Tim Kerin, Casa Dare To Dream — From DC Cleaning Boss to Costa Rica Luxury Villa Builder
Tim Kerin is a multi-business entrepreneur who built and ran large commercial cleaning and construction companies before launching a high-touch luxury villa brand in Costa Rica. He’s also the author of 10 Lessons Learned… How to Build a Successful Business, and his story is packed with real-world tactics on cash flow, networking, and scaling the smart way. If you want a playbook for moving from “in the trenches” to owner/operator—and knowing when to pivot—this episode delivers.
Top 5 Takeaways from the Episode:
Niche and proximity win. Tim and his wife started in residential cleaning by hosting a rooftop mixer at a high-income DC building, then stacked clients in the same tower to cut travel time and boost margins.
Work in the business before you work on it. Early on, they cleaned themselves—then hired, documented, and backed away as they grew into commercial accounts.
Learn via franchise, then graduate. He used a commercial cleaning franchise to grasp operations, later negotiated to take over vulnerable accounts and phase out royalties as his team out-performed.
Scale adjacently. After reaching 4M+ sq ft/night and 135 employees, Tim added commercial construction for the same customers—“if we’re in the building mopping, we can be in the building painting.”
Costa Rica play: concierge, pre-sell, debt-free. They bought/finished a villa, ran it like a full-service experience (manager, chef, driver, tours), exited profitably, and are building a larger, wedding-ready property—pre-booked and funded in cash to keep cash flow strong.
Watch the full episode now on YouTube: https://www.youtube.com/watch?v=7klVS_aQqR0
Memorable Quote:
“Cash flow is king.”