy, create board advocates, or develop a comprehensive legacy giving program, I'd love to discuss how we can work together.