Allison Flanders
Family Office Advisor | Multi-generational family office
Our first spotlight of 2025 is Learning Community standout Allison Flanders, an accomplished family office advisor based in St Thomas, U.S. Virgin Islands. Her bio on 21/64 Connect is perfect: “I advise a multi-generational family on articulating, documenting, and growing their legacy through philanthropy & next gen education. Ask me about baking!”
Of course, even as she speaks about baking Allison is able to eloquently weave it back to the larger themes that imbue her self and role “The last show I binge-watched was The Great British Bake-Off. My favorite part of the show and what keeps me coming back to watch season after season is how supportive all the contestants are of one another. They each want to win, but they don’t let that get in the way of their humanity and helping another person in a pinch.”
Indeed, “finding humanity” is very much what drives Allison. As she reflects on the best parts of her work, her words convey a deep appreciation for humanity and relationships. “I love seeing the smiles that giving puts on everyone’s faces, and the joy and connection that comes from doing it together. I put together a short photo montage from our ‘Enterprise Day of Giving’ where groups from across our organization volunteered together, and my heart was bursting with happiness to see everyone’s radiant smiles.
Allison says the title of her yet unrealized book would be “Where to next?” She not only loves to travel and see new places, but this title also captures her desire to identify the next goal and make a plan for achieving it. So where to next for Allison? “We’ve been spending hurricane season in Maine these past few years but haven’t really established much of a community. So in 2025, my husband and I will be more intentional about building a community and connecting with new people.”
Thanks for helping to build the 21/64 Certified Advisor community Allison! And thank you for answering our questions. More below …
WHO HAS HAD A PROFOUND INFLUENCE ON YOU? My grandmothers. They could not have been more different, one fiercely independent and unwilling to conform to the societal expectations of her day; the other happiest gathering her family to feed them food prepared with so much love. Growing up with these two examples and seeing that both held family as one of their highest values, taught me a great deal about how the expression of a value can look different in different people’s lives.
WHAT IS ONE VALUE THAT MOTIVATES YOU AND HOW HAVE YOU BROUGHT THIS INTO YOUR WORK? Relationships. Building relationships with those I work with is motivating to me. I want to get to know the person as an individual, in addition to their role within their larger family, so that I can consider points of connection. This is a value I’ve brought to my work with the next gen specifically, seeking to get to know each of them and their interests, and then incorporating those interests into the education sessions we’ve designed.
HOW HAVE 21/64 TRAININGS CHANGED THE WAY YOU THINK ABOUT WORKING WITHIN A FAMILY ENTERPRISE? The concept I’ve returned to most from Approach Training is the Philanthropic Identity Equation. I’ve used it as the backdrop to the next gen learning program we’ve designed, as well as in building our family office philanthropy strategy. I continue to use it as a touchstone and reminder when things start to feel overly complex – what am I inheriting, who am I, what do I want to do about it. I find that returning to these fundamental questions and making sure we’re clear on the answers helps bring things back into focus.
HOW HAS THIS WORK CHANGED YOU? By helping others better define the legacy they want to create, I’ve taken more time to consider my own legacy. This work has made me realize we’re each on a journey to consider what we want our legacy to be and how best to create meaning with our lives.