Podcast:Acquiring Minds Published On: Mon Jan 12 2026 Description: 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!! - https://bit.ly/3YtLIvpFrom W2 to Owner Mindset: How to Think About Your Take-Home Pay - Jan 15th - https://bit.ly/4qJ1Xk5Topics in Matt’s interview:Investment properties as a side hustleEvolving short-term rental ecosystemDifficult transition with the sellerInfluence of Airbnb on customer expectationsImportance of clear communicationRolling up property management companiesConcentrating on one region of the countryDifference between urban and rural marketsLaunching a membership programPutting the brand first when making decisionsReferences and how to contact Matt:LinkedInInstagramRed CottageGet complimentary due diligence on your acquisition's insurance & benefits program:Oberle Risk Strategies - Search Fund TeamGet 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 MindsGet a complimentary IT audit of your target business:Email Nick Akers at nick@inzotechnologies.com, and tell him you’re a searcherConnect with Acquiring Minds:See past + future interviews on the YouTube channelConnect with host Will Smith on LinkedInFollow Will on TwitterEdited by Anton RohozovProduced by Pam Cameron