Kevin Penner.
Operator. Founder. Retreat Owner.
Fortune-100 exit. Owner of Wilderness Edge, a 28-cabin retreat center on 140 acres in the Pacific Northwest. Founder of Everybooking, the AI-first booking platform he built after five years of being on-site 24/7 answering inquiry emails. He hasn't been on-site in 8 months.
From Fortune 100 to retreat operator.
Kevin spent the first chapter of his career in enterprise software at a Fortune-100 firm. After a successful exit, he and his wife bought a parcel of land in the Pacific Northwest and opened Wilderness Edge, originally eight cabins, now 28, on 140 acres.
For five years, Kevin ran the retreat center as a hands-on operator. He answered every inquiry email himself. He learned what worked, what didn't, what software fell short, and where the bottlenecks were. The bottleneck was him, specifically his inbox.
In 2024, he started building what would become Everybooking. By late 2025, the agent was running at Wilderness Edge. By 2026, he hadn't been on-site for eight months and was bringing the software to public release.
- →Fortune-100 enterprise software exit
- →Founder, Everybooking (2024–present)
- →Owner / Operator, Wilderness Edge Retreat Center (2019–present)
- →27+ years in operations, sales, and software
- →160+ AI agents shipped to retreat / venue operators
What Kevin writes about.
Talk To Kevin Directly.
Founding customers get a direct line to Kevin during onboarding and ongoing.