Acquiring Minds Buying for Brand (Then Growing 4x)
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Jan 12, 2026 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.
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Short-Term Rentals Are Still Early
- The short-term rental ecosystem is still early and rapidly professionalizing despite Airbnb's age.
- New software and services create large opportunities for buyers and builders in the space.
Bought The Brand He Loved
- Matt had stayed with Red Cottage as a guest since 2012 and targeted it off-market because he loved the brand.
- He competed with institutional buyers by pitching to preserve and build the brand rather than roll it into a platform.
Value Managers On Commission Multiples
- Value STR managers primarily as a multiple of their management commissions, then adjust for contracts and team.
- Use 1.25x–1.75x of trailing commission revenue as a baseline and move it for portfolio quality.