Buying for Brand (Then Growing 4x)

January 12, 2026
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U

nlike most guests on Acquiring Minds, today's did not come to his acquisition as a self-identified "searcher."

Instead, Matt Orley was an entrepreneurial guy who'd found an industry he really wanted to get into, and buying a business there was his path to do so.

The industry is short-term rentals.

That is, the property owners who rent their properties on the likes of Airbnb, and the growing ecosystem of vendors that serve those owners.

As you know, this is a category that has exploded in recent years, thanks first to the advent of Airbnb and later to Covid.

And you will hear Matt's passion for it; there is founder energy to Matt.

Brand is another differentiator of today's story. Matt is solidly a brand guy, and you'll hear how he is building Red Cottage as a brand-forward business.

In the 3 years since he acquired it, Matt has grown Red Cottage from 50 homes under management to over 200, and from about a million in top line to mid-7 figures.

In terms of short-term rentals in Matt's geographical market, the TAM is 250,000 homes.

So with infrastructure, brand, and innovative product offerings, growing his own business to 500 or 1,000 homes under management is "absolutely achievable," says Matt.

Please enjoy this conversation with Matt Orley, owner of Red Cottage.

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Buying for Brand (Then Growing 4x)

Matt Orley wanted to enter the short-term rentals space. Buying a business — and a brand he admired — was his way in.

Key Takeaways

Introduction

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U

nlike most guests on Acquiring Minds, today's did not come to his acquisition as a self-identified "searcher."

Instead, Matt Orley was an entrepreneurial guy who'd found an industry he really wanted to get into, and buying a business there was his path to do so.

The industry is short-term rentals.

That is, the property owners who rent their properties on the likes of Airbnb, and the growing ecosystem of vendors that serve those owners.

As you know, this is a category that has exploded in recent years, thanks first to the advent of Airbnb and later to Covid.

And you will hear Matt's passion for it; there is founder energy to Matt.

Brand is another differentiator of today's story. Matt is solidly a brand guy, and you'll hear how he is building Red Cottage as a brand-forward business.

In the 3 years since he acquired it, Matt has grown Red Cottage from 50 homes under management to over 200, and from about a million in top line to mid-7 figures.

In terms of short-term rentals in Matt's geographical market, the TAM is 250,000 homes.

So with infrastructure, brand, and innovative product offerings, growing his own business to 500 or 1,000 homes under management is "absolutely achievable," says Matt.

Please enjoy this conversation with Matt Orley, owner of Red Cottage.

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Matt Orley

Matt Orley
Matt Orley

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