Annual Retreat 2026: Punta Cana

May brought another successful team retreat for PaperStreet. Our three-day retreat to Punta Cana felt a little like a reset, a spark, and a reminder of why the work works. Our 2026 annual retreat brought 23 teammates together in Punta Cana from all over –Argentina, Colorado, Georgia, South Florida, Philadelphia, Southwest Florida, New Jersey, Central Florida, Tampa, and Turks and Caicos. (Yes, Robin flew and then drove three hours to join us!)

For three days, we stepped out of our usual routines and into a setting that made collaboration feel lighter, conversations feel easier, and ideas feel bigger.

Training, Strategy, and Building What’s Next

While the ocean was never far away, the focus of the trip was forward-looking. We dedicated time to training and deeper strategic work, mainly digging into AI, exploring how it can shape our workflows, and defining goals for new internal programs and initiatives.

A major highlight was working alongside an AI champion to begin mapping and even coding early versions of the initiatives we had outlined. Instead of keeping ideas theoretical, we started turning them into something tangible… right there, in real time.

It was a reminder that innovation doesn’t always need a boardroom. Sometimes it just needs the right people in the right place with the willingness to build.

Team Building, But Actually Fun

Not everything was strategy sessions and screens. We leaned into some classic (and slightly chaotic) team-building games that brought out a different side of everyone. Our team building games succeeded in connection, and we had a fair amount of laughs as well.

Conversations That Don’t Fit in a Calendar Block

Some of the most valuable parts of the retreat didn’t happen on an agenda. They happened between sessions, at lunch tables, walking back from the beach, or sitting around after dinner.

When people who normally collaborate across time zones and states finally sit in the same physical space, the conversations change. They get more honest, more creative, and more human. This is the reason we continute to priortize traveling together every summer.

Our 2026 annual retreat left us feeling aligned on where we’re headed, how we’re using technology like AI, and how we continue building as a distributed team that still manages to feel close.