Name: 2nd Annual Founder's Retreat
Start: 2026-09-08T15:00:00-04:00
End: 2026-09-10T13:00:00-04:00
Location: Prospect Berkshires

Running a family business means carrying a lot at once — keeping the business moving, your people engaged and productive, and your relationships strong with family and non-family alike.

Our 2nd Annual Founder’s Retreat brings the Stride community together in the Berkshires for two and a half days of connection, candid conversation, and genuine downtime. Last year, 6 families — 17 of us in all — came together for the first time and felt something rare: finally being in a room with people who share the same family-enterprise experiences. This year, we’re gathering again, and we’re warmly encouraging you to bring the whole family. At least two generations attending together is strongly encouraged — it’s a chance to get on, and stay on, the same page in all things business and family. This year we’re keeping it intentionally small — limited to 10 families — so that by the second day, everyone knows everyone.

You’ll leave with plans you can act on and connections that last. We begin at 3 PM on September 8th and wrap by midday on the 10th.

What to Expect

Speakers who share hard-won wisdom in honest, small-group settings
An opening keynote you won’t forget — dinner, laughs, and family-business trivia by the water, capped by a keynote from Sara Sturgess, Founder & CEO of R.J. Balson & Son USA, England’s oldest family business (founded 1515) and the first woman in 26 generations to lead a branch of her family’s enterprise
Genuine downtime together — the sauna and cold plunge, the water and the boat, and s’mores under the stars
Dinner at the historic Red Lion Inn, a family-run Berkshires institution established in 1773, including a talk by family owner/operator Sarah Eustis
Breakout sessions by role — whether you’re the current owner, next-gen owner, non-operating owner, or spouse/influencer, you’ll connect with others who carry the same weight
Connections that last — you’ll leave knowing you’re not alone in your challenges

How the Weekend Unfolds

Tuesday, September 8 — Arrive & Connect. We begin at 3 PM. Settle in, meet your fellow families, and ease into the weekend with an outdoor cocktail reception, a lively family-business trivia night led by Corey Finkle, our Chief Story Officer, and a keynote dinner full of laughs and honest conversation, and s’mores by the lake to close out the night.

Wednesday, September 9 — Do the Work. Then Celebrate. The heart of the retreat. We gather as a full community in the morning for a candid, workshop-style conversation about the real challenges facing family enterprises right now — succession, ownership, the next generation, and what the future actually looks like. After lunch, we split into smaller groups by role, so every seat at the table gets the conversation they actually need — from building a real next-gen development plan to using proven operating systems to make succession a roadmap instead of a source of tension. The afternoon is yours — a boat ride, a cold plunge, a walk in the woods. That evening, we drive together to the historic Red Lion Inn in Stockbridge for dinner and a talk by Sarah Eustis, whose family has owned and operated the inn since 1773.

Thursday, September 10 — Integrate & Leave Ready. A relaxed morning breakfast, a final session on how to stay connected and keep moving forward, and a box lunch before you head home — with a plan, with people, and with a lot less of that feeling that you’re doing this alone.