Inside the OTA Playbook Explained
Podcast Summary
Carl Shepherd is a pioneer of the sharing economy and co-founder of HomeAway, which he launched with Brian Sharples in 2005. As Chief Strategic and Development Officer, he led the company’s acquisition strategy, closing 22 deals that helped scale HomeAway into a global short-term rental marketplace. The company went public in 2011 and was acquired by Expedia for $3.9 billion in 2015, where Shepherd remained on the board until the sale. Earlier in his career, he held executive roles at Hoover’s Online and served as CFO for publishing firms. He has served on the boards of RVShare, Turnkey Vacation Rentals, and others, and is currently the Senior Non-Executive Director of HostelWorld PLC. He and his wife Suzanne are dedicated advocates for people with intellectual disabilities, inspired by their son Jack.
Carl doesn’t hold back in this one. From the early HomeAway days to what’s broken in short-term rentals today, this is a candid look at where we’ve been and where we’re heading.
In this conversation, we discuss:
- How Carl Shepherd and Brian Sharples turned a business plan into a $3.9B HomeAway empire
- Why HomeAway started as an information company and how that early vision shaped the short-term rental industry
- How the OTA model has changed and what Carl believes Expedia got wrong after acquiring HomeAway
- Carl’s take on Airbnb’s fee structure change and what it means for hosts, managers, and guests
- Why short-term rentals became "cookie-cutter" and what needs to change to bring back uniqueness
- Why Carl believes the future of professional property management depends on franchising, not centralization
- What tech-enabled property managers are still getting wrong and why software alone is not the solution
We Say What Others Won’t
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Resources mentioned in the show:
- AJL Atelier– Global STR Consulting. 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 Carl Shepherd on LinkedIn.
Guest Appearing in this Episode
Simon Lehmann
Simon Lehmann is the CEO of AJL Atelier, a strategic advisory firm for the global short-term rental industry. He has decades of experience in vacation rentals, travel tech, and hospitality, and has advised hundreds of operators, startups, and investors across EMEA, North America, APAC, and LATAM. He’s also a frequent speaker and moderator at global events like VRMA, Phocuswright, and Skift, covering STR tech, market consolidation, and professional hosting. Simon was Co-Founder & Chairman of Vacasa Europe, President of PhocusWright, and a Board Member of HomeAway. He also held executive roles at Interhome, Hotelplan Group, and Swissport.
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