For more than twenty years, David Stillman has been a leading voice on what makes generations tick. He’s helped companies, nonprofits, and family enterprises understand how Gen X, Millennials, and Gen Z differ in their motivations, communication styles, and decision-making.

A sought-after speaker and coauthor of When Generations Collide, The M-Factor, and Gen Z @ Work, David has spent his career advising leaders on how to recruit, retain, manage, and meaningfully engage people across age cohorts.

This year (2025), we welcome David to 21/64 as a Senior Fellow, where he’ll collaborate with our team to deepen intergenerational understanding and enrich the experience of advisors and families navigating values, identity, and legacy across generations. While his work reaches Fortune 500 companies and global audiences, David brings a deeply personal lens to the topic, particularly through his years of collaboration with his son, Jonah, a Gen Zer whose presence in David’s professional life has sharpened his appreciation for the power (and inevitability) of generational diversity.

As a Fellow, David will contribute thought leadership, offer insights to our team, and help bridge the worlds of generational research and multigenerational family engagement. He is also developing a new learning experience for our community that explores how each generation approaches philanthropy and decision-making, work we look forward to sharing more about in the months ahead. We’re delighted to introduce him to our community through this month’s Spotlight.

What are your core motivational values?
Authenticity is a core value for me. I am very honest not only with others, but especially with myself. If I am aware of what I’m good at and where I need help, I find the best work gets done. Curiosity is also at the top of my list. If I remain curious, it forces me to work harder and improve each day.

What did you learn through working closely with your son? Any unexpected outcomes?
I learned firsthand what I’ve spent a career teaching about the different generations: no one generation is right, wrong, better, or worse. They’re just different. I’m Gen X; he’s Gen Z. We click and clash all the time. From dress to communication styles, he’s much more casual than I am. He was raised with a faster pace of communication and prefers soundbites over long narratives. I feel like the luckiest dad in the world and have learned just as much as I’d like to think I’ve taught him.

Why 21/64?
I saw Sharna Goldseker speak at a conference and was ignited. I have been speaking with organizations about how best to bridge generation gaps, but had never looked through the lens of philanthropy. She really shined a light on how to invite the next generation to the table. I also believe that the world is not short on tactical solutions when it comes to managing all aspects of wealth. But the soft skills – where people and organizations often struggle – are where 21/64 excels. I’ve always admired how 21/64 teaches and demonstrates the ability to navigate tough conversations, and then puts thoughtful strategies in place so positive change and true evolution can happen. My decades of experience helping industries work across generations, combined with 21/64’s proven methodologies, make this a great home to bridge generational gaps. I’ve been dazzled by the 21/64 team and feel honored to be a new member.

What would the name of a book about you be?
My late brother had a saying I’ve always loved: “You can’t fall off the floor.” I’ve lived my life knowing that no matter how challenging the day is, it can and will always get better. I’d want my book to be motivating in some way, and hopefully really funny. I’ll admit that no one finds me funnier than me.

Where might we find you when you’re not working?
Doing something active and spending time with my kids, family, and friends. My happiest place is snowboarding in the mountains.