Matt Orley
Entrepreneur and founder/owner of Red Cottage, a short-term rental management brand that grew from ~50 to over 200 homes under management and launched membership and loyalty products.
Best podcasts with Matt Orley
Ranked by the Snipd community
12 snips
Jan 12, 2026 • 1h 25min
Buying for Brand (Then Growing 4x)
In this engaging conversation, Matt Orley, an entrepreneur and founder of Red Cottage, shares his inspiring journey in the short-term rental sector. He discusses his strategic decision to acquire a brand he admired, emphasizing the importance of authenticity in branding. Matt elaborates on the challenges of transitioning post-acquisition, particularly with the seller, and the operational fixes he implemented. He also highlights the potential for significant growth in the market and the innovative $500/year membership program that enhances guest loyalty.
Aug 9, 2024 • 37min
10 Entrepreneurs Building the Future of Hospitality That You Should Follow (If You Don’t Already)
In this discussion, a group of ten groundbreaking entrepreneurs share their insights into the future of hospitality. Justin Potts promotes lifestyle through creative media, while Sara Roitman and Nick Purslow craft unique outdoor experiences. Boris and Susan specialize in immersive camping, alongside Hillary Flur's luxurious travel ventures. Matt Orley and Brian Meyer revolutionize the cottage and home services industry. Plus, Becca Schulman Havemeyer and Janice Smith offer cozy coastal and outdoor experiences. David Garber adds a touch of wine, while Amber and Charlie Pl. adventure in hospitality!
