Acquiring Minds · 2026-01-12 · 1h 25m
Matt Orley wanted to enter the short-term rentals space. Buying a business - and a brand he admired - was his way in. Register for the webinars: DO’s and DON'Ts of the LOI - TOMORROW!! - From W2 to Owner Mindset: How to Think About Your Take-Home Pay - Jan 15th - Topics in Matt’s interview: Investment properties as a side hustle Evolving short-term rental ecosystem Difficult transition with the seller Influence of Airbnb on customer expectations Importance of clear communication Rolling up property management companies Concentrating on one region of the country Difference between urban and rural markets Launching a membership program Putting the brand first when making decisions References and how to contact Matt: LinkedIn Instagram Red Cottage Get complimentary due diligence on your acquisition's insurance & benefits program: Oberle Risk Strategies - Search Fund Team Get a free review of your books & financial ops from System Six (a $500 value): Book a call with Tim or hello@systemsix.com and mention Acquiring Minds Get a complimentary IT audit of your target business: Email Nick Akers at nick@inzotechnologies.com , and tell him you’re a searcher
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