In this episode of Alex & Annie: The Real Women of Vacation Rentals, we are joined by Bob Milne, President and COO of First Chair Destinations.
Bob has spent decades in the vacation rental industry, with leadership experience across Steamboat Resorts, Wyndham Vacation Rentals, Vacasa, Casago, and now First Chair Destinations. His career has taken him from building a local vacation rental company in Colorado to helping lead large-scale portfolios across some of the most recognizable names in the industry.
Now, with First Chair Destinations, Bob is returning to a more focused, locally grounded model of vacation rental management.
Throughout the conversation, Bob shares what he has learned from building and scaling vacation rental companies, what the industry can take away from the Vacasa to Casago transition, and why the future of vacation rental management still depends on strong local teams, trusted owner relationships, and consistent guest hospitality.
He also discusses the role of technology, AI, distribution, OTAs, private equity, and consolidation in shaping what comes next for the industry.
Episode Chapters:
00:00 - Welcome to the show
03:22 - Bob’s path through Steamboat, Wyndham, Vacasa, Casago, and First Chair
06:26 - What the Vacasa to Casago transition revealed about the industry
10:25 - How First Chair is approaching its next chapter
15:29 - What rapid growth has taught the vacation rental industry
16:18 - Why local teams still matter in a scaled industry
17:05 - How hospitality can get lost as companies grow
23:56 - What operators can learn from the Vacasa to Casago transition
27:51 - What consolidation could mean for the industry
30:06 - Where AI can support vacation rental operations
33:16 - Building a hospitality-first culture across local teams
40:47 - Why OTAs still play a major role in distribution
46:56 - How owner expectations around channel visibility are changing
49:34 - Why the future of vacation rentals is still local
51:57 - How guest expectations are changing
Connect with Bob:
LinkedIn: https://www.linkedin.com/in/robertemilne/
Website: https://www.firstchair.com/
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#vacationrentals #shorttermrentals #local