What happens when a frustrated Airbnb host builds a tool to solve his own problem—and ends up launching one of the most influential platforms in short-term rentals?
In this episode, we sit down with Pierre-Camille Hamana, CEO and founder of Hospitable, to explore his surprising journey from law school dropout to tech entrepreneur. What began as a simple solution to automate guest messaging for his own rental has grown into a powerhouse property management platform supporting tens of thousands of listings across the globe.
Pierre shares the real story behind Hospitable’s evolution—from a basic tool for solo hosts to a full-fledged system tackling everything from platform integration to direct bookings.
We dive into the complexities of building software for hosts, the future of short-term rental automation, and why simplicity is the key to scaling. Whether you're a seasoned host, a budding entrepreneur, or just fascinated by startup journeys, this episode is packed with insight, inspiration, and behind-the-scenes moments from a founder who’s quietly reshaping the future of hospitality tech.
Things we discussed in this episode:
- Founder’s Origin: Pierre Hamana began by renting out a room on Airbnb and built
- Hospitable to automate his own guest messaging.
- Early Focus: Designed for small hosts managing fewer than 7 properties.
- Direct Bookings: Built-in booking engine with ID checks, rental agreements, and deposit handling.
- OTA Integrations: Navigated complex relationships with platforms like Airbnb and Booking.com.
- Community Input: Product roadmap shaped by user forums and direct feedback.
- Support Culture: Globally distributed team known for fast, friendly help—often using memes.
- Vision: Exploring marketplace tools and STR property investments.
- Small Host Challenges: Tackled issues like payment processing and lack of support from traditional vendors.
- Platform Growth: Evolved from a messaging tool to an all-in-one host solution.
- Tech Democratization: Making powerful tools accessible to individual hosts and self-managers.
Get in touch with Pierre:
- Facebook -
/ 20ad6664f78b17b8fed5 - LinkedIn -
/ - Instagram -
/ - Website - Hospitable
➢ Subscribe: 
/ @smartstayshow
- 0:00:00 Origin Story
- 0:00:48 Birth of Hospitable
- 0:03:33 Accidental Entrepreneur
- 0:08:03 OTA Integration Challenges
- 0:12:55 Community-Driven Platform
- 0:16:47 Product Roadmap Insights
- 0:19:16 Customer Support Magic
- 0:21:15 Direct Bookings Future
- 0:26:05 Industry Evolution
- 0:31:43 Market Trends and Opportunities
- 0:35:50 Beyond Messaging
- 0:40:16 Entrepreneurial Advice
- 0:45:38 Future Vision
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