Helen Brown Group

By

The Giving Journey: From Training Wheels to Purposeful Impact

by: Melissa Bank Stepno, President & CEO

I’ve had the privilege of hearing directly from several philanthropists about how they’re approaching the concept of multi-generational giving. These conversations have been candid, reflective and revealing, not just how families think about legacy, but how they actively shape it through intentional choices, shared values, and evolving strategies.

These conversations feel especially timely given the pending intergenerational wealth transfer, a shift that my colleague Heather Willis explored in her recent Intelligent Edge post, Next-Gen Donors and AI: Changing the Game of Philanthropy Forever, noting that the scale of this transfer is unprecedented.

The pending transfer is also prompting many donor families to ask deeper questions: How do we prepare the next generation not just to inherit wealth, but to steward it wisely?  What’s clear is that multi-generational philanthropy isn’t just about passing down assets—it’s about passing down purpose.

I’ll share the sentiments and stories from a few of these families, all anonymized:

The Adlers are a first-generation philanthropist couple—by which I mean a couple with self-made wealth who are now figuring out how to give it away with intention.  They have reimagined the Hanukkah tradition which typically involves parents giving their children eight gifts, one to represent each night of the Jewish holiday. But in their home, the couple’s children receive seven gifts. On the eighth night, the spotlight spins: instead of receiving their own gift, the children are invited to select a charity for their parents to support on their behalf.  For them, it is a simple but powerful way to make generosity part of the family rhythm.

Barbara is a second-generation philanthropist, whose father built and sold the family business.  Before he died, he told her something like, “It was hard to make this money—but even harder to give it away.” That stuck with Barbara.  Now Barbara and her husband take a thoughtful, strategic approach to their giving, and they always include their young son. Their guiding question is: “What kind of family do we want to be, and how do we want to show up in the world?” It’s not just about writing checks—it’s about shaping values.

Charles, a third-generation philanthropist, grew up in a philanthropic home and remembers conversations around his grandparents’ dining room table similar to the ones Barbara is now having with her son. Fast forward to today, Charles chairs the family foundation that his grandfather created. It’s grown so much that most of the board members aren’t even family anymore.  His role reflects a shift from intimate family stewardship to institutional leadership, that still honors his family legacy.

What ties the Adler family, Barbara, and Charles together is a shared understanding that becoming a philanthropist isn’t automatic—it’s something you grow into. Each of them shows, in their own way, that thoughtful preparation matters. Whether it’s through family traditions, strategic planning, or early exposure to giving, they’ve all embraced philanthropy as a journey, not just a role.

A helpful analogy might be learning to ride a bike. You start with training wheels, then move on to a basic bike with foot brakes, eventually graduating to a ten-speed, and maybe even a racing bike. It takes time, practice, and intention—just ask anyone who’s trained for the Pan-Mass Challenge or followed the path of a professional like Lance Armstrong. In the same way, many philanthropists see their journey as a gradual build: learning, refining, and growing into the role.

But what happens when someone’s handed a racing bike before they’ve even learned to pedal? Barbara and Charles both shared examples of next-gen’s who were “voluntold” they’d be joining the family foundation board (or similar), often without being asked if they were interested. When that happens, philanthropy stops feeling like a privilege and starts feeling like a chore.

For Charles, soon after he graduated from college, he found himself on the board of his family’s foundation.  A requirement of being a trustee was that he attend twice-yearly in-person board meetings.  For him, this meant using approximately half of his vacation time in any given year to travel home for board meetings. This can be something that is difficult for a younger person to truly embrace.

Barbara said it best when she articulated that giving should always be a “joy.”

Charles echoed Barbara’s sentiment, with more weight.  He spoke candidly about the weight of his grandfather’s legacy, and the pressure he feels to honor it well. While he’s deeply aware of the privilege he holds, he also feels the burden of stewarding money he didn’t earn, and the responsibility to distribute it in ways his grandfather would have respected.

Dana: in one final example, a fourth-generation philanthropist’s great-great-grandparents set up a private foundation with the purpose of providing charitable dollars within the local community where they lived.  Now, a century or so later, Dana and her cousins, who are the current trustees, are spread across the country, no longer tied to that original hometown.

Rather than letting geography dilute their connection to the foundation’s original purpose, they have found a creative way to honor it.  Each cousin has opened a donor advised fund at the community foundation located near their great-grandparents’ home. They make grants from the family foundation into these DAFs, ensuring that the money first flows through the original community, just as intended. Then, from those donor advised funds, each cousin supports causes in their own local community—bringing the spirit of the original mission into the places they now call home.

It is a balancing-act: staying true to the letter of the foundation’s founding vision while also embracing its deeper meaning.

For many of us in this field, our day-to-day work can often feel distant from the human beings who are donors.  Focused on data, capacity ratings, and business summaries, it is sometimes easy to forget that behind every profile, every spreadsheet, every analysis, there is a real person with a story. With these examples, I hope to bring the living and breathing individuals back into view.

The people represented in our work are often deeply thoughtful about their giving. For them, philanthropy isn’t just transactional.  Rather, it’s intentional, strategic, personal, and powerful. And more often than not, they’re thinking not just about their own impact, but about the families they come from, the legacies they carry, and the futures they hope to shape.

 

For more reading: https://ssir.org/podcasts/entry/building-trust-and-managing-conflict-in-family-philanthropy (note that none of the interviewees in this podcast are The Adlers, Barbara, Charles or Dana!)

 

Image Credit: Toy Bicycle Rider, Smithsonian American Art Museum, Gift of Alan and Ann Rothschild (found at: https://www.si.edu/object/toy-bicycle-rider:saam_2011.37.11)

By

Connect Me!

By: Senior Consultant, Debbi Olley

Debbie Olley

Debbi Olley

It’s a hyperconnected world, we’re told, and you’ve likely used some sort of connecting relationships in your own life. Maybe you’ve played a version of Six Degrees of Kevin Bacon with your friends. Or maybe, when looking for a new job, you’ve engaged in what my late mother (and plenty of others) called “networking.” Thanks to growing up in a household that valued personal introductions and making connections, I also love to connect people whenever I can. (“Oh, you’re going to Rome in a week? You should look up my college professor, who’s working on a book there right now!”)

In prospect development, our version of making connections—relationship mapping—is a topic that comes up often. Here at HBG, our founder, Helen Brown, wrote about it a month before COVID shutdowns hit. Helen’s post remains relevant more than five years later, since we continue to wrestle with these same questions. In the past few weeks alone, I’ve seen plenty of posts on PRSPCT-L about this topic. And so, in the spirit of Helen’s original piece, I’ve talked to my fellow researchers at HBG and have also used my own experience as a springboard. I hope it can be a helpful guide for you, too!

What Are We Hoping to Find?

My colleague Catherine sums this up beautifully below; her guidelines can help when deciding what you want for your own shop.

In general, the things she’s looking for in a good relationship mapping tool:

  • A robust database of names with up-to-date data;
  • Something that will answer the two most common relationship mapping questions:
    • “How can our organization connect to this person?”
    • “Who can this person introduce to our organization?”
  • A way to create lists, definitely for individuals but ideally also for organizations;
  • A user-friendly interface that lets me easily see the details behind each connection (both first and second degree connections);
  • A way to export my findings into something relatively tidy so that I can show the results to clients.

Connections with a Cost

Altrata now owns some of the major connectors researchers have long relied on, including BoardEx, Boardroom Insiders, RelSci, WealthEngine, and Wealth-X. Kaleidoscope will be unveiling a new product soon, Path Explorer. Products such as Kindsight (iWave) also offer connections tabs on its profiles. For confirming family relationships or trying to trace family trees, Ancestry can be a terrific resource. Nexis for Development Professionals will also list relatives, neighbors, and other known associates.

As always, there are caveats with what each product can provide and areas where they may fall short. Best practices in prospect development makes it imperative to test products thoroughly before committing to it for your shop or team.

The Hard Work of Free Results

I’m going to bring in my HBG colleague Viola’s suggestion below to start this section off, since managing expectations is a key part of relationship mapping.

Relationship mapping can be really time consuming. What she often suggests is to handle it in a phased approach:

  • Provide lists of current affiliations [to the client] (boards they’re currently serving on, other people that work for the same current employer).
  • Let them eyeball the list to see if they know anyone.
  • If they don’t, the names can be checked against the organization database to see if they have records.
  • If that still doesn’t produce anyone, provide lists of former affiliations (boards they previously served on, people who were previously on a board with them but have since left the board, previous co-workers).
  • Let them eyeball the list to see if they know anyone.
  • If they don’t, the names can be checked against the organization database to see if they have records.

Viola also shared the following tips:

  • Use the Wayback Machine internet archive (https://archive.org) to see previous versions of a board list.
  • Don’t forget to look in your organization database. Some have a Relationship Tree that you can use to see who’s connected to who. Also, you can use queries to see who they might know (e.g., which other alumni attended during the same timeframe). You can also search for people who live on the same street or work in the same profession.
  • Google the person’s name and site: org to see what organization affiliations they might have. You can also do that with site: edu to find education affiliations.

HBGer Maura uses an approach with one of her clients that is a version of something I’ve used in the past, too. I’ll bet others reading this have done something similar. Essentially, create a running spreadsheet of your organization’s board members/main connectors and add possible connections as you prospect and/or try to make connections between other donors. You can run keyword searches in your master spreadsheet to see if there may be a relationship.

More recently, I used a Frankenstein’s monster combination of free sources, including LinkedIn, Impala, ProPublica, and, as Helen put it in her previous post, “search-string ingenuity,” to find possible connections for a client. As Viola observed, relationship mapping can be time-consuming, but sometimes it really is a matter of digging in all sorts of places to yield a single possible relationship.

Make That Connection: It’s Good for You!

PRSPCT-L is always a fabulous source for tips, tricks, and sometimes simple validation that your fellow researchers often struggle with the same issues. A recent poster indicated a switch back to a more “manual” approach, creating relationship maps for senior leadership to identify. (That sounds a lot like what Viola and Maura recommended above!)

All this talk about relationship mapping should be a good reminder for all of us, both in our workplace and in our “regular” life, of the absolute necessity of creating, fostering, and maintaining strong, lasting relationships. While so many companies have monetized and capitalized upon the idea of making healthy, happy connections, the reality is that many of us continue to struggle with loneliness every single day. It is gratifying to know that my mom, with her long-ago focus on networking and making connections between people, was a bit of an oracle in this particular realm. And so, as we continue to work hard for in our workplaces, let’s also create strong, healthy, and vital relationships for all of us!

 

Follow Us: Linkedin
617-393-1983
info@helenbrowngroup.com
Helen Brown Group