SpeakEasy 2025
October 22–25, 2025 | Location: Seattle, Washington
Built by Next Gens, FOR Next Gens (and their families) — Conversational catalysts for those “behind-closed-doors” kind of topics.
Next Gens — ever feel like you need to have those hard conversations with your parents but you don’t know where to start? Or you’ve tried a thousand times, but it just goes nowhere? We get it. That’s why we built SpeakEasy.
SpeakEasy is a one-of-a-kind gathering for Next Gens, parents, and advisors in family enterprise who are ready for something different. This is not your standard conference where you ingest learning materials and then are left to your own devices to incorporate them….At SpeakEasy, we create conversational contexts and catalysts for families who want to actually communicate constructively, but who just haven’t quite figured out how to stop walking on eggshells.
Because let’s be real — Wanting to FIX a problem shouldn’t BE the problem. Using humor, vitality, fun, pragmatic compassion, and paradigm-shifting education, we create both aha-moments and haha-moments for parents and NextGens alike. Equal parts legitimate learning, irreverent play, and unforgettable glamour (because who doesn’t like an excuse to get dressed up??), this event blends candid conversations with immersive experiences unlike any family office conference you’ve ever been to.
What to Expect
October 22nd; Arrival & Welcome
Kick off with a stylish cocktail party sponsored by advisors—your first chance to unwind, connect, and feel at home in this community.
October 23rd: Conversation Catalysts — Let’s get down to business.
Crash courses designed to cut through the noise:
Don’t Make Me Hate You: No Seriously, We REALLY need to talk about what happens after you die – Estate planning made real. A course designed by and for millennials who would like to start having productive conversations with their parents about end of life and beyond.
Family Systems 101 – A crash course; Understand how family systems work, and how they impact your business.
Family Office 101 – Next Gen perspectives (and a parent refresher). Namely, does your family need a family office? What even is a family office? Are they all built the same? How should you be thinking about managing, growing, building, or designing one? How does family office transformation occur across time?
How to Get Your Family to Work on Their Sh*t – Real talk best practices and strategies for handling even the most complicated, complex, avoidant or entrenched family structures.
Intergenerational Collaboration in Family Business– What’s normal, what’s not, and how to last the long haul.
October 23rd : The SPEAKEASY Soirée
Our crown jewel: a black-tie, ballgown-level evening where guests are encouraged to go all out. Think music, elegance, and maybe even a little matchmaking magic!! (Singles, start your engines!)
October 24th: Workshop Intensives & Play
Interactive, therapist-guided, improv-infused sessions that get to the heart of communication, conflict, and collaboration. Covering everything from peer support to reality checks on estrangement, grief, addiction, and the hard stuff families face.
9:00 – 10:15 AM – Workshop 1: Don’t Make Me Hate You – Peer Group.
10:30 – 11:45 AM – Workshop 2: Communication 101 (Awareness Wheel) – Guided by 3 therapists; designed to teach you how to communicate effectively, especially when things get heated.
12:00 – 1:15 PM – Workshop 3: Yo, I Wanna Love You Better – Parent/child role play, improv, hilarity.
1:15 – 2:30 PM – Lunch.
2:30 – 3:45 PM – Workshop 4: Reality Check: Handling the Hard Sh*t – Estrangement, grief, addiction, mental health, and more. Candid conversations with other people who get it.
Afternoon – Free decompression time (spa, walks, naps, optional advisory 1:1s).
7:00 – 9:30 PM – House Dinners – Small-group dinners in private homes with curated guest lists set the stage for deep connection.
10:00 PM – Late – Next Gen Capture the Flag – Midnight mischief, energy release.
October 25th; Closing Brunch
A celebratory send-off!
Why SpeakEasy?
Because even the strongest balance sheet can’t fix a broken conversation. SpeakEasy is about courage, candor, and connection—helping families in enterprise thrive together across generations.