In this special extended episode of The Playeasy Warmup, co-founders Kerri and Sean sit down for an honest, behind-the-scenes conversation about the company’s journey.
From a spontaneous conversation on a Boston roof deck in 2017 to navigating the uncertainty of COVID-19, Sean and Kerri share the pivotal moments that shaped Playeasy’s evolution.
The conversation explores how the company moved from a simple idea, helping people find sports facilities, into a platform connecting destinations, event organizers, venues, and visitors across the sports tourism and destination marketing ecosystems.
They also introduce Destination Experience Co., the parent company behind Playeasy and Compass, and how new technologies like AI are shaping the next generation of destination engagement.
This episode is a candid reflection on entrepreneurship, resilience, and the power of community in building something that lasts.
Episode Chapters
00:00 – Introduction: Why We’re Sharing the Full Story
04:33 – The Origin of Playeasy
26:45 – Discovering Sports Tourism & Finding Product-Market Fit
34:30 – Surviving COVID and Reinventing the Platform
1:06:00 – The Catalyst Behind Our New Company Evolution
1:16:30 – Introducing Destination Experience Co. & Compass
1:20:00 – Looking Ahead to the 2026 Innovators Summit