Carl Shepherd is the Co-Founder of HomeAway, the marketplace that helped define the modern short-term rental industry. Before Airbnb became a household name, Carl and his co-founder Brian Sharples built HomeAway into a global platform that changed how people rent and manage vacation homes. The company went public in 2011 and was later acquired by Expedia for $3.9 billion.

If you want to understand how today’s OTA landscape was built, and where it’s breaking, this episode is essential listening. Carl shares how HomeAway scaled through acquisitions, why the industry lost its uniqueness, and what professional property managers must do to stay relevant in a platform-dominated market.

In this conversation, we discuss:

• How Carl and Brian turned an information business into a $3.9B global marketplace
• Why HomeAway’s original model changed the future of short-term rentals
• What Expedia got wrong after acquiring HomeAway and how it reshaped the OTA model
• Carl’s view on Airbnb’s fee structure shift and its long-term effects on hosts and managers
• Why professional property management must evolve toward a franchise model
• What tech-enabled PMs often misunderstand about software, service, and brand consistency
• Why the next phase of STR growth depends on quality control and trust

Explore more:

• Connect with Carl Shepherd on LinkedIn [linkedin.com/in/carl-shepherd-1152924/].

Resources

• AJL Atelier – Global STR Consulting [https://www.ajlatelier.com]. Led by our host Simon Lehmann, AJL Atelier is a boutique advisory firm helping professional hosts, property managers, and investors succeed in the short-term rental industry.
• Connect with Simon Lehmann on LinkedIn [https://www.linkedin.com/in/simon-lehmann-8375753b/]

Stay connected:

• Apple Podcasts: https://podcasts.apple.com/us/podcast/str-global-unlocked-with-simon-lehmann-unfiltered/id1842946960
• Spotify: https://open.spotify.com/show/3kke4wOx0tNv0duq9MMWtO
• Youtube: https://www.youtube.com/playlist?list=PLWVkmUOkmhSHcFjzi28AhaQNR98vaG65O
• Website: https://www.ajlatelier.com/podcasts
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